Episodes

Rob Walling:
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Welcome back to another episode of Startups For the Rest Of Us, I’m your host for Rob Walling and in this episode I’m going to answer several listener questions and I’m going to pull in one of my remote correspondence to help out with one of the first questions. Before we dive into that, I want to let you know about the best online community for SaaS founders. It’s called MicroConf Connect. You can go to MicroConf connect.com. We charge $50 a month and that keeps the quality of the conversation and the folks who are in the community very high. We also have an application process and we do in fact reject. It’s not just a fake one where we let a hundred percent of the people in, we reject applicants who we don’t think are going to bring value to the community, who are going to come in and sell or who frankly don’t qualify and aren’t going to improve the quality of the conversation. MicroConf Connect has been around for five years now and there are hundreds and hundreds of founders in there discussing things like, give me feedback on my landing page, or How do I validate this? Or I’m doing 1.5 million a RR, how should I be thinking about delegating certain tasks? If you’ve only been part of free online communities that are very high noise to signal and often have low quality conversations, you should check out MicroConf connect.com. And with that, let’s dive into my first listener question.  

Speaker 2:
Hi Rob. This is ZA from France. In the SaaS playbook you gave key values for a churn rate and saying for example, that a churn rate above 10% is catastrophic and a churn rate under 2% is great. As I am launching my hub, I try to analyze more of a retention rate than the churn rate. And my question is, do you also have key values of range for retention rate that can say if it’s good or not good? I mean, I can see the number of people who install the app and keep the app, and I wish to know which is a good percentage of people that keep the app compared to the one, but just install the app and live straight away and just to specify this kind of free offer where customer can try the app based on the value metrics. So this is why I ask this question. Thanks a  

Rob Walling:
Lot. This is a great question. Thank you for asking it. And to help me answer this question, I’m going to call in the startups For the Rest Of Us remote freemium correspondent, one of the foremost experts in the world on freemium that I turn to when I have a question like this. Ruben Gomez.  

Ruben Gamez :
Thanks Rob. Freemium retention. So this is an interesting topic. It’s also really hard to find good numbers in the way that you would find for churn or trial conversion rates. I’ve worked on this myself over the years for my SaaS Sewell. I’ve also talked to founder friends, I’ve done a bunch of research on this and the numbers are kind of all over the place. And then founders just often don’t really know what their activation rate is and especially what their retention rate is on free plans, free users. So all that said for SaaS, usually going to want to keep it above 20% if it starts to go into 15%. If I have a SaaS and it has a 5% free user retention rate, then I’m definitely jumping on that and there’s something going on. The free plan isn’t working or we’re targeting the wrong free users or something. 

Now that’s very different than retention rate on mobile free users. And I mentioned mobile because you said the word install, which made me curious and I looked into the app that you have and it does seem to be mobile consumer. So the retention rate on mobile users is actually way lower. Think something like three to 5%. But I was talking to a friend just recently and asked him about his retention rate on, he has mobile app, he has millions of users, and his retention rate was somewhere around 1%, which seems like really low. But this is another thing when it comes to retention rate on free users is that the more volume you’re working with, the harder it is for your retention rate to be high just because your funnel is so wide and probably your top of funnel is so wide and you’re just getting so many users and the targeting tends to be a little bit off. 

And if you get very few free users, they’re often pretty targeted and maybe they’re more highly motivated and you’re probably going to have a higher retention rate. It doesn’t mean that you can’t improve your retention rate, it’s just what you tend to see depending on the type of volume that you’re working with. The more important thing to know, and the thing that I would really focus on is that your retention curve, this is like if you’re looking at a chart and you have a hundred percent at the top and 0% bottom, this is the percentage of users that you keep and you measure this over time, over a week or over several weeks or months or whatever, and you have this line that sort of starts at a hundred percent and as it moves to the right, it drops. And what you want to avoid is for this line to get down to zero, you want it to flatten out at some point eventually just kind of stay steady and that’s the most important thing. 

If it doesn’t stay steady and it’s just dropping to zero, then you have a problem. So it’s almost like retention rate is so different depending on the type of app that you have and whether it’s something that’s supposed to be used daily or if it’s consumer, if it’s a habit sort of thing, that it’s more important to look at that pattern and whether it flattens out or not. The reason why flattening it out is important is because then you can over time as you get new cohorts in, you layer that in. Sure you have like 15%, 20% of your free users stick around after day 30, but then there’s another 20% after day 30 and for each cohort and that kind of builds over time. So if you don’t have that and it eventually always goes to zero, you’re kind of just starting over each month each week or whatever each day. So those are the main things that I’d look out for if I’m trying to improve my free users’ retention rate. I think that’s it. Over to you Rob.  

Rob Walling:
Thanks for that, Ruben. This question actually got me thinking that next time Ruben comes on the podcast, I think I’d like to dig into freemium a bit more, maybe not for the whole episode, but to have a topic where we don’t just talk about retention rates, but there are things that Ruben will say when we get in conversations about freemium that I just wasn’t aware of because the last free plan I had, well, I guess we had one at Drip after we were acquired, and then I had one with hit tail as well. So I have had freemium plans, but I never dove into it the way that Reuben has. And I’d like to not only talk about retention rates, but if you have a free plan, what’s the range of conversion to paid that you should be looking for? Because Reuben said something that surprised me. 

I dunno, it was a year or two ago. He and I were just BSing at some point and someone had, I believe a 7% freemium to paid conversion rate within X months. And Ruben made the comment, and I hope I’m not misquoting him, but he made the comment, oh, that’s too high. And I was like, what do you mean too? How can it be too high? Right? That’s like saying my trial to paid conversion rate is too high and it’s like, don’t you want that to be as high as possible? And he had just an amazing take on why he had concerns about the structure of that free plan. And so I think next time Ruben comes on, I’ll make a note to have a conversation around that. So thanks for that question Xavier, and thanks for answering that with all the detail that you lend Ruben. My next question comes from longtime listener, longtime MicroConf attendee and speaker Ted Pitts, the co-founder of More Aware Software. Fun fact, Ted and his co-founder Harry attended the very first MicroConf in 2011 as well as several subsequent MicroConf, but they run more aware software, which is a very successful SaaS for countertop installers. And Ted has a question about delegating the core four SaaS skills.  

Speaker 4:
Hey Rob, this is Ted. I enjoyed your comments in episode 8 0 7 about the core four SaaS skills. I agree with what you said for early stage companies about founders needing to own those roles. I don’t think founders have to start out good at every one of the core four as long as they take ownership of it and commit the time to getting good. That’s a little different than saying you have to already be an expert in all four of those areas to succeed. So I’d be interested to hear your experience with how this concept evolves as the company grows because if you want to be an owner of your business without also being an employee or if you want to sell to someone who doesn’t want to buy a job, you may want to delegate these at some point. I mean, it’s normal to have other employees help execute on these four functions, but I’ve found that it’s challenging and high consequence to delegate full ownership of these functions to non founder employees. Can you talk more about how you have seen founders successfully delegate the core four as they grow  

Rob Walling:
Grow? Honestly, Ted, this is a really good question and I’m glad you asked it because it instantly got me thinking. I have seen this done many, many times and I love the thought process of A how do you do it so you’re not just doing all these things forever and B, how do you do it well, when do you do it? How do you not abdicate it? How can you delegate not abdicate probably? How do you hire for this? So there’s a lot here and just as a refresher for folks who didn’t listen to my episode when, I guess it was about three, four episodes ago where I talked about the core four SA skills and what I said is I get these questions of, Hey, I’m trying to find a co-founder, do I need a co-founder? And what I’ve finally kind of landed on as my stance is there are four skills that I think are absolutely critical to have operating at an owner level or a founder level. 

And so usually if you’re bootstrapped, that means that the founders, founder or founders between them have to own these skills in the early days, and I talk about it for like 15, 20 minutes on that episode. You can hear all the nuance there. But the core four are sales or marketing, depending on if you’re high or low touch product and development. The easiest one to delegate of course is development, especially if you are a technical founder. But again, I already went through this for 20 minutes so I won’t dive in here. The question that Ted has asked is when do you delegate these? And I guess I’ll start with I think at different stages. The way I’ve seen it done well, and this is across my investments, this is the TinySeed companies as well as my independent investments. I think I need to rerun the number, but I think it’s 234, maybe 2 35 SaaS B2B SaaS companies that I have insight into as well as of course thousands across MicroConf and startups For the Rest Of Us where I have a little less exposure, but I have a lot more data across the state of independent SaaS and such, development is the easiest slash one that I would consider the earliest because it is so time intensive and especially if you already have that skillset on your founding team, I’m going to say it’s not that hard. 

It’s not that hard to find a really good developer that can help you. It’s not easy, but it’s not that hard compared to finding a product person that’s going to come in and understand your product and make decisions of what to build and how to build it. So I’ve seen great developers bring on help at 10 KMRR, right? And in fact, with Drip as an example, I think I had two devs, I had Derek Rimer, and then we had a junior dev by the time we were at maybe 10 or 15 KMRR. But keep in mind that was a market that really needed a lot of features. If you’re going to build an ESP or marketing automation, you need a couple years of person hours into development just to build the feature set to be table stakes in that realm. So if you’re in a tighter vertical where there isn’t that much competition, maybe you hire a dev at 10, 20 30 KMRR, and that will be a huge weight off your shoulders now delegating the technical direction of the company, all the tech leadership and the architectural decisions, that’s the kind of stuff that I would keep on the founding team until much later, and I’ll get into that in a couple minutes. 

Sales, in terms of sales demos and closing sales, I’ve seen folks, founders get a repeatable sales process by the time they’re doing. I’ve seen some 2030 KMRR and if it really is repeatable, I mean I handed off sales. We were at about that 2025 KMRR because I had done enough sales calls and they were very similar to each other that I was able to hire Anna who did customer success and sales for us. But then I’ve also seen folks, if the sales process is more of an enterprise procurement situation, I’ve seen folks wait until they’re at a million a RR or even beyond that, I hear some sales coaches who are more in the VC backed space saying founders should definitely do it until one or 2 million, and that’s good guidance, but I think that you can do it earlier than that if your sales process is not super complicated, especially if it’s like a one or a two call close and you find there’s a lot of repeatability. 

If you have a dual funnel and you’re doing sales at the low end, let’s say 500 a month, and then you have 5,000 a month as a founder, I’d probably retain the 5,000 a month sales calls. So you get the idea there for marketing is a tough one because marketing is 20 different things, right? It’s being an individual contributor and actually pushing the buttons in a Facebook ads console. That’s something I think you can delegate to contractors or a freelancer or an agency really early on. It’s just a black box. Does it work, does it not? But marketing strategy and marketing project management are two layers above that, right? The strategy is figuring out what we’re going to test, how we’re going to test it, monitoring it, looking at the analytics and project management is just keeping everything going and making sure that if you have contractors or in-house folks, they’re doing the thing and giving them guidance and keeping ’em on task. 

Project management, I think you could delegate relatively early if you had budget. It’s all going to be budget constrained. The marketing strategy is pretty tough. It’s hard to find someone that can take you, especially if you’re at the zero to one level where you’re still trying new marketing approaches. But if you have two that are working or three that are working, that’s the kind of stuff that you can definitely hand on once it’s working. And I don’t think it’s really an MRR goal or an MRR level where you would hand that off, but I think of it more as how repeatable is this process comes back to my certainty versus uncertainty framework of what founders should be working on Once a marketing approach is fairly repeatable, you can hire folks to crank out the SEO articles or create the videos or do what it is that you’ve been doing versus marketing strategy. 

I’ll tell you the earliest, I’ve seen founders like the most successful founders in TinySeed that are doing seven figures and up in a RR the earliest I’ve seen any of them really bring someone in to collaborate on strategy. And I’ll say they didn’t hand it off completely, but it’s probably about certainly above a million A RRI would lean towards 1.5 to maybe 2 million a RR. And this depends on a lot of things, but I am giving you loose ranges. It’s further along than most founders want, right? A lot of developer founders want to be like, how can I just outsource sales and marketing? And they’re doing five KA month and it’s like I’ve never seen a founder outsource marketing strategy and doing sales calls, sales demos and closing sales that early and have success with it Doesn’t mean you can’t bring people in to help you with it, but the founder has to drive it. 

That’s what I mean when I talk about the core four is even if you hire help, you really need to own most of these things to above, I’d say about a million product is the other one. I think you’re probably, it’s definitely one to 2 million is the earliest I would consider bringing someone else in to start making product decisions. What you build in what order, getting customer feedback, understanding your space, deciding how things are built, really having product management or product ownership on your team is probably going to be at a minimum to, man, that might even be two or 3 million. I can’t think of any TinySeed companies that have brought in outside help for 3 million on the product front. And so I’ve talked a lot about when you should consider delegating some of the core four, and I do think it’s a good idea by the time you hit a million or 2 million that you really start delegating these things. 

But hopefully what you’ve come away with is that you don’t necessarily need to hand off all of marketing. You can hand off pieces of it, hire a project manager if you have budget, hire individual contributors, whether the W2 freelance, it doesn’t really matter who are pushing the actual buttons on the marketing channels. And then maybe hire someone to at first collaborate with you on marketing strategy and hire someone to come in and shadow you for sales and eventually hand off the lower end deals. And then maybe if they’re doing great, then they work their way up to the more expensive deals. And similarly with product Man that, I mean Derek and I made every single product decision on Drip until we were doing, I would think we were doing at least five, 6 million at the time it was post-acquisition. And we brought in a product person whom you’ve heard on this podcast, his name is Brendan Fortune, and he came on here to talk about product management. 

And that was a tough hire. And in fact, hiring a product person is very, a really good one, is very expensive. And at least the way we architected it, it was very much a collaborative process where the three of us then made all the product decisions. And then as Derek and I transitioned out of the company, then Brendan really took over the leadership of that. So how would I think about doing this? Well, certainly if I had the core four on my founding team, let’s say it’s two founders and we split these two things, I would absolutely be thinking about delegating slash hiring some senior engineers to start taking over even to the point of architectural decisions as I’m doing single digit millions. And to me it’s always a collaboration. It’s like if I spend two hours a week, three hours a week talking to my senior dev lead who’s running the whole thing, you can have a lot of impact in those couple of hours where you’re almost an advisor or a consultant to that team and you bring someone on over time. 

I mean, I can’t imagine just bringing someone in, being great here. You make all the decisions. Now, it would have to be a really slow burn for me to feel comfortable with it on any of these fronts. But the thing to keep in mind I think is hire someone who they need the experience. They need to have been a senior at all four, not all four of these things, but at any individual thing that you hire them for. So whether that’s marketing strategy or sales or development or product, you take your best shot and you hire someone senior, you bring ’em in and you collaborate for a while and then you slowly draw down your time moving from being the operator, making the decisions day to day, to slowly stepping back to like, I’m going to let you take that piece over customer interviews that I used to do. 

I want you to do this now and just report back to me. And then there’s a little bit of coaching that happens there. And then I used to create the kind of backlog all the features that we could feasibly build and why don’t you start doing that and I’m just going to monitor. And then you slowly, as it’s done well, you slowly just let go a piece at a time. So at least the way I view it is probably more like a bootstrapper does where everything’s a slow move. It’s slower than if it is like we raised $10 million, I’m going to hire all these people all at once and you need to go to headcount of 50 within a year, or your venture capitalists are busting your chops. It’s a very different game. And I’ve seen that done well and I’ve seen it done poorly mostly I’ve seen it done poorly just moving so quickly. 

But for me it is a slow process and it gives you time to kind of suss out, oh, where are this person’s strengths and weaknesses? Where do I need to either hire an additional person to give them help if they have a blind spot or a weakness in an area, or where do I need to still stay involved? And then one of the ultimate delegation moves that I’ve seen is folks running a SaaS company doing several million and hiring a COO to take over management of those areas and even moving them to CEO to where you really are just working on your areas of expertise, your zone of genius. Because as founders, we are Jacks or Jills of all trades, but usually there’s one or two that we’re really good at. And sticking in that zone of genius and not having to spend so much time working on the others I think is probably a long-term goal, especially if you’re going to make it a sustainable company that you want to run for years or decades or even if you want to sell it so you’re not so tied to the day-to-day operations. 

So that was an excellent question, Ted. Thank you for sending it in. And if you or anyone else feels like I missed any aspects of it or there’s more to discuss, please send in a follow-up question and I will either talk more about it or have a guest on to bat it back and forth with me. I think given that this whole idea of the Core four is like a month old, it just kind of hit me one day while I was recording an episode. I think there’s more to discuss here and more to be thinking about. So really appreciate the question. Hope that was helpful. My next question is from Twitter and its Val Soapy, longtime listener of the pod as well as many time MicroConf attendee and Val asks, I’m always wondering if a great founder with all the Core four sales, marketing, product and dev can succeed with any product or the product first and foremost must have legs. 

Where’s the cutoff? This is a fun thought experiment. I think. Here’s my opinion, there are founders out there. I often, they’ll either come on the show or I will mention them as just being someone who’s going to kind of succeed at anything. And I think for those founders, even if they have, let’s say it’s a bad market or a bad product idea that they launch into, they pivot and they figure it out. And I’ve seen founders, this is the Ruben Gomez’s and on a bigger stage with Jason Cohen and Heat and Shaw, and we look at HubSpot and how they pivoted in the early days. There’s just folks who I do think if they have those Core four, they will figure it out. It doesn’t necessarily mean inevitably, doesn’t mean they’re right the first time, but it means that they will keep grinding and look at that product sense and get that sense of the customers and kind of look for market poll into an entirely different vertical or an entirely different space and they just figure it out. 

I feel like there’s always a little bit of luck involved in hindsight, but I’ll see the same founders having success after success after success, and eventually I’m like, they’re just going to kind of figure it out with whatever they’re doing. David cancels another example. I believe he’s sold five startups. They’re all successful. I could go on a laundry list of folks who could just kind of do it. But with that said, I think your market and your product are a multiplier on your strength. As a founder, and I can’t remember where I talked about this, I don’t think it’s in a book. It might be in the SaaS launchpad course at SaaS launchpad.co or maybe a YouTube video. I’m going to need to look back. But I talk about how the founder skillset and ability to execute is a multiplier on the idea and the market. 

And I’m trying to think if I had two or three things multiplied together, was it like founder times product times market? Maybe it wasn’t just founder times market because I can go into a market and build a product no one needs, so it has to be, I almost think it’s these three things multiplied together. It’s the founder times how you’re solving the problem itself, like the product times the market itself, like how hungry it is, how willing it is to spend money. We can go back to the 5:00 PM framework and look at those categories. So let’s say we have founder times product, times market, and each is on a one to 10 scale. Just to keep things simple. If the founder is world-class, the product idea is amazing and the market is super hungry and growing. You might think of this as a WP Engine type situation where you have Jason Cohen launching into a growing market at the right time, and his product idea, it was very, very smart. 

Maybe that’s a 10 times 10 times 10. So you have, what is that, a thousand? Yeah, a thousand. I don’t think any idea product or market is a 10 out of 10. So maybe it’s nine or nine plus times nine times nine, but let’s say you have a really small market that’s not growing very quickly and people’s willingness to pay is pretty low. Maybe that’s a one or a two. And if the founder’s really good, let’s say they’re an eight or a nine and the product is really good, it’s a seven. You can imagine. I mean this is all kind of made up, but you get the ideas that it’s multiplicative. That’s how I think about this. And so we could go down to gruesome detail and be like, well, your particular product knowledge, you’re like an eight out of 10 or your product abilities, and as a dev you’re like a six out of 10. 

I think we’re going down such a theoretical rabbit hole. I would just say the founder, I would rate myself as, I don’t know, among all founders, maybe I’m a seven out of 10 or an eight out of 10. And then this product and this idea, these are all kind of made up numbers, but you get the idea, it’s directionally correct. I like the idea of a multiplier. You don’t just want to add them together. It can actually 10 times 10 versus 10 plus 10. It’s a logarithmic scale. I do think the best markets like the nine or the 10 out of 10 markets are significantly easier slash better to enter into than ones that are not. And for the astute listeners who have listened to this show for a while, you’re probably thinking to yourself, well, what about hard work, luck and skill? And I do think that the founder themselves, if you’re going to rate yourself I a one to 10 hard work and skill, go into that. 

How hard do you work? What are your skills in the areas you need to be a founder? I think that all just gets lumped in your one to 10, but luck is not covered anywhere. When I say, Hey, it’s founder times product times market. So maybe there’s a fourth of yeah, if you got really lucky, it could bump it up. I don’t know that that’s particularly helpful because I think some people attach to luck as an excuse so they don’t feel bad if they fail. But we could add that as a fourth as well. So those are my off the cuff thoughts. Val, I really appreciate that question. I hope it was helpful. My next question, I’m going to leave as anonymous. I believe they gave me permission to mention unstar For the Rest Of Us, but I think it’s just easier if I leave them as anonymous. 

They basically wrote in and said they’re using off the shelf software, and I don’t know if it’s an open source package or if it’s a commercial package, but that’s the underlying software that they have adapted for their SaaS. And I think they do not have development experience on their founding team. So they are missing one of the core four. And the problem is, is they’re hitting roadblocks in terms of being able to adapt to the market. And so they’re going to need to completely rewrite their tech. And there were a couple of things around this. One was a question around whether a TinySeed would fund a company like theirs. And the other one was a question that I think I came up with myself, which was more like, is this a good path? Is this a viable path or should founders avoid this? So to answer the first question around whether TinySeed would fund a company like this, I lump companies together where either the underlying tech has been vibe coded or it is a platform that the founders don’t control, like in this case or if it’s no code, all three of those are cases. 

And there are probably others where I know that the code-based is going to need to be rewritten fairly early on, completely from scratch. And maybe that’s at 10 KMRR, maybe it’s at 20. I do not think you can get to a million in RR in any repeatable fashion. There’s probably one example that someone can bring up. But as a rule, I think this experience is going to be a very common one. TinySeed has funded a couple no code, code bases, and I don’t honestly know the exact number. It might be two and it may be a size four. I don’t think we’ve funded a vibe, coded code base. We are now asking that in interviews because I want to know if you’re going to need to stand still for six months and rewrite this code base before you can really scale and get to seven or eight figures in a RR. 

So the answer is would we might, but it is not a hard no, but it’s a factor that counts against you because to me it’s a factor that counts against your possibility of success. It’s going to be a drag on your momentum. And I have a tough time imagining all of the most, the TinySeed money being invested into a business that then has to stand still for 3, 5, 6 months to recode an entire code base. So the answer is it depends because let’s say it’s not a huge code base and you could code the entire thing in a month or two. Great. And as I said, we have funded a few of these, but it has inevitably been a big pain for them and it has been a bit of standing still hard to keep up with the market. And so it is not a hard no, but it is a factor against them. 

And if you think about it, that may be the answer to the second one as well. Is it a, you should never do any of these things? I don’t think so, but I wouldn’t do them if I could avoid it if there was any way around using no code. And again, this is, I’m not saying for 5,000 or a $10,000 lifestyle business, if you’re an indie hacker and you want to quit your day job, that’s great. You can do whatever you want, scrap get by, and I’ve done that. I’ve had crappy code bases that just kind of limped along, right? That’s okay. But if you want to become a seven or eight figure a RR SaaS company, I would try to avoid this if at all possible, and I would want to take more time upfront to be in control of the code and not have the platform risk and have the ability to be agile with a lowercase a. 

Now, with all that said, one could make the argument well, but what if you have to spend three to six months coding? Isn’t that a lot of risk upfront? You could validate the market with no code or with a vibe coded thing or with a third party platform as this founder has done. And the answer is, yeah, but then what happens when you validate that market and you have some folks paying you and you get to 2, 3, 5 KA month? The question is, are you going to then stand still for six months while you’re rebuilt the tech? And for me, for my money as a founder, that’s not something that I would enjoy doing. That would be very painful. I mean, I remember in the early days of direct even having to stand still for a month while we migrated to, I don’t know, a new database provider and had to rewrite some things to be more performant and that was agonizing. 

So I can’t imagine not being able to serve our customers in the way that I want to and not being able to respond to the needs of the market in the early days of your app, which is exactly when you need to be doing those things. That’s one of your advantages over big competitors, over entrenched incumbents is that you have the ability to ship so fast and your feature velocity can be super high. You don’t have a bunch of tech debt, and that is one of your competitive advantages as a small bootstrapped or mostly bootstrapped startup. And I have a really hard time imagining giving up that flexibility, especially in the early days. Those are all the questions I have time for today. If you have a question for the show, feel free to email it to Questions at Startups For the Rest Of Us dot com or head to the website, click ask a question in the top nav that’s startups For the Rest Of Us dot com. And you can send an audio or video question to go to the top of the stack, or a more advanced question also goes to the top of the stack. But all questions are welcome and it looks like I only have about 20 questions in the backlog right now, so can definitely use more. Thank you for joining me this week and every week. This is Rob Walling signing off from episode 811.  

Rob Walling (00:00):
Welcome back to another episode of Startups For the Rest Of Us. I’m your host, Rob Walling, and in this episode I welcome Derek Reimer back for another round of listener questions. We talk about the best AI coding stacks, how to balance shipping fast with UI polish, when and how much to think about security and more listener questions. Before we dive into those, I want to make a call for speakers for MicroConf us. You can head to MicroConf dot com slash pitches if you feel like you have an incredible framework, a unique insight, or something else to share with 275 of your favorite bootstrapped and mostly bootstrapped founder friends. MicroConf us is in Portland, Oregon in mid-April, and we are filling out the speaker docket as we speak. MicroComp is unlike any other event I’ve ever attended. We don’t let people sit and pitch their product. We’re looking for great talks from folks who are in the trenches, whether you’re a founder or an advisor or a consultant, a freelancer. If you are working in SaaS or on a topic that can really help SaaS founders and you feel like you can deliver it and you have proven experience on stage that has been recorded at least once, you should add to MicroConf dot com slash pitches. And with that, let’s dive into listener questions with Derek.  

(01:34):
Derek Rimer, welcome back to Startups For the Rest Of Us. Thanks for having me. It’s great to have you, man. I believe this is your 22nd appearance, but who’s counting? I’m really into numbers, so we are going to answer some listener questions. You’re back by Popular Demand. I mean, honestly, not a month goes by that someone doesn’t either comment on an episode you’ve been on or say, Hey, when are you going to have Derek back on the show? And I’m always, pretty soon. Pretty soon. So you’re a fan favorite  

Derrick Reimer (02:01):
Too kind, too kind. I’m honored.  

Rob Walling (02:03):
Let’s dive into our first question. I have a mix today. There were some questions that have just come to the main startups For the Rest Of Us line, but then a couple days ago I posted on X Twitter and said, Hey, Derek’s coming on the show. What questions do you have specifically for him? And the first couple will be along those lines. So Brandon Manson on Twitter asked as a solo founder with a two month old and a three-year-old and two plus hours of commuting per day, I found AI coding to be an absolute game changer for me. I use Claude Code plus GitHub coding agent to do what is essentially spec driven and development. What tools and or workflows are you using?  

Derrick Reimer (02:44):
Two month old, 3-year-old, two plus hours of commuting a day? Oh my gosh. Brutal, brutal,  

Rob Walling (02:50):
Brutal. Yeah, let’s just have a moment of silence for your productivity right now. And they won’t be permanent, but my kids are four years apart, but that’s a lot. AI is going to help you  

Derrick Reimer (03:02):
And it is nice to have AI to help accelerate things, especially when you have those types of constraints. So my current tooling, and I feel like this is always needs to be caveated with the timestamp of, we’re in November of 2025, so this may be completely outdated three months from now, but as of right now, I’m still using Windsurf as my main editor, which is sort of an alternative to Cursor. The only reason I’m using Windsurf is because someone convinced me to give that one a try first and then I’ve just stuck with it. But I think Cursor’s probably a little more popular than Windsurf and they basically do the same thing. They have a little agent panel built in that communicates with the major models and helps you edit your code with ai. So that’s my main editor and I actually don’t use the agent functionality in windsurf much anymore.  

(03:53):
I’ve kind of switched over to Claude code for that. And you can actually install Claude Code into Windsurf or any VS code based editor so that it sort of natively integrates as if you were using the agent in Windsurf or Cursor. And I’ve done that because Windsurf went through a period of time where they were, OpenAI was flirting with buying them, and then Anthropic cut off their cloud access for the best models and then cloud code was coming out around the same time. And it seems like cloud code gets first party access that others don’t because Anthropic is the one that’s developing it. So they build the model and the agent so they’re able to make sure it works really well and they probably give themselves priority on compute and all that. So I use that. But in Windsurf, they still have tab completion type of functionality.  

(04:44):
So as I’m bouncing around, if I put my cursor somewhere in the middle of a code file and I’m thinking about modifying that code about, I don’t know, 60% of the time, it’s able to guess what I want to do and kind of show the auto complete style. Here’s the proposed change and I can just hit tab and accept the change. And that for the longest time didn’t using that type of thing. That was sort of how GitHub copilot worked a couple years ago. That was the main way that you would use GitHub copilot. And for me, it always felt like someone was trying to finish my sentences before I had time to think through what I was going to say and it interfered with my thought process, but these days, the tab completion stuff is getting really good and it feels like it’s reading my mind half the time.  

(05:28):
So that’s kind of my two main tools while writing code, GitHub code has their new plan mode thing, so you can ask it to do something and to make a plan first, and that’s sort of natively built in to the editor, and so it’ll propose a plan and then you can flip it into kind of auto accept edits mode. And so it’ll make changes, run the tests, read the test output, make more changes, and kind of iterate on its own, which is really nice. It used to ask a lot more frequently, do you want me to do this? Do you want me to do this? And I think it’s getting a little bit more refined in its ability to just sort of iterate on its own. So that’s been cool.  

Rob Walling (06:09):
Cool. So it sounds like overlap though with him, like Claude Code seems to be the leader in this space.  

Derrick Reimer (06:16):
I think so. I mean, I will say that I’m, I feel like every week I’m hearing about some new thing that people are using and I’m not one to necessarily jump right on it. I kind of wait to see, okay, it seemed like there’s enough critical mass here where everybody’s talking about this thing. Okay, maybe I’ll give it a try, but I can only allocate so much time to trying out something new and potentially changing my workflow maybe to my detriment, but it’s just moving so fast.  

Rob Walling (06:45):
Here’s the thing, so I think of being an early adopter as either it’s a hobby that I’m doing nights and weekends or I have a day job and I have a bunch of downtime, which I used to work at a credit card company. I was a developer and I had 40, 50 hours a week that I was there. And oftentimes I’d take an hour and just kind of screw around with stuff. If I were running my own company and I was coding on my, I wouldn’t do that, right? It becomes a lost opportunity cost. And so early adopters, it’s the same way we used to build our own PCs, right? I’m sure you remember that. And then at a certain point I’m like, when I became a consultant and I was billing whatever, a hundred donut, 50 an hour, I stopped building my own PCs because an hour of downtime because my graphics card went down, became catastrophic. And this is what you’re in now where it’s like every minute counts and productivity is more important. And so it is that balance of I don’t want to try the new AI model or the new JavaScript library that comes out every week.  

Derrick Reimer (07:42):
The nice thing about these is I found in general a lot of these AI tools, they try to make extremely smooth to adopt. So trying out cloud code, initially it was in the terminal and then at a certain point I started seeing, I don’t even know how I discovered it, but it was like, Hey, do you want to install this into VS code? And I was just like, yes. And then it just did. It was very seamless. So the nice thing is a lot of these tools are, I mean, it’s a land grab right now and they’re all trying to be as easy as possible to adopt. So that has been the nice thing compared to other technologies in the past where it’s like, oh boy, okay, I got to roll up my sleeves and read a bunch of docs and learn this thing. Thankfully, a lot of these things are pretty quick to be able to try out.  

(08:25):
There’s a new one called Tide Wave from, I think actually some of the people behind Elixir Language are working on this, but they’re not just building it for Elixir, they’re doing it for Rails and Python and JavaScript and these different ecosystems. And it gives you kind of two things. It gives you an MCP server for your code base. So I can have Claude Code have some first party tool access to my code base. It can ask Wave to search all the functions that are defined in a module as opposed to it doing a string search. So it has just a little bit higher fidelity and it also knows what packages are installed in my project and can read the docs for those. So it has a direct line to the doc site, so it just helps it be a little bit better at what it does. So there’s that, and then I think they’re also adding a kind of Claude code esque editor in the browser, so it’ll open up your project on the side, have a panel, and then you can ask it to make changes to the page that’s currently showing and it’ll live edit for you. I saw  

Rob Walling (09:30):
Someone demo this. I was really impressed with this. Yeah, I saw it on a YouTube video. I was like, whoa. Yeah, that’s really cool. If you had told me 10 years ago that Microsoft would have the leading one of the leading editors with VS code, I’d have been like, no, no, no, no, no. There’s no way the rails and the open source and the elixir developers are ever going to use a Microsoft product. You remember I always loved Visual Studio back in the day when I was a net developer because it was just so good. Everything was strongly typed and you’d type out your object, hit dot, and then you’d see all your methods and all this stuff. It was just really, really engineered very well. And I know VS code is not exactly that, but when it came out I was like, good luck Microsoft per usual, and then suddenly it’s everywhere. I feel like everyone uses it  

Derrick Reimer (10:16):
And I think the fact that it’s open source, yeah, built on kind of deep open source foundations with Electron and I dunno, it’s like the fact that it’s open source and it’s been able to be forked by Cursor and Windsurf and others to then layer on this functionality has just made it even more entrenched I think, which is kind of cool. There’s interoperability with all the VS. Code extensions now also work in Cursor and windsurf, so it’s a smart strategic play. There’s a lot of jokes out there about how there’s these multi-billion dollar companies that are built on top of a fork of VS code, but hey, I mean it’s a land grab  

Rob Walling (10:54):
That’s open source. Yep. Yeah, so thanks for that question Brandon, and I really appreciate your insights on that, Derek. I know some folks are out there kind of looking for, maybe they haven’t figured out their AI coding stack or maybe they’re just dipping in. It’s helpful to have just a perspective or two in this case from the two of you guys, from folks who are doing it day to day. Our next question is from at j Geek, SEO on X Twitter, and they ask, how does Derrick balance shipping fast with maintaining design polish in solo projects? That daily trade-off fascinates me and I typed out a response to this asker and did not send it and my jokey response was, Derrick does not. He just gives up on the polish. Have you seen how crappy his product was? And then I thought, someone’s going to take me serious. It was a very dry, just a sarcastic dumb thing to say, but I’m saying it here because yeah. Anyways, there we are. That sets you up how you maintain this balance. I want exactly how you do it. Don’t tell me. It depends. If you say it depends. I will cut your mic.  

Derrick Reimer (12:00):
I know these questions are always so tricky. I wish I had a really good answer because yeah, it’s not a formula. It’s like I was trying to think of the best way to characterize it without just sounding, you just have to be awesome at it. But I do think it’s a learned  

Rob Walling (12:16):
Intuition.  

Derrick Reimer (12:17):
Yeah, yeah, just intuition. I really like it’s a learned skill and you have to build up your intuition on when to call it on something, when something is good enough. And I think it does depend on your context. How important is a high degree of polish in this area? I would say not every part of my products are polished to the level that I would ideally want them to be, but every time we’re building a feature, it’s like, okay, we have this dropdown and yeah, it’d be nice if we had all the icons for all the things showing in this dropdown that would look really cool. Is that really that important right here? No. And that’s going to add an extra couple hours to the task and we need to move on to other things. Nope, let’s call it. So I think it’s a never ending series of judgment calls and I think you can kind of refine this over time and build up your skillset around it.  

(13:09):
I’ll also say this is some other practical things as I reflect on how my process has changed over time and how technology has changed over time. These days, UI component libraries have gotten really popular and I didn’t rush to adopt them right away. I was sort of the mind that every element in your app needs to match the aesthetic of your kind of internal design system. So you should just design all your form inputs and selects and check boxes and radio buttons, design all these things from scratch to match your internal design system. And I feel like we’ve sort of moved in the direction where a lot of these things we’re always just kind of looking for them to look basically native. A good default, a good sensible default is like do your form inputs kind of look operating system native. And there’s actually a lot that goes into making a lot of these controls truly accessible following all of the Aria accessibility guidelines and does you have keyboard navigation in your dropdowns and all this stuff that you ideally want to have.  

(14:18):
And there’s not a lot of value these days in trying to re-implement a lot of that stuff. So adopting either a catalyst from Tailwind or Shad CN or Flux or there’s a bunch of these for all the different kind of flavors of front end that people work with. And I started using this in all of my projects and Savvy Cal meetings are the older savvy Cal product kind of has some handbuilt components, but we’re gradually moving over to catalyst components just because it’s like I don’t want to be thinking about styling all of these things. I want to lean on things that people have put hundreds of hours into carefully crafting. And so adopting some primitives that other designers have spent a lot of time on shortcuts the process for sure. And then I think about for higher level components, it’s like having the discipline to say, all right, I built this, say it’s like a filtering UI at the top of a list page and I figured out the structure for this thing and maybe I’ll have other pages where I need filters, having the diligence to extract that into a reusable component. So then the next time I need to go and add filters, I’m not having to think about, alright, let’s duplicate this code over and what’s different about it if you do the thinking upfront when you first design something, then you’ve given yourself the gift of having something reusable later on and you don’t have to spend a bunch of time on it.  

Rob Walling (15:42):
Yeah, the discipline, I like that word discipline. It’s hard to do when it’s like, this doesn’t buy me anytime right now, but my future self will thank me. And then how do you not overdo that because you can, oh, I’ve seen people gold plate their code where everything is super reusable and so that’s again that judgment call of  

(16:01):
It’s just enough. And I think here’s the thing, you have to unlearn. If you’ve worked at big companies and had, again, infinity hours per week to just ship a thing and worked on a big team where you’re working on one piece, you can really gold plate stuff and it’s fine. And I know I had to unlearn those habits when I started building my own stuff. I needed to move it two to three times the speed. And so it’s like, what do I cut? What corners do I cut? There are corners that you need to cut in order to keep your velocity going. And it sounds to me like I would say you have a very, very refined kind of design and ux, like UI taste or editorial eye we could say. And if I were to say, all right Derek, you’re going to design this settings page design and build and code out the settings page versus the main interface to Savvy Cal that everyone sees every day, you would want the main interface to be a nine out of 10 plus nine plus out of 10 and the settings page, maybe you could do a five out of 10 where it is like, eh, there’s some check boxes still.  

(17:04):
They’re not even sliders. And that part is the judgment call, but you have to develop that editorial eye first or that taste right if you don’t know what if you don’t know the difference. There’s people who just will look at a UI and say, I don’t know, is this good? Is this great? Is this a two out of 10? A 10 out of 10 that you also have to develop that. I think  

Derrick Reimer (17:24):
It’s funny how the things that large famous software that we all know, the things they can get away with. You go to the Gmail settings sometime, just take a look at that Catastrophic. Yeah, I was in ’em the other day. It’s still so bad. Yeah, I mean stuff is really tightly packed in there. There’s the save button that’s tiny way down at the bottom, super easy to miss. Just so many things wrong with that. I will say if you’re a newer entrant to the market, making sure you have a reputation of a certain level of quality is often important. Gmail can get away with that because it’s Gmail, but your new app that’s trying to be viewed as credible, you can’t get away with that level of sloppiness. But just to say that, yeah, there’s especially certain parts of your interface, like a settings panel where I think we tend to perfectionists me tend to want to obsess too much over that. And it’s like just keeping that in check. Alright, you can always come back and refine that later. Keep that in your mind. Maybe there will come a time where you have some downtime and it’s like, you know what? I’m going to take a couple hours and make that page much prettier, but is that really the most important use of your time or should you go build another high value feature?  

Rob Walling (18:38):
That’s a good thing to point out. There might be two extremes there where big company interfaces, you say, well, Salesforce and Gmail and whatever, these other big apps, even HubSpot or whoever we could think of, they have really bad interfaces and especially parts of them are clunky. And so I can build a really bad interface too and it’s like probably not, but let’s flip to the other side while I was in Basecamp version three and everything’s polished, just gold plated everywhere. So that’s how I have to be. And it’s like Basecamp has infinity time to ship whatever they want and that’s an amazing luxury that they earned by building Basecamp and they executed well. They got a little lucky, we know they’re doing nine figure or we think they’re doing nine figures of revenue, tens of millions of net profit. They can do whatever they want.  

(19:20):
You can’t do either of those extremes. So if you’re going to model yourself, also don’t model yourself after Apple because they also have infinity resources to do things model after people who are constrained and who have a Derek Rimer, any TinySeed company, maybe some of the indie hackers that have taste. I dunno, we can point to some people, but I don’t like it when people use Steve Jobs as an example of anything usually because you’re not Steve Jobs, you don’t have his resources or his ability. And I don’t tend to like it when people use Basecamp as an example because like you’re not Basecamp guys and if you are great, go do that, but try to be a little more moderated or I guess measured in your opinions and look at other folks who are succeeding as you are as maybe a single founder or a small bootstrap team.  

Derrick Reimer (20:06):
Yeah, because that’s basically the skill. The intuition you’re developing is like resource allocation. That’s what it comes down to. You think about the fact that nothing you do is free because there’s an opportunity cost of what you could have spent that time on. And the more you get that ingrained into the way you think about things, the more you’re able to be at peace with something that’s not perfect, but you’re like, no, but I feel deeply at peace with this because I know that if I spend time on this thing, I’m robbing that time from something else and we can’t afford to spend all that time on stuff that’s low value. So appreciate  

Rob Walling (20:42):
The question Jules, I hope our thoughts were helpful for you. Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today’s sponsor Design Lee. They specialize in helping founders like you who are stuck with messy code, unclear roadmaps, or a dev team that just doesn’t get it. And for listeners of the pod design, Lee is offering their Impact week completely free. That’s a one week no obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next. If it’s a fit, you can move on to Solution Lab, a three week sprint where design lead takes over your code base and architects of real roadmap for growth led by a full-time cross-functional team. This isn’t just another dev shop cranking out features. Every sprint is tied to measurable business outcomes so you can scale with confidence and enjoy the process. If your tech is the bottleneck to your next stage of growth, check them out@designli.co slash For the Rest Of Us, that’s D-E-S-I-G-N-L i.co/ For the Rest Of Us.  

(21:55):
Moving on to our next question, it’s from Pablo Fernandez on Twitter and Pablo asks, I have a question for both of you. Do you think with AI we are seeing a shift from market risk to feasibility risk when looking at startup ideas? I used to think, would anyone want this? Where today I find myself thinking, can AI do this yet? What I mean is most idea validation in the startup world, especially bootstrapping has been about quashing market risk. Now I see a lot of bootstrappers that also need to quash feasibility risk and I’m not sure I agree with the terms feasibility implies to me is this feasible to build at all? But I think what he’s saying is almost there’s a weird platform risk that we all are having that AI could just subsume your business market risk. If folks aren’t familiar with that, it’s like is there a market for this idea that I have, Derek and I, you and I could come up with a software that helps people lay out books for printing in paperback and whatever, and it’s like, well I dunno, does that exist already?  

(23:01):
Is there really a need for this? Is the book industry dying customer development? We’d have conversations, should we build this rather than just going off? That’d be kind of fun to build, Hey, let’s do it. But we would want to question, does anyone want this? And in what volume and can we reach them? But what he’s asking is interesting because there are some tools that AI just kind of has wiped off the face of the earth a little bit or at least it’s chomping at their margins. And I think that these days is only getting better. How are you thinking about  

Derrick Reimer (23:32):
This? Yeah, it’s interesting. I was trying to come up with some examples of products that have truly been upended by ai. One that came to mind is Grammarly. I don’t know how they’re doing these days. I know they bought Superhuman, the email editor. I think they’re trying to pivot their company basically because Grammarly, you either type in or you paste in an email or a paper or something you’re trying to write and then it gives you a bunch of suggestions on stuff and obviously LLMs are extremely good at that. So a product like that, yeah, probably sees a lot of threat from LLMs and then there’s, I dunno the bigger question of it’s a whole category going to shift. This was a question for me as a scheduling link provider, are scheduling links just going to be dead? Are we just going to be using AI chat to negotiate times to meet?  

(24:22):
I tend to think stuff is not going to shift as much as people often jump to initially. I still think there’s a place for the user interface that has well-crafted inputs for you to get something done. I still think that beats chat interfaces in many cases. Now, whether you’ll need to incorporate AI into the functionality in order to stay competitive is a different question I think, but completely being replaced by ai. I don’t know. I think there’s still so many things out there because ultimately customers, they still have jobs to be done that they’re hiring software companies to help them do. And I kind of reject the notion that someone said this or this is something that’s just out there in the ether. Like yeah, everyone’s just going to be building their own bespoke software to do things. They’re not going to pay for SaaS anymore. And I’m like, that’s they’re not complete bs.  

Rob Walling (25:19):
Yeah, that’s not going  

Derrick Reimer (25:20):
To happen. No, I still need team communication software. I need a calendar, I need project management tools, I need an email client, I need a CRM, I need error monitoring. I’m not going to build any of this stuff myself just because I may have some specific requirements or I’m not so happy that Honey Badger doesn’t do this thing, so I’m going to ask AI to build an entire error monitoring system for me and then I’m going to maintain that infrastructure and host it myself. And no, that’s not going to happen. So I think yeah, SaaS is not anywhere close to dead because of ai. I don’t think that’s what Pablo is saying, but I’m just making the point that I think there’s still a ton of opportunity to automate things with software and sell it on a subscription basis. But I think the question of how much is an industry going to move because of the way that people are now relying on ai, I brought up the calendar link example, I don’t know, a lot of this stuff is to be determined. We’ll see how the lines are drawn around, how much does chat GPT itself become the level of influence that Google is in people’s lives where some businesses that maybe were standalone before would have to be become a chat GPT plugin because that’s where everybody’s going to do a certain job or something. So I think it’s hard to know where to draw the boundaries around products, but I don’t think opportunities to build new software is vanishing.  

Rob Walling (26:46):
Yeah, I would agree. The way I think about it, and admittedly I haven’t given this particular question a ton of thought, but seeing Pablo’s question made me think about it and the examples that I could think of, I went down the same exercise of how many apps, Salesforce is not going away. It’s going to change and we could build a different Salesforce from scratch right now or a different CRM with AI first, blah blah, blah. We could build a different one and maybe in the long term that subsumes it, but it’s not like Claude or Jet GPT or any of these other models are just going to do everything that it can. But the place where I think the apps that I think have been or can be pretty easily replaced by AI are these apps that are more utilities where it’s almost a single feature.  

(27:30):
Alright, so let’s talk about if you had an app, and there are some out there where you, you’d go in, you’d type in your URL and this is pre AI and it would help you generate a bunch of images and ad copy for Facebook ads and it would do it and it had a big library and it would pull ’em together. It’s like it’s kind of a single feature, but it doesn’t mean it wasn’t important. I think AI, just as we know, just can do that really well these days and probably at a higher level. So unless they really integrate AI into that app, and even if they used to charge 20, 30, $40 a month just for that, and I’m paying $20 a month for chat GBT and it can just kind of do 80% of that, then it’ll kill it, right? I think back to hit tail, which was a single feature, all it was was for those who don’t know, you installed a snippet of JavaScript on your website.  

(28:21):
It looked at your search engine traffic. Well later on after not provided it actually had to hit the, what was it, Google search console or something like that, but it then looked at the keywords people were already finding you for, but you didn’t rank on the first page four and it would recommend these keywords that you should probably target these a bit more. You have a high potential to rank for them. Well, couldn’t you just download a CSV now put it into JGBT, do the exact same thing because it’s a single feature. There was nothing beyond that. And that I think is a big differentiator, at least in my simplistic view right now, is if your app is a single feature, the beauty of app being a single feature is the development can be done, it can be done. These are great indie hacker lifestyle, step one, step two businesses.  

(29:06):
You don’t have to constantly build an add and compete. But the danger there is that I think those are the big ones that boom, AI can swipe. I mean, I met people at MicroConf who had a guy built a half a million dollar a year business. It was at MicroConf Europe several years ago, and it was converters, it was like a PDF to JPEG online converter or an MP three to some. That’s all it was, was a utility to do that. And of course the world needs that and he ranked number one in Google for a bunch of these terms. Do you need that now? It’s that type of thing. And if you have simple ideas like that that are all these like, Hey, I’m just going to do this one thing and I’m going to create headshots for you and charge for it. It’s like, well, AI can do that.  

Derrick Reimer (29:46):
Yeah, I think those are cases where you could still potentially make something work by getting the distribution and being really good at marketing. It’s like the companies that are going to start a new canned water or something, it’s like, okay, bottled water has been done over and over again. So it’s just purely a marketing play. It’s purely a let’s get this in front of people in the right spot and there’s something else there that’s just unrelated to the level of commoditization that the product has that gets them to buy. And I think pre AI was, I guess you could try to make technology more defensible. You could say, well, there’s some special sauce here and we do some good marketing and now it’s a certain class of software, it’s so easy to replicate with AI or just like Chachi Boutique can just do it. So then that makes you have to have a high degree of skill on marketing and messaging and getting stuff in the right place in front of your potential buyers. And it skews the strategy there for sure.  

Rob Walling (30:49):
Yeah, and the other thing to think about, I like what you said, it’s basically like distribution because there will always be consumers, there are a lot of consumers these days. If my mom wanted to add captions to a video, she would just go to Google and type in how to do that. She doesn’t use chat GPT, and so she’s going to go to the top result, which is probably V do io if I know them, they’re really good at this type of SEO and if she wanted to get headshot, she would use headshot AI instead of using you, and I would just use an AI tool, right? A dolly or whatever to do it. So there will always be some of that, but it really also depends on, look, are you trying to build a 10,000, $20,000 a month lifestyle business that’s kind of on autopilot or you’re trying to build a multimillion dollar SaaS?  

(31:36):
It does depend on your goals. So thanks for that question, Pablo. Appreciate you sending it in. Our last question for the day comes from Daniel Huon. He has sent in many questions to the show over the years, and he had a question about security. He said, Stelli mentioned security in episode 766, and I’m curious how much of an existential risk security is in a business that’s doing let’s say seven or eight figures, and what’s the appropriate amount to be concerned about as the business grows if founders are only thinking about things after they happen? I’m curious how much time, effort, and energy folks should be putting into this thought process. And look, Daniel brings up some other points. It’s not just penetration testing or cross site scripting, but if you have 10 employees and there’s phishing attacks, I get phished with TinySeed specific where they will send it to an email address and say, and make it look like it’s from me and say, pay this invoice and attach a PDF to a fake thing.  

(32:51):
And it’s really obvious that it’s fake, but I always have to chime in and be like, this is fake. Don’t believe this. So there’s phishing, there’s all kinds of stuff like this and you can buy, there’s software and there’s training to help your employees not get phished. But really the question I think is around, and maybe it’s two questions, maybe it’s application and tech security and then it’s the social engineering type. How do you educate your employees and how much time should we spend thinking about this as founders at what stage? So with that very broad question, I’m going to pass it to you.  

Derrick Reimer (33:24):
I mean, I haven’t thought a ton about the social engineering side just because I’m generally in a really small context where it’s not that it’s impossible for someone to try to do it, but the likelihood of it succeeding is low. I think if you’re a 10, 50, a hundred person company, the risk starts to go up as you have just more people, more chances for people to get scammed and stuff. So I think like you said, there’s training software and software that will fish people to try to use it as an education tool intentionally. So I think there’s services out there that will help with that. When’s the right time to adopt those things? I don’t think I have a well calibrated judgment barometer on that. It is probably earlier than a lot of people think that it is because I think we just tend to be idealistic and think like, well, that’s a big company problem, and it’s like it can probably kick in at a smaller stage than you’d be comfortable with. So I don’t know if you have a sense before I go any further, do you have a sense on that? What’s the right size when you’d start thinking about actually paying for something to help your team not be exposed to phishing attacks?  

Rob Walling (34:37):
I have, and it depends because I think it does depend on the industry that your app is in. So if you are a FinTech, I think you need it probably from day one and maybe from a SOC two or an ISO 27 0 0 1, like those compliance frameworks, I might implement something at that point if I was going to get those. If you’re FinTech, if you’re in crypto, if you’re in any type of finance, if you’re handling people’s money payment processing, if you’re where there’s a real vector for someone to do harm and to transfer money, big sums of money of client money out, I think you have to have crazy lockdown pretty early. If you’re building a utility for SEO keywords or for AI headshots and your team is 10 people, I mean, I don’t know. Yeah, it would suck if someone got phished and they got your credentials and whatever, they took your server down or something, but the risk there is a lot lower.  

(35:34):
So I do feel like it relates to for it’s headcount that it relates to, because that’s the vector, right? It’s like I could be doing $10 million and if it’s just you and I, I’m not paying for it. I know that it’s when we get to, what do you think, 15, 20 employees, 25, 30, there’s some number in there, it’s not 50, it’s below that for me and 10 feels safe, 10 feels fine, but I will say TinySeed MicroConf 11 people and we get phishing stuff all the time. And so we’ve had to talk to our team about it and make sure they’re savvy. I think it also depends on the savviness of your employees. If you have a call center, let’s say you had three or four people who are making 12 bucks an hour answering phones versus everyone is like a developer or a product person or just a more, I dunno, a tech savvy person who’s on computers all day and is really aware of it. I think there’s kind of a judgment call there, but I do echo your thought that it’s probably way earlier than we think and way earlier than we want to. How about that?  

Derrick Reimer (36:35):
Yeah, totally. And I think the same holds true for the kind of application side, making sure your code base is not vulnerable to abuse. So the next point I was going to make is that if you have any kind of service exposed to the public internet, bad actors will try to abuse that system in some fashion at some point. It’s just inevitable. They can find your website by scanning IP addresses and looking for servers. So even if you don’t have much SEO going on, they’ll find your service if it’s exposed on a port publicly. And there’s a bunch of different ways that people try to abuse systems. They try to do card testing if you have some kind of checkout page to see if stolen credit cards will go through. If that happens a lot on a page that is yours, it can get you in trouble with your payment processor and interfere with that.  

(37:31):
They can try to send spam of any kind through any place where your application kicks out, email that takes user supplied content. This is why you’ve probably noticed those emails that you get that are confirm your email address after signing up for a service usually has almost no information in it because that’s a very common one. It’s the first email that gets kicked out from a system. So if someone can sign up for your service with an email address that they want to send spam to and then inject spammy content into the name, then when it says hi insert name, confirm your email address, it’ll be like, hi, Viagra, Bitcoin, whatever. And so any place where your app kicks out emails or confirmation emails invites, invite a team member, well that sends an email and that’s an opportunity for spammers to abuse it. Anything that you have public facing, like Savvy Cal has profile pages and we’ve had people try to use our profile pages to link out to pirated movies on some BitTorrent site just as a way to host a public website that links to this thing.  

(38:39):
So I think in general it’s important for developers to always be thinking, getting in the mind of a spammer, how could this thing possibly be abused? And I have some general tips that I just sort of jotted down based off of what I’ve done with Savvy Cal and just other apps over the years. First one is put rate limits on everything. Most things in your app don’t need to happen, be able to happen a hundred times a minute from the same user or same IP address. So ideally you have some kind of, whether you use a third party service that sort of sits as a firewall or you do it at your application layer inside of your code base. There’s a lot of middleware libraries in most ecosystems that you can put into your request processing pipeline and you can just say, okay, this endpoint where someone can send an invitation, how many invitations should they be able to send per minute or per 10 minutes or per hour and just set it somewhere that’s at a reasonable level.  

(39:37):
So that backstops you from someone writing a little script and suddenly they’ve kicked out 10,000 invites to spammy email addresses. I think limiting capabilities before someone pays for your, so if you have a trial experience or you can sign up and you can look around before you upgrade to paid, make sure that you limit things as much as possible. The less people can do, the better. That’s one of the hidden costs of having a free plan is you have to deal with potential abuse because you’re allowing full capabilities of your product without a credit card, which is just a nice deterrent layer. People can obviously steal credit cards, but you can’t do it at the same scale. I like to, well have an easy way to block or ban IP addresses. So if you see something bad happening from an IP address, being able to within a minute just immediately block it to stop the bleeding is good.  

(40:29):
Being able to easily ban an account, have a button in your admin interface that’s like, okay, this person is a spammer, block ’em immediately to shut ’em down. And I just also have various channels that I have a feed that’s like anyone who signs up for savvy their email address and names show up in this feed and I can just sort of dip in there and keep an eye on stuff. If I see a big batch of signups come through and they’re all from Russian email addresses, like, okay, that’s a little bit of a red flag, I might take a peek at what’s going on there. And you could start to spot some of these things, which ideally you would have automated systems to catch it, but sometimes just having a human eye is what’s needed in order to figure out what’s the signal here.  

(41:11):
And then if something does start to become a recurring pattern, then you can implement automated things to monitor for that signal. But it’s kind of hard to know universally what are the different vectors that you’re going to experience. I think having some feeds where you can keep an eye on stuff like keeping an eye on web analytics if you have a huge spike in traffic, something to look into if you have a huge spike, if your spam rates spike in your transactional email sending, you should be keeping an eye on that. So just the core metrics of the leading indicators when something’s going wrong and just keeping an eye on those.  

Rob Walling (41:51):
All that sounds great and that’s a nice balance of not gold plating it or overdoing it. These are kind of sensible things to bake in from the start. It’s not so much extra effort. Obviously you could go five times as restrictive or as secure and if you were building military grade software for going to war or whatever, you would have a lot more. But this is a really nice baseline. I like the way to think about that and it’s a lot about outliers, like you said. It’s like, oh, you monitor if this spikes, if that spikes just have something throw up an alert and you can go in and you’re either going to be pleasantly surprised like, oh, hey, we just had a really big customer send a big thing and we’re going to make more money this month because of it. Or we are presently being hacked and we need to figure out what to do.  

(42:33):
So it’s always a balance. These are the really, I think, challenging topics where it depends on the industry, it depends on exactly what kind of software you’re building like we’re saying. But it also depends, I think on, it’s kind of like how big of a vector you have. Meaning when you just start out and you have 10 people coming to the website a month, it’s just nothing’s going to happen. But there will hit a point where you have 10,000 uniques, a hundred thousand uniques, whatever it is where you get noticed on the internet. And then once that happens, you usually wind up on some type of list somewhere on the dark web and people really start coming in. And so having the basics kind of tied down or dialed in I think is good because there’s always going to be, no matter how much you do upfront, they’ll always find another vector and that’s when you just have to start figuring out how to plug those other holes as well.  

Derrick Reimer (43:25):
Yeah, that’s where stuff like rate limiting, it doesn’t prevent people from doing any kind of spam, but it hopefully just mitigates the level of damage. So when you’re just putting a hard cap on how much volume, because that’s really the worst thing. It’s like if someone does figure out some vector and then you wake up in the morning and they’ve sent 150,000 spam messages and now your transactional bill is a thousand dollars and you’ve been blocked because you’ve exceeded your spam rates, that’s when stuff really gets into a bad place. So if you’re just mitigating volume, that can go a long way in just capping the bleeding.  

Rob Walling (44:06):
Yeah, that’s a good way to think about it. Derek Rimer, thanks so much for joining me on the show. Again, you are at Derek Rimer on Twitter and of course savvy if folks want to check out the best scheduling link on the internet, but it’s not just scheduling for meetings, it is also scheduling for appointments. And do you want to give folks an idea of what’s going on with the appointment side?  

Derrick Reimer (44:30):
Yeah, so I’ve teased about or talked about this on the show before, but yeah, avial appointments new product line from Thesal team. And with this product, we’re really trying to be sort of an infrastructure layer for businesses that need to build in custom scheduling flow into their existing stack, whether it’s like a medical clinic that needs to take initial consultations through a custom form, and as part of that, they need to present time slots for the providers in the office who can be on rotation to take these appointments. That’s just one example. We’re looking at kind of platform level integrations where if you want to offer sort of appointment scheduling in a box for your CRM product, we could potentially be your partner for that. So I think there’s a lot of opportunity here to take some of our best learnings from building Savvy Cal the meetings scheduling product and apply it to sort of these more custom setups where people need scheduling capability, but you don’t want to build everything from scratch. So that’s what we’re playing in.  

Rob Walling (45:35):
So if you’re either an agency freelancer and you are building this for, as you said, medical clinics or other appointment scheduling type businesses, you should reach out to Derek. Or if you have a product like you said, A CRM or any other thing where you’re thinking about this, you can hit him up at D-E-R-R-I-C k@sical.com. Thanks again for joining me, man. Thanks so much to Derek for taking an hour out of his day and coming back on the show. It’s been great having you here listening to this show, whether it’s been one week, one year or 10 years. Thanks for listening this week and every week. This is Rob Walling signing off from episode 810. If you’re listening to this, you made it to the hidden track. This is where I ambush Derek without any prior notice. He thought that we were going to dive into listener questions and in fact, we are diving into questions about one of his favorite streaming shows selling Sunset. So I have confidential informants around the world.  

Derrick Reimer (47:26):
Oh my gosh.  

Rob Walling (47:27):
And I ask them about my guests and Derek, somebody outed you. My  

Derrick Reimer (47:31):
Guilty pleasure has been  

Rob Walling (47:33):
Exposed fan telling sunset Seasons one through four only I’ve been told. And if folks haven’t ever heard of or seen the show, do you want to give them a 32nd overview of what it is it? I think it’s on Netflix.  

Derrick Reimer (47:47):
It’s on Netflix, yeah. Yeah. I’ve kind of gone up and down on different types of TV shows that I like to I hear you couching  

Rob Walling (47:58):
This. Are you trying to justify it  

Derrick Reimer (47:59):
Already unwind with, okay. And I do like me some real estate. It’s always fun to see fancy houses and great views and all that kind of stuff. And I’ve also discovered that I find a little bit of reality drama is sometimes just a fun way to disconnect from real reality. And so I would say selling Sunset and the similar types of shows are about 80% reality drama, 20% real estate. I think you’re just following along the lives of these people who have strong personalities and interesting interpersonal dynamics like any reality show and with a little bit of luxury real estate sprinkled in  

Rob Walling (48:48):
And you’re like, Ooh, nice house. Oh boy, here’s the argument again. Why are they breaking up or getting married again or whatever.  

Speaker 3 (48:55):
Yeah.  

Rob Walling (48:55):
Alright, so I have a few trivia questions for you. Seasons one through four only I’ve been informed that you’ve seen and tried, make them not  

Derrick Reimer (49:05):
Still plow my way through it.  

Rob Walling (49:07):
I think there are nine seasons when I researched it, I’m like, I’ve never even heard of this show. What is this? Well, that’s  

Derrick Reimer (49:12):
The other thing I like sometimes when you can just get into a storyline and then there’s just a lot of meat on the bone there, you can just sit with it for a while. It’s kind a bummer when you start a show and it’s like, oh, nine episodes and then it’s done and you’re like, great.  

Rob Walling (49:27):
And it’s a bummer to sit down every night and be like, well, what do you want to watch? I don’t know. What do I want to watch? And if you know you’re into something, you just roll with it. You  

Derrick Reimer (49:35):
Can just dip back into the stream, catch a little bit of entertainment and dip back out.  

Rob Walling (49:41):
Alright, so these questions are going to be an increasing order of difficulty, I’m guessing, of all the listeners, there’s like two that have even heard of this show. So it’s what is happening right now. Alright, starting with the easy question. What Los Angeles based real estate brokerage is featured in selling Sunset? The  

Derrick Reimer (49:59):
Oppenheim Group.  

Rob Walling (50:01):
Alright, very nice one for one. A hundred percent. Which cast member was known early on for her bold fashion choices and frequent drama with coworkers.  

Derrick Reimer (50:12):
It’s got to be Christine,  

Rob Walling (50:14):
It is  

Derrick Reimer (50:15):
Christine Quinn. Oh yeah, she’s the villain. She’s the villain.  

Rob Walling (50:22):
Do they make her out to be the villain or is she kind of actually the villain?  

Derrick Reimer (50:25):
Here’s the thing, I don’t know how much, I don’t really know what goes on behind the scenes of these reality shows and how much the producers are stoking the drama or telling this person like, Hey, you should come in really hot into this argument. So I don’t know how manipulated it is, but boy, she sure seems like a villain just in her natural personality.  

Rob Walling (50:45):
Yeah. Alright, so far, two for two. Before joining Real estate, which selling Sunset Agent was a soap opera actress on Days of Our Lives  

Derrick Reimer (50:55):
Was Oh, oh, was that Kelle?  

Rob Walling (50:58):
It is Kelle. STAs. STAs,  

Derrick Reimer (51:02):
Yeah. Yep.  

Rob Walling (51:03):
All right. Three for three. Brett Oppenheim eventually left the Oppenheim Group to start his own firm. What was it called?  

Derrick Reimer (51:15):
Oh my gosh, I don’t think I’m there yet.  

Rob Walling (51:17):
What? Jesse alert. I’m so sorry. Oh no, this is brutal.  

Derrick Reimer (51:22):
That’s alright. You  

Rob Walling (51:23):
Spoiler of a reality TV show. Yeah,  

Derrick Reimer (51:27):
I do occasionally look up something. There’s a lot of tech gazillionaires that end up showing up on this show. Someone’s dating some guy who’s shopping for a $60 million house. And of course, nine times out of 10 it’s like, I made a bunch of money in tech. So I’ll go look him up, like, who is this guy? Have I heard of his company? Then I often will just get numerous spoilers in the process of trying to figure out some detail like that.  

Rob Walling (51:51):
Yeah. Oh boy, that’s coming up. That’s what you have to look forward to, dude.  

Derrick Reimer (51:55):
Yes.  

Rob Walling (51:56):
Okay. Alright. You got three for three? Let’s do one more. Hopefully this is, I mean, maybe any of these are spoilers at this point. I said Chad GT one, four. Are you done with season four or you just in the middle of it?  

Derrick Reimer (52:06):
I guess I could be partway through season four. I honestly don’t remember.  

Rob Walling (52:11):
Alright, let’s try this one. Which agent joins the cast in season four and becomes a central figure in the conflict involving Christine and the alleged bribe situation,  

Derrick Reimer (52:22):
Bribe situation.  

Rob Walling (52:25):
I wonder if this is also a spoiler.  

Derrick Reimer (52:29):
I’m trying to think. That could be construed. Is it Vanessa? It’s not Vanessa.  

Rob Walling (52:34):
Someone named Emma.  

Derrick Reimer (52:35):
Emma. Emma, yeah. Yeah, yeah. Okay. Yeah, I don’t know if I’ve heard about the bribe, but maybe  

Rob Walling (52:40):
That’s, see this is, ah, all right, well let’s try one more. We’re going to throw that one out. Last one. This is season three. According to chat, GBT, this is your last, so you’re three for three in season three. What made event in Chelle’s personal life becomes a major storyline and affects her relationship at the brokerage?  

Derrick Reimer (52:56):
Okay. She got a divorce and then she started. Okay. Alright. And then she’s dating the owner of the brokerage right now, which was very shocking to see. Yeah, Jason, the Forever bachelor, Jason. So we’ll see how that plays out.  

Rob Walling (53:14):
Alright, well yeah, you truly do know a shocking amount about this show. Much. An embarrassing amount. This is a little creepy. Is there any way, yeah, you could dial down that brain section and maybe know a little more about, I don’t know, espresso  

Derrick Reimer (53:33):
Or So, dude, I was hoping you would fail this just for your own integrity’s sake. I kind of  

Rob Walling (53:39):
Was a little bit, everyone, you were being so judged by tens of listeners who have stuck with us this far.  

Rob Walling:
AI is completely changing how people discover brands and content online. And hres has built a full blown SaaS marketing platform to help you stay ahead with over 15 years of real world web data. An AI that actually understands marketing. Hres helps you measure your brand presence, build authority, and monitor reputation across search, social and AI platforms like Chat, GPT, Google AI overviews, perplexity and more. You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do helping you create content that ranks and drive new traffic to your business. There’s no need to juggle a bunch of disconnected tools. Get hres all in one platform to make your brand unmissable in a fast moving world. Try it free@ahhfs.com slash a wt. That’s the letter A-H-R-E-F s.com/a wt. This is startup For the Rest Of Us. I’m your host, Rob Walling. In this episode, I sit down with Craig Hewitt, the founder of Casto, many time guests on this podcast, and we dig in to his 100 days of AI series that he did on YouTube. 

So we talked through the things he learned from that series as he dove into all the tools that you hear people talking about, and frankly, I wanted to find out from him which tools I should consider using. And by the time we get halfway through the episode, he kind of blew my mind and basically says, yeah, no one in our space should really be using chat GPT. There is a much better tool that can do all that and more. And I’m going to make you listen to the episode to find out which tool he recommends. Before we dive into the episode, MicroComp us. Our next flagship event is April 12th through the 14th 2026. It’s in Portland, Oregon. We’re putting together an amazing speaker lineup. This event will sell out. We’ve sold out our last four or five events for the last few years, and this one, especially given the reach and the depth of our audience in the Portland and surrounding area, we will definitely sell this event out. So if you want to attend, don’t make the mistake of missing out on your ticket microcomp.com/us. And with that, let’s dive into my conversation with Craig. 

Craig Hewitt, welcome back to the show.  

Craig Hewitt:
Rob. How’s it going?  

Rob Walling:
So good man. And you are bumping, you’re increasing by one. Your number of appearances on this podcast. You’re catching up to Derek Rimer who is the current leader. I think he has  

Craig Hewitt:
21  

Rob Walling:
Appearances and I tweeted out a while back about the number of appearances you were in that list. Do you remember? You remember your number?  

Craig Hewitt:
I don’t remember my number, but I think it’s a little bit of a cheat if you put the TinySeed tails on there. I think I ran the table for a while, so you did. That’s a little cheaty, but honestly, if I wanted to talk to somebody, super interesting, Derek would be way up there. I don’t know if you’ve had Jesse Hanley on the podcast.  

Rob Walling:
I heard you interview him on your show though.  

Craig Hewitt:
Super interesting. Dude, he’s in Japan, so time zone would be tough. And then Jordan’s been on a lot and Reuben, I mean, yeah, you have the people on who I would want to talk to, which is why I think everybody listens, so hopefully I can fill the bit or whatever today. Yeah,  

Rob Walling:
Indeed. And for folks who aren’t familiar with you, you are the founder of Cast Doses. Your H one is from audience to income Cast doses makes it possible. Transform your podcast from a hobby into an income earning machine, your podcast hosting plus production. You have a productized service under that, and you were season one of TinySeed Tails and you’re now doing low seven figures of a RR. You’ve been on the show many times and I was going to bring you in today honestly to to-do listener questions, but then I realized it would be such a wasted opportunity to not talk about ai. And I think there’s a certain group of folks out there who really want to hear more about it and have it kind of broken down a little bit more and hear thoughts. And there’s a certain group who’s going to delete this episode the moment they see AI in the title, but for them it’s just fine. You have recorded 100 YouTube videos, you did 100 days of AI on your YouTube channel, which is a staggering accomplishment. And I think I do want to talk to you a little bit later on in the show about how you possibly got a hundred YouTube videos done in that amount of time, but realistically high level, you start this a hundred days of ai, what did you learn that you were super, super surprised that you learned in that a hundred days or any high level stuff?  

Craig Hewitt:
Yeah, yeah. I guess just for kind of context on my podcast, which has been on break, I think fairly so because I’ve been publishing YouTube videos for three months straight. I had Brendan Huffer on, you probably know Brendan, he does Growth sprints, super interesting guy. He was telling me on our podcast interview, he kind of came on the scene as he said because he did a hundred days of SEO and this is about 120 days ago. I was like, that is a freaking great idea. I was going to do sales. At first, I was like going to do a hundred days of sales, I have sales background, and I was like, you know what? AI is the topic du jour. I should do this. And so I did and it was super freaking hard. We can talk about the production and the process and all that kind of stuff, but what I learned at a high level, it’s incredible and not there all at the same time. 

What I mean by that is it’s all the stuff you see on Twitter. It’s the, oh, I automated my entire life with AI and this N eight N workflow with 87 nodes and all this kind of stuff. That a hundred percent exists and I’ve built that and it works about 80% of the time. And so it’s that 20% that is still the human in the loop or the human augmented or amplified experience with ai. That’s where we are today. And that applies to everything that applies to voice and video and code and marketing and sales and data. In my experience, it’s not taking any of our jobs entirely today. I think at a macro level what’s happening is exactly what we see. Like Amazon this week, 14,000 people, they’re laying off because you just don’t need that many people to do the same amount of work.  

Rob Walling:
And as founders, that’s a benefit to us because that’s always our time is always the most restrictive thing versus at a large or if you’re an employee of a large company, that’s not a good thing because you’re going to lose your job. So that is the dichotomy of this in the a hundred days of ai, and I heard you talking about this on Jordan GA’s offsite podcast. You talked about a few categories of tools and what you consider the best in class for each, and there’s coding and there was I think just a general purpose kind of chat interface and I especially want to stop and talk about, you have some very opinionated thoughts about chat GBT, which I think are great and then maybe some other, I don’t know what all the categories are, if there’s three or four of ’em, but you want to talk us through that. 

And here what I want to give people an idea is this podcast, the single topic that it focuses on is how to start and grow an incredible company that changes your life. And if you want to go raise funding, you do that and still listen to this podcast because everything I say will apply if you want to use AI or not. Well, everyone is eventually going to have to use AI as founders, but it’s not that this podcast is going to start focusing on that, that I want to educate you as a founder or someone who’s maybe on a founding team, the topics that are super relevant today and that you can’t, there are no books on this stuff yet because it’s changing too fast. There are some YouTube channels that are talking about it like yours, but even those, they’re out of date within a few months. I’m not saying a hundred days will be, but a lot of stuff that I go to seek out education I seek out about AI is out of date because stuff’s changing so fast. So that’s what I want to call out is we’re here to help founders hopefully have some stuff that they can hang onto and kind of frame their thinking around how can I use AI and what if I just want it handed to me the information. That’s what I’m looking for. So let’s go through those categories.  

Craig Hewitt:
So I think probably the easiest one is for code, Claude Code is the answer. Claude code is a bit of a misnomer because you can use it for everything. I built a really powerful SEO and content writing tool with Claude code and if you look at Lenny’s newsletter, he has some really cool examples of this, which is kind of where I got some of the inspiration for that. But imagine Claude code as the best analogy I heard is imagine just taking the rails off of AI and going bare metal with it. It’s in the terminal, you add files and context and all this stuff. So it’s like if you take the chat interface away from something like chat GBT and get to do stuff and plug things into it, that’s what Claude code. So Claude Code is an agent, it has access tools and memory and you can expand it and plug things into it like MCP, but it’s an incredible coding tool. 

So Claude Code, you might say, Craig, that’s dumb, it’s code X or Cursors, new composer model, whatever, some kind of agentic coding tool. Claude code is it for me, I don’t care for chat GPT for almost everything because it’s a consumer product. It’s the thing my wife uses to talk about the stuff she’s interested in. It’s the thing my kids cheat on their homework with. It’s like all this stuff, but the only place I see use in chat GT is in the gpt. So we’ve created some GPT for our teams and use with customers. That’s really cool. So GPT are kind of reusable bits where you do a very specific thing and you can share those and the shareability of ’em and  

Rob Walling:
You train them, you kind of train it and you say, here’s my book, or here’s a bunch of docs, here’s our whole knowledge base, and now you know that that’s  

Craig Hewitt:
How you  

Rob Walling:
Describe it.  

Craig Hewitt:
Yeah. Yep. Or I want to write this very specific type of marketing email for product announcements and you just plug in, here’s the page, go write the email. That would be a good use for A GBT. There’s a bunch of other ways you can do it. Like a Claude project can do the same thing. Probably the tool, if I decided Craig, you get to use one tool, it would be Manus and producer Ron messaged me last night. He’s like, holy shit, I just used Manus for the first time and it’s incredible. It’s incredible. So Manus is basically Claude code with a web interface. It’s an agentic AI tool that uses Claude under the hood and it’s incredible. It has a browser, so it’s a agentic. If you use chat GT’s agent model like hey, go to booking.com and book me a hotel in Rio for two nights. 

It would do terrible, but Manus would probably nail it, it can write code, it can create reports, it can do all this kind of stuff. And so specifically I’ve been in kind of product creation mode, how I use Manus as like, Hey, I’m thinking about this thing. Help me think through this and help me go do market research, put together a brief for me, help me refine my thinking here. And it’s not just the dumb back and forth with chat g pt, it goes and gets data and provides briefs to you and documents and scripts and all this kind of stuff.  

Rob Walling:
What LLM, is it using Claude? Is it using Claude? Yeah. Okay, so it is Claude  

Craig Hewitt:
Underneath. Yeah,  

Rob Walling:
So as someone, the only AI tool that I use personally, our team uses a bunch of stuff, pod scan and pod squeeze and things to prep show notes, and of course everybody’s using, I think a lot of ’em are using Claude. A better writer is what I keep everyone, everyone who use it says it’s a better writer than chatt, but I really only use chatt and I use a lot. I’m in it multiple times a day and I’m in it. Would Manus be superior for just chat interface stuff?  

Craig Hewitt:
Yeah, it is. So it has either agent mode, adaptive mode, which lets it choose or just chat mode and so you can use it however you  

Rob Walling:
Want. Fascinating.  

Craig Hewitt:
Okay. Yeah.  

Rob Walling:
Chat GPT. Oh no, I feel now I already feel outdated. I remember when I was using chay bet, I started paying for it the first time you could pay for it and I’m like, look how ahead of the ground. 

I’m not an early adopter. In fact, I hate being an early adopter. I don’t like when changes and I don’t like when it messed up my workflow. I was one of the first back in the day, let’s say 20, 25 years ago as a developer, we all built our own machines. You you got all the components, you did that. I was one of the first guys to be like, I’m just buying a Dell now. And people were like, whoa. Oh no. The dark side, you’re no longer technical. It’s like I’m tired of messing around with the printer card. That doesn’t work. I don’t have time for that anymore. I’m billing a hundred dollars an hour writing code. I don’t want to fuck with this. So I tend to want stuff that is pretty streamlined and just works and new stuff often is a little janky. So anyways, I feel like I was ran early on chat GBT and now I’m already falling behind. Man, this stuff changes so quickly.  

Craig Hewitt:
Yeah, so I’ll give you an example of something I did yesterday for one of our clients at CAOs production. So we have a client that’s kind of revamping their podcast and they’re having a hard time nailing the intro section, which is especially on YouTube is so important is you got to nail that first 30 seconds to keep people so that YouTube keeps promoting your stuff. I said to Manus, so by the way, my third one I guess would be super whisper or whisper flow, so I’m kind of voice to text amazing. Or you just talk into your microphone and it types for you. So I said to Manus, I said, go and get the latest 20 videos from Jay Klaus’s YouTube channel. Jay is a big kind of creator economy guy. He does really good podcast on YouTube, which as you know is hard. Get the latest 20 episodes, download the transcript and then analyze the transcript and create a rubric or a framework for how we can input a topic into that and you give me three different intro options and it did, it took about 20 minutes, but it did it and you just can’t imagine chat GBT doing that.  

Rob Walling:
No,  

Craig Hewitt:
You see it, it’s writing code, it’s launching 20 different browsers, it’s downloading this stuff, it’s aggregating it, it’s doing all this Python stuff. That’s the kind of stuff Manis does.  

Rob Walling:
I have run into limitations of Jet GPT where I’m asking it to do just a little too much and I can tell it just tries and it can’t. Oftentimes for me it’s like I have this MP three of something, I don’t have a transcript for it. You’re screwed. You just got to go get that transcribed somewhere else, go to Rev and then bring it over. And I’m like, come on chat GPT, you should be able to do this. This is not that hard. I’ll pay extra, but you should be able to do this and it can’t. I’m guessing if Manus can do that, I would completely change my workflow. Huh. All right, well I guess I got to change that shortcut. This man has to remove a chat GPT from I have so many GPTs already trained. This is going to be the hard thing is there is actually a switching cost for me at a certain point.  

Craig Hewitt:
Yeah, I probably can’t leave chat GPT, but I just don’t use it. I mean it’s 20 bucks, so it’s not going to kill me. But yeah. The one other I would really consider folks to look into is talking about agents or automations is some kind of automation or agent builder. There’s a bunch, there’s Innate N, which talked about, there’s Lindy, there’s relevance, there’s Google Opal. I saw Google came out with another thing today. I think however you slice it, whichever tool you use, you probably should be trying to find ways in your business to automate this stuff with either just make.com style automations or these kind of more AI forward AgTech automation platforms. And if you imagine if you just did one of these a month, where would you be next year?  

Rob Walling:
Yeah, tell me, you’ve used this term AgTech a lot on the show already and I have a mental model of what that means. I’m not sure my mental, how accurate my mental model actually is. So just in case folks are listening, maybe they’ve never heard that term before or maybe they’ve heard it as much as I have and they’re kind of like, I’ve never built an agent. I get the idea that it’s a, Hey, it’s a GPT that can then go do some stuff and is monitoring things, and so it’s more like, I think of it as more like a make automation and a Zapier type automation that has AI built into it, but I think that’s actually a limiting description based on what you know, want to talk us through just what agents are and how different they are than just a chat interface type thing.  

Craig Hewitt:
Yeah, so I guess we’re talking about three separate things. One, I would just call a chat bot, right? So chat g bt your claw.ai, you go, you log talk to an LLM. That’s cool. That’s really useful. I do it a lot. I think everybody does that. An AI automation would be kind of stringing together a bunch of if this then thats or loops or whatever with calls to an LLM by itself or an agent. And so that I’d call out an automation and so that’s make.com and ADA and Lendy, all these kind of things. An AI agent has three components to me. It has three components. It has an LLM, so it’s going to call Claude or it’s going to call chat GBT or it’s going to call grok. It has memory. So you think about a chat bot, have I been asked this thing before? Yeah. Okay. I probably don’t need to go call chat GT to find the answer. I can just serve the answer up and it has access to one or multiple tools, so email or calendar or your knowledge bases in a vector store, like a pine cone or rag thing or the web or whatever. So those are the three elements of an agent and an agent can be part of an automation and in the case of Manus, the chat interface is an agent because it has access to tools and has memory.  

Rob Walling:
Yeah, yeah, as you said to all that stuff. Yeah. Here’s the thing I heard, I think it was Andrew Wilkinson on my first million three, four months ago, and he was talking about agents and they’re like, he’s talking about agents. I’m like, great. And he has all these agents that he’s built and I listened to it and I was like, none of these do much. These are toys and I am not going to go through the time to build them because they don’t win me anything. It was like before I get on a call, my agent looks at who’s going to be on that Zoom call and it goes and researches online and then gives me a bulleted list of kind of a bio and a this and that, and it’s like, okay, that’s fine, but I don’t need that. And if I did, I guess it’d be interesting that it would save a little bit of time. There were three or four examples like that, and I’m like, I’m not sold on this idea that it’s going to be worth the building and the maintaining of these things, but I will be sold eventually. I know I will, but I’m just waiting for that. There are a few, an killer example or two of an agent that someone’s using that I’m like, oh, I have to have that. Do you have any examples like that that you’re using or that of?  

Craig Hewitt:
I think a good example of an agent is a customer support agent, and so we absolutely do. We implemented it six months ago. It’s called Doc Spot and it’s kind of from an indie hacker guy. It’s amazing. It’s cut our customer support burden in half at CAOs and we have 4,000 customers. So it’s like a lot of customers every day. It diverts handfuls of conversations from our support team. All it is is it takes our entire knowledge base and most of our website and puts it into vector stores. Vector stores, like easy way for AI to look up the right things and then people ask you questions and it gives them answers. That’s super valuable. We pay 80 bucks a month I think, for it, and I would pay 80 bucks all day to have two salaries essentially and let them go do more interesting things.  

Rob Walling:
Yeah, that’s a big deal. And of course the first question any founder thinks is, but is it pissing your customers off? Is it doing the endless when I’m on the fricking Verizon wireless chat thing and I’m like, you so angry right now. You’re such and such. Yeah, you, such and such. So have you. I’m totally when John, John, I’m going to be dead way before John Connor leads the uprising because of how annoyed I’m at chatbots, but how do you keep it from doing that? How have you kept it from being annoying?  

Craig Hewitt:
Yeah, so I mean I guess first of all, Laura Rotor suggested this tool to me. So Laura, I’ve been on the show a few times. She was the one that turned me onto it. It has an escape hatch, so in every response it’s like, I want to talk to you human. There’s a button at the bottom, and if you do that just for us, it dismisses that and then pulls up the Help Scout contact page where you can send a ticket into the team. So we let people get out of the chat bot mode really quickly. Then our team monitors all the logs and all the conversations from the chat bot every week. Basically the cool thing is it’s made our documentation better because the chat bot only references the docs. They’re able to see, oh, it answered this question wrong. The docs are actually kind of vague here or misleading, so it’s getting better all the time. 

Not the bot is better, but because our documentation is better. But to answer your question more kind of holistically, I went through a bit of a identity crisis about 70 episodes, I’ll call them episodes into the a hundred days of ai. I realized I’ve built all this shit that is totally worthless. I built some really cool stuff. I created a AI avatar myself, and I cloned my voice and I did all this stuff like nano banana image generation. It’s like, what the hell? What are we doing all this stuff for? And I pivoted to being like, I’m just going to build products because I find it really interesting because exactly your point is like, yeah, a lot of these AI automations and agents just aren’t helpful right now.  

Rob Walling:
Speaking of 70 days in and having a realization as someone who for a couple years, I forget how long we did it, two and a half years maybe. I did 52 YouTube videos a year and it was brutal. It was so much time and work and the team, it wasn’t just me, it was many people working on it, and I almost tapped out at a certain point and just said, I’m done with YouTube, but we went to every other week. It’s been much simpler since then. I want to talk just a little inside baseball on this, on YouTube, and then I want to move to your, you have a big reveal, an announcement per se that we’re going to get to right at the end and then Cliff hang this, but how did you possibly crank out a hundred videos in a hundred days?  

Craig Hewitt:
It was a lot of work, I think is the easy answer. There’s no magic ai, blah, blah, blah to it. Really, there was almost no AI at all to the whole production process. I had a notion board where I just kept ideas. I borrowed, and I think this is good baseball. I borrowed a lot of ideas off of other channels in my space, so talking about AI automations, the first couple of videos are about AI automation and I kind of borrowed ideas that other people had built and I built my own. There are a couple of what I would call AI thought leader and news channels, and I would kind of follow what they do and make similar videos to, and everybody in YouTube does this. Right later I started trying to do a bit of news jacking, which is like, oh, Google nano Banana. 

This is my first big hit was I dropped the video on 12 Google AI products. You need to know. I dropped it the day that Google’s big image generator dropped just by chance. And then later I started trying to really do last second videos on to do a video on the day something was released and then later most of it was around building product with cloud code. So I think I mentioned all that because ideation is the hardest part. How do you come up with a hundred ideas? The execution of it’s not that hard, it’s just like, God, what do I want to talk about today that I haven’t already talked about? That’s interesting and that I could actually have you watch. It’s a little bit of everything, a little bit of inspiration from the space, a little bit of just what I want to do. 

A little bit of this probably would work, this a listicle or a best X or whatever. I had two times when I wasn’t sure if I would get a video out. The worst was I had done a video that day and the recording didn’t take for some reason the wrong camera was selected or something, and I went to export it at like 9 45 at night and it was wrong, and I was just like, I was sick and I was like, I just don’t want to do this. And so I got something out for the next day. I have an editor who’s part of our team at Casto Productions. He did 85 of the videos probably, and he was incredible. He was incredible. He worked on the weekends. I was never more than a couple of days ahead, and so he would work on the weekends and stuff. 

That was huge. I used a tool called Creator hooks. Creator hooks.com. It’s an AI tool where you put in, what’s the video about, and it’ll give you title and thumbnail suggestions. I had Jake Thomas on my podcast a couple of times. He’s the guy behind Creator Hooks. That was cool. I didn’t have to come up with title and thumbnail every time, and so it’d give you a bunch of different title suggestions and then just the text overlay for the image and then just, I made the image in Canva, but that was kind of the workflow.  

Rob Walling:
Yeah, that’s impressive, man. I can’t imagine trying to do that. But you grew your subscriber base up to what, 11,000 subscribers?  

Craig Hewitt:
Yeah, 11,000. Yeah, we hit 10,000 last weekend, which was incredible. You probably can relate, we had two videos, I think over 50,000, and neither of them are the video that I want to be known for.  

Rob Walling:
Yep, totally been there.  

Craig Hewitt:
They’re just two different listicle videos really. And I think you get a bunch of tam, I guess a bunch of reach on those kind of videos, but the ones I want are the video I did about making the Claude Code project for content marketing. That’s me. That’s super interesting. That’s really super aligned with this MicroConf founder or person, but just the reach of those is not there and the mass appeal.  

Rob Walling:
Yeah, no, we feel the same way. It’s always the push and pull of bigger the audience, but it isn’t actually within, it’s not even ICP, but it’s within the person that I want listening. It’s not the audience that I’m seeking. So as we move on to our final topic, I get the feeling, am I guessing right, that you got into Claude Code and the last 30 videos you started building something and then at certain point did you think, huh, I might want to build this for real. Is that what happened where you’re like, because something you said you’re going to start talking about is what the thing you’re doing at CAOs?  

Craig Hewitt:
Yeah, so just really transparently, I think give folks a little bit of context. We’re eight years in at CAOs and amazing company, amazing, stable, profitable, growing a little bit business, but the podcasting space is challenging. I think competitive. Everyone’s competitive, but I want my own airplane. I want my own jet. And that’s kind of the yardstick for everything is like, is this going to get me My private jet? Casto as itself is not a hundred million dollars company. And so I’m kind of sitting here saying like, Ooh, AI is a giant lever either using AI to do a thing or building in the AI space. Can that get me my private jet? Can it help me return a whole bunch of money to TinySeed and my other investors? And I think the answer at a high strategic level is cast dose by itself as a podcast dosing platform. 

Not a 20 million company I don’t think, but can I layer on a product or to have a suite of things that are complimentary that we can cross-sell because we have an email list of almost 40,000 people and we have 4,000 customers. What can we do to leverage the thing we already have to expand our base if we say that just making the current thing a lot better maybe isn’t the answer, which to be honest, I just don’t think the easiest way to grow the company. And so yeah, I have three different things that I’m in kind of product validation on right now and I’ll talk about, it’s funny being 10 years into this, thinking through how to validate a new product is really different than the first time, which I answered your survey the other day of how did you validate your first product? I was like, we just decided to do it. 

I, I think this will be helpful for folks. I had this conversation with Manus the other day because it was helping me think through some of this. I said, I want to create a product that is in this space, kind of like I can cross sell to my existing customers, but I want it to have these few attributes. The first is it needs to be at least $50 a month at least. We’re going to start at a hundred I think for all of these because selling a $20 a month thing is super or hard. So a hundred bucks a month, absolute entry point for anything that I do these days. And I think for most people, if you can’t come up with an idea to sell a hundred dollars a month thing, I would probably think harder. It needs to have expansion revenue built into the model. So an ESP or a CRM or a usage-based thing, a lot of AI things or usage-based. So the more you like it and you’re successful, our P goes up through expansion revenue and it needs to be aligned with our current customer base and audience at CAOs. There’s a lot of things I want to build that, but that’s hard mode. I’ve already done the hard part of creating a brand that we can just expand on from there.  

Rob Walling:
So that brought you to then a list of three products that you’re evaluating to build as a second product under the CAOs umbrella.  

Craig Hewitt:
And I can share that, man, I don’t know if I’m ready to share.  

Rob Walling:
You don’t have to share. You don’t have to share the ideas if you don’t want to. The thing I’m trying to get at is, it’s interesting to me, there would even be three ideas I would think, but is that the Manus speaking? Because I feel like I’d have a really tough time coming up with a list of viable ideas and that one of them for me would just leap out and grab me and I would just get the madness for it and be like, I want to build that right now versus having three that I was actually validating.  

Craig Hewitt:
So that’s a really good point. So I think there objectively several different good options. One of them talks to me personally more than the others, and I think that is pretty important because one thing I’ve seen with CAOs in my whole kind of cycle with it is I got to be excited about showing up every day and doing this, especially starting from scratch. So I’ll talk through the three ideas. One is I started on a channel, it’s called Link Berry, link berry.ai. It’s a AI writing tool for LinkedIn. So the idea is a lot of people that I talk to cast us are like, I know I need to be on LinkedIn where all the thought leaders are, but it sucks and I hate it and I hate writing for it, and I just don’t want to do thought leadership content. And so we’re like, cool, how can we go get the ilk of who you are from other content you have online and just create content for you? 

That’s pretty compelling. So basically saying instead of you hiring a ghost writing agency that’s like two grand a month to pay a hundred bucks for us and we create 20 days or 30 days of content for you at a time, that’s pretty compelling. I think the other is a tool that we built internally, which is this AI content writing tool. Dude, it creates such amazing content, but it’s in code and I have to freaking open up cursor and go into the terminal and do this stuff to have it right, because just like that, taking the rails off of AI that Claude code allows for, it’s like, cool, can we sify that, give a ton of context to it and have it create really good content. So like an AI SEO tool, there’s a lot of value in that. I think the market for that is much bigger. I think the challenge of that is it’s probably harder for people to see the value of that.  

Rob Walling:
There’s just too many competitors. The way I see it too many is too strong, but there are a hundred tools that are basically saying they can bring up blog content. And here’s the thing, yours is really good and it’s better than all of those. No one else will believe you when you say that. You know what I mean? It’s like that’ll be the big challenge there is how do you prove to other folks that when they’re evaluating, should I buy this one or this other one? But anyways, but you’re right, the market for that one is bigger.  

Craig Hewitt:
And the third one is kind of an offs spin of that, which is talking about agents and you’re like, I think I noted agent is, but is we are creating, and we’re using it in Casto, a few really specialized AI agents like, Hey, go get me the SEO data from our website, our Google Analytics data, go get me a Google search console information, go write this article for me in Slack. And so commanding army of marketing agents from Slack. And so the writing agent that we have is kind of a part of that, but so are like, Hey, go write me a LinkedIn article, go me LinkedIn post, go write me ad for Facebook ad. I think that’s probably like, I’m just not there yet because that’s the first one and the second one put together along with a Slack bot and a bunch of really complex stuff. So yeah, I might do that in the future, but it’s probably, I think we should go raise a bunch of money if we do that. It would be a really good business, but that’s a different kind of train.  

Rob Walling:
Yeah, that makes sense. It’s a bigger, more ambitious, more competitive, there’s more to build, right?  

Craig Hewitt:
Yep.  

Rob Walling:
Huh, interesting. How are you feeling about building a second product talked about on this show with Ruben? I get this question every once in a while of should I build a second product? And it’s like by default, no, but the not build a second product thing, it’s usually somebody who’s got 20 grand a month in revenue and it’s like, that’s not your, don’t build a second product. This is not happening. You’re obviously in a very different situation than that being eight years in. And as you said, you kind of hit the S-curve a little bit. You’ve heard about the S-curve that dmh, I mean, it’s before DMEs, but basically every product plateaus at a certain point, and sometimes that’s half a million and sometimes that’s 30 million. But it happens eventually. And then you do, you look at HubSpot and Salesforce and all these big companies, they’ve had to layer on multiple products in order to keep growing. 

You just can’t. The total reachable market for these things isn’t that big. But beyond that, not about do you think you should be building this product because you think you should, right? You’re like, no, this is the way to grow it. You’ve already talked about that, but as a founder, there’s got to be some excitement in it, but there’s got to be, is there a little bit of kind of dread or anxiety around it’s the pro and the plus the thing that makes you happy and the thing that makes you squirrelly? What are those emotions?  

Craig Hewitt:
Yeah, I think that you shouldn’t do this. We have tried to grow organically and I mean organically within the kind confines of what Castus is to achieve significant growth for a long time and have brought in some extremely talented, smart people to help us and it’s not happened. And so the one thing I would say to everybody else is don’t think go building another tool just because tried to grow for a month is the answer. We’ve been trying for a year and a half and have brought in the most talented marketing people that I know and paid a lot of money and it’s just not happening. I think we’re at that natural point in our business and yeah, I’ve talked to Reuben about this and he’s like, Hey man, it’s just not going to happen. 

And so we have a responsibility to ourselves and our investors to make a ton of money. And so if that’s not the way, then this is the way I am very excited about building a new product. I think Link Barry is a really compelling value prop when you say, we’ll create a month of LinkedIn content for you so you don’t have to, and it’s a hundred bucks, people are like, oh yeah, amazing. Take my money. I think in the AI era, you kind of almost need to work backwards from the aha moment to the product, and that’s, it is like, what’s the problem we’re solving? Which is like people need to post on LinkedIn, but it kind of sucks and they don’t want to, we’ll just kind of do it for ’em. We’ll just pull a bunch of information from them from the internet, aggregate it and kind of spin it into content and it does a really good job. So I’m excited about it from a product perspective. I’m starting to bring the team into it a little bit, which that’s a whole dynamic. I’m nervous that we’re starting from scratch and it’s been eight years since we’ve had no customers, and I’m scared that it’s not going to work. And I get this in talking to founders who have exited a lot, they’re like, was it luck the first time? Can I do this again? And so I’m having that from within the company still.  

Rob Walling:
It’s got to be exciting. I love the fact that you, because and I have been, obviously we talk pretty frequently and I have watched you try all the avenues to get CAOs growing faster, and it is frustrating when none of those work, and I feel like in a business that’s not growing for me, I’m going to speak for myself. I’ve got bored gotten demotivated. It’s like, I’m not going to keep spending my time here doing this if it isn’t working. And so it’s like what’s the excitement? What do founders actually get their juice from? I know that we talk about, well, it’s to change your life. Money is a goal I think of almost all of us, and that’s great. I have no problem with that. But also it’s the excitement, it’s the learning. It’s the seeing something go up into the right, it’s seeing more customers or more MRR. There’s always got to be something, right? And I think the thing that maybe has been lacking for you for a bit of just to keep you motivation, right?  

Craig Hewitt:
Yeah. I mean motivation, a little bit of fear and excitement, I guess. Casto is a stable business, for better or worse. It’s really stable. Yeah, I need to sizzle it up a little.  

Rob Walling:
Well, I’m excited for you, man, and folks who have known you for a long time is running cast hosts, the podcast host. We all got to kind of expand our thinking and that’s it. Yeah. And going to get excited to see as you launch this, folks want to keep up with you on X Twitter, you are v Craig Hewitt and on YouTube, youtube.com/the Craig Hewitt. And if folks were interested in, they’re like, I want to see what you build email. Do you have an email newsletter where you’re going to be like, Hey, this is what I’ve settled on? Yeah. Is that@craighewitt.com?  

Craig Hewitt:
Yeah, Craig hewitt.com. There’s a little button in the top right to join the newsletter. Yeah, I send the newsletter out as often as I can, which is about every other week. And then if folks want to check out Link, Barry link, barry.ai, we have wait lists there now of a few hundred folks, and we’ll be opening doors for early access in a few weeks. So a week or two after this comes out,  

Rob Walling:
Going to link barry.ai right now to enter my email address. And yeah, it’s been great having you on the show, man. Thanks for coming back.  

Craig Hewitt:
Awesome. Thanks Rob.  

Rob Walling:
Thanks so much to Craig for coming back on the show, and make sure you follow him either on Twitter or YouTube or sign up for his email list to see what he’s up to, because he’s putting out a lot of really interesting content. And I, for one, am looking forward to where he’s headed as he starts building this second product. Thanks for listening this week and every week. This is Rob Walling signing off from episode 809.  

Rob Walling :
The big question I would ask myself if I were in your shoes would probably be, do I want to be running this business in five years and do I think it’s a viable business in five years? Probably same question for 10. And then I would ask myself, do I have the motivation and the desire to keep pushing my founder level energy into this business? You are listening to startups. For the Rest Of Us as always, I’m your host, Rob Walling. Welcome back to another episode where we dive in to what it’s really like to build, launch, grow, sometimes exit, sometimes shut down, sometimes fail in spectacular fashion and sometimes completely change your life through software entrepreneurship. These days it’s SaaS. Maybe in 10 years it’ll be something different, but right now it’s about staying in control, bootstrapping, and mostly bootstrapping incredible businesses that change your life and the life of those around you. 

This is episode 808 of this show, and I’ve been doing it for more than 15 years. Today I comb through listener questions and in fact, we are getting a little low on questions. If you could head to startups For the Rest Of Us dot com and click ask a question in the top nav, I would much appreciate it. Audio and video go to the top of the stack as well as intermediate to advanced level questions Before I dive into my first question, discretion Capital is the premier m and a advisor for SaaS founders doing between two and 20 million of a RR. You’ve heard the founder of Discretion here on this podcast, our very own a r vol set. He knows more about the sell side of that range of SaaS than anyone I know, and he has been a proponent and an advocate for SaaS founders in the MicroComp community for well over a decade. He’s attended MicroComp since the mid 20 teens, and many of you have probably met him. You’ve seen him speak on stage, you’ve heard him on this podcast, and several of you out there have even worked with him to achieve a life-changing exit. Whether you’re thinking about selling now or in a year or two, it’s never a bad time to reach out to a r and the amazing team he’s put together over@discretioncapital.com. And with that, let’s dive into our first question.  

Speaker 2:
Hi, Rob. Steven here, longtime listener, second time caller. I have a question and before I can ask the question, I feel like I need to give you some background on my business. I have a step one business. It’s an iOS B2C app. It’s not however step one type revenue, at least typical step one type revenue. We’re doing a little bit north of 500 KAR. I have multiple employees. It’s in a very large market. We have a little slice of the market. I have multiple competitors doing nine figures of a RR. I’ve grown the app through a SO and sales funnel performance, so I focus a lot on activation rates, free trial conversion rates, churn, all those numbers are looking great. I’ve hit a point though where I’ve plateaued and I’ve plateaued for a while. It’s a really calm and fun business. So I have some mindset in just some ideas that I wanted to ask you just your perspectives on, not to give me an answer, but as far as just how would you go about thinking about this? 

I’ve listened to your episodes on plateaued businesses, but what I wasn’t sure about was what do you do in a case with a step one B2C business? Is it worth continuing to invest in that versus looking at some of the other options? So I do see a number of options as I’m looking at moving forward. One is I can continue as I’ve been going. Basically, the business probably won’t grow with that, but it will keep it from declining. There’s a lot of competition in the space, a lot of fun, super calm, really enjoy doing that great lifestyle. I see a lot of change coming with ai. Should I quote skate tour? The puck will be, it’s risky, but trying to get ahead of it. The third thing I’ve been thinking about is focusing on a EO. That’s answer engine optimization. I feel like there’s tons of opportunity in this space that’s actually a marketing channel that’s brand new. There’s a lot of lack type of tactics and tricks people are using. The other one is trying to go after a whole new app in the AI space. What are your thoughts just about ideas as far as how I should be thinking about this and questions I should be asking myself? Thank you.  

Rob Walling :
I love this question. Thanks for sending it in Steven and for being a second time question asker. I think what’s interesting is I don’t know that it matters that you have a B2C versus a B2B business. I actually think of myself back in 20 11, 20 12 where I had hit tail, which was B2B as an SEO keyword tool, and it was doing, let’s say it peaked at about 30,000 a month, and it was just me and I had a few contractors, so it was like 90% net profit. It was incredibly profitable. It changed our life and it was relatively high churn and it had plateaued in the mid twenties to 30,000. And you are kind of in a similar boat, although it sounds like you have a team and you’re a little further along in terms of the a RR, but you do have a team that’s working on it. 

And the big question I asked myself around hit tail was, is this a five or 10 year business? Meaning do I think this business will survive that long and do I want to be running it in five or 10 years? And the answer was no on both counts. And so I had to go through exactly this decision of do I keep pushing on it to try to push it past this natural plateau? Do I have more ideas? Do I have motivation? Do I go and sell it or do I try to autopilot it and I’m going to come back to autopilot? Put an asterisk by that term because autopilot doesn’t actually exist. If put something on autopilot in any space that we deal in, it will decline over six to 18 months tops. Even if you have all this automated SEO, blah blah blah, you’ll just slide and the business will just slowly melt like a iceberg or a nice cube in this case. 

And so by autopilot, what I really mean is try to keep it flat and if it starts shrinking, try to minimize how quickly revenue is dropping and then diversify into another idea. And I think those are really your three main options, right? I mean, there’s other options you could sell part of it, things that we kind of get, I dunno getting a little crazy with, but the big question I would ask myself if I were in your shoes would probably be, do I want to be running this business in five years and do I think it’s a viable business in five years? Probably same question for 10. And then I would ask myself, do I have the motivation and the desire to keep pushing my founder level energy into this business? Because you as a founder have an incredible opportunity cost of every minute, every hour, every day you spend working on something that isn’t working. 

It’s not just that you’ve spent that day, it’s that day hasn’t been spent on something new that could be growing at 2, 5, 10 times the rate that could be worth two, five or 10 times the valuation and therefore 2, 5, 10 times your net worth. That’s the issue with being a founder. And a lot of this depends on age. If you’re 25 versus 55, how many more at bats do you have? Is the clock ticking is something to think about. But a big thing I asked myself around hit tail was not just do I want to run it in five or 10 years, but it was like, am I kind of bored of this or do I still have that founder energy, the founder activation energy to really get a flat business moving again because it requires a tremendous amount of energy to do that. So those are the questions I’d ask. 

And if the answer is yes and I’m excited about this a EO that you mentioned, then why not take a crack at that and give yourself three months, six months and see if you can get some results out of it. It is typically easier to not have to build a grand new product from scratch and find product-market fit and then get growth engines in place. You already have a good chunk of product-market fit it sounds like, and you would just need to get the ball rolling again. And that’s going to be simpler than building a new product. Question of course is do you have the motivation and the desire and ideas on how to do that? And it sounds like a EO is the idea that you have. So why not take three to six months and get that engine in place? And it’s probably going to start by you having to do a bunch of research and you doing some of it and then having some of your team take that over and then hand it off to them such that you’re not doing the day-to-day right? 

So that’s one option. Second option is just to sell it, take the cash and move on to your next thing. And of course the third option is to, like I said, with hit tail, autopilot it with an asterisk to mothball it and have your team run it and try to stay flat and not decline and then go off and build your next thing. Third option is what I did with Drip, and that is it was late 2012 where I had the idea for Drip. I hired a contract developer, we broke ground on it, and that was to diversify because I saw building in the email space as just a longer term play than an SEO keyword tool that was really kind of smacked around by Google every six to 12 months. And basically the business was almost put out of business multiple times just because of the way it worked. 

So after Drip was successful during that time, hit Tail did in fact decline relatively significantly. It lost MRR almost every month, even though I was still pushing on some things and doing marketing on the side, doing things on the side doesn’t work that well. And this is one of 10 products I had that I autopiloted by this time. I knew that that isn’t a real thing, that it will certainly, if it’s growing, it’ll plateau and if it plateaus, it’ll start to shrink. Hit Tail did that, but I never regretted it, made a great bunch of profit on Hit Tail, I acquired it, I rehabbed it. And as I said, the money, I mean, I think I’ve said on this podcast before, all of the revenue plus the exit price was $1 million and I paid $30,000 for it and everything else was my time and the expenses were minimal. 

I don’t know if I had a hundred thousand in expenses, I don’t think the entire time I ran it, it was probably more close to like $50,000 of expenses. So it was one of those life-changing moments. It wasn’t never have to work again money, but in fact it did by the time I sold it. And I looked back and I thought that was a great experience. I learned a ton from it and it allowed me to stair-step my way up into Drip, which was obviously an even larger success. So realistically, those are your three options, and just because it worked out for me to diversify and start Drip doesn’t mean that was the right answer, right? It just happened to be that was what I was motivated to do. The right answer is probably what you’re really championing at the bit to do as the founder because wherever your energy is, that is the most likely path to success. 

And again, coming back to, I don’t know that it matters that it’s B2C versus B2B, maybe if it’s high churn, it’s B2C, I would guess, and one time payments or maybe low subscription fees. It sounds like it’s a little bit like hit tail. So if anything, it’s even similar to the situation I found myself in and the big thing as I was coming off of hit Tail was I wanted something that was higher priced than hit tail. Hit tail was like $10 a month. 20 and $40 a month were the three lowest plans. And so it was low priced, high churn, tons of platform risk, and I wanted bit higher priced. I wanted lower churn, I wanted much less platform risk. On and on. You could see that I had seen the weaknesses in the business even though it treated me very well. And in fact, I have no regrets about doing it, but when I stepped up, I was like, I want the next one to be 10 or 20 times larger. 

That was just what I was looking to learn. It was what I was looking to do in my own career, and that’s what I did. So those are the things I’d be thinking about in your shoes. Do you keep pushing and do the A EO? It’s like, do you have the motivation? Do you have the ideas? Do you sell it? Or autopilot and diversify. So thanks so much for that question, Steven. Hope it was helpful. My next question comes to us from Pratt and he says, longtime listener, third time questioner. I have a small tech firm, K tmbs.com. Oh yeah, see these written questions? They go way back. This goes back to September of 2023. So while the question itself may not be relevant to Pratt, I do think the thought process is interesting. So back to the email, I have a small tech firm and have been providing software consulting services to clients around the world. 

Lately I’ve been collaborating with startups and providing them with very budget friendly MVP development in a partnership model. I’ve been asking such partners to only cover the salary of my developer, which is very minimal. So prova has a consulting firm or an agency and has developers working for ’em. I feel like this is a risky move as I am losing my income. However, I really want to encourage startups and make them feel like application development until an MVP could be done at a very low cost. I will however, want to be part of the company once the application scales. Any suggestions you could give me or anything I need to be considering before I take in more partners? Yeah, really interesting. Yeah, you are losing income and opportunity costs and all the things I talk about. I think the biggest thing I would be concerned about is you say, I want to be part of the company. 

Once the application scales, what does that mean exactly? And where is that in writing? Because if you’re effectively working for free, and I know they’re paying for your developer, but you are doing whatever it is, project management and hiring and training and keeping folks on staff so to speak, and that’s for free, there needs to be a tremendous amount of upside because nine out of 10 of those companies when you’re building an MVP will fail. Maybe it’s 19 out of 20. And so the one that works, you are going to want a significant amount of upside in that company. And this is partially the venture capital model or any type of investing in startups is that most will fail. And so this is a risky model for you because it seems like there’s a lot of time that you’re investing in this, and I personally probably I wouldn’t feel comfortable doing this myself. 

If anything, what are you going to want? 10%, 15%, 20% of each 20 sounds like a lot, but 10 15% of each company that goes through. And so again, if you have to build 20 of these MVPs, I dunno how long they take you, and these days with ai, it’s probably a little faster, but 20 to get one or 10 to get one. I mean that is a tremendous amount of darts to throw at the wall. Yeah, I wouldn’t do this unless I had something in writing. I wouldn’t do it unless I had some idea of the math of this because so many MVPs, even one in 20, is that being too ambitious? It really depends on who’s coming to you for this, to be honest, is it second time entrepreneurs? Is it just random people who have a B2C two-sided marketplace idea? I mean, this is where I’d apply kind of you have to maybe de-risk this and turn clients away in this case using the 5:00 PM framework, right? 

This puts a lot of burden on you to validate and think, is there a chance that this idea is successful? So all that said, I don’t know when I was back doing this, when I was building MVPs, but it was before we called them MVPs, but 2000 to 2006, maybe 2007, I was a developer and then I ran a micro agency, which was just me plus a few contractors. I used that as an opportunity to charge market rates, which were a hundred to $150 an hour. And then I took the market rate and I banked that money and that allowed me to then go buy Doted invoice and to take some time off or work a few days less per month to then go build my own stuff. So I looked at it differently rather than trying to attach to other people launching and hope they succeed and hope that I can be a part of that success. I took a different tack to it. So I dunno what you’re doing. Again, I don’t want to overstate it, but it does definitely sound risky. And if I were doing this, I would want something in writing that I have equity or upside in each of these businesses. So thanks for that question per bot. I hope it was helpful. 

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My next question is from Message masses writes, hope you’re doing well. I’m a MicroComp member building a product to simplify and lower the cost of getting and staying compliant with standards like SOC two and ISO 27 0 0 1. We built it after getting ISO compliant and realized we overspent on it. My team and I were reflecting on how little founders actually talk about compliance until they’re deep in the process. We’d love to better understand how this plays out in real startups and not just our own lived experiences. What was your experience with SOC two or other compliance while bootstrapping Drip? Have you noticed any patterns or shifts in how founders deal with this now? Anything you wish you’d known earlier? See founders consistently get wrong. When do you think they should start thinking about it? When do you think they should start getting certificates? Yeah, a lot of questions here, but I think I can boil ’em all down. 

The answer is we didn’t think about it at all with Drip because we didn’t have to. My broad advice across this because with TinySeed across my entire portfolio, TinySeed plus private investments, I’m about to be at like 2 34, 2 35 companies and probably if I were to guess, it’s maybe 10%, 15% of those have a SOC, two or an iso. So 20, 30 ish companies, 40 sounds like a lot, but you get the idea. And inevitably my answer is always, don’t do this until you need it. This is an insurance, this is filing for an LLC. This is like anything that isn’t moving the business forward until you absolutely need it to move the business forward. And I think that founders that actually think about this too early are the folks who are kind of playing business, they get the business cards and they get the domain and they pay a lot of money for the design. 

And it’s like, how about sell something, build something that people are paying you for and many folks get off the ground and are doing fine without SOC two, as long as your customer type is not enterprise. I mean if it’s enterprise, obviously that is a different ball game and some founders from day one know that they’re going to need SOC two and ISO compliance and other folks just wait, put it off as long as possible. Honestly, and I know that’s not particularly what you want to hear as someone who is building software to help folks do that, but this is one thing where if you’re not getting requests for it and you’re not losing deals over not having it, I wouldn’t put the time into it. I do think this is a very interesting space. I know Van is here and there’s several competitors to them. 

So I think it’ll be an interesting space that you enter in terms of trying to improve on what’s already there because obviously just building the same thing that’s out there isn’t going to get you much because people are going to use the brand names and I guess you could come out and try to be cheaper in the early days, but longer term, what will be your unique selling proposition or your unique value that you can add to this space and position yourself and carve out a corner of this market in order to take on the Vanta and the other big players in this space. So thanks for that question. Hope it was helpful. My next question is from Brandon and he says, Hey Rob, I’m a couple of months into starting a business. I’ve really gravitated towards you and your content. My wife and I welcomed our second child about a month ago while in parallel trying to adapt a four day return to office mandate. 

That puts me on the road two plus hours a day rather than spending the time with the family. It’s a huge factor in why I decided to finally start shipping. My question is how did you balance a full-time job and building a SaaS business on the side while also combating an unpredictable sleep schedule? I was making great progress before a baby was born, but have not been able to find much time since. I know this phase is temporary, but I feel like I’m falling behind. Yeah, there’s no silver bullet here. And realistically, the way that I did it is when we had young kids, I didn’t try to build and launch stuff. I went into autopilot mode and I either tooled around on little step one businesses that didn’t require a cajillion hours to ship or when our second child was born, that’s when I did the four hour work week thing where it was right before I bought tail actually. 

And I kind of, again, autopiloted all of my stuff. I spent about 10, 12 hours a week working on it, but I’d already quit my day job. So I didn’t have the day job by the time I had the second one. But with the first child, yeah, I backed off all my side projects, had a little bit of product income from two to $4,000 maybe a month of product income from a couple of things that I had going. And I did not try to move forward when I had young kids and I mean babies that were waking me up as well as I’d never had a two hour commute. I worked from home intentionally and I guess one of my jobs had about a 20 minute commute each way. So I mean, my big thing is how do you recapture hours of your day? Well, you try to find a work from home job or one where you’re not on the road two hours a day. 

This comes from someone who used to live in the Bay Area and I used to commute 70 minutes each way. It was 13 miles, I think it was down six 80 and it was brutal, 70 minutes each way. It was just all basically nonstop the whole way. And it infuriated me and severely reduced my quality of life, which is why I don’t live in the Bay Area anymore. And I guess these days if I lived there, I’d work from home. But you get the idea. So yeah, you have to make a choice of either slowing down for let’s say six months and doing what you can during that time and launching something smaller. You don’t want to do a standalone SaaS app. I say you don’t. I don’t want to make an edict. I wouldn’t want to do a standalone SaaS app in your shoes because it’s just too much. 

It takes too much time to get it going. That’s where the stairs step method is so fricking helpful is where you don’t a cajillion hours every day or every week and you can ship it in little bits and get it live and learn. And I was the first person I know who lived the stair step method and I had a bunch of little products that I either built or acquired and I was able to kind of dip in on them and make some small things here and there. But I did not have this big lumbering drip type standalone SaaS app. That’s great and can get huge, but is really, really hard to manage when you have what, a handful of hours a week. So that’s the type of thing I would be thinking about as well as is there a way I can get a work from home job and reduce or eliminate my commute altogether? So thanks for that question. Alright, my last question of the day comes to us from Conrad.  

Speaker 3:
Hi Rob. Covenant Boak here, you listener from Poland. So I have a question now with the era of all the AI coding and all those tools, I see that one thing that can help us boots, strapper, especially to stand out in the crowd is having our intellectual property, but in it, what’s your intellectual property? Like patents, grants, it’s super hard and it takes years of research sometimes like for some algorithms r and d projects. But I recently heard about building your IP as open source projects and maintaining them and at some point growing them to apply where other people start to help you maintain it. What’s your thing? Maybe you have also some nice guys you could invite to the discussion for this. Thanks.  

Rob Walling :
So Conrad, I’m not sure I accept the premise of your question. You’re saying that to stand out in the crowd, you need to have intellectual property and I don’t agree with that. To stand out in a crowd, you need really good marketing, really good sales, really good positioning and potentially a product that is actually differentiated or at least one that you position and differentiate it. Because as far as I know, no one uses MailChimp because MailChimp has six patents or they have some secret sauce intellectual property that the other ESPs don’t. It’s a capitalist system where people are paying for the best tool at the best price that does what they need to do. Unless you’re talking about really very complex ip like when Google first built the search engine or they didn’t invent the search engine but built their search engine and their algorithm out of Sergei and Larry Page’s, PhD doctoral dissertations or open ai, yeah, that’s IP because we can’t just build that. 

But the SaaS apps that we’re talking about that you’re going to bootstrap and mostly bootstrapped are not based on some secret ip. And this is why approximately zero founders in the MicroConf TinySeed startups For the Rest Of Us ecosystem have patents. There are some exceptions. That’s why I say approximately zero. So yes, I can point out two right now, but there are more than what is 125,000 folks in the ecosystem, maybe 150,000 in our audience. And so it’s approximately zero. So as a result, I don’t even know how to weigh in since I don’t agree with your basic premise. You’re saying you can open source your IP so that other people build it and start to maintain it. And my understanding from folks I know who’ve open sourced things is unless you have a very successful project, it’s still a lot of work for you. 

Even if other people write code, you then have to review that code. You have to make sure it’s not malicious. You need to make sure that it’s actually making the product better. You’re rejecting it if it doesn’t. And then you get people who are upset because you rejected their poll request because they’re trying to put something self-serving in, there’s no silver bullet here with I’m going to make it open source and then someone’s going to build out my ip. And even if it is your ip, then can’t anyone come along and it’s open source, they can then fork that and compete with you tomorrow. So if you don’t have the marketing sales positioning that I mentioned earlier, there are some exceptions. Obviously there are the big open source companies that have done very well with this like Laravel, WordPress, tailwind, CSS, and many others. There’s not only a few sidekick I think is one, but there aren’t thousands. 

There aren’t tens of thousands. There are so many more successful SaaS closed source SaaS companies. Then there are successful companies that have been built on open source. And it’s not even like, oh, it’s half as many. I would guess it’s a hundred to one ratio or something like that, give or take. And so I dunno if that’s the world you’re in and you want to go deeper in that, I would find the startups For the Rest Of Us for open source. And I would listen to all the interviews with Adam Wain and with the founder of Sidekick. I interviewed him here on the show, Mike Perham, I think his name was. And with all I would really dive deep into that, but I would be careful with painting the idea that somehow open sourcing is going to make things a lot easier for me in terms of building out intellectual property or in somehow getting your code base built faster. Because if it did, a lot more companies would do it. So thanks for that question, Conrad, that wraps us up for today. Thanks so much for joining me again, listener questions are always fun. And again, I’m running low, so if you want to head to startup For the Rest Of Us dot com, click ask a question in the top nav. I’d love to answer your question in a future episode. Thanks for listening this week and every week. This is Rob Walling signing off from episode 808.  

Rob Walling:
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You are listening to startups. For the Rest Of Us, I’m your host, Rob Walling, and in this episode I answer listener questions covering topics from whether I should find a sales and marketing co-founder dealing with big company customers that make a lot of changes to your deals. This deal is getting worse all the time. What to do with huge traffic of users who aren’t in your ICP and more listener questions before we get rolling on those. If you are thinking that you might sell your SaaS company in the next few years and you expect that your a RR will be between two and 20 million when you go to market, you should reach out to interval@discretioncapital.com. A r From his many appearances, I think he’s up to 10 or 12 appearances on this show and he’s been on Hot Tech Tuesdays. He comes on to explain venture funding and growth equity and he for years has been my go-to person for B2B SaaS M and a and discretion Capital advises B2B SaaS founders who are looking to get incredible, incredible outcomes for their SaaS doing between two and 20 million a RR. They have a great track record of dealing with strategics and private equity in a way that can optimize your outcome. Discretion has been a long time partner of MicroConf and TinySeed and if you’re curious, even if you’re not planning on selling in the next six to 12 months, but you want to reach out, have a conversation about how to optimize the value of your business discretion capital.com. And with that, let’s roll into our first listener question.  

Speaker 2:
Hey Rob, love the podcast. I listen to an episode every day on my evening walks. My question is, should I find a business co-founder? As a technical founder, I built the MVP myself, now comes sales and marketing, which I have no experience in. Should I look for a business co-founder to handle that side of the company or hire an agency or a contractor or even do it myself? This is different to the usual question of whether to find a technical co-founder and comes with a different set of pain points that I would love to hear your thoughts on. Thanks.  

Rob Walling:
So as he said, this is a variation of a question that I get on this show. What do we think? At least every month? I get it. I don’t always answer it, but it’s always, Hey, I’m a developer. Should I find a sales and marketing? I don’t call ’em a business co-founder, by the way. What does a business person do? What do they set up a bank account and file for an LLC? If they don’t have sales and or marketing experience and the ability to execute in this space, they don’t get half the company because the most valuable things in a SaaS business, the most valuable skills I’ve talked about are sales and marketing. Depending on there are some SaaS you can build with those sales, right? So I’m going to group them together, but you can uncouple them. If you build a true self-serve SaaS, then there is no sales. 

So you can remove that and realize it’s just all about marketing, all about driving leads and converting, but sales and marketing and then a product like the ability to decide to follow that gut, to find product-market fit, to decide what gets built, what gets built into the product, what features get built, how they get built, even if you don’t build them yourself, right? That’s product and then development, which is still a crucial skill, but it is lower on the hierarchy. I’ve seen so many companies, SaaS companies succeed with development not being that strong and sales and marketing being extremely strong. Now, longer term they have technical debt, their feature velocity slows down. But it’s amazing what you can go back and solve if you’ve bootstrapped to two, three, $4 million in a RR because your sales and marketing are so strong and technical debt is nothing that I want or that you want as a developer, but it is something that can be fixable. 

So what I want to do instead of just answering this question is I actually want to outline, it’s a new framework ish. It’s probably technically not a framework, but it is maybe a mental model is a better way to put it. And since I do get this question or a variation of it so often this is what helps me build these rules of thumb. And for this one, this question of should I get a co-founder to do X, Y, Z or should I hire it out? Should I outsource it? Should I hire my first employee to do it? I want to reflect on what I call the core four, which are, in my opinion, the most crucial aspects of building, launching and growing a SaaS company. So these are the four skill sets or areas of expertise that in a perfect world you would have all of them on your founding team and they’re very, very difficult to outsource. 

Certainly hiring someone on Upwork is not going to get these done. Best case, you’re going to find someone very expensive who’s very knowledgeable, who can maybe do these. And when I look at all the, I’ve talked about this, how there are dozens of TinySeed companies doing seven or eight figures in a RR and when I go down this list, none of them hired for or outsourced any of these core four before they were doing about one and a half to 2 million a RR when I used to run and build my companies, I never outsourced these core four until I was doing seven figures of a RR. So I think my rule of thumb is probably going to be, hey, in a perfect world, maybe 2 million a RR. Still, I could see as you hit a million, you could think about hiring out some of these, especially that development is one of them. There’s a stage early on where I think if you hire, you can hire competent people and manage them if you yourself are a developer. 

That’s the thing with these Core four is it becomes so much easier to hire for them and then to manage them if you’ve done them yourself. And so there is a difference here. Were you a developer even if you’re not coding anymore, have you hired and managed developers in the past then hiring a developer, not co-founder, but like a founding engineer or an employee number one or someone who is going to write a lot of the core product code that is feasible? It’s feasible to do that, but if you are not a dev and you’ve never managed devs, then no, it’s not that it’s impossible. There are certainly some companies that do it and you might be listening to this and be like, Hey, that’s me. And there are founders like Craig Hewitt who’ve done it. There are a handful of TinySeed companies, it’s not very many that don’t have a developer or co-founder, but the number one struggle that they have inevitably month after month is we have too many bugs. 

New agency wants to rewrite our entire code base. We can’t make progress because we can’t ship features fast enough and it just becomes the number one headwind for them over the long term. And I think if you removed that headwind by them having a founding engineer or a dev co-founder who really owned the code base, it’d be a significantly different business in almost every case that I’ve seen. So what are the core four? Well I’ve already defined them in the last five minutes. Sales, marketing, product and development. Those are the core four elements of a SaaS company and if you go on social media or you listen to podcasts or you see founders who are trying to succeed and failing over and over, usually they’re missing one or more of these. Usually they’re really good at product and maybe development too. Maybe they teach themselves how to code, but they really aren’t that good at sales and marketing. 

And by sales and marketing, I don’t mean posting on Twitter, I don’t mean audience building because that is not a core skillset of building a SaaS company as you’ve heard me rant about. And then there are some folks who are really good at sales and marketing and they start a company without product knowledge and they hire an engineer or an agency to build their product and they can kickstart that product to something based on their audience size or based on their reach or how good they’re at driving SEO traffic. But they inevitably hit a couple things. Number one, they can’t find product-market fit and their churn is extremely high. I’ve talked about the four stages of product-market fit on my YouTube channel. I dunno that I brought it into this podcast yet, but I’ll have to at some point. But all that said, the high churn is a sign of non-existent or weak product-market fit. 

And the big kind of info marketers or the marketers that I’ve seen who’ve tried to lean true SaaS and who don’t know product well, they don’t know what they should build. They don’t really know how to iterate on a product because when you’re an infomarketer, it’s just the headline, right? Hey, what does this thing do to you? This helps make you a million dollars great product inside. Does it really matter what’s in it? People pay you a one time fee and if they never use it, they is like many people ask for a refund versus if you’re building SaaS, you have to be able to take feedback and iterate and know how software works and be able to build something people want and are willing to pay for. And that’s really hard and that is that’s the job of the founder. That’s the product skillset. 

I’ve also seen sales and marketing founders with no development expertise and that’s where you get into the code bases that just you basically grind to a halt after 12, 18, 24 months because of the technical debt. So the core four are the four skill sets that in a perfect world I want to see on every founding team, and this is, it’s not the only way to do it, it’s not a hundred percent, but boy, 90 plus percent, 95%, these are the companies that I see just hitting on all cylinders. Sometimes the core four are spread across three co-founders, sometimes it’s two and every once in a while you get a Ruben Gomez who has all four. You get an Iran Galran who has all four of these who came on and talked about selling gym desk for it was a majority buy for 32.5 million. That’s the headline number, but it’s implied that the valuation was higher than that and he in fact has all four of these and I could go on there. 

There are other folks, but it is a rare combination to have it in one individual. And so the reason I’m saying all of this is with that mental framework in mind, the question is do you have the core four? And if your answer is no, then the question is are you willing to learn the ones that you don’t have? And I’m not saying you have to be 100% certain that you can be a master of all these because let’s be honest, none of us, even those that have tried to do all four of these as a single founder, none of us master them. But can you do them well enough to scrap and get by and build something that people want? And if the answer is yes and you’re willing to try, then I would say you don’t need a co-founder if you feel like you have the ability to potentially do well enough at these to get along because as a founder, you’re usually going to be Jack or Jill of all the trades and a master of none of them, then no, you don’t need a co-founder. 

But the more common answer to this is people say, I don’t want to learn this or it’s going to take me too long, or can’t I just hire for this? Won’t that be faster? No, it won’t be faster and it’s much, much more likely to fail. That’s what I’m saying. That’s what I’ve seen across the thousands and thousands of bootstrapped, mostly bootstrap SaaS companies that I’ve interacted with across the last 20 years of doing this. So if you’re willing to learn and develop and grow into all four of these, then I’d say a no co-founder. Now if you’re not, I see there’s still a couple options. One is you get a co-founder or you, as I said, you hire that you need a founder level person. So let’s just put, if you’re not willing to learn them, then one option is to get a founder level person in that place, whether you give them equity or whether you’re paying a full salary so to speak. 

But there’s also one other option, which is to build your product to basically restrict your idea and probably your growth to make up for this deficiency of only having the core three or the core two. Notice how core two and core three don’t sound nearly as poetic as Core four, implying that perhaps Core four is the right way to think about it. What I’m saying is you can limit your product ideas or your growth if you build a product where you don’t need all of the four. So what are examples of that? Well, I think you always need product expertise. Someone needs to decide what are we? This is founder level. You can’t build something people want by accident. It almost never happens and you need some type of product mind of deciding what gets built, how it gets built in what order, listening to customers getting all this stuff done to build a great product. 

So I don’t think you can get around that one period. You’re going to want to learn that hiring a developer, hiring a project manager at an agency. No, this isn’t it. This product expertise is probably the biggest thing that I see missing on teams that just can’t get it right and can’t find that market fit and can’t iterate to make better and better products for their customers. So let’s say product is some knowledge of what to build in what order I think is critical. So let’s say can you build something that doesn’t need development though? Well, you’re not going to build a full-blown SaaS app with that because everything needs development even these days with no code. If you are going to build Drip or Gym Desk or Sign Well or Al or any of the full-blown SaaS apps, you need development skills. So you have to restrict yourself if you’re going to not need development, and I think you can build simple apps with no code and I think you can vibe code. 

You’ve heard us talk on the show, you can vibe code Simpler apps. If you recall, I had an analogy of having Derek Grimer over to my house and he and I with really no carpentry skills. We could build an outhouse that would be fine and would stand up and not tip over. We could build a shed like a tool shed the moment he and I tried to build a garage or a single family home or a two story home or a commercial building, that’s when it falls over because he and I would basically be vibe building small structures and at a certain point it just tips over and fails. That’s what Vibe Coating does is you can build a little utility, it’ll work great. I’m going to take a PDF, turn it into audio fine go vibe code that I’m sure it’ll be fine. It’s not hard to maintain. 

It’s 10 lines of code, 50 lines of code, whatever, whatever it winds up being, you’re set. So what I’m saying is if you don’t want to have development requirements, if you don’t want to need development skill on your team, then you need to pick something very simple and minimalistic and something that can either be built out with the existing no-code tools or with five coding. The problem is how are you going to know? I could look at it and say, oh, that’s too complicated. You need a developer, but how are you going to know? I dunno, ask a friend, ask a developer as far as I can take it is if you want to try to get around development, you can’t just build what everyone else is building when they are a developer or when they have developers. That I think is a huge fallacy. 

So what about not having sales expertise and not wanting to learn it? Well pick an app that is marketing only that doesn’t need sales, and this is kind of the indie hacker dream, right? It’s the bootstrapper dream of 15, 20 years ago. Self-serve SaaS usually has a lower price point, usually has higher churn. It depends on the space, but you can do that. It’s rarer these days and in fact, unfortunately I guess for those who want to do that, the fastest growing companies and the ones that grow into the seven and eight figures within my investment portfolio of 200, what is it? It’s 224 companies, but it’s about to bump up into the two thirties about to fund the next TinySeed batch, but the ones that are growing the fastest are doing sales inevitably. I mean when we started Drip, I wanted it to be self-serve and then what I realized is people would come in with a million person list and I’m like, I don’t remember what the pricing was, but let’s say it was a thousand dollars, $2,000 a month. 

Well, they did at least want to have one or two conversations and that was worth it because of lifetime value with net negative churn and the lifetime value of one or $2,000 a month for a long, long, long time, it’s just totally worth it. And so if you want to be wildly successful and grow fast, still grow organically, but grow really quickly, you will inevitably want to learn how to do sales. But what I’m saying is you can certainly get off the ground. I don’t think I did any sales calls until we were at 10 or 15, probably 15 or 20,000 MRR with Drip and then I started doing ’em and realized, oh my gosh, I closed so many more deals and we were growing faster. Then I went and hired a customer success person to not only do the sales calls but then to also do customer success and get people onboarded. 

So what’s the last of the core four is marketing. How do you get around not having marketing? Well, I mean I guess you could think about it if you were really good at sales and you’re really good at outbound and you have a good network and your unique advantage is you have a huge network within a space you could do not a ton of marketing. If you’re in that position, then good If you’re not and you’re just going to build cold and build an app in a space you don’t have a bunch of reach in. This is where step one businesses work. This is why they work is not only do I think step one businesses are simpler apps and so they kind of can check the box of need less development to maybe where they could be built with no code or with vibe coding. 

But at marketplaces where if you go to search MicroConf list of 80 app marketplaces, and I don’t know how many we have on the list at this point, but these are the Shopify app stores, the HubSpot, the Heroku, all these add-ons that you can build. It’s not that you don’t need any marketing, but you just need to learn one channel with a step one business. And this is why stair stepping works, and this is why I preach it to folks, especially where it’s your first time or if you don’t have the core four, you should get a co-founder or you should step one, you should stair step. I mean I think the more I think about it and the more I dug into this topic that’s now my answer to this and I’ll likely take what I’ve just said on the podcast the past 20 minutes and put it into my next book because it feels like when you get to a certain point, you make a decision, you’re like, oh, that’s the right decision. 

It slotted in for me, it just clicked for me of like, yeah, if you’re going to ask this question as the question asker did, should I get a sales and marketing? Or if you’re a sales and marketing and you’re looking for a developer, my question is going to be do you have all the core four? And if you don’t, maybe get a co-founder or founder of a person. And if not, if you don’t want to do that, then you need to limit yourself to ideas to where you don’t need the core four. And someone might come in and say, well, isn’t customer support a core four or customer success or I don’t know what is their legal operations? Hr? No, they’re not core to SaaS companies. You’ll figure this out. It’s project management. Customer support is responding to emails and tickets and chat customer success and getting people onboarded. 

These are all disciplines, but they’re all things that founders can do. And if you do them, obviously the better you do them, the better off your reputation and the brand you build. But even if you don’t do them that well, if you really execute on the core four product dev, sales and marketing, you can still build an incredible business with, unfortunately it’s not a path I would take, but with crappy support, with crappy customer success, with crappy internal operations and messy finances and blah blah, blah. Now when you go to raise money or when you go to sell, it’ll all come to come back to haunt you, but you get the idea of what I’m saying. I’m just talking about building the product and getting to a point of having revenue and having significant revenue and growth and product-market fit and feeling like, oh, I’ve built something great. So all that said in answer to the question of I’m a solo technical founder, should I hire someone out? I think I’ve answered it here with the first 20 minutes of this podcast episode. So thanks for that question. Hope it was helpful. Now let’s roll into our next question.  

Speaker 3:
Hi Rob. I have a question about startups doing deals with much larger companies. I’m in talks with a very large company and things are going well, but every now and then they’ll come back to me and say, management can’t do this even though we agreed on it or they want to change that part of the deal. And it seems unfair, like they’re taking two bites of the apple. They know that I’m the ultimate decision maker within my company, and so I’m not going to play this. I have to ask my wife card. I wonder if you have any suggestions for how to deal with this sort of tactic that larger companies play when doing business with smaller companies? Thank you.  

Rob Walling:
Yeah, this is a good question Anon. Thanks for asking. So there’s a couple separate questions here, a couple nuances. One is you’re saying, how do I deal with big customers just changing the deal? And that’s the first question. The second one is, and then they blame it on, it’s the used car thing where it’s like, oh, my manager said, right, they blame it on this other person and that’s how they get around it. I think I’ll start with the second one. You don’t have to tell them upfront that you are the solo co-founder and the solo decision maker. You can be vague about it when you get into these deals and you can play the same game of like, well, no, my co-founder didn’t agree. You can also have even policies like, you know what? Our policy doesn’t allow us to do that. There are things that you can bring to play to also blame, and if you’re in the middle of a deal now obviously that is not going to make sense, but from here on I think it’s something that you might want to do such that you can blame an external factor in the same way that they’re doing. 

Aside from that, the question is their big company, they’re throwing their weight around, they’re changing the deal. Yeah, they do that and big companies can do that and it sucks, and I don’t know of an easy way around that other than to say, no, we just don’t do that. We aren’t allowed to do that, or we can do that, but it’s an extra thousand dollars upfront or it’s an extra five grand a year. That’s our enterprise plan. Now that price goes up, you get to make that choice of it. Feeling unfair is one thing, but it being a bad deal for you is another. And when I worked in construction, one of the project managers would, he told me several times, I always liked this, he said, there are no bad jobs, meaning we would bid jobs, right? We’d estimate our is a $5 million job and sometimes you’re high and sometimes you’re low, sometimes you get it, sometimes you don’t. 

But he said, there are no bad jobs. There are only jobs without enough money in them, meaning even jobs that are complete grind, if you make a load of money, it doesn’t matter and within reason, not a bad idea. And so my big thing is make it worth your while. Know that you are pricing these deals to the point where even as they change the deal over time, you’re still okay with it. So if you’re doing an enterprise with procurement and marking up your Ts and Cs, to me it’s a minimum $35,000 a year contract. That’s USD and I see people doing $250,000 a year contracts. I say people, these are B2B SaaS companies, right in TinySeed some outside of that. And so you just have to make sure there’s enough money in it to make you worthwhile and this is the hassle of it cuts both ways. 

Big deals are great. They put a bunch of MRR on your books and they’re annual and they don’t tend to churn and there’s all that, and big deals suck because of everything you’re laying out because of all the time it takes. So whether you do it from the start and you price it accordingly such that dealing with the headache is worth it or whether you get into it and if they really start jerking you around changing the deal, you just say, we can’t do it, and you’re willing to lose the deal or you say, we can do it and it’s this extra cost, realizing that you’re willing to lose the deal, maybe that’s a way to play it. The big thing, I was giving a founder advice a couple of weeks ago and I said, the biggest thing you don’t want to do is quote them a price that if they say yes, you say, oh shit, and you don’t actually want to do it. 

Make sure there’s enough money in it that if they say yes, you’re relieved and you’re like, wow, this is totally worth it. There are no bad jobs, only jobs without enough money in them. So thanks for that question. I hope it was helpful. My next question is not a question at all, but a word of thanks from anonymous. He says, Hey Rob, just wanted to drop you a message to thank you for your content and podcast, which I’ve listened to for a long time. I started a bootstrap side project in 2018 that became my full-time focus in 2021. I’ve now exited this week for a life-changing sum of money, and this was sent looks like four or five months ago in mid 2025, back to his email, he says it was a slow burn, but a worthwhile one. Thank you. Keep up the good work as I believe the work you do is vitally important. Exit strategy has helped me during this process as well. I’ll be tuning in again next Tuesday. Exit strategy, if you don’t know, is my latest book, exit strategy book.com if you want to check it out. But thank you so much for the email anonymous. It really means a lot to hear from folks like you who’ve been impacted by the pod. And now let’s dive into our final question of the day.  

Speaker 4:
Hey Rob, how’s it going? I’m Marcelo from Brazil. I’m a listener of the podcast for quite some time right now. I love the show, love the content, and yeah, I’m the founder of SaaS platform that’s called Beauty Forge. We’re mostly focused on generating PDF templates using LLM and using no-code builder to generate PDFs at scale. So my main ICP now is mostly SaaS who need to generate lots of different PDF DF templates like okay, n to generates invoice reports and stuff like that. And no-code builders also use all the product, and I usually had 30 to 40 signups every week on my product, but because of my page that I made, which was create your PDF in seconds, query your PDF template in seconds using ai, I began to receive a lot of traffic from the internet and trying to generate one-off documents. So I received 400 new subscribers each week, and so around 2000 subscribers per month, and I tried to build an MVP around it. 

I figured most of the users would be like B two cso, one time payment, no recurrent low tickets, and the product didn’t go through the MVP. So I figured, okay, I should abandon this product, but what do I do with all this audience that I’m getting on my subscribers? Do I diverge them to another product as an affiliate link? Do I take down the page and stop receiving these users altogether because they are actually taking a cost to me because on my onboarding they use a lot of the features to try the product out, but yeah, I don’t think I want to sell to them. So what’s your hint on how to act on that? Thank you.  

Rob Walling:
This feels like a nuanced question, and it’s almost like having a free plan. Should I kill the free plan? I don’t know if you ever fully free plan or not, but you’re getting, I mean, I’ve seen stuff like this before where you kind of have non ICP customers because they only want to do one-off things, but enough of them stick around that it makes it worthwhile. That’s what I would try to do is actually look, if a hundred percent of them, there’s no value to you and it’s not generating any backlinks. I would think with a tool like this, you’d be getting back links. Is there no virality to it? This is kind of like a free plan question. I think that’s why it clicked in my mind of being similar. If this blog post slash tool or this blog post that is bringing in marketing leads truly is no one’s converting and there’s no virality and it’s not bringing any backlinks, so it’s not bringing any SEO juice, so it’s not bringing any of the benefits of a potential free plan and that’s costing you money, then yeah, I’m not sure why I would keep this around, but something in the back of my mind says, I feel like maybe you should be or are getting some backlinks from it. 

I feel like you’re getting some value from it. It’s just a gut feel and I can’t prove that to you, but I would want to get more data about is this worthwhile leaving this up? I hate to turn away from a source of traffic that could potentially, even if it’s a low conversion rate of these folks that actually stick around and become customers, is that worthwhile? Now, if they’re high churn, then no. If it drives your churn up, then that’s not worth the weight on the business. But I feel like I would do a little more investigating and potentially ask someone more experience with this type of thing. If you have an advisor or if you have a founder who’s further along or hire a growth coach or someone who can kind of help you dig into it and see it with a fresh set of eyes, that’s probably what I would think about. 

You can do this yourself too, but of course it’s hard when you’re kind of embedded in the business and you have your preconceived notions of it. While I definitely don’t like the idea of having people coming in and using my SaaS tool one time costing me money, support headaches, it messes with your metrics. Then it’s like, well, we got, like you said, hundreds of signups, but our conversion rate to paid is whatever is 2% and it should be 10 or 15%, but it’s muddied. That’s annoying. And so I think I would do a bit more research, not even research, but dig into the numbers as much as you can to see if there’s any value. And then if not, then yeah, I don’t see, could you put it on affiliate, an affiliation? Sure, you’re going to make tens of dollars a month, maybe hundreds. I’ve tended, in my career, I’ve made huge sums of money from a small number of things, and anytime I had this idea of, oh, I’m just going to like this, do an affiliate thing, they’re set up and linking out, and then I’m tracking the affiliate down, and then in the end I make in the lifetime of the entire deal, thousands of dollars, a few thousand dollars versus if I just took that time and put it into my SaaS. 

The compounding of of the enterprise value of every dollar of MRR, as you’ve heard me talk about on this show before, is worth so much more than that, and I just value the focus. So again, it’s up to you. You’ve been thinking about this probably for months, and I’ve been thinking about it for about four and a half minutes, so take that with a grain of salt, but that is my gut feeling based on the info you gave. So thanks for that question, Marcelo. I hope it was helpful and that wraps us up for today. Thanks as always for joining me. I’m actually running low on listener questions, and so if you have a question for the show, please do go to startup For the Rest Of Us dot com. Click ask a question in the top nav, and you can send audio, video or text, audio and video. Go to the top of the stack as well as any intermediate to later stage question. I’ll still answer beginner questions, but I just think there’s more meat and more interesting variety in the ones that are folks that are, if it’s questions that would be for someone doing at least five or 10 K of MRR up into the seven and eight figures of a RR as a SaaS company, those are the ones that I really want to tackle on the show. So thanks as always for listening. This is Rob Walling signing off from episode 807.  

Rob Walling:
Welcome to Startup For the Rest Of Us. I’m your host, Rob Walling. This is the podcast where I help developers, designers, and entrepreneurs be awesome at building, launching, and growing software products. Today I interview Philippe eu, the co-founder of Missive, about how he and his two co-founders bootstrapped to $8 million in a RR and 16 team members. It’s a really interesting story and what an incredible amount of leverage they have as founders to be able to build such an incredibly profitable bootstrapped company. Before we dive in to their story, if you are a SaaS founder doing at least a million in a RR, you should check out the SaaS Institute that’s at SaaS institute.com. This is my premium coaching program where you get access to top your coaches, seasoned mentors, and a curated community of founders. We give you the support and the connection that frankly, it’s very hard to find anywhere else. 

It’s an application only community, and we want to get you the systems and the support that you need to scale from 1 million to 10 million and beyond. We have founders in the program doing all manner of revenue. It’s not just a million, but we have people doing four, five, $6 million and you’ll be grouped into a highly curated mastermind. You will have a one-on-one coaching. We have some incredible coaches, and of course you’ll be able to get advice from me. That’s SaaS institute.com. If you want to check it out and apply, it’s great because it’s still early. So it’s a small group and it’s again, really highly curated and high value SaaS institute.com. And with that, let’s start my conversation with Philippe about how they bootstrapped missive to $8 million of a RR Philippe. Welcome to the show. Hey Rob, great to have you on here, man. As someone who has bootstrapped a company to 8 million in a RR, my numbers from producer Ron were 7 million and you’re like, nah, it’s more than that now. Impressive man. And let’s talk about your H one here on your website, missive app.com and your H one is inbox collaboration for teams that run on email, see what’s going on, know who’s doing what, and collaborate behind the scenes without changing your workflow. So I kind of understand what you do from that, and I know of other apps that do this. I think of front is one that I know where it’s like inbox collaboration. Would you equate missive to being in that category?  

Philippe-Antoine Lehoux:
Yeah, definitely. One big difference, I think there’s no product like missive in that aspect is we really respect the email aspect of it. So any action you do in missive, we really work hard to make it work with your email server. So whatever you do in missive, and there’s a lot that can happen because it’s a collaborative tool. We sync it back to your email servers, which is mostly not the case. Now with those bigger collaborative solution,  

Rob Walling:
They do it all in the browser type thing. You have to use the app.  

Philippe-Antoine Lehoux:
Well, some will just not sync both ways.  

Rob Walling:
I  

Philippe-Antoine Lehoux:
See. Basically they will ingest the emails and apply collaboration in, but that don’t deal with the syncing, which kind of is hard to not become a mass.  

Rob Walling:
Yeah.  

Philippe-Antoine Lehoux:
So if you use missive, you can use it for five months and then all your emails are still in your email server. Everything is archival. Marcus read as it should. So we really respect that aspect of it.  

Rob Walling:
And when I think about this space, there’s a lot of competitors that do something similar to this. I even think of this being a support inbox for a SaaS company of course, where my mind goes. And if go into, if support is a category, we’re talking hundreds and hundreds of competitors, how have you possibly bootstrapped into this space to 8 million a r, your team size is 16 fully remote or mostly remote more than 4,500 customers with 30,000 users net negative churn. How did you get here? It feels like an impossible thing these days.  

Philippe-Antoine Lehoux:
I would say one step at a time, but I mean I know it’s not a good answer, but we always respected the email aspect of it. We’re an email client first and foremost, so when you start using missive, even if you’re a solo user, we want to make it a great experience. And I think there’s a lot of businesses in that space that kind of forget that first and foremost, they’re an email client. We’re not like a customer support L desks, we’re an email client with a collaboration. A lot, lot businesses prefer to use that over outdesk because they do a lot of emails in a lot of contexts, not just support. And the other aspects is we embrace that we are SMBs like small and medium. We don’t really go towards the enterprise market even though we do have bigger customers now because for the smaller businesses, one of their main issue in life right now is they have too many tools and they certainly use email for communication and they also need to chat. 

And with Mississippi you can kind of do both, so you can pretty much ditch a lot of silos by basically just using our app and by respecting email, you can actually stop using your Outlook or your Gmail, so it’s one less place to go look at things. And I think for those reasons, we were able to create a lot of loyalty by our customers. There’s a lot of customers that would say, every time I check my SaaS bills, missive Clear is the only one I wouldn’t change. I’m too dependent on it. There’s nothing else on the market and it’s sometimes hard to realize, like you said, there’s a lot of competitors, but there’s not a lot that respect email and the email aspect of it.  

Rob Walling:
Interesting. Yeah, I would not have thought of that as a unique selling proposition that respecting email would be the big deal. Now, did you build missive for yourself for a need that you had at a prior company? Yeah. Let’s talk through that because the inception of the idea I think is intriguing. And then next I’m going to ask how’d you get your first 50 customers? But yeah, talk us through where the idea came from and why you built it.  

Philippe-Antoine Lehoux:
Basically, me and my two co-founders, we were building another project called conference batch.com, which got to profitability quite quickly and quickly. We were like, that’s a done product, we want to work on something else and we start to brainstorm. A lot of indie would do you spend weeks trying to find your next ideas and for us, at one point it was just me doing a lot of typos in my emails and my co-founders would like, ah man, so wouldn’t be nice if we could just a Google doc just collaborate on your draft. That was before AI obviously. So nowadays typos are a bit harder to do, but previously, and that was the first prototype, let’s do a collaborative draft editors connected to Gmail and then we’re like, well, that’s not kind of, okay, let’s build an email client over it and then oh, let’s chat. And then slowly the prototype become a full-fledged email client. Then when we launch a collaborative email client  

Rob Walling:
And with conference badge, then you said it was a done product, which I find to be, it’s kind of an interesting concept, but folks who listen to this show are well familiar with the stair step method of entrepreneurship that I’ve been talking about for almost 15 years now, where you start something and usually eventually it just has a limit and you kind of can’t push it past that without making a serious change to it. Adding a second product or really changing what it does or expanding was conference badge kind of like that where it was just a limited, it was a single feature or a couple features, and once it was done, it was done. What did it do?  

Philippe-Antoine Lehoux:
Yeah, basically it was like Vistaprint for badges. So you would go there, connect your br, and then design couple of different badges and then associate through a spreadsheet or your EverBrite data, those guys should have that badge, those one, this one, and then we would print and ship them.  

Rob Walling:
And so you built Missive to help you with conference badge, and then so now you have one customer, which is you. How did you find your next 50 or 40, 30 whatever number makes sense.  

Philippe-Antoine Lehoux:
It’s funny, it’s been 10 years now we’re building missive, right? So it’s kind of a blur, but the beginnings were hard. I remember launching and I was still the product and craze, I think we found our first customer, Kenny, which is still a customer, Cadney is a feedback board that we still use at Missive, and those guys found us through our product on launch, and I think that after that launch, what I did is that every single time people were talking about email issues related to businesses, I would just jump in the Twitter tread and just mention my product. And to my surprise, initially, 99% of the time people were really excited about it and maybe the product wasn’t made sure enough for them, but they were like, oh, that’s a pretty cool concept. So it gave us the fool to kind of persist and go to our first 50 customer and whatnot. 

And the second phases of growth was riding the wave of investment from big Silicon Valley startups that would raise a lot of money and build that collaborative space. And for us as a bootstrap company, we didn’t have any dollars marketing dollars, but because those startups front superhuman were kind of creating a lot of content about email and collaboration, we were able to kind of inject ourself in those conversation, put on the a EO aspect, but also in social media, but not a lot of dollars. We could insert ourself in the conversation of people that knew they had a problem, they knew they needed a solution, and they found those big startup VC back solution and us, and that really helped us get to that first million dollar. That one versus page with both superhuman and front probably drove most of our initial customers.  

Rob Walling:
Got it. The versus pages are big, and so people were finding, did you have superhuman versus front? Was that the versus  

Philippe-Antoine Lehoux:
No, we worded Superman alternative front alternative,  

Rob Walling:
The alternative two. Yep, yep, yep. Yeah, versus works better when you are a brand. Now people are searching for missive, but alternative twos are a big one,  

Philippe-Antoine Lehoux:
So alternative twos and back in the days, those Versa space, you would find them obviously already at that point, but they were pretty simple, just bullet points and the same one for every single competitors. In our case, it was like a 5,000 words essay, all of the feature, how they are better in front, but better and submissive and always keeping that we’re an email client first. Maybe you should go for those guys if you’re for those things, but if you really want to be emailed first, you should at least try us and play with it.  

Rob Walling:
Yeah. Again, coming back to that unique selling proposition, I have entrepreneurs who either come on the show or who I advise, and a big thing I talk to them about, especially with SaaS is I don’t mind if you copy another product or enter a category that exists, but the big question is if you copy or if you do something similar, why would anyone use you? And don’t tell me it’s you’re cheaper. What are you actually doing differently? Once you have a brand, you’re doing millions a year, you have thousands of customers, it becomes different. People use you because you are Salesforce or because you’re missive and they just know it and you’re in the conversation. But to get there, there has to be some compelling reason and it can be ux, but it’s often not enough. That’s not a defensible, you know what I mean? And it sounds like for you, it just keeps being the email first, the respect for the email inbox and the server, as you said, you sync it all back. Did you ever consider, because you’re a horizontal tool, did you ever consider niching down and attacking just a few verticals or were you horizontal from the start and that’s just worked for you?  

Philippe-Antoine Lehoux:
Yeah, I’m a pretty stubborn guy and that has been a lot of people would say that to me like, oh, you should go transportation business, build the one collaboration inbox to them or lawyers or whatnot, and I was like, nah, I like being that Gmail or Outlook for businesses. I was building a product for me, first and foremost, we like building it because we use it on a daily basis, hours a day still today obviously we do emails in it, but we do every single thing about the business in it. It’s like our Slack. We do everything, so it would be sad for me to sell and stop working on that thing.  

Rob Walling:
No, that makes a lot of sense. Email is a space. Having built myself an ESP, it’s a space where you can have a lot of success and that negative churn as a horizontal play, there are other spaces where that’s harder. There’s something about that stickiness of email and it’s so permanent. You see this, you have someone who’s been with you for 10 years, your very first customer is still a customer. That’s huge. It’s a huge testament to your product and your support, but also to this  

Philippe-Antoine Lehoux:
Space. And there’s a big bar to entry. I mean, just try to remember how many email client has launched in the last five years that you can remember. It’s not a lot. It’s just because really long to get something that work. And so for that reason, that made us defensible, right? There’s not a lot of competition.  

Rob Walling:
The roadmap for a horizontal product can be tough. You are getting a lot of feature requests. I’m guessing you’re going to have a real estate agent asking for an MLS integration and a support team asking for SLA timers and marketing team asking for social media, just all the features all the time. How do you do this? How do you decide which ideas to build, which are distractions? Do you have a framework for triaging?  

Philippe-Antoine Lehoux:
Well, initially it was mainly, do I want this for me as well, right? Because you get bombarded with feature requests, but because you use your product a lot, you’re like, wow, I wouldn’t use that myself, so I don’t care. And to be truthful, at first you pretty much say yes to everything. You really want those first customers, but as you grow, it’s just the number of feature requests possible is to infinity. So there’s just more and more as you have more customer, there’s more feature requests, and then it’s pretty much becomes impossible. Even if we would add a thousand developers, we create a bad product. So as we grow, I go back to the first inch, which is would I use that myself? It’s the same conversation we have with the team when we are trying to understand what we should work on next. So there’s not a complex roadmap or complex workflow to decide what we’re working on. 

It’s pretty much like all the things we’ve received in the last few weeks, which one I think would improve our workflow the most, and that’s what we work on. That’s the freedom. Also being bootstrapped, there’s a bit less pressure to get to certain milestones so you don’t have that pressure to sign that next big customer to push that feature that you absolutely need. We don’t really have that pressure. So it comes with disadvantage as well. But on the roadmap aspect, it gives us more time to reflect and not be pressured to push things. That makes no sense.  

Rob Walling:
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Philippe-Antoine Lehoux:
I mean, initially we did apply to YC because for us it was like, oh, that’s like if we ever want to raise money, that’s the school to go to because I don’t know, I am from Quebec City, I know nobody that raised money and whatnot, and those didn’t work out. We got to sf, the interview didn’t work out, and after that we were like, well, we’re making money with conference badge. We can sustain ourself. We’re pretty lean small team, so let’s just get going as long as we can. And then we had a couple of conversations with VCs, but it was always like our growth rate. I mean, it’s not stellar. It’s not like we’re tripling the company every six months. So it wasn’t like didn’t fly to our door with money. It was like, hi, what’s your name? Tell us our number, maybe we should have another call, whatnot. And then after a few of those we were like, well, that’s leading to nowhere. If one day someone shows up at my door with money, maybe it, I’ll say that guy’s really serious. But to that point it’s just emails and phone calls. So you see, we’re maybe not that sexy because we’re bootstrap because we’re doing the long game, and I think it kind of showed they’re not looking for that anyway.  

Rob Walling:
And have you been approached by strategics or private equity that want to acquire you and has that ever crossed your mind?  

Philippe-Antoine Lehoux:
Oh, every day.  

Rob Walling:
That’s what I was guessing. Yeah, ever. As someone who I didn’t think I was going to sell my last company, and then I kept getting, I got five inbound, serious inbound in 18 months and was just like, huh, maybe I should think about this. And then it was like, well, but I need this number. That’s obviously not going to happen. And then that number happened. I was like, oh, okay, I guess I’m selling this, but I’m curious how you’re thinking about  

Philippe-Antoine Lehoux:
It. Yeah, I never got to those that deep in the conversation, I receive a lot of emails, but obviously you go to LinkedIn and those people are just out of the university, mainly r vesting deals, potential deals and whatnot. Sometimes it’s for more senior people and I might sometimes take those call, but I’m always saying I’m not interested to sell. It’s profitable. We’re growing and that’s kind of the right playbook anyway if you want a big number. So it’s like if someone is really interested one day it’s going to show, and to this point it’s still like, nah, nobody is really that interested and I don’t want to lose time digging into it too much. I prefer investing my time in my business.  

Rob Walling:
And I didn’t ask you at the top, but do you have a co-founder or are you solo?  

Philippe-Antoine Lehoux:
Yeah,  

Rob Walling:
You have a co-founder? Three co-founders. Three  

Philippe-Antoine Lehoux:
Total. Three total? Yeah.  

Rob Walling:
Okay. What are the role breakdowns? I dunno if you have a development background or sales.  

Philippe-Antoine Lehoux:
So all developers, so we all code still today. I’m the generalist, so initially I would do both front end and backend code and my other co-founder is like pull backend, we call is the CTO right now. Really perfectionist makes things work perfectly. My other co-founder is frontend masters, so nails all details about the app itself as a great combination. That would be the one who is more business oriented. Let’s focus on growth, let’s move to another other stage of the business, and they’re really the perfectionists that helped me make it happen. So we really have a great combination.  

Rob Walling:
Yeah, it sounds like a very complimentary skills even though because there’s danger in having two or three developers as founders is build, build, build, build, build. Somebody has to be driving sales and doing some marketing, which I guess it sounds like that, was that you? Were you more of the marketing sales side?  

Philippe-Antoine Lehoux:
Yeah, it was me, but again, for some reason I still feel I was doing that part-time for a lot of years and I don’t know if it’s a good if I ever started another business. To us the conclusion is kind of like we build it and they come, which is usually not it, right?  

Rob Walling:
No, that’s the message. I don’t want to spread on this podcast. I always say, well, you get a little lucky, you make yourself your own luck. But  

Philippe-Antoine Lehoux:
I think the reality is that’s kind of my, if you look back, I did a lot of things that are right, it’s just that I don’t consider them, to me marketing is paid ads. It’s not that I really care about those versus page. I really care about those social media conversation. I did a lot of small things that to me weren’t really straight up big marketing. I don’t even know today what is marketing really apart from building a great product and talking about it, which is probably just it, right? I’m not a marketing guy, but yeah,  

Rob Walling:
No, that makes sense. Yeah, I’m not either. I’m classically a developer who now builds audiences and write books, writes books and advises people. But when I had built a product and I loved it and I knew that it could help people, I couldn’t stop talking about it. And so it sounds like do similar things to you or it’s like, oh, there’s conversation on Reddit about X, Y, Z or on X or on LinkedIn and content was a big thing for us. First it was written and then I started a podcast, this very podcast that you’re on, this is 15 years old now, and then YouTube channel now with 110,000 subscribers. That all kind of became a thing that I did, but what else did you do? You said the verses or the alternative two pages, which is content marketing. It’s getting found in Google and you get that stuff converts really well and then social media, but it wasn’t audience building. You don’t have a big audience. It was participating in existing conversations and it’s probably Reddit product hunt for sure. Hacker News if something’s up there. Twitter. Yeah, Twitter maybe Quora back when it was a thing. It’s much less of a concern now.  

Philippe-Antoine Lehoux:
Yeah, a couple of posts, but also now we have affiliate program that we built ourself that we host in the app. Then people are like, why did you build your own affiliate program? Backhand, right? No  

Rob Walling:
One does that. That’s  

Philippe-Antoine Lehoux:
Funny. Yeah, exactly. The reason is privacy. We’re always skeptical of implanting all the marketing toolkit in the app itself just because we’re dealing with sensitive stuff. So for us, the app itself is free of any trackers. It’s all on the website, and then we have kind of a flow to make it link to the registration that happened on the app, on the website, but in the app itself, there’s nothing and for that we build it ourself. I guess we could have not built it ourself, but still to that day it drives a lot of revenue. Maybe 30% of the growth now of the new users come from the athlete program.  

Rob Walling:
That’s big. Now, did you typically affiliate, I’d say affiliate marketing or affiliate programs is usually enterprise sales because you have to go out and you have to find the affiliates and you have to recruit them almost, right? They’re influencers busy, they’re not out there looking for affiliate. Has that been your experience as well?  

Philippe-Antoine Lehoux:
Well, initially a bit, I guess we were stupid is that there is no enforcement. You could actually take it and do ads yourself on the massive term or brand or whatnot. So for us it was like we we’re just three guys. We don’t have the time to do Google paid ads. Let’s build a EL program so somebody can arbitrage it and if they make money with it, fine with us. But at some point we got a brand, we do have some brand recognition now, so there’s a lot of people typing just missive. So it started to make less sense. So we started to enforce you guys, you can’t actually advertise using missive, right? You need to go for new customers. But I would say no. Most of the people that signs up through the affiliate programs are pretty classical missive users, like SMBs, that can be anything. They’re really like lawyers, transportation, business mostly in the us but also uk, Australia, like Anglos Fair countries.  

Rob Walling:
And so you must not have, there’s typically with affiliate programs, there’s a concentration where you have a thousand affiliates and three of them drive 95% of your revenue or something like that, that you do have that. So you have just a few.  

Philippe-Antoine Lehoux:
It’s people that arbitrage the fact that we’re bad at marketing and that we don’t do paid marketing. Got it. That’s still to this day, interesting. I mean they’re still profitable for them even without using the missive brand. So they’re going to advertise on the competitors and in other countries, and they’re really, this guide is a big, big, big nerds. They do that on the side of work in Silicon Valley and probably make some money with us. I don’t know how, but how much, but  

Rob Walling:
Well, I want to get back to this idea of it being difficult to be a horizontal product, and yet you’ve been successful in spite of potential headwinds, specifically your marketing website. It has to speak in language that works for a cajillion, different job titles, for example, when you think about writing a homepage copy, how do you make it compelling and specific enough to be compelling, but general enough to be inclusive?  

Philippe-Antoine Lehoux:
So we’re trying to ize some of our marketing nowadays. For instance, we did a campaign with accountants, a couple of accountants, influencer did YouTube videos podcast mentioned, and then created dedicated landing page with a lot of quotes from existing customer. So both the influencer words, Hey, that’s a pretty cool solution for your accountant problems. If I say it, I’m like, Phil, the submissive developers, they don’t trust me. So that’s why we’re trying to go to create vertical content through influencer. So we did accountant that’s working, we’re going to do lawyers, and then we’re looking for the other ones, but it’s kind of really hard, so many possibilities that it’s more what type of answer, answer in each of those industries and which one are kind of respectable and have enough network that it can actually work for us. So we’re playing with that. As for the OnPage itself, our goal was to make it about emails. 

You would be surprised how many people are like, well, I tried all those new product, but in the end, my business is always an email and it just sucks to have to go to all of those other apps. So when you tell them, well, there’s actually an app that respect email, but just make it a bit better that you could least use and solve all of your email problems because you have them, right? Everybody received too many emails and they’re drowning and they can’t collaborate and whatnot. So sticking to the email messaging in the OnPage and then we’re trying to create vertical landing page for some industries. That’s what we’re trying now.  

Rob Walling:
Yeah, makes a lot of sense. That would be, that’s a playbook that I’ve seen work with horizontal folks. I guess I have a question about, back to kind of building features. It’s like you’re not just competing with other horizontal tools. You’re competing with probably a thousand vertical specific tools. So a law firm comes to use missive, but they have legal practice management tool that probably has email built in. So what’s the pitch for beating that?  

Philippe-Antoine Lehoux:
A lot of those, for instance, we have a immigration law firm in New York. They’re like 150 now in missive, and the way they can use missive and or other more lawyer tool is that they build bridge in between the two solutions. So whatever they’re doing in their more specialized app that they usually don’t like, because when you’re doing a vertical app, you have less insensitive to make it, right? You have less competition, so the UX is less good and whatnot. So missive is their dually driver and they’re going to create integration with their own stack in missive. So those bigger customer, that’s what they’re doing. But now because of ai, we’re seeing even smaller businesses, like 20 employees building really complex custom integration built in missive with all the different tool in their stack. They would say, well, you guys had the Asana integration, but I actually wanted the Asana task plus mash it up with whatever backend I have, and I kind of did it with chat to PT and now it’s working. So missive is their daily driver because of emails and they’re using the integration aspect to integrate themself with their own stack. Initially we were also building integration, but you can’t build them all yourself, right?  

Rob Walling:
Yeah. It just becomes too much. At a certain point, do you feel like staying horizontal has maybe even provided you a form of defensibility? Does it make you less vulnerable to shifts in any single industry as well as since the market, the TAM is so much bigger, I don’t talk much about Tamer, but it just being horizontal, it can be an advantage there if you can compete.  

Philippe-Antoine Lehoux:
Yes. The answer is yes, because if you look at the pie chart of the industries using missive, I think that the biggest pot is like 6%, so it’s like 6% retail, and then it’s just like 5.5, 5.4 and then goes on. Yeah,  

Rob Walling:
It’s all long tail. There’s no head. It’s all long tail  

Philippe-Antoine Lehoux:
And the spread of the seats in organization as well.  

Rob Walling:
Yeah,  

Philippe-Antoine Lehoux:
Right. So I think the median org is like six, seven, but it goes, it’s not like half of the customers are businesses are seven. It goes like 1, 2, 3, 4, 5, 6, 7, and then slowly to, the biggest one we have now is 400 seats.  

Rob Walling:
And you don’t do, I mean 400 seats to give folks an idea. Your pricing is, it’s $12 per seat, $24, and there are a $48 plan or something like that, obviously with more features. So 400 seats times any of those numbers is an enterprise big plan. Do you do sales calls? Did you do enterprise sales for  

Philippe-Antoine Lehoux:
That? Well, I used to do all of them, close them. We wouldn’t go after them. It was mainly inbound, and usually the bigger customer are using another solution before 

And they would know and actively be looking for something to fix their issues or they don’t like the platform or evolve in something they didn’t want. And so they’re looking for an alternative. And for us, winning those deals has always been kind of easy for some reason. I know you said it should not, but we’re cheaper than most of our VC backed competitors. Not by a lot, because usually those, they will show a big price on their own page, but it’s not actually the price people are paying for us, it’s usually the price people are paying. There’s not a lot of, we’re a small team, we don’t want to negotiate, so it’s like, Hey, that’s the price. If you don’t want, you can go negotiate, but we won’t do a quote for you to negotiate with your previous provider.  

Rob Walling:
Right. Yeah, no, I was asking, do you do enterprise sales much or is it mostly self-serve?  

Philippe-Antoine Lehoux:
It’s inbound, but we do close them in a sales is fashion, so we’re going to do whatever document they need, SOC two, security questionnaire, meetings with IT, security, we’re going to do it obviously. Yeah,  

Rob Walling:
To get the big deals you’ve gotten SOC two?  

Philippe-Antoine Lehoux:
Yeah.  

Rob Walling:
Yeah. How was that? A lot of TinySeed companies that I’m invested in, windy, biding, SOC two. Did you find it relatively easy or relatively painful?  

Philippe-Antoine Lehoux:
Yeah, so SOC two, because we were a small team of four or five, I don’t remember adapting new processes was easy for us, so we just need to learn them and apply them in our stack. And we used drta. I think there’s Drta and what’s the other one? I think I would not advise somebody to not use one of those solutions. It’s just like they streamline everything. It’s as a service. I can’t imagine doing that without those service. A couple of buttons, you get a lot of templates for the different processes, you accept them. And for us, we had, so two before we start ING people, so when we are people, we already had the checklist process of what service I’m onboarding them in, they need to sign those couple of legal documents and whatnot.  

Rob Walling:
Philippe, thanks so much for joining me on the show today. If folks want to keep up with you on the internet, you are at P-L-E-H-O-U-X on X, Twitter, and of course missive app.com if they want to see the pretty incredible company you’ve been bootstrapping for the last 10  

Philippe-Antoine Lehoux:
Years. Thanks, Mars.  

Rob Walling:
Yeah, thanks so much for joining me on the show.  

Philippe-Antoine Lehoux:
Awesome, thanks.  

Rob Walling:
Thanks again to Philippe for coming on the show, and thanks to you for listening this week and every week. This is Rob Walling sending off from episode 806.  

Rob Walling:
Today’s sponsor is Ahrefs built a full-blown SaaS marketing platform to help make your business discoverable. They recently launched a tool called Brand Radar, which helps you analyze your visibility in ai, chatbots like chat, GPT, or perplexity and compare against competitors. There’s no need to juggle a bunch of disconnected tools. Get hres all in one platform to make your brand unmissable in a fast moving world. Get started today at hfs.com/awt. That’s A HRE fs.com/awt. It’s another episode of Startups For the Rest Of Us, I’m your host, Rob Walling. In this episode, I cover a handful of solo topics talking about gatekeeping versus paying dues. I contrast the value of a raw material versus a refined or handcrafted version of that raw material. Talk about how people who are winning don’t usually have a problem with other people winning, and maybe even another couple topics depending on time. 

Before I dive into that, MicroConf remote is tomorrow November 5th. It’s a completely virtual event. Tickets are I think either 65 or $75, so we try to keep it really inexpensive and you get the recordings. Even if you can’t show up, you can use promo code Startups 15 for $15 off. We have amazing talks lined up. Sonny Hunt will be talking about a 15 minute intelligence framework so you can stop stocking your competitors. Victor Hot Faludi will talk about turning demos into your best discovery tool. Greg Hewitt will be focusing on AI tools and as I said, the recording from this event will be available for ticket holders microcomp.com/remote if you are interested and use code startups 15 for $15 off. 

My first topic of the day is around the difference between gatekeeping and paying your dues, specifically as a new startup founder. And I wish that when I emailed this to my Trello board that I had included a reference to what triggered this in me. It was probably something on social media I’m guessing, but someone was contrasting the difference between gatekeeping, meaning keeping folks out of an inside circle or of a circle where successful people mingle and kind of where it’s more about who rather than what you know, and they contrasted that with having to pay dues and not being able to just enter a community when you are a complete newbie and not do any research and not do any work and ask the same newbie questions that the other newbies last week asked. We were all new at one time, but what I didn’t do was come into a community and say, how do I find an idea here? 

I have an idea. Is this a good idea? I’ve built something. How do I market it? It’s these same questions that we see on the Reddit threads and on Hacker News and any other social media where folks want to be handed the answer, and that’s kind of why we can’t have nice things in these founder circles, right, is that if you are a new founder and you are coming in expecting other people to hand you the answer or to allow you into the inner circles with super experienced founders and to come in and ask very basic questions that you haven’t put any work into to answer for yourself by asking chatt, by googling it, by buying a book on the topic, by listening to any podcast from anyone reputable in your space who’s talking about this? If you haven’t listened to 50 episodes of Startups For the Rest Of Us or Lenny’s podcast or Jordan Gall’s offsite podcast or Omar Zen Holmes a hundred dollars MBA, there are a bunch of reputable startup podcasts, and if you haven’t done a bit of work to educate yourself on the fundamentals that are pretty, they’re out there either for free or for very low cost. 

There’s a reason that the SaaS playbook and start small state, small hall and exit strategy. All my books you can get for $10 on Kindle or you can buy them direct from me in DRM free PDFs. Links are available from Rob Walling dot com. But there’s a reason that I want those books to be in people’s hands for very little expense is I think that they are a part of a rising tide that raises all boats. So if you’re coming new into a space and claiming that folks are gatekeeping you, maybe that’s true. I think in the founder space, the odds are more likely that you have some dues to pay. You have some education, some upskilling. I talk about it being hard work luck and skill, put in some hard work and learn some skills, and sometimes learning those skills is just paying attention to what folks are doing around you and building and shipping something into the world, making a few mistakes and learning from that. 

When someone asks me a question, whether it’s on the show or in person or via email or via a contact form, if they haven’t put any effort into what they’re doing or any deep thought or any type of trial and error, I’m much less likely to give them a detailed answer, especially when the question is something like, how do I market this? I could write not just one book, but multiple books on how to market this. It doesn’t matter what this is. It is a huge topic. Narrow your questions and the best questions you hear on startups For the Rest Of Us are folks that have tried a bunch of things and are at a crossroads and say, this is what I’m thinking. What is your take on this? But there’s guardrails and there’s details. The worst questions you see are usually super, super general because the asker hasn’t put in the time or the effort either to craft the question or even to know what they really should be asking, and they want me as the person answering to do their work for them. 

And if you’re an experienced founder, I of course would encourage you not to gatekeep. I think that’s been my mission for 20 years, right? Since I started blogging in 2005 and writing my first book in oh nine, published it in 2010, and this podcast and the other books and MicroComp, I like to see that there are things available for free for $10 one time costs, and then going deeper for those who have more resources or who get further into their journey, things that can help folks at every stage. So if you were an experienced founder, I think I’ve already talked about, if you’re a new founder, as I said, build up your skills, educate yourself a bit more, put effort in, and if you’re a more experienced founder, certainly don’t gatekeep. I mean, I don’t think that’s a good approach at all, but if founders, I think there’s a two-sided balance to this of if a lot of new founders are asking basic questions, try to help educate them on, Hey, that question should be asked like this. 

You need to go put in some effort and come back with a better way to phrase that or a better way, bring something to the table. Don’t just expect us to give, give and at the same time realize that for your energy as an experience founder, you might be able to put a little bit of time and energy into new founders, and I think we kind of all should to raise up the next generation of folks, but also reserve good chunk of your time and energy for yourself, right? In your masterminds with your, whether it’s investors, advisors, co-founders, other mastermind folks, other experienced founders that you can find in a room at a MicroConf, right? Where almost 30% of the attendees are above a million in a RR, the SaaS Institute, our premium coaching program, everyone’s at seven or eight figures a RR, and if the majority of your time is spent with those folks, then it kind of builds you up and it allows you to continue growing and learning and always remembering to maybe give a little back to those folks that are coming up behind us, the new founders, I think of the, I don’t know, is it five generations of founders now? 

There was a really early generation. I mean there was Joel Spolsky, Paul Graham, MailChimp, so Ben Chestnut, there was a couple others there pre oh five, pre 2005 and six, and then there was maybe a second wave. That was me, PEL d, Patrick McKenzie, Andy Bryce, it was the Joel and software, the business of software forums, and then I remember the Ruben Gomez’s and the Dave Augh round 2010 coming up, and then there was another wave in 2013 and 14, and so there’s been several waves of new founders coming on the scene, and that’s good. It keeps our ecosystem vibrant and it keeps it alive, and so there’s no reason to gatekeep, but I do think that there is a certain value to having standards of folks who are educating themselves and kind of paying their dues by actually launching stuff and doing things in public, getting things out there and not just post, I don’t mean posting on social media, I mean getting code into production and actually iterating and trying to get better and not launching 20 things in 25 days or whatever. 

I mean, my take on that, but in closing to realize that there is this balance between being someone new, coming on a scene and feeling like, oh, I’m getting talked down to, or people aren’t answering my questions. But if you’re not putting the effort in yourself to answer your own questions based on all the amazing information that’s out there, then you’re doing yourself and the community a disservice. My second topic of today is about the value of a raw material versus a refined version of that material. And I either got this from Facebook or Instagram. I have a screenshot of it on my phone if I’m honest. It looks like Neil deGrasse Tyson maybe posted this, and here’s the post. It’s got a picture of a 1000 gram iron bar. It says, this is a 1000 gram iron bar. Its raw value is about a hundred dollars. 

If you choose to make horseshoes, it’s value will rise to $250. If instead you make sewing needles, the value will rise to about $70,000. If you make watch springs in gears, the value will rise to about $6 million, but if you make precision laser parts from it like those used in lithography, it will be worth $15 million. Your value is not only in what you are made of, but most of all in how you make the best of who you are. And I love this analogy for founders and for founders and for startup ideas as well. We’ve been told that ideas are worthless and it’s all about execution, and we know that’s not true. We know there are some ideas that are just better than others. Derek Sives has a really good framework around ideas and how they’re a multiplier of execution. He says Ideas are worth nothing unless executed. 

They’re just a multiplier. And so you can imagine an awful idea is minus one and a weak idea is a one. Soso idea is a five. A good idea is a 10. A great idea is a 15. A brilliant idea is a 20, right? So from negative one to 20, and then he puts a dollar amount on no execution, up to brilliant execution, and no execution is a dollar, and brilliant execution is $10 million. And so if you multiply the two, you can imagine brilliant idea, brilliant execution is you don’t have the math in front of you, but it’s $200 million versus an awful idea with no execution is negative $1. I love that you lose a dollar, but a weak idea and no execution is a dollar, right? And the idea is he’s saying it is a multiplier. There’s a logarithmic or an algorithmic scale to it and that it’s not that ideas don’t have value, it’s that you also need execution. 

And the better your idea and the better, the more desiring the market is, and the more unfair advantages you have and the better execution, the better off you’re going to do. I mean, we see it over and over. I see this in companies that I invest in, companies that I don’t invest in. And so what I like about this post from Neil deGrasse Tyson is that it’s not just about where you start from, and it’s not just about having the raw material because you can waste it. I’ve talked to my kids about this. My kids are each gifted in different things, and I’ve told them both, just being gifted won’t get you anything. You also have to put in hard work. Think about my hard work, luck and skill framework in this context. When I have a 15 and a 19-year-old think about their giftedness of being an exceptional musician or exceptional athlete or exceptionally intelligent as being a skill for now, maybe we could say it’s a talent or a skill, but you get the idea. 

It’s that raw ability to do something and do it well. And of course, luck can’t control that, can we? So I talked to them, the way you are going to succeed is not just through raw talent or skills. It’s going to be by pairing hard work with that. And in fact, everything in my life that I’ve achieved, I had a bit of skill or raw talent that I then built upon, built upon, built upon, but I got better at that by applying hard work to it over not just months, but years. And this was some of my athletic success in high school and then college, my professional success as an entrepreneur, complete outsider, not knowing a single entrepreneur growing up, living in the Bay Area, but being in the construction industry essentially, like my dad was an electrician. My brother still runs an electrical contractor there. 

That was where I was brought up. And as you know, coming out of college, I’m working a job as an electrician, laying pipe and installing fixtures, and at a certain point, digging ditches. I think I’ve talked about the story here on the show before, but that was really transformative for me was that there was raw material there. But if I had not started going to the library nights and weekends, taught myself Pearl and PHP and a SP, was it 2.0, 3.0, I don’t even remember. It was 1.0, but taught me those raw skills. That was the value that I was adding to this raw material. Obviously, looking back, it’s like, oh, I have a knack for left brain thinking, and I have a knack for logic, and I have a knack apparently for programming computers and for thinking about frameworks. There’s a bunch of things. 

Maybe I’m not a bad writer. I’ve written five books. Good or bad is probably debatable, but at least I can get the books to print. But all that said, in retrospect, it feels obvious to me now, but it wasn’t. I was just an iron bar 25, 30 years ago like everyone else, and so that’s what I want to drive home. I was really struck by this because if you are a founder, an entrepreneur, an aspiring entrepreneur, realize that it takes both. And this is why I often talk about what’s your unfair advantage? What are you exceptionally good at? If you’re really good with people, well, maybe you want a co-founder who is a complete code junkie and you’re going to do the sales and they’re going to do the coding. And if you’re really a left brain marketer and you’re good writer and you can copyright, realize that you can capitalize and build on that, that there’s probably some raw material or some proclivity that you have. 

And don’t go with the proclivity of, oh, I just want to build a great product and have everybody use it. It’s just not going to work. Don’t convince yourself that eating ice cream is going to help you lose weight. You have to be within the realm of what works, but also look at the raw material that you have and think about how much time, effort, and energy you can put in into building up your skills, building up your experience over time, potentially by stair stepping your way up until you can potentially make precision laser parts from who you are and become worth $15 million. I don’t mean exactly that number, but you get the idea. I also, what I love about this is it really is a stair step, right? He says, if you’re just the kilogram iron bar, then you’re worth a hundred. If you make horseshoe, you’re worth two 50. 

If you make so many needles, you’re worth 70,000. Each of these is a stair step. So that is my second topic of the day. My third topic is a word of thanks from an anonymous listener, and he says, Hey, Rob, just wanted to drop you a message to thank you for your content in the podcast, which I’ve listened to for a long time. I started a bootstrap side project in 2018 that became my full-time focus in 2021. I’ve now exited this week for a life-changing amount of money, a slow burn, but a worthwhile one. Thank you. Keep up the good work as I believe the work you do is vitally important. Exit strategy has helped me during this process as well. I’ll be tuning in again next Tuesday. Kind regards, these are the types of emails and messages that I get that remind me of why it is that I do this. 

Why it is that my mission is to multiply the world’s population of independent self-sustaining startups, and it doesn’t get old. Hearing this and hearing the lives that are changed, not just by this podcast or this ecosystem or words that come out of my mouth, it’s by us. It’s the community. The multiplicative effect of the MicroConf and TinySeed and startups For the Rest Of Us community is 10 times, a hundred times a thousand times more than any one individual can do because on my own, I can only do so much. I can only say and write and think so many words and invent frameworks. It’s not that. It’s the folks out in the audience helping one another. It’s this community of bootstrapped and mostly bootstrapped founders, whether you’ve attended a MicroConf, whether you’re in a Mastermind, whether you’re in MicroConf Connect, or whether you’re just doing your own thing and finding other founders and supporting one another, this is why we’re here. 

So thanks for that email anonymous. It means a lot every time I receive one of these. Thank you. My next topic is about how people who are winning don’t have a problem with other people winning. I also wish I had referenced a source. I think this was a tweet that I saw, and this sends me back to a blog post I wrote years ago, which is it’s easy to criticize from the stands, and usually, especially as I was coming up, and I think as anyone’s coming up, you’re going to get criticism on social media or even before social media. It was like you had a blog and people would comment on it. They’d send you direct emails. If you’re launching a product, people will message you, say how crappy it is, try to give you feedback that’s not super helpful, that they feel is constructive. 

Or maybe they’re just being jerks. And 99.5% of the time, the people who are giving you the harshest criticism and feedback and kind of trying to tear you down, not actually trying to help, let’s separate those. The people who are actually trying to help or at least think they are, okay, we’ll give ’em a pass. But the folks who dig in and are really trying to tear you down, usually to make themselves feel better, make themselves feel superior, those are usually the people who haven’t done anything. They haven’t shipped anything worthwhile. They have not had success. Every once in a while I’ll find that it’s someone who’s had success, and then I’m usually like, why are you punching down? It’s a bad look. This is not great. But so many of the people that you’ll hear from are folks who are not winning and who don’t know the difference between failure and success and who don’t know what it’s like to work hard nights and weekends while you have a day job, while you’re raising that family, while you’re trying to balance everything and make it all work, and you’re struggling and you’re putting in a ton of effort to change your life, and it’s the folks who are either half-assing it or just not having the success and not making the progress that want to tear other folks down. 

The idea that people who are winning don’t have a problem with other people. Winning holds true. In my experience. I love this summary of this, and this feeds into the idea of surrounding yourself with people, whether they’re winning or not, they’re at least optimistic. They’re at least positive. They’re saying, we can win. I can win. We can launch something and build a product against all odds, right? Make something that people want and are willing to pay for. And in all my years of being an entrepreneur, I’ve gotten so much more out of being around people who are positive and at least trying to win, rather than the ones who are tearing themselves or others around them down. And it’s interesting that in my early years of being an entrepreneur, since I didn’t really know anyone else who was doing it, I had to start distancing myself from some college friends and some just post-college friends who kind of wanted to, when I talked about entrepreneurship, or I had, what did I have? 

Ink Magazine or Business 2.0 or Entrepreneur Magazine, whatever it was. I mean, again, this is a while ago. It was a long time ago. So magazines were a bit more of a going concern at the point, but they would poke fun at it and say, oh, you think you’re going to be an entrepreneur? You think you can do this? Or just really, and I don’t know what the motivation was, tall poppy syndrome where they’re trying to tear other folks down, maybe because they can’t do it, or maybe they’re just looking at something to rag on someone for being different or having an aspiration. And the hard part is sometimes it’s is family. Oftentimes it’s probably family and sometimes it’s friends, and sometimes it’s acquaintances or whatever. But realizing that surrounding yourself with folks who either are winning, and what do I mean by winning? I mean, I’m not talking about hashtag winning Charlie Sheen, or I’m not talking about being some always be closing sales, bro. 

I’m just talking about folks who are trying to better their lives and change the lives of themselves and those around them through entrepreneurship. That’s what I mean is folks who are positive and trying to improve their little corner of the world. To me, someone who is doing that is optimistic about it and who’s driving it forward is someone who’s winning. So since you have a choice around this matter, try to surround yourself with people who were doing that because they won’t have a problem if you are winning. I remember in my early days of starting to share what I’ve learned, I was a few years in maybe four or five years, and I had successes under my belt, and I was doing well. Some of the folks that were learning from me that had read my first book, that had read my blog, started things and became more successful than me, they would tell me, oh, my MRR is 50 KA month or something. 

And I hadn’t gotten there yet. And I remember a twinge of jealousy at the start before I felt a tidal wave of happiness for them. I was winning enough. They were ahead of me, and they had learned from me, and they deserved it because they’d put in hard work and skill made a little bit of their own luck. Just because they had learned from me doesn’t mean that they didn’t deserve to be wildly more successful than I am. And there are TinySeed founders that have sold their companies for more money than I’ve ever sold a company for. There are TinySeed founders that have more money in the bank than I have in the bank. It is similar. I know what they’ve sold for and I am nothing but happy for them. Just because someone is winning a little more than you, if you have the right mentality and the right thought process around it, and don’t see this as a zero sum game, you see this as an abundance mindset rather than a scarcity mindset. 

You’re not going to mind if other people are winning. So the key takeaways here in summary are surround yourself with those folks who are winning, who genuinely want you to succeed, and figure out who those folks are that are thinking and doing the opposite, and realize that you want a lot more of the former in your life. Speaking of winning, you made it to the end of another episode of Startups For the Rest Of Us, thanks so much for joining me today. It’s always an amazing experience to spend another half hour with you. This is Rob Walling signing off from episode 805.  

Rob Walling:
Some folks I know never want to be in their comfort zone and they’re always out doing new things and they bounce from one thing to the next to the next, and that’s not good. And some folks always want to be in their comfort zone and they stay within it even if the business needs other things like sales and marketing and that’s not good either. And some people stick with things for way too long and they’ll ride a losing business for years and years and years and just stick with it because they don’t know what else to do and that’s not good either. So the idea is to figure out which of these are you. 

This is startups For the Rest Of Us. I’m your host, Rob Walling. In this episode I answer listener questions ranging from how to position a product, whether to focus on horizontal, vertical, orthogonal as a bootstrapper, whether you should invent a category when there maybe are exceptions to the rule to not do so whether to market locally or globally. And I’ll answer another listener question or two depending on the time we have. Before I dive into questions. MicroConf remote is happening on November 5th, 2025. So far we have talks from Sunny Hunt about stop stalking your competitors, your 15 minute intelligence framework, a talk from Victor Hot Faludi, who is a B2B sales consultant and trainer on turning your demos into your best discovery tool to get your deals unstuck. The theme of this MicroConf remote that is a totally virtual event is ship it. It’s about getting launched. 

The recordings from this event of course will be available to all ticket holders, but if you show up live, you can ask questions of the speakers. And after the talks, we’re going to have our patented founder by founder session. It’s not actually patented, it’s just an expression, which is like a digital version of our hallway track where you can meet other bootstrapped and mostly bootstrap founders. We keep the ticket prices extremely reasonable to make it a no-brainer for you, and the event is completely online. And if you buy your ticket, we’re going to throw in a bunch of extra talk videos from MicroConf Remote Spring 2025 and our talk videos from MicroConf us the live version we had just a few months back in New Orleans tickets are $65, but if you use the promo code startups 15, you can get $15 off. And with that, let’s dive into our first question about positioning.  

Speaker 2:
Hi Rob, thanks so much for all the content that you provide. I have been listening for the last four years and it helped tremendously. You talk a lot about niching down and not chasing other markets too early, but for the last months, me and my co-founders have been discussing if we should niche and position ourselves in a more horizontal or orthogonal way. The context is this. We are scraping thousands of publicly available regional data sources and combining the structured and enriched data into a single dashboard, all with notifications about new data filters and collaborative features for our users. We have deep expertise in renewable energy, so that was the first market segment we targeted before we came along. They were spending hundreds of hours searching through these sources manually. We got great feedback and already closed a good chunk of the biggest players, but now there are three ways forward. 

We could double down on renewables, adding more features for their specific needs, but also dealing with the volatility of the market and new legislation changing customer needs. Or since we already have all this data, we could go more orthogonal and also target other markets with similar needs to renewables. Here we would have a first mover advantage since nobody is providing this much needed data outside the renewable sector, but we would lack the industry knowledge or we could go more horizontal and become what’s stripes for payments providing access to a unified data API for everyone that needs it. What do you think about this? What are the conditions for considering vertical orthogonal and horizontal positioning? I would love to hear thoughts and again, thanks for all that you do.  

Rob Walling:
I like this question and this really is a one with a big, it depends, but of course, as you know, I like to say it depends and then go through different scenarios instead of just punting on it and using that as a cop out to not actually answer the question. I don’t think there’s a single unifying theory that I’ve heard or that I have around when to go orthogonal vertical or horizontal. It’s kind of a case by case basis, but there’s certainly more guardrails than that, right? There are times when it’s kind of obvious that you should be in one versus the other. Choose that vertical, horizontal or orthogonal. I think the two things that I think about are, number one, how much does the product have to change to go with one of those three options? Is it kind of broadly the same across all three and two is do I have any reach? 

Do I know how to market and sell to any of these versus one of the others? So that was kind of a weird convoluted way to say it, but obviously in the vertical that you’ve chosen the renewable energy, you had some type of advantage. So is there a way to then add other verticals that are adjacent to renewable energy? And when I say adjacent, lemme give you an example. I have this exact conversation once a quarter at least, maybe more often with either TinySeed companies or companies that apply to be in TinySeed where we’re talking about the idea that you can start with a vertical and add more later. You can start with multiple verticals and narrow down. You can start horizontal and narrow down to a few verticals that become the most profitable or easiest to serve or sell to. There’s all zoom in and zoom out pivots. 

That’s the phrase for these. None of these is right or wrong, and I don’t think there is a one size fits all. You’ll often hear me say, oh, my default if I’m launching a new B2B SaaS is to have a credit card. But there are times when you don’t have to. There are exceptions to that kind of rule of thumb. I don’t have a rule of thumb on this yet and maybe I will develop it over time if I think more about it and see more examples. Usually I develop these rules of thumb based on seeing dozens if not hundreds of examples of something and seeing the patterns and then coming up with a theory and the framework around it, and I don’t have a strong one on this particular conversation yet, but I was talking about if you’re going to move into another vertical, try to make it adjacent to the vertical you’re in. 

And the examples of that are like if you are serving realtors, real estate agents who sell homes, then adjacent to that is mortgage brokers who might underwrite loans or at least broker loans in the real estate sector. And then are there title companies, are there real estate attorneys or just in general attorneys? Are there accountants? It’s these professional services folks that are similar enough in need and may even talk to each other, like realtors talk to mortgage brokers that it kind of translates. There’s an adjacency between those two spaces versus saying something like, I am currently catering to realtors and we’re going to switch to catering to folks who do lawn maintenance. It’s not a similar market. They might not even have similar needs in the product. They’re not going to talk to one another. There’s very little overlap or adjacency, and that’s what I mean by that. 

So the question is, in your shoes, would I stick with and double down on renewables? Would I go orthogonal or more orthogonal and add more verticals or would I go horizontal And I come back to how I started this, which is how much does the product have to change to serve these three? And I would probably just wing it and take a guess. Is there zero hours? Is there a hundred hours? Is there a thousand hours for each of these three paths? And my guess is the product, well, my guess is the product doesn’t have to change that much, but I include in that the need to write crawlers and scrapers and pull in that data. That’s a product task. And so if going horizontal is a ton more work, then there’s more opportunity there. But then I ask myself, okay, so is horizontal for anyone, and I’m this, as you said, unified data, API for everyone. 

How as a bootstrapper am I going to find everyone? How do I market that? Is there a search for a unified data api? Is there a search for the terms that I would become? Because right now if I’m a renewable data source and folks are seeking that, then you have that advantage. You have customers that are relatively aware of their need versus going horizontal. If it removes that and it makes it really hard to sell broadly, then I would shy away from that. The idea of adding more verticals, I’m never opposed to that. It’s always an experiment. It’s always a question and a hypothesis of can I either target some keywords, create some content, do cold outreach, go to in-person events in order to find folks in these adjacent verticals, or if it’s just a single adjacent vertical, you get the idea. I think there’s a lot less risk in adding another vertical or two. 

Now that doesn’t mean it’s the right choice, just because less risky doesn’t mean it’s the way you should go, but with no other information beyond what you’ve presented, I’m not sure I see the path to going horizontal unless you see a compelling case to go there. But I do see adding more verticals as potentially a stepping stone that you start where you are, you add verticals, you eventually get to horizontal. To wrap this up, I would ask myself, is what we’re doing now working by just being in this one vertical or is it broken, right? Do I need to fix it? Or if I keep doubling down, will I get to a million a RR? I mean it depends on what your goals are, right? But it’s like if I were you, I’d be trying to get to 1,000,002 million and 3 million a RR and can I get there with it as it’s been going or is it too slow? 

And you said there’s volatility in the market, and the question then is, okay, so if I add another vertical, then do I even out my volatility and am I adding a lot of work to do that? Is it the two-sided marketplace problem, not literally two-sided marketplace, but the idea that now I’m marketing to two audiences and so it doubles the amount of work that I have to do to bring folks in or is there overlap because they’re adjacent? Lastly, you made the comment, we have first mover advantage if we add new verticals and why that is not a silver bullet by any means. I’m intrigued by that. I like first mover advantages. I would just make sure that the marketing and sales plan, the strategy, the tactics, that there’s some type of validation there. This is where folks will come and say, well, I don’t like the term validation and I want to validate and then just build in launch. 

And it’s like you’re validating until you sell that company, you’re still validating do people need this feature? You’re validating that every expansion, every strategic decision, every move you make, every marketing approach you add kind of doing some validation in advance, right? I never just launched a new marketing effort without having some idea of whether it was going to work or what it would look like if it was going to work or not. And so that’d be the thing I’d be thinking about and looking at is like, how can I get just a little more data on each of these? Or if I have a gut feel that I want to add more verticals, how can I have some conversations, build some landing pages, start some SEO and outreach before I go full bore into trying to actually build the product out and ramping everything up? So thanks for that question. Hope it was helpful. My next question about starting a new product category.  

Speaker 3:
Hey Rob, Andrew ASINs here from Meta Monster. First off, thank you so much for everything that you do. I have devoured startups For the Rest Of Us over the last few years. Somehow I came to the podcast late and as someone who’s been working on building bootstrapped startups and tried a bunch of times and failed miserably for years, I so wish I had found your content sooner. It has been tremendously helpful to me. And so just thank you for everything that you do. Really appreciate it. So the tool that I’m working on building, I think I want to describe as an SEO automation tool. It’s an AI native SEO tool and we’ve been struggling to figure out how to position it. We started off calling it a site audit tool or AI powered Screaming Frog or an SEO crawler that fixes issues for you and we’re really leaning more thinking. 

The thing is more in this automation piece, but the problem with that is that doesn’t seem to be a super well-defined category, and I know your advice and advice that I have seen firsthand play out is that bootstrappers should never ever start a new product category, but that feels like the direction we’re being pulled in. And so I’m basically trying to figure out how big of a mistake is this? Is AI changing things? Is there something natural happening here that we can tap into and grow with? Is AI making it easier for bootstrappers to create product categories? Would love to hear your thoughts on some of this and happy to give you more details if you need them. Thanks again for everything you do. Look forward to hearing from you.  

Rob Walling:
Thanks for the kind words at the top of that voicemail. I hear that a lot. I’ll be honest of I wish I’d found your show earlier. So I really do. It means a lot coming from you and I really do appreciate that. My thoughts here, there’s a couple things, right? On the one hand, if your H one says what your product does, we audit and fix the SEO issues on your website, then I’m more lenient with the need to even have your product category defined on your website. Do you need to be in a category? I mean, I guess if you’re on Capterra and you need a category there, right? So you’d be an SEO tool of some kind or maybe you’d be the SEO audit if there’s an SEO auditing or site audit or whatever to get more granular. But the thing I think defining categories is tough when it’s far afield from the existing stuff and where it takes you an entire sentence or two to describe what your tool does, that’s when it gets difficult. 

And when you’re trying to cram that into an H one where it’s like we are email automation that also does this other thing and talks to all your customers at the right time and this and that, and you go into this long explanation, it’s like, gosh, that’s your H one. That’s brutal. Rather than saying, we are the best email service provider for accountants, that makes sense. Email service provider is a category and your vertical is accountants. In your case, if you’re getting customer poll to fix the issues and not just audit and unearth the issues, I’m not sure I would resist that. And what your product does can be, I won’t say different than your category, but it can be more than just your category. Again, let’s say your product category is an SEO tool or an SEO site audit tool. I don’t dunno if that’s a full-blown, it depends on how we define product categories, but let’s say that it is, it’s a site audit tool is the category, and then you also using AI fix the issues. 

I mean, that’s kind of a neat bonus and I don’t know that you’re saying it’s SEO automation. I don’t think I would use that term on my homepage. The danger is that you say a phrase that means something to you, that doesn’t mean anything to anyone else. That’s the real danger. And I guess what I’m saying as I’m talking this through is I would piggyback off of an existing category. As you said, you kind of started as a site audit tool and it’s like you’re trying to pivot away from that. But if you still do site auditing and then just fix people’s issues, I don’t know that I would define that as a new category. If you say SEO automation, I’m not sure what that means. Does that mean you write articles, post them on external websites and build back links to me, plus you do onsite auditing and this and that, it’s just not specific enough. 

The reason when I say email service provider to you, if that wasn’t a category, you’d be like, wait, ESP, is Gmail an ESP is a OL an ESP hotmail or is it a MailChimp? Is it thing that sends emails for you? Email service, you provide email. The reason that these categories work, CRM is another one. Customer relationship management. So that helps me communicate with my customers. It helps me manage my relationship with my customers. It doesn’t. It’s a sales tool. It’s for salespeople because the description of a category or the title of a category, the name of it, it really is kind of inside baseball, right? It is jargon or words that have come to have meaning in our minds. And so if you say SEO automation and no one’s heard that before, most people haven’t, it’s not helpful. It’s not a shortcut. It’s confusing. 

And that is of course why we say most people who talk about who have tried to create categories and who’ve seen people try to create categories as bootstrappers. My thing is if you don’t have millions of dollars and three to five years to build a category to start one, don’t do it. And that’s why most of us say it because we have seen a lot more folks fail at it than not. So to wrap up my thoughts here, is AI making it easier for bootstrappers to create categories? No, because if you think about it, creating a category is kind of like building a brand on hard mode. So building a brand is where you build hopefully a great product and you get a bunch of people using it and then they start talking about it and then that name, your name has meaning, right? So MailChimp evokes a certain emotion in us, right? 

Startups For the Rest Of Us, MicroConf, TinySeed, each of these has a brand with people who have heard the name and who associate it with something. If you are trying to build a category, you are trying to build a brand for an entire grouping of software and everyone else who’s in that grouping is going to resist being under that brand, especially if you coined it. So I don’t think AI makes any of that any easier. AI makes building products easier and it means the type of products we can build are more varied and we can build maybe some new new product types or categories, but building a product category and fleshing that out I think is as difficult as ever. So thanks to that question, Andrew. Hope it was helpful. 

If you know me, you know that I started TinySeed, which is the SaaS accelerator for ambitious B2B founders. To date, we’ve invested in more than 200 companies and we’ve raised $60 million across all of our funds. We’re about to close fund three, and if you want to hear from TinySeed founders, you can go back to episode 783 of this podcast where Pierre de Wolff talked about having an eight figure all cash exit with Scraping Bee and episode 728 with Gym Desk where the top line number, the headline number was 32.5 million, but that was for a partial acquisition of Iran galperin share of Gym Desk. The vast majority of our investors are B2B SaaS founders themselves, either current founders who have companies that are throwing off enough money that they can be accredited or folks who have exited, check out the full thesis@tinyc.com slash invest. And if you want to take some money out of the public markets and get them into ambitious, highly vetted and so far, highly successful B2B SaaS founders, you should head to tiny c.com/invest. If you fill out that form, it goes directly to a R’S inbox. My next question is about getting through mental blocks of launching.  

Speaker 4:
Hey, Rob and the team, it’s Farish from London again, and had a question on focusing one thing at a time when you guys started working on Drip, how did you discipline yourself to focus on the product? What signals did you have on a daily or weekly basis that kept you motivated to work on shipping it fast and out the door? I’m getting stuck shipping and mostly procrastinating when I’m nearly at the point of launching just a landing page. I get excited for weeks working on it, but I feel drained out just thinking about publishing and I get to the point of just changing the idea just before launching. Do you have any tips on trying to get out of this mental  

Rob Walling:
Block? I think the majority of entrepreneurial success is managing your own psychology. Just like so much of your job as a founder is making hard decisions with incomplete information. Both of those apply here. The biggest thing is to know yourself. It’s to learn about yourself and when you have resistance, because we all resist different stages and different activities, a lot of developers resist anything but coding because it’s their comfort zone. Some folks I know never want to be in their comfort zone and they’re always out doing new things and they bounce from one thing to the next to the next, and that’s not good. And some folks always want to be in their comfort zone and they stay within it even if the business needs other things like sales and marketing, and that’s not good either. And some people stick with things for way too long and they’ll ride a losing business for years and years and years and just stick with it. 

They don’t know what else to do and that’s not good either. And then the folks who spray and pray 20 things at once or who just are serial launchers looking for that dopamine hit, that’s not good either. So the idea is to figure out which of these are you, and it sounds like something you struggle with is really getting through that resistance of actually shipping it that you build and work and it’s fun and ooh, this is great, and I’m getting the dopamine hit because I’m imagining what it’s going to be like and it’s so fun to build and building is fun, and I get it. I get it. I’m a maker too. I’ve been writing music and writing code and I used to write fiction. This is something I’ve done for decades and decades, but the trap is that the and the making, unless you’re doing it purely as a hobby or just as art, you’re sitting down just to make a thing that no one else will ever consume unless that’s your goal, then it has to get in people’s hands. 

And so the way that I got over this was to realize very actively and very left brain that rationally I have a resistance around this time, and so I am going to counter that resistance and I’m going to brute force it. You’ll hear me say that expression on the show. I was just going to brute force it. What does that mean? It means to fight my own instincts to fight not only the voice in my head, but when it’s not even a voice in your head and it’s just this internal lizard brain resistance that is kind of guiding me. The folks I see, some of the folks I see making the same mistakes over and over and always getting in their own way. They don’t have the self-awareness and the self-knowledge to see that they’re sabotaging themselves. I talk about having weaknesses and all of us have weaknesses, but a weakness that you are not aware of is a blind spot, and blind spots are catastrophic for entrepreneurial success, frankly, success in a lot of realms. 

So the idea is to learn what your blind spots are, and it sounds like you kind of already know what yours is. You called it out of I build and build and then I just don’t launch and I change it last minute because I’m uncertain. And so you can do it on your own, you can. I’ve done it. I’ve gotten over a lot of my blind spots and turned them into weaknesses. So it’s a blind spot I’m aware of and fought through them. You can do it with the help of other people. This is where a mastermind comes in, mastermind for accountability. Potentially it’s your spouse or significant other. It is unlikely to be unless you have a very special relationship with that person. Sherry, my wife of 25 years is not that for me, and that’s fine. It’s just not the role that we play for each other. 

You can get this from an investor, an advisor, a co-founder, a friend. You see what I’m getting at? There’s someone external here that you might need to find who can bust your chops. An accountability buddy. A coach might be someone you pay, might be someone that you return the favor for that if you can’t do it on your own, much like going to the gym. Some people just don’t do it unless they’re going to let their friend down by not meeting them. That might be the case in this case is that you have to figure out a way to fight your programming. And each of us has these things that will trip us up over and over if we don’t A, recognize them and B, put systems in place to figure out how to get through them. I happen to not have the best memory for, I don’t even know what it is, but it’s like items in the future, like Sherry will tell me, oh, we’re going to do this on this day, or we have this appointment on and it doesn’t sink in for me. 

So my system is everything that I’m going to do goes on a calendar and anything I need to remember is always in writing somewhere and it will pop up. It’s an email that is snoozed until that day or it is, like I said, a calendar item. This is very simple, but you get the idea is that I know what I’m strong at and I in general know what my weaknesses are. And you can build systems around your weaknesses if you know what they are. And so to answer your original question, which was as we were building Drip, how did you focus? Well, number one, we kept getting feedback, right? Because we weren’t just building in a basement for six months. It took six months. No, it took at least five or six months from the first line of code until it was in Patient Zero’s hands, customer zero’s, hands. 

And along the way though, I was out there marketing and building a list and getting interest in having conversations and emailing folks and sending out surveys or episodes of this podcast where I talk about the surveys I was sending to the mailing list. So I was getting that the dopamine hit and a little bit of motivation from that as Derek was coding. He was coding halftime for me as a contractor at the time, but we had that feedback loop of, oh, at least people are interested. So that was one. The other thing is Derek and I were working together on it, and so there was some little bit of accountability there and some motivation. I was also in maybe two masterminds at that time and I was telling people about it and I was committing that we were going to try to get it out and this is the progress and this is how we’re thinking about it. So you can see the scaffolding that I put in place to keep us moving forward. So thanks for that question. Hope it was helpful. My next question is about marketing locally versus globally.  

Speaker 5:
Hey Rob, how can I market to my local group of people without hurting my reach for a wider audience? Or should I just ignore the wider audience until later? I’m working on a SaaS app with Target customers that can be in any country, but I can sell it better in my own country. New Zealand, is it better to make landing pages on a New Zealand domain that will have a higher chance of showing locally but less internationally? Or is it better to keep marketing as wide as possible with the downside of being somewhat less effective and reaching people locally? Thanks, Rob. Love the podcast.  

Rob Walling:
Similar to the earlier question about positioning. I mean, this reminds me of does the product have to change and does the marketing slash sales have to change, and how much does it have to do local versus global? The way I would think about it is the odds are probably good. I don’t know the space, so I’m making assumptions. The odds are probably good. You’re eventually going to want to make it into other countries, Australia, the uk, Canada, the us. So I would plan longer term for that to be the plan. And therefore I would not personally, this is not advice, this is what I would do. I would not do a.co nz domain because it will be detrimental, especially if you try to market into the us. I can’t speak for all the other countries, but in general, I think folks who live in a particular country or area are biased towards that area. 

And.com is just the most kind generic or whatever ly, whatever you wind up landing on. The idea is I would allow that flexibility. I wouldn’t want to change domains later. Now, could I see having a.com and having language on the site that says, Hey, we are this for New Zealand. I could, I dunno if you need that, if you think it’ll help do it and change it later, it’s an H one on a homepage, you can change that later. If you don’t think it’ll help that much, then just don’t add the restriction to it. And I think marketing and selling into your home country to start with and to prove it out and to get a feel for it is really quite a good idea. Again, assuming you think it will be some type of advantage, like certain tools, I just don’t think it matters. We were just talking about Drip because the prior question asker asked about it, I just don’t think it would’ve made any difference if Drip was, let’s say Drip was built in Canada or Drip was built in New Zealand, and it’s like we are email marketing automation for New Zealander. 

It just doesn’t matter. And so it does depend on whether or not your product becomes more attractive or easier to market or easier to sell or easier to build because it focuses on your own country. That would be a big part of the decision for me. And then as I said, I would try to keep that flexibility longer term and not make big decisions like it wouldn’t include NZ or New Zealand in the name of it or in the domain. If I thought, eh, that’s probably a pretty good chance I’m going to add other countries or just go globally later without additional information. I’m not sure I have a more concrete answer, but those are my thoughts thanks to the question. Then my final voicemail of the day is not a question. It is more of a thought around validating ideas. And Sean who sent this in is hearkening back to my prediction that I made about self-driving cars in 2025, really accelerating, so to speak, forgive the pun, but their growth and adoption really accelerating and he had some thoughts on why they may or may not do that.  

Speaker 6:
Hey, Rob, Sean Murphy here, a fellow co-founder based in the Twin Cities like you. In your recent podcast where you made predictions about 2025, you predicted about the rise of self-driving cars or self-driving taxis. And as part of that, you used a data point. And I thought it was really interesting to think about how entrepreneurs like all of us can use data to make business decisions or identify business opportunities. And in this case, the example you used was that there are 50,000 traffic desks per year, and it’s estimated self-driving cars could save or reduce 90% of those deaths every year. And so that would take it from 50,000 deaths per year to 5,000 deaths per year. And that made a really compelling case for why these self-driving cars should take off. But I also think that this is a great example that all entrepreneurs should be fluent at doing, which is to reverse a statistic and see are there business opportunities or reasons why something won’t work In this case, you can imagine that that still leaves 5,000 deaths per year, in which if there’s only a handful of companies that provide these platforms, let’s say five of ’em, that’d be a thousand deaths per year that each company was responsible for or three people per day. 

And so it’s pretty hard to imagine a company that could handle, that could survive where their users of their products are dying three per day. And so that could be a strong counter argument against that business idea, or it could be thought provoking idea for entrepreneurs to say, well, what must be true to enable this? And so are there business opportunities there in saving lives or in handling the grief or issues that come out of this other thing? So I was super thought provoking. I love the idea that you had there and I thought the technique was something to share with the audience. Love what you’re doing with the show. Thanks.  

Rob Walling:
Thanks for writing in Sean. I appreciated your insights and I think you make a valid point and I guess we’ll get to see how it plays out in the coming years. Thanks so much for joining me. For listener questions today, if you have a question for the show, you should head to startups For the Rest Of Us dot com. Click ask a question in the top NAB and right from your phone, you can record an audio question, a video question or just type a text question, audio and video. Of course, go to the top of the stack as do any questions that are intermediate to advanced. I did ask one beginner mindset question today. I like to trickle ’em in because there’s a tremendous backlog of them, but realistically, the beginner questions have, we’ve covered so many of them so many times on the show that I’m kind of trying to optimize more for intermediate and advanced questions. Thank you for listening this week and every week. This is Rob Walling signing off from episode 804.  

Rob Walling:
You’re listening to Startups. For the Rest Of Us, I’m your host, Rob Walling. In this episode, I talk through the eight key takeaways from MicroConf Europe 2025, which happened just a couple of weeks ago, and I talk these through with the founder of Rual, Laura Sprinkle, who attended the event, and this was her very first MicroConf. As I said, Laura runs Rootabl, which is a TinySeed company, and this was her first exposure to the broader MicroConf community. So it’s really nice that we each have obviously different exposure. I’ve been to 25 flagship MicroConf, and this was her first. And we weigh in on the key takeaways that we pulled away from the talks and the hallway track. Before we dive in, early bird tickets for MicroConf US 2026 are on sale. So if you listen to this episode and you’re thinking, I want to get in a room with 275 amazing bootstrapped and mostly bootstrap founders, you should head to MicroConf dot com slash us. 

The next event is in Portland, Oregon from April 12th through the 14th of 2026, and we have sold out our last several events. We’ve already sold a big chunk of early bird tickets and prices on these tickets will go up on October 22nd or when the first a hundred tickets have sold. If you’re planning to come, you do want to get your tickets now. The tickets today are as cheap as they will ever be. That’s MicroConf dot com slash us and use promo code Rob 50 for $50 off. And with that, let’s dive into the key takeaways from MicroConf Europe 2025. Laura Sprinkle, welcome to the show.  

Laura Sprinkle:
Thanks for having me.  

Rob Walling:
It is great to have you on for your first ever appearance on startups. For the Rest Of Us, we’re going to be talking through MicroConf Europe 2025 that just happened in Istanbul, Turkey. And before we get into that, I want to give folks just one or two minutes about who you are and your expertise. You are the founder of routable. It’s R-O-O-T-A-B l.com. Your H one is create an affiliate program that gets you more leads and more revenue. So you are affiliate management if we were to categorize it, but unlike a lot of founders who enter a category, you have a ton of background and experience in this space. Do you want to give folks just a snapshot of how long you’ve been doing it and maybe some bon fetus?  

Laura Sprinkle:
Sure. Yeah. I mean, it’s been almost a decade in the affiliate space and I’ve done every witch thing. You could think about affiliate management for clients. I had a course, I did consulting, I had an agency, so I’m really all up in the business of affiliate marketing, affiliate management, and worked with some of the top course creators in the world and just done millions in revenue with them, and it’s been a wild ride.  

Rob Walling:
Any top course creator names you want to just drop here on the floor as we’re getting started?  

Laura Sprinkle:
Sure. It’s funny, when I come into this space, I’ll drop a name expecting like, whoa, and then no one knows who they are, but like Amy Porterfield, Todd Herman, Kate Northup. So yeah, lots of folks in the creator space,  

Rob Walling:
Lot of big names. And you actually gave a lightning talk at this event that we’ll get to a little later about affiliate management or really it was affiliate programs made ridiculously easy. That’s a good title. So let’s dive in a little bit, give folks some background, and then we’re going to do, I think we’ll have eight key takeaways from MicroConf Europe 2025 to give folks the lay of the land, whether they’ve been listening to this podcast for 10 years or 10 minutes. We tend to have, in Europe, it’s a smaller audience than our US event. And so we had think a record breaking audience of 160, 1 65 in that range. Oftentimes Europe has been more in the 1 25 to one 30 range, so it’s a little bigger, still felt nice and intimate. I felt like I got to talk to a lot of people, maybe not everybody, but I got to talk to a lot of folks. 

We did sell this event out, it’s like our third or fourth in a row that we’ve sold out. 40 countries were represented, which is a record for any MicroConf that we’ve ever run. And to give folks an idea, I believe, including our local events, we used to run, this is our 39th MicroConf and just counting our flagship events from US to Europe. This was our 25th, and then I believe it was the 12th MicroConf Europe. But who’s counting? I’m not a numbers guy. See, I rattle these things. I totally, I do pay attention to ’em. And some of the crazy stats, which I don’t know if we weren’t collecting these before or if they’ve just gone up over time, but 90% of our attendees at this event had a product with revenue, and at 30% of attendees had at least a hundred thousand dollars in MRR. So 30% seven figure a RR companies, which that’s a significant number that I’m not sure I was aware of. Again, over time, I don’t know if it’s always been that high. I feel like it’s kind of creeping up. This is my 25th flagship MicroConf Fit was your first, I’m curious to set the stage. Is it what you expected? What did you expect, and was it same or different than what you thought it would be?  

Laura Sprinkle:
Yeah, I think we had a conversation back in April in San Diego and chatting about the difference between Europe and the us. And I will say one thing I was surprised about was there were actually more women than I expected. Not that there were a ton, but it was still more, and also, this is going to sound like I thought it was going to be terrible. I didn’t, but everyone was so friendly. I’m thinking, oh, these are all going to be nerdy programmers. They’re going to be standing by the wall. But no, everyone was so excited to chat and so kind, so that was a surprise.  

Rob Walling:
Yeah, that’s cool. Nerdy programmers can be friendly too. You know that as a nerdy programmer myself. No, I agree. And that’s something that, it’s not like we’ve cultivated that on purpose, but a little bit. I think folks who are attracted Microcom spring out of this show, this podcast, and Mike Taber, who I started the podcast with and myself, tend to be just pretty nice people. And so I think people who are drawn to us tend to be pretty nice people. They’re obviously more polarizing personalities in the startup space. I could be a total startup bro and be super aggressive and be like, fuck everybody. And the people who are drawn to me then are of that personality. I think that’s the people who would be at the event. So that’s how we kind of view it. And it is nice, as you said, the vibe of this event in particular, all microscopes are like this. 

They’re positive. But the vibe of this one, I felt like people were really going out of their way to almost offer to help one another. I mean, I was just standing around talking to people, signing books and stuff, and I would watch people come up and be like, oh, how can, oh, I’m really good at this type of marketing and here’s some advice on SEO, or you should talk to my buddy who’s a blah, blah, blah. And I was like, this is so cool to see this in real life. It’s like an extension of the TinySeed Slack is right where it’s like everybody is here, they’re there to learn and help themselves, but also there’s a real, they felt like a really giving environment.  

Laura Sprinkle:
And I think everybody too was they just asked really great questions and you could not tell when you said the 30% were over a millionaire R, there was no, you didn’t know that. Walking up to somebody, everybody was very chill.  

Rob Walling:
Yeah, that’s part of what I enjoy about it is it’s pretty rare. There are egos at a MicroConf, and there are folks doing a hundred KARR, a million a r, 10 million. I mean, there was somebody there, there’s several folks there doing eight figures a RR, and they’re as humble as anyone else, and you really have to dig. I mean, I remember one guy was telling me, yeah, I’ve never been to a MicroComp and listed your podcast for a while, really liked your book. And I was like, oh, cool. And I’m just like, so you have a product? Have you started working on something? And he’s like, we have 70 employees and we’re completely bootstrapped and we’re doing north of 10 million. And I was like, oh boy. And you just couldn’t tell. So  

Laura Sprinkle:
That  

Rob Walling:
Was really fun. Now we’re going to dive into the sessions in a second and kind of pull out some key takeaways from each of them, but I wanted to call out the fact that this is the first time, not only we’ve done a MicroConf in Istanbul, but it was my first time in Istanbul, and I believe it was my first time that far east in Europe because I mean I’ve, I’ve been to Thailand, so I’ve been east in the world. But it was a pretty cool experience for me. I got a guidebook, of course, the Rick Steves guidebook and did a walk through Old Town, is that what it’s called? Yeah, old Town and saw 2000 year old mosques and such history there as Istanbul slash Constant denoble ran the world. It was the world trade or a world trade, a center of world trade for hundreds of years. Had you been to Istanbul before and what was your take on it?  

Laura Sprinkle:
Yeah, it was my first time as well, and it was the furthest east that I have ever been. And I am sad that I did not go to the Asian side while I was there, but the history is just incredible. We went to the Basilica, the cistern on one of the days before the event, and I was just struck by how they were reusing product and materials from ruins from way before that was built. That’s crazy to me.  

Rob Walling:
Yeah. Alright, and with that, let’s dive in to our first talk and a good takeaway or two from it. We’re going to go kind of in order. I actually don’t remember the exact order. So I went from memory, and I’m sure I’m a little bit out of order, but folks, there was only 160 people there, the other tens of thousands who were listening to this, don’t care about the order. But the first talk on the first day that kind of kicked us off and set the stage was from Mark Thomas. Folks have heard him on this podcast. He’s also a coach in our SaaS Institute program for seven figure founders. His talk was what to do when growth feels like it has ground to a halt. And he talked a lot about what lead magnets, lifecycle marketing, sending emails, and really taking advantage of your current lead flow rather than just defaulting to looking at top of the funnel and more and more leads. And this is in line, it’s not always the right answer, much raising prices. It’s not always the right answer, but oftentimes it is. And if you’re not thinking about it, it’s probably something you should pay attention to. And I went on a rant a couple episodes ago about this, about, it wasn’t even a rant, but it was some advice of like, Hey, it’s not always just more leads. Make sure your funnel follows these rules of thumb and has pretty good conversion rates and such. What else did you take away from Mark’s talk?  

Laura Sprinkle:
Yeah, I really loved how he was talking about the, he kept calling it an addiction to acquisition of more leads. And I really, as someone who talks about affiliates a lot, I was like, oh, people need to follow exactly what Mark is doing first before they go get more traffic, whether it’s paid or organic or affiliates. And I am actually going to book a call with him as part of the TinySeed mentorship because I’m like, I want to implement lifecycle marketing. And it’s so hard to, what’s that phrase? See the bottle through the label? No, see the label from the bottle or whatever it is. So I’m excited to tap into that. And it was interesting seeing the room and how people were like, Ooh, send more emails. That feels like a lot, but really, why else do we have the email list? It’s not to build an email list. It’s to grow our business.  

Rob Walling:
And then we had a couple talks after that by names. Most people who are listening to this will know, and these talks were kind of related. They rhymed. They had some similarities. Michelle Hanson, author of Deploy Empathy and co-founder Geo Coio, and now a multi-time MicroConf speaker. The title, her talk was Unlock What You Came here for. And it was a little bit of a workshop where she gave people some work to do around tables and figure out why are you here? And that was followed by John Knox who did a lightning talk called Networking for Introverted Founders. And so a lot of it was about making connections in relationship. And if folks have been to a MicroConf, they know that the second slide of every MicroConf, I talk about strategies, tactics, inspiration, and relationships. And we started by focusing on strategies, tactics, inspiration comes along just, you always get a good founder story here and there, but the relationships is actually what will get you through the hard times. What did you think about Michelle and John’s talks?  

Laura Sprinkle:
Yeah, I loved how John really focused on, he did a lot of Star Wars references, so I was like all these really nailing it in as far as relationships and making sure to prioritize that at the event. And it was great that we were able to speak with our table during Michelle’s. Oftentimes you’re just sitting at a table but listening. And so that interactive piece was helpful too.  

Rob Walling:
And then we had excursions at the end of that day, and excursions are something we’ve only implemented, we were going to implement in the first year was 2020, and then we canceled all the micro comps. And so I believe the first excursions we ever did, were probably late 2021 or 2022, and this is where we take half the day. And instead of just doing more talks, we put founders in a place where they can have conversations with other founders. It’s the networking, it’s the relationships, it’s just stuff stern in your head from those morning talks and you get to know the people and you can kind of build relationships with ’em. So we had things ranging from hopping on a boat to a, I think it was like a rooftop, I don’t know if it was a bar tour, a rooftop restaurant tour. And there was a Hamam, which is a Turkish bath, and I believe, is that the excursion that you went on?  

Laura Sprinkle:
It is, yes. We did the Turkish bath and then met up with those who were in the bazaar doing the coffee workshop,  

Rob Walling:
The coffee workshop. And the bazaar was pretty cool. It was a low shopping area. How did you feel about, well, I guess to start, have you been to a conference before where it is a mix of talks and getting out and doing things, and then how did this experience feel to you?  

Laura Sprinkle:
Yeah, so no, I mean, I host an event, but it was like 40 people and there were a lot of outdoor excursions, but the fact that y’all organized for 160 people to do excursions is next level. And that there were options and so many different things. And I think that was my favorite part of having chosen to go to MicroConf Europe over something in America. And I probably will do more here, but it was like I’m visiting a place. So it was fun to get out in the community, and that’s also why I chose the, it felt the most Turkish of all the options.  

Rob Walling:
Yep. No, I agree. I think if I would’ve gone on one, I actually took that time to kind of take a breath, make sure my talk was really dialed in. I like to do the excursions, but it can be a bit much for me given that I am running crazy the whole time. The other opportunities that we make available for the founders and attendees are these receptions. There’s a welcome one on Sunday night, and then there’s one on Monday and on Tuesday night, and we really try hard to have an outdoor place, otherwise it gets so loud. We’ve been doing this for a few years, and so all the do’s and don’ts, pitfalls of running in a, Hey, let’s have a seven or eight foot marble ceiling and a marble floor and get 200 people in a room. It’s so deafening. So it was nice here that we did have outdoor space, although one of the days, I think it was raining, but this is probably where I got to do the most mingling with attendees. And these were two hour receptions right before dinner. And I talked to dozens and dozens of founders introduce myself. Some folks had been to many MicroConf and some folks had, there was a lot about, it was about 50 50 new versus returning, which was cool. It means that there are 80 people there that I’ve never met, but are somewhere within this MicroConf ecosystem, whether they’re listening to startups For the Rest Of Us or they’ve bought my books or what have you. Any key learnings or meetings or thoughts around the receptions.  

Laura Sprinkle:
I remember actually Michelle said in her talk something about leaving the circle open, so never having just a closed group of people. So there’s always space to welcome a new person to the conversation. And that was so true at these receptions. You could just walk up and it never felt, Ooh, I’m interrupting something. And everyone always caught you up to speed and no, I just met a lot of people. And there was also an opportunity if you did need to rest before dinner or make plans for dinner, you were never just solo unless you wanted to be.  

Rob Walling:
Yeah, which is really nice at an event, especially if you’re new. The second day we kicked off with Tiny Seed’s, very own a R vol set, and he talked about, oh, it was pitfalls of selling B2B SaaS and it was value buyers and how you can kind of be, tricked is a strong word, but how you can sell for less than you’re worth. If folks build a relationship with you and then run a process, you don’t get a lot of bitters. So he did a lightning talk, and then I dove in with my AI talk, begrudgingly talked about ai. It is so funny when I surveyed TinySeed in the slack and then I asked on Twitter and I just said, I’m going to talk in two months at MicroConf Europe. What do you want to hear me talk about? And it was super helpful. A lot of people, how do you use ai? What do you think about ai? And I was like, I don’t really want to talk about that. But what I realized, I picked a completely different idea, started writing that talk, and it just wasn’t very good. I didn’t have a soul. I, I  

Laura Sprinkle:
Dunno what it was,  

Rob Walling:
Wasn’t going to great. I might give it again later. Yeah, I liked the idea of it. The implementation was challenging for me. So do you know the book, the Hard Thing about Hard Things by Ben Horowitz? No. It’s basically the story of, so Andreesen Horowitz is Mark Andreesen and Ben Horowitz. Ben Horowitz was a startup founder and raised venture and sold, I don’t even remember the name of the company now, but made, I think it was like a B2B security company or something and sold it for a billion or 2 billion. The whole book is the story of that, and it’s just all the hard things, all the shit that went wrong and all the hard moments. And I believe each chapter is an anecdote of, and then this catastrophe happened and then this catastrophe happened and then this, you know what I mean? So it’s kind of a cool title, hard thing about hard things. 

Ruben Founder Sewell said, no one talks about that for Bootstrappers. So do that. Write a talk. That is the stories. And so I was going to have one section of, and it was going to be a case study where I was going to interview a founder, likely a TinySeed founder. I have easy access to ’em, but maybe a MicroComp was going to have to anonymize some of them, but it was going to be getting a cease and desist, getting hacked and ransom, having your data ransom, who have, I know founders where all of these have happened, right? Co-founder splits, selling your company imploding, shutting your company down, running out of money. I dunno, I had this whole list of things and it was like, Ooh, these are going to be good stories. But when I actually looked at it, I’m like, look, what’s the action here? Maybe it’s a better podcast series. You know what I mean? Just for me, a talk, especially at MicroConf from me has to come with some, got to, it has to make you think deeper than just it’s going to be scary. And that was it. You know what I mean? Or things are going to go wrong and I’m normalizing it, but that didn’t feel like a great talk to me and I got a ways in and then I gave up and said, forget it. I’m talking about ai.  

Laura Sprinkle:
I want to hear those stories.  

Rob Walling:
Yeah, yeah. No, I know ’em all. I know. I wonder if man, producer Ron will kill me if I do this. If I did a series, you know how we do the Tiny Sea tales where it’s like narrative and there’s voiceovers in music. It’s like, tell me the hard thing. The hard thing about bootstrapping series wouldn’t be kind of rough. I mean in a good way, right? Hearing the story, we could anonymize voices even with AI now and I could do an interview. We are so far off track, you’ve completely derailed podcast, Laura, that’s a great call. Whatcha you doing? You’ve not only derailed the podcast, but you’ve made me volunteer for some crazy, crazy side quest questing. Alright, bringing us back my talk on everyone. Just forget everything that I just said. No one email or hit me up on Twitter asking me to record that. 

So my talk was from gimmick to growth, how to use AI and SaaS, and what it forced me to do honestly was to sit and think for hours and hours and hours and do research and write things out and then ask TinySeed founders. Once I had kind of a thesis, what I was trying to do was get my arms around what are all the ways that we can use AI in a SaaS company and then in a SaaS product. And I got close. I don’t think I nailed it because actually right after I had five and five ways to use AI in SaaS, in a SaaS company, which actually by the time this goes live, that might be live on the YouTube channel. I recorded like a 10, 12 minute YouTube video about that specific thing, but then how to use AI in your product and what AI can do as a SaaS founder. 

That’s the part that I really struggled with. And I came up with three use cases, generalized use cases, and then a fourth. And then when I surveyed TinySeed founders and said, give me all the examples of AI of how you’re using AI in SaaS. I was like, oh, my categories don’t fit. And so it made me rework it and I loved that It’s a little bit of a scientific process. It’s more qualitative than truly quantitative. I had about 20 different examples that I spread out across five uses of ai, but I in the end was pleased. I was happy with how the talk turned out. It was grueling to write. It was one of the harder talks I’ve written because I didn’t have, a lot of times I’m writing a talk, which is like, I already know what I want to say. I just need to get slides. 

This was like, I think I know what I want to say. Got the slides from the designer, I mapped it all out and then was like, Nope, this is wrong. I already have slides and half of these don’t even work. So then in a panic like four days before the event I posted in TinySeed Slack, you probably saw it. Advice needed, dear founders, please send me examples of what you do with AI to make sure I don’t have a talk that’s just completely wrong. And it was really helpful for shaping it, and I have so much more confidence in it now that it’s mostly right. I think the only thing I missed, or I missed it slash kind of left it left out on kind of purposes, MCP, which is making your SaaS available to LLMs, where they’re chatbots and such that they can hit you. It’s an API for blah, blah, blah. So I think if I give it again, I probably will give it again in MicroConf Portland, and I will probably add that sixth thing in and then make sure it’s dialed in. So overall, I think it was helpful. Was there anything, are you thinking about the use of AI in readable and did it spark any thoughts in your product mind?  

Laura Sprinkle:
Yeah, I mean I took a ton of notes also. I loved that all of my mastermind buddies from tiny C got shout outs in there.  

Rob Walling:
Oh yeah. Is that right? That’s great pictures. That’s just coincidence. But yeah, that’s fun.  

Laura Sprinkle:
I was like, yay. And I loved what you said about not just adding it to add it. You were like, is this truly going to be helpful for the user then do it? Because that is something I’ve been thinking about and I do think there are ways that it could be helpful for readable, but if I’m going to do it, I want to do it really, really well.  

Rob Walling:
And then our very own, Laura Sprinkle gave a Lightning Talk affiliate programs made ridiculously easy and I loved, it was a great overview and then you dove in to some pretty detailed elements. It was just very obvious that it’s not like you’re a dabbler in the affiliate space of like, Hey, I have some thoughts about being an affiliate. You’re just like, all right, how do I distill a decade of knowledge into 12 minutes and this whole thing is an exercise for the reader? Go do that on your own time. I thought the talk was great. I heard people mentioning it in conversations of like, oh yeah, I haven’t done enough with affiliates or I want to kind get into that. I’m curious how it felt to you to show up to give a talk on something you’re obviously an expert at.  

Laura Sprinkle:
Yeah, it felt great. Someone asked me what was the highlight of the experience, and I said my talk, but not from this place of like, oh, my talk was the best, but more just the experience of doing it felt so fun, and there was a moment getting on stage being like, oh, wait, I’m doing the talk and I’ve got 12 minutes. I better hurry up and get to it. But it was so fun and the fact that there were people there to talk to me afterwards, Michelle Hansen also mentioned doing a talk is this friend catcher because you talk about something you’re passionate about and then people find you. And I was like, that definitely happened.  

Rob Walling:
Yeah, that’s a real plus of being a speaker at an event, so thanks for doing that. I know it takes time to put it together and really appreciated you given the talk at the event. Thought it was really, really good. It was great. Our next talk was from Jesse Shoberg, another Lightning Talk, and this one got people talking ranking in chat, GPT and Google’s AI overview lessons learned from Tess on 2000 websites. Jesse is the founder of Drop in Blog. H one is the only blogging platform you’ll ever need, and so as a blogging platform, he sees what he sees. I see they have a whole rank and chat GPT plugin or some functionality built into that as a feature. And so what I really liked about his is there was theory and then there were super concrete examples and just screenshots calling things out. All of these talks will be available for purchase if you didn’t attend MicroConf, and I believe that we usually price ’em around $99 for the run of ’em. They’ll be available within a month or two after the event, and we sprinkle a few of them out on the YouTube channel. But make sure to check microsoft.com/events if you want to check it out, because a few of these really are meaty in terms of implementation, and I thought Jesse’s was just that with some really specific advice. What did you take away from his talk?  

Laura Sprinkle:
Yeah, I loved how specific it was. Everyone was like furiously screenshotting, taking notes, chatting about after, and felt like he just kept saying, this is something that you can do for all of your old content. So it wasn’t like, oh, I need to go create a whole new strategy or go reinvent the wheel. It’s like, how can I optimize what I have? And I loved that about his talk.  

Rob Walling:
Then we had attendee led workshops. This is a brand new, I’ll say it was experimental, but it’s been requested for years and years, probably 15 years of people saying, Hey, what about the attendees leading workshops? And in the early days, we didn’t have space or budget for breakout rooms. Now we do. So in the afternoon on the second day, well like a month or two prior, we let attendees volunteer to lead a workshop on a topic, and then folks signed up for their workshops. And it wasn’t just a talk, it was a small group where Brennan Dunn talked about personalization and gathering more data about folks on your website. That’s just one example, but I think there were six or seven of them. I’m super curious to hear the feedback on them in the survey that we sent at the end of the event, but I’m curious which one you attended and what your feedback is. Was it good or was it kind like, eh, that’s always my concern, right? With attendee created content, is it going to let people down because the MicroConf stamps on this, and if you go to a session that isn’t good, that’s kind of a bummer.  

Laura Sprinkle:
Yeah, so I actually did go to Brennan’s. I thought it was great. I think the one feedback, which I already gave as well was I think taking up the whole hour for one would’ve been great, so we could really dive in and actually workshop. He did a lot of talking. We had a great handout, but I’m like, all right, now I want to implement this for my business. Let’s do this here.  

Rob Walling:
Yeah, got it. Yeah, we had two 30 minute slots and you switched workshops. It was 30 minutes. So yeah, having it an hour. Ooh, that could be really interesting. Another session we did on that second day was an interview with the co-founder of Scraping Bee. Kevin Sahe, obviously a TinySeed founder, and Kevin’s co-founder Pierre appeared on this very podcast just a few months ago talking about being mostly bootstrapped to their eight figure cash exit. And so it was a q and a fireside chat where I interviewed him, and then we got some really insightful audience questions. So his session was called Bootstrap to Eight Figures, scraping Bees Journey. Any notable things that you remember or took away from the conversation with Kevin?  

Laura Sprinkle:
Yeah, I was talking with a few people after of how he was at 2 million before he hired anybody else, and we were all like, whoa, that’s wild. And also, I was interested to chat with him of what specifically he would’ve done differently, but I loved how he was just so blunt and honest about answering the questions you asked him.  

Rob Walling:
Yeah, he was prepared and he basically, yeah, they were at 2 million with two co-founders, zero employees, and I said, oh, our advice was like, don’t do that. We were telling them along, you need to hire. And they’re like, oh, we don’t want to. I said, what would you tell someone who’s doing that today? And he said, I would tell them not to do that. He’s like, it was a huge mistake. And I was like, I know you need to listen to us. It was really funny. I actually didn’t expect him to say that. I would not prompting him. I thought he might say, you know what? It was cool and we figured it out, and then we decided blah, blah, blah. But he was like, no, it was a big mistake. It was burning him out. And realistically, two co-founders at 2 million, if you’re thinking about selling at some point, there’s not much of business there without the co-founders. 

And so you’re saddled to it where you can’t step away. And it’s like then they really need you to stick around for two or three years to run the business instead of having a team that can do it. Rounding out the day. We had two more talks. We had one from Hana, she was a second time MicroConf speaker, former CEO of Thrive themes. Her talk was how solo founders and nimble teams can leverage AI to multiply their marketing efforts. I think it’s no accident that we had three talks that touched on ai. As much as I think I kind of start rolling my eyes when I hear a lot about it and other people are like, do I really want to hear more about ai? I felt like the talks though were practical. It was Jesse’s, it was mine, and then it was Hannah’s, and they all covered different elements. And I’m curious, what if you had any takeaways or want to add more summary of what she talked about?  

Laura Sprinkle:
Yeah, I thought it was great because I think a lot of folks in that room in particular think about AI in terms of product. So reminding them like, Hey, we also have to market our businesses was great. And then I loved her examples of using automations, so not just going to chat GBT of how do I do this thing, but really, okay, you can input some stuff. And then each, wow, I’m so not technical as you can tell, but each agent is going to do a different thing for you. And I’m like, oh, that was a good reminder for me that I need to set those up.  

Rob Walling:
Our last talk of MicroConf Fear of 2025 was from James Mooring, the co-founder of Asty who appeared on this show maybe eight or nine months ago. And his talk was momentum over mayhem, what bootstrapping to 2 million A RR really looks like. And he talked about how they’re now at about two and a half million, and they have a pretty SELT team, and they’ve gotten there actually quite quickly in terms of when he’s always like, it’s kind of a CRM for the NDIS, which is the Australian, it’s a scheme and whatever. He describes it. I’m like, I totally get that and I’m going to forget what that is in 12 seconds. But the fact, if you were to tell me I’m going to build a SaaS like that, I’d be like, great. That’s going to be a great little tiny business and it’s going to grow slowly. And he’s like, no. I mean, they’ve gotten there in a handful of years. I loved, I mean, it’s a classic MicroConf talk of a founder story of how they got there, what they did, the ups and downs, and then key takeaways, what I learned from this, and maybe some advice that I can give you the audience as to how you can do it better, easier, not make the same mistakes that I did. Anything you took away from James’s talk.  

Laura Sprinkle:
So I had sat next to him just accidentally at a table the day before, and it was one of those, oh, I would have no idea that you are this multi seven figure a RR business because you’re so down to earth and so generous with your time. Apparently I have this bad view of people with a lot of money, but no, geez, seriously, he was just so kind and helpful, and that translated so well into his talk. And also, I loved how he talked about doing the not scalable thing and just really showing up and creating a great product and being helpful to your customers and how that’s helped them grow.  

Rob Walling:
Yeah, so thanks to all the MicroComp speakers for taking time out of their busy schedules. It’s a lot of founders who are flying halfway across the world to basically give talks to give back to the community. Yourself included, and thanks for taking the time to join me here on this recap episode. If folks want to keep up with you on the internet, of course they can check out reputable.com, R-O-O-T-A-B l.com. It is the best affiliate management software on the internet. Laura Sprinkle, thanks again for joining me on the show.  

Laura Sprinkle:
Thanks so much for having me. This was awesome.  

Rob Walling:
Thanks again to Laura for joining me on the show, and thanks to you for listening to this and every episode of Startups For the Rest Of Us, as I mentioned at the top, if this event sounds incredible, it was, you should try to make our Portland, Oregon event in April of 2026 work for you. Head to microcomp.com/us and use promo code Rob 50 for $50 off. Thanks for listening this week and every week. This is Rob Walling signing off from episode 803.  

 

Rob Walling:
They say life’s like a box of chocolates. You never know what you’re going to get except every Tuesday morning you’re going to get another episode of Startups. For the Rest Of Us, which is what you’re listening to right now, I’m going to be diving into listener questions today, covering topics ranging from marketing that’s not scaling, having a product and then trying to figure out how to best find product-market fit, best places to publish content, and if I should start a media business to get eyeballs before building my SaaS. Before we dive into those delicious listener questions, I want to let you know about MicroConf Remote. It’s on November 5th and as the name indicates, it is a fully remote event that you can join from anywhere in the world. We’re actually switching up the theme this time around and the talks are going to be around shipping and validating fast and landing. 

Your first customers speakers include Sunny Hunt and several others. We have yet to announce. I of course will be there. MCing doing magic tricks, telling bad jokes. The recordings from the event will be available for ticket holders and when you show up live, you can ask questions from the speakers and after the talks we’ll have our Founder by Founder session, which is like the digital version of our hallway track to get all the details and snag your ticket. They’re really inexpensive. You really should grab one in case you want to watch the videos, microcomp.com/remote promo code startups 15 for $15 off. Let’s dive into our first listener question from longtime listener, MicroConf attendee and speaker and many time question asker. James Kennedy.  

Speaker 2:
Hey Sherry and Rob, I just finished Exit Strategy. Really worthwhile read, even if you’ve read all the books about exiting at a fresh take, and I’m glad I read it, recommend it. I have a follow on question which is, have you ever heard of people doing a management buyout, so that means their team actually buying the company because I’m honest, the one thing I got from the book was, wow, this exit stuff is way more stressful than I thought it was going to be. If it ever happened or whatever, I thought it’d been a much nicer actually to be able to sell my company to my team one day when I want to go and do something else. Maybe you have, maybe you haven’t, but either way, awesome book. Highly recommend it.  

Rob Walling:
Congratulations. Thanks for the compliments on the book, James. Sharon and I are really proud of this one and I think it’s going to help a lot of people out as they exit. I like your question around management buyouts, so my answer is I have heard of approximately zero startup founders doing that. It of course exists. We do talk about it a little bit, but I don’t blame you for missing it. I think we have half a page on it where we talk about who buys companies and we go in order from top to bottom in terms of who we see usually paying the most, and so strategic buyers are at the top, private equity and then search funds. Then high net worth individuals, then your co-founders, and at the very bottom we have your network, your customers or your employees, and that would of course include a management buyout. 

These are much more common with traditional, I’d say brick and mortars and manufacturing. There’s certain segments where this makes sense where you either have a lot of employees in the business is extremely stable and they can get a loan or some type of seller financing makes sense and the multiples aren’t huge and it’s based on ebitda, right? It’s based on net profit per year, and so if you sell for whatever the multiple is, three years, four years, five years, if you keep running the business, well you’re going to make that money back, be able to pay back the seller financing or the loan. The challenge I think with SaaS is since the multiples are high, and if you’re doing 2 million or more per year and you’re growing, you’re going to get a revenue multiple most likely. And so yeah, let’s say you take a 2 million a r, a SaaS company that’s making almost, that’s basically break even, but growing quickly and you sell it for 10, 12, 14 million manage and buying that out would be tough. 

Now, on the flip side, I have heard of one founder who has sold a small software product that I believe let’s say was doing half a million a RR and it was stable but flat and the team is super small and one of the employees, one of the team members wanted to buy it, and so they did just kind of work out a deal for a super low multiple and the founder was happy because he was able to kind of pass it along to someone who really wanted to grow it and the team member was happy because they wanted to be an entrepreneur, but obviously it’s hard with a day job to do at nights and weekends. So I have seen it done and I think it works especially well if you don’t have other options to sell for higher multiples. If you’re growing quickly and you can get these really accelerated aggressive SaaS multiples, management buyout just isn’t, it’s not going to compare to that. 

But if you are mostly flat declining, maybe growing just a little bit and you think, well, maybe I’d only get a one to two XARR multiple, let’s say you’re doing a million dollars and you think you might be able to get 2 million or you get an appraisal or you get an offer for 2 million and you are a profitable company. Let’s say you’re making half a million a year including your salary and whatever else you take out of the business in terms of covering expenses, what’s only a four x EBITDA multiple? Is that something where they could, they being your management team could each put, let’s say again loose math here, but let’s say you have four managers on your executive team and they each put a hundred thousand dollars down, so you walk away with 400 grand or they each put 200 grand down, so you walk away with 800 grand and then they just pay the rest off over. 

You give ’em a bunch of seller’s note and they pay the rest off over three years or four years or whatever it takes. It might work. I think it’s a creative approach, it’s just not something that I’ve traditionally seen in our space because our space does have those frothy multiples and I think a lot of people, well, a lot of people kind of want to walk away and not a lot of founders want to walk away and not be kind of saddled to the business, but I love creative approaches like this, especially if, as I said, you’re not going to get that aggressive multiple anyways if you’re going to get a low purchase price and you can hand it off to someone you trust, maybe you are willing to extend the time that it would take for you to get the full purchase price. I appreciate your questions as always, James, thanks for writing in. 

Our next question comes from Ali on Twitter. Ali’s the co-founder of Seja and his username is, hello, it’s Ali. By the time this goes live, I think I might be in Istanbul, probably high fiving Ali over a welcome reception, but Ali posted a tweet, gosh, this was five months ago that it gives you an idea of the backlog of questions and at mentioned me and said, really curious if you have any thoughts. Now, I’m guessing the situation has changed since then, but I still think it’s interesting. So Ali said, Seja just hit $65,000 of MRR, but I’ve hit my limit. We have a bunch of marketing channels that work, but we can’t scale any of them. And then he runs through paid powered by link, SEO, lead magnets affiliates and kind of how they’re not scaling. Plus 45% of signups are unattributed in post hog. 

I switched between relentlessly working on one channel to working on all of them to focusing on product. To be honest, I don’t know what is driving branded search. I don’t know if I should keep pushing when it seems to have little impact or just accept things as they are. We have consistent growth and add about $4,000 of MRR net each month, but we’ll plateau when our 4% churn represents more customers than we can acquire in the same period. I lost in feeling overwhelmed. Anyone have thoughts? I really like this question because there’s a lot of detail and there’s obviously no silver bullet obvious right answer that we can just, oh, we’ll do this and this will totally work. I do like that Ollie gives all the numbers and that he says 45% of senates are unattributed in post hog, so you don’t actually know where folks are coming from, so do you stop doing something? 

That’s where it gets tough, right? I did check out Ollie’s profile and I dunno if it’s up to date, but it says Sanja just hit 75,000 MRR, so we do know that they’ve grown 10 K in the last five months. So I have a couple thoughts here of how I would think about this. So a couple things. There’s is several leverage to pull. One is you have 45%, almost half are unattributed in postdoc. If you don’t have it already, I would definitely have a popup, right? When someone signs up, how did you hear about us and try to do my best to attribute rest of those. You’re never going to get to a hundred percent, but if you’re at 55% now you can get to 75 or 80%. You just have a little bit more data. I mean, geez, that’s 50% more data to make decisions with. 

Second thing I would look at 4% churn is okay, but I’m wondering how much time you’ve spent working on that. Have you hired anyone to come in and help you improve that at this point? Either product things or tactics that you can use. There’s a bunch of churn reduction tactics you can check out churn key. It’s for example, it’s a TinySeed company. If you get that down to three or two and a half really changes the equation. So those are the obvious levers that I see right up front. And the other one of course is well drive more leads and Ollie talks about not being able to increase any of these channels, and this is the interesting thing when people say, oh, my churn is low, it’s only 5%, 5% is high and 4% is okay, and the reason is exactly this is at a certain point you can’t outrun churn. 

That’s that high you’re going to tap out, and when I say this, I’ve said this on the podcast and on YouTube and especially on YouTube, I get comments like, yeah, he said, you’ll with 4% churn, you’ll tap out at a hundred thousand dollars a month and I would kill for a hundred thousand dollars a month business. I don’t care about the 4% churn. And it’s like, that’s fine. If you’ve never started a company and that is your goal and you’re willing to do that, it’s fine, but once you get there, if your market is a 4% churn market, it is very, very, very hard to outrun that and you do then have a flat business doing a hundred thousand dollars a month, great, you didn’t have that several years ago, but you also put in years and years of work to get there. And so it’s a thing of this is why when we talk about it, I got in a conversation in the last month on X Twitter and I said, eight to 10% churn is catastrophic business on fire. 

And someone weighed in and said, well, no, that’s like an old way of looking at it. And it’s like, no, that’s not. There are spaces that are eight to 10% churn and it’s consumers prosumers, indie hackers, hobbyists and other folks who think like consumers and those are not great SaaS businesses. They can be okay SaaS businesses, but they will plateau. Those are step one and step two businesses. If your churn is that high, if you want to get to a step three business and you want to be an ambitious SaaS founder and build a healthy, fast-growing seven or eight figure company, you cannot have churn that high. And I want to circle back to Ali, 4% churn is not catastrophic, but between four and 3% it would change the economics of this business pretty substantially and getting it down to two and a half. Similarly, and I’m not saying that’s easy, but I would definitely think about how to do that or if there are ways that I could approach that. 

Lastly, and you’ll notice I’m getting to just adding more leads as kind of the last thing. Ollie already has eight channels going, or I guess one of them is engineering is marketing and he says, don’t have the resource. And social selling and listening is low. ROI, which I would definitely agree and social and build in public is not scaling, which yeah, that’s not a surprise at all. You have an audience, you build the SaaS and if you buy and most churn and then that’s it, your audience, unless you dramatically grow your audience every month, that’s not going to. So it really is concentrated in five areas. It’s paid, powered by link, SEO, lead magnets and affiliates. And I think what I would do is probably ask my, because this is a good list, I mean I don’t want to suggest we start adding more. I would think about if you have not already brought in a consultant, an outside hand that you can pay, for example with your paid acquisition, Ali says, increasing spend causes CAC to skyrocket. 

I wonder, have you had a consultant or to look at that? Because man, if you can get paid to work just a little better, that would be a big one. What I would do is I’d look at this list and figure out which am I most interested in, which do I think has the most potential if I can get them to work? And when I look at this, I think paid is super interesting. SEO is super interesting. All he said can’t find a trusted partner. Signups are from branded terms. Cool. I would find a trusted partner. I know that’s easier said than done, but ask at MicroConf, try to find someone who can refer you to a trusted partner. It would be a big goal of mine to get one or both of those working better. Now, affiliates, I’m curious about this. Three affiliates send 99% of referrals. 

Great. So have you talked to those three affiliates about whether they would like to co-promote with a webinar? When was the last time they sent a dedicated email to their list or did a dedicated social post and then get ’em in A CRM and by that I mean boomerang or snooze an email and every six months reach out to them and ask, Hey, how can we collaborate to get more promotion? Next thing is how do I find more affiliates just like them? People with audiences maybe of their size, similar size with similar demographics or whatever. Affiliate marketing is enterprise sales. It’s finding affiliates who are willing to promote it. It’s not actually affiliate marketing, it’s finding affiliates who have big audiences that are willing to promote your product. And that’s not actually that easy to do if you’re outreaching cold. And this is why I say if you’re going to build SaaS, build your network, not your audience. 

If you have an amazing network, you can usually find influential affiliates who will be able to help with this. So those are my top line thoughts. I mean, the next thought of course is go down the SaaS playbook and figure out are there any other marketing approaches you want to spin up? But man, you have a lot going on already, and I know Ali doesn’t have a large team. They are bootstrapped, so I don’t like that suggestion. I think what you have here can be optimized before you need to start over from scratch basically with a new approach. So Ali, sorry I didn’t respond on X Twitter, you can tell that I had seven or eight minutes of thoughts on it and I didn’t want to try to fit that into a tweet. Might be too little too late because it’s been months. But I hope my thoughts were helpful and thanks for mentioning me as always. 

Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today’s sponsor Design Lee. They specialize in helping founders like you who are stuck with messy code, unclear roadmaps, or a dev team that just doesn’t get it. And for listeners of the pod design, Lee is offering their Impact week completely free. That’s a one week no obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next. If it’s a fit, you can move on to Solution Lab, a three week sprint where design lead takes over your code base and architects of real roadmap for growth led by a full-time cross-functional team. This isn’t just another dev shop cranking out features. Every sprint is tied to measurable business outcomes so you can scale with confidence and enjoy the process. If your tech is the bottleneck to your next stage of growth, check them out@designlead.co slash For the Rest Of Us, that’s D-E-S-I-G-N-L i.co/ For the Rest Of Us. My next question is about validation and product-market fit. If you already have a product comes to us from Russ.  

Speaker 3:
Good day. Rob Russ here from New Zealand only been listening a couple of weeks. Feels real good to be amongst other bootstrappers. My question is around the age old handed down philosophy of not building first and instead validating first, which I totally get, but I find I’m getting a bit annoyed with this statement, much like anything that appears to portray life as being black and white as it doesn’t adequately cover gray areas like my own. Recently I had been working on a side project while employed as a developer at my last company and it solved a real problem that myself and my now co-founder had seen many, many times in our careers and the intention was to deploy it within that company. But then last October I got laid off, I had a chat to my wife and given that she’d known I’d always wanted to follow my IT entrepreneur father and that we had savings to do so, we made the switch to me working full-time on the product, which as an MVP is fairly polished. We’ve been working since our marketing efforts and while trying hard me to stay off the tools. So my question is a little nebulous. Have you seen others in a similar position where they already had a product for whatever reason and like myself who may have had firsthand experience with the vertical in which their ICP worked? What advice did or would you give them with respect to marketing with the aim of discovering product-market fit? Thanks H Rob.  

Rob Walling:
Here’s the thing about validation. It’s an ongoing process. It’s not something you do upfront and get an absolute answer and then stop with the 2 2200 framework. I talk about spending two hours with research hours with landing page conversations and then 200 hours trying to get an MVP out or get something into the hands of people to see if they actually use it, if it actually solves their problems, they’re willing to pay for it, all that stuff. That’s a simplified framework. More than that. Every day you’re still validating every day, even when you’re live and you have customers using it, you’re trying to have conversations and you are trying to gauge interest and figure out you’re validating assumptions at that point. Which features should we build next? How should we update our marketing, our positioning, our ideal customer profile? There’s all this stuff that is constantly in fluxing. 

I mean, I remember being at 50,000 MRR growing five grand a month and still validating a bunch of assumptions we were trying to figure out. So I mean validation is obviously not a binary, it’s a spectrum and it’s really an ongoing thing. So the biggest thing I’d be doing is having conversations. I think if you have seen this problem come up over and over so you have verified it is a problem, that’s great. Just finding a problem can be hard. The next question I have is your solution something that actually solves the problem in a way that makes it worthwhile for your customers? This is called searching for problem, a solution fit. Have you built a solution to a problem that actually works and that people will use because you can build a piece of software to solve the problem of I want to add two numbers together. 

And you could be like, that’s a problem people have. They’re searching for it in Google, so I’m going to build calculate that addition.com. Boy don’t register that. And people are going to log in, they’re going to create an account. I’m going to ask ’em a few questions and then they’re going to type in numbers and I’m going to solve the problem. This is a contrived example, but you get what I’m saying that is not worth it because people can just go to, it’s easier to just go to Excel, go to a calculator, go to a Google sheet, do it in their head, your solution is not going to work. And so again, while that was an overly simplistic example, you get the idea of you can technically solve a problem but not do it in a way that your customers will use because it’s still more cumbersome or it’s more confusing or they don’t want to learn it or they don’t want to switch the way they do it, or they’ve always done it on paper and they don’t want to move to whatever tool you have. 

There’s all these objections. And so in this case, it kind of depends on your space, the vertical that you’re going into, but I would be having conversations showing people screenshots, getting people to try the app, does this look interesting? Does this solve a problem? Then the next question is, will they pay for it and will they pay enough to make it worth your while? Because you can build amazing software that solves a very hard problem and if a business is willing to pay $50 for it, but for you to find customers and support them and support the software, it’s a hundred dollars a month to make that happen. Obviously the unit economics don’t work and usually a huge cost of unit economics is the cost to acquire a customer because marketing sales are hard and they’re really expensive. So that’s probably, these are in order. 

The next things I would be trying to figure out, it’s not just the problem exists that people are solving it today using something. Usually it’s Excel or clipboards. Those are the most common things. I say Google sheets, Excel, some type of spreadsheet and clipboards. And so then you’re trying to figure out does mine solve it better or in a way that people will switch from a free tool and will switch away from the way they’ve been doing it for 30 years. And then you start asking that question, can I find more of them? And so one way to answer the question I can’t find more of ’em is just to start doing outreach right now. And you can do it on LinkedIn, you can do it on any of your socials, but you can do direct cold outreach, you can scrape lists or buy lists or whatever, and you do this cold DMing and cold emailing. 

And of course if you have a network in the space, you do it warm as well, like, Hey, we’ve solved this problem. And you can tell them, I have nothing to sell you right now, but I would like your opinion. Would you be willing to jump on a call and chat about this? Or would you be willing to exchange back and forth via email or send me a loom depending on how sophisticated the customer is? So that’s how I would be thinking about the next steps, the what’s next. Now, if the phrase validation bothers you, then don’t use it. You just talk about what are next steps? What are the riskiest parts of this business right now? That’s the question you should ask yourself every day when you wake up because the riskiest part is not that you can answer a support email. It’s not that you can write another line of code or build another feature. 

I don’t think any of us are doing incredibly technically challenging development of stuff of can this be built? That’s usually not the question. The risk is part of the business is usually, does this solve a problem that anyone cares about? Will they be willing to pay for it? Can I find more customers like the ones that I have in mind or that are already using it at a cost that makes this a viable business? And of course, in terms of finding product-market fit, which was part of Russ’s question, I have an entire chapter on that in my book, the SaaS Playbook. It is the market chapter, and it’s a tight 19 pages. It’s the first chapter. Get into SaaS playbook.com if you’d like to buy that book for $10. Of course it’s available on Amazon and Audible where you can of course hear the sweet Dulcet tones of this voice puts you to sleep by telling you about SaaS G codes like net negative churn. So thanks for that question, Russ. I hope it was helpful. My next question is about content marketing.  

Speaker 4:
Hey Rob. I’m starting a SaaS app. It’s still pre-launch at the point where I am looking to do some pre-launch content, a little bit of writing. I would also love the chance to continue writing after launch and build a bit of a following because at this point, I have none. I know that the best place to do this kind of thing used to be medium, but I think that people have changed their minds on that. The option for starting a standalone blog is there, but the maintenance kind of scares me. And also the risk of calling myself a blogger scares me for some reason. It’s just, it feels easier and more approachable for me to post on an existing platform. Are you aware of anything else other than medium these days where people can write about bootstrapping and it’s a good place to be? I’d love to hear your thoughts on it. Thank you very much.  

Rob Walling:
Yeah, this is a good question. And I will admit we tried Medium back in 2014 or 15, and I hate building on other people’s platforms because all platforms eventually turn to is really what happens, right? There’s this whole Cory doctor who talks about the ification process. You can Google it if you haven’t seen that. But basically every platform starts for the users and then they pivot to be for the advertisers, and then eventually they pivot to be, it is not a pivot, but they adjust their algorithm or whatever else to be for the company and the company’s bottom line. And that process means that wherever you build, and we’ve seen this over and over and over with social media, I mean, every social media platform ever eventually just screws, its users and screws, its advertisers, so to speak, in terms of just really making advertising expensive and harder to reach and all that. 

So with all that said, I never would’ve built a presence on Medium or Quora or other platforms like that. I think of them as a hub and a spoke. So my hub has always been my domain, Rob Walling dot com, and you can go to Rob Walling dot com slash blog I believe, or you can just go there and see my essays link in the top. And if I were to post on Quora or Reddit or Medium or anywhere else, it would either be a summary or a short think piece that basically references my hub. And if you want to read the full piece, you have to come to my website. And of course, these places all resist that. And Twitter these days, it makes posts or tweets with links less what? Less viral. These are all anti-US Pro platform moves. And so yeah, I would do it on my own website is what I would do. 

And then you learn how to promote it, how to submit it to Hacker News, how to figure out how to get it on Reddit, how to mention it on cor, if that’s still worth doing. There’s a bunch of playbooks of how to get your content out there on social media, and I would want to own the domain authority and I would want to own the link, any link juice that comes from those pieces. And the trade-off is you don’t get that instant distribution, right? If you go to Medium and you hit the algorithm or your posting on Reddit and you hit the algorithm, ooh, you get this big boost, the challenge is those customers are not yours. Those readers are really not yours and they don’t stick around in any form or fashion compared to say, having their email address and posting on Medium, it’s going to be really tough to do that. 

The only thing I might consider is I have heard that it, I don’t use it, but I’ve heard that it is a way to have an email. I like email, email even today. It just outperforms everything else, social media and all the other stuff in terms of reach and engagement. And so substack is something I might consider, but for me, if I was going to start writing about a topic, I would want to own that domain and own the SEO around it. So thanks to that question, I hope it was helpful. And my last question of the day comes from X Twitter. So I posted back in June of 24 that I was recording an episode of the show looking for some questions or Azule said, my hypothesis is that if I focus on building a media business and get enough eyeballs, then the right monetization channels will appear. 

And so I should focus mainly on valuable content creation. Is this a legitimate hypothesis or should I also explore monetization more actively? And so I have a couple different answers to this. One is, if you’re building a SaaS, just don’t do this. Don’t build a media company. If you’re building a SaaS, unless you’re HubSpot or Zapier or one of these massive, massive, when you’re doing nine figures of a RR or you’ve raised nine figures of funding, go ahead and build a media business until then. Don’t. And I think it was an entire episode, or at least a segment on a solo episode called Don’t Build a Media Company. You can go find that in the archives. If you are talking about building an info product course and kind of creator maker business, then yeah, I wouldn’t call it a media business, but basically you want to get eyeballs, you want to build an audience. 

And if I was thinking about that, I would think up ahead at least have ideas of how I was going to monetize that because the right monetization channels just appearing almost never happens. I really want to say never happens. I think it never happens, but basically it’s going to be like, oh, I’ll put ads on it. And if you’ve never done ads, you don’t realize how low the ad rates are and how even with an audience like me slash MicroComp TinySeed, my whole ecosystem, if we tried to monetize this with ads, we wouldn’t even be able to afford my house payment. That’s how much money it would bring in a trivial, trivial amount of money. And we have pretty significant reach built over 15 years, significant reach for our niche, not significant compared to Joe Rogan or Tim Ferriss. But the thought that a monetization channel will appear is no, I would not do that. 

I do like the idea. Again, this is info products and courses, not SaaS, that if you want to create valuable content, then do that and think about Hub and Spoke. And your hub is going to be some website use set up where you get people back there, you want to get ’em on your email list, and that’s where you start pitching and selling them on stuff. And that first thing might be a $10 ebook, and then you can do a 50 or a hundred dollars video course. And there’s a playbook for doing all of that I won’t go into on this program. And then you map out, well, what are my media channels? What are my spokes? And it depends on what you’re good at, depends on what you want to learn. Do you want to do YouTube, LinkedIn? There’s all the social medias, there’s TikTok. 

Depends on the topic. There’s a whole thought process I would go through to think about how I would do that. You can’t do them all. Well, this is the myth is people will say, well, you know what I’m going to do? I’m going to record a video, a 10 minute video on a topic, then I’m going to cut it up into shorts. I’m going to put those shorts on TikTok and on YouTube, and I’ll put the 10 minute video on YouTube, and then I’m going to have chat GPT, summarize it, put it into a LinkedIn post and a tweet thread. And I don’t take a still and put it on Instagram. You can do video on Instagram. So I do 90 seconds on Instagram and I’ll break it up. That won’t work. It doesn’t work that way. Anytime you repurpose a single piece of content into a bunch of pieces, most of them do not work. 

We have tried this over and over and over in different iterations. And what I have found in my 15, well, I’ve been blogging since oh five, so in my 20 years of content creation, but realistically, let’s say 15 years of podcasting and a little slightly less of that on YouTube obviously, is that native content that is focused on exactly hitting that channel’s algorithm and that channels users and what they expect. That’s what it’s going to require. So you’re not going to do seven channels at once. You’re going to pick a couple, and you’re going to get really knowledgeable and really good at them. And you are going to do, I mean, I like the jab, jab, right hook framework from Gary V. You’re going to do content, content, and then you’re going to ask for sale or ask to get on the email list, and you’re going to just rinse and repeat. 

So in conclusion, I do not like the idea of getting enough eyeballs and then having the right monetization channel up here or finding it. I think you should go in with at least a hypothesis of, I’m going to monetize it this way and look at other people who have done this or who are doing this because you are not inventing the wheel here. There are, I guarantee you, there are folks who have done what you’re thinking of doing, and maybe they’re in the development niche or the AI niche or the entrepreneur founder niche or the designer niche, or just pick one and see, oh, what have they done? What has worked? And you might want to reach out to ’em and ask them questions or find out if they’ve been on a podcast and talked about what has worked and what hasn’t. And again, that is for courses, info products. 

If you want to build an audience-based business, if you want to build SaaS, do not do this. Please ignore my advice at your peril. That’s all we have for today. Thank you so much again for joining me here in this episode of Startups For the Rest Of Us, it’s great to have you. As always. If we are not connected on X Twitter, I’m at Rob Walling. Please hit me up there and if you were at MicroConf in Istanbul, I hope you had a great time and I hope you came up and said hi. This is Rob Walling signing off from episode 802.