Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions

Rob Walling:
Welcome back to Startups For, the Rest, Of Us. As always, I’m your host, Rob Walling. In this episode, I’m going to be answering later stage questions. I received a ton of good questions on X Twitter a month or so ago when I did a call for them, and I had gotten a little weary of answering the same questions about idea validation and early stage stuff. So these are all folks doing six or seven figures in a RR that have questions ranging from regrets for things you didn’t delegate how to decide to DIY, versus hiring a growth agency, deciding whether a customer type is worth selling to or targeting. And more. Before we dive into the episode, my new course, the SaaS Launchpad, has been live for a few weeks. It has been receiving rave reviews, SaaS launchpad.co. If you want to check it out, it’s for the earliest stage SaaS founders. 

So if you’re looking for an idea, if you want to vet an idea to validate it, if you want to build a launch list, if you want to build an MVP launch your product, this is the course for you. It is the best course I’ve ever put together and it’s really the first course I’ve built in about 14 years. So you can head to SaaS launchpad.co for full details and to check out the course. And one more thing, MicroConf us 2025 tickets have just gone on sale. Every event we’ve run for the past 18 months, I believe maybe more, has sold out and I expect MicroConf US 2025 to be no different. It’s going to take place in New Orleans, March 16th through the 18th of 2025, and right now our lowest priced tickets are available on sale. They will never be lower priced than they are now. We’ve just wrapped up our Dubrovnik event that one sold out, and again, I expect this New Orleans event to sell out. All the details are at microcomp.com/us. Be sure to check it out soon if you’re interested in joining me. And two, 250 of your best founder friends that you’ve known on Twitter that you’ve met in person that you’ve aspired to meet in New Orleans next March. 

My first question for today comes from Tobe. He is Tobe builds on X Twitter. His question is, is there anything you regret doing yourself instead of delegating while trying to grow to 10 KMRR? And I’ll do you one better. I won’t just talk about things I regret, but the most common mistakes I see early stage founders making, and these are founders who listen to startups, For, the Rest, Of, Us, these are TinySeed founders, these are MicroComp founders, and there are some pretty common anti-patterns in this early stage of learning how and when to delegate. Now, delegating is a balance, especially in this early stage if you’re bootstrapping, because oftentimes you should delegate or outsource a bunch of things, but you don’t have the money, right? You don’t have the luxury of a funded competitor who can hire a chief of staff on day one or who can hire a staff to do things that you don’t want to do. 

So there is this balance between your willingness to delegate and the budget you have to do so. But with that said, I think a couple things that I commonly see founders keep doing that they shouldn’t be doing in these early stages are things like bookkeeping or doing your own books in general, doing your own accounting, not hiring a CPA DIYing your own legal. This is one that I did a couple times. I never knock on wood, wound up regretting it, but certainly things that I could easily ever regretted. It had those gone sideways when I downloaded a template for a contract and edited it myself. I think founders who are doing audio video editing in the early days are doing themselves quite a disservice. Audio and video editing are so fulfilling. I dunno if you’ve done it, but it just feels like you’re getting stuff done. 

You’re doing something with your hands and when you ship it, it’s a better end product. It feels really good to do, but it is a tremendous waste of time because audio and video editors even really good ones are what, 15 to $30 an hour? I mean, obviously more expensive and less expensive, but this is an easy one to outsource. Another one that I see founders doing and kind of making a reason for it is continuing to handle their email and live chat support. Now this one depends because if you’re doing high touch sales with a high ticket product and you’re only doing a few sales now and again, then you probably don’t need a support person. But if you do have a wider funnel, lower touch funnel where you have a lot of volume coming through, email support and live chat support if you offer it are some of the first things that I look to outsource. 

Now, the reason I hear a lot of founders keep doing it for way too long as well, it’s only 30 minutes a day and I want to be in communication with my customers. This is the way I keep in touch and get their feedback and hear what should develop in the product. Now, both of those are kind of reasonable. However, I will say that with pretty much every product I’ve launched, I have hired part-time support help. Sometimes that part-time support help would swing across multiple products I owned. Sometimes I would just overpay them for the hours they were working to say, look, you get a minimum of 10 hours a week. I know I don’t have 10 hours of support yet, but I’m going to bring you in and you can write KB docs or you can help with onboarding or there’s a ton of other stuff that I can find depending on your skillset I can find for you to do to kind of fill that time. 

So even if you don’t have a ton of support or it’s sporadic, I’ve always figured out a way around that. So I just don’t believe it as an excuse because it’s never one that I’ve used and I’ve always outsourced support within a few months of taking over or launching an application. The other thing about not being in touch with your customers is that I tend to be known for being in really close contact with my customers. Whether I was running SaaS companies or now MicroConf, TinySeed writing books, I talk with people a lot and putting a support person between me and all the end users did nothing to curb that. It did nothing to dissuade me from talking to and hearing from my customers because my support guy, Andy would say anytime there was new feedback, new input, anything he thought was novel or that I should know, he would either cc me on it or he’d just sign it to me. 

Once it was resolved, any of the rote tasks or the rote responses that he could just hammer out, he would get back to ’em. He would close. I didn’t need to see over and over that someone wanted to reset their password or someone had a question about pricing. Now, if those questions came in a lot, Andy would then say, Hey, a lot of people having questions about pricing, can we clarify this on this page? So there is a key factor here of hiring someone in that support role who is good and is willing to escalate things to you or at least pass things along that they think are notable. Another thing that I regretted, I remember regretting this in the days of Drip was continuing to handle social media for my products. It’s not that I should have hired it out, I just don’t think I should have done any of it. 

I really don’t. Social media did so little for us as a SaaS tool. We were not Intercom and HubSpot and Salesforce. We were a tiny bootstrapped product that was growing and social media was nothing but a headache if you want to know the truth. And if it drove five customers in the entire history of the company, I’d be shocked. And so what I would do these days, I would just get off social media. I wouldn’t try to hire someone for it. I wouldn’t use it as a marketing approach. For now, I would focus on blocking and tackling on SEO, on content, on sales, on real inbound marketing, on integration marketing, on attending live events, on going on podcasts, on talking to my customers. There’s so many other things that I would be doing to not waste time because social media is a distraction that masquerades itself as productivity, and people justify it by saying, well, I’m working well, I’m marketing. 

No, you’re not. You’re not marketing. You’re getting on social media and you’re frankly feeding an addiction that these apps are really good at feeding and they have entire teams engineered to make us feel this way to make us feel productive when it’s actually a distraction. So if I were just starting out today, I would focus on marketing and sales, and I would ignore social media altogether until such a point that it became important. And frankly, there are TinySeed companies doing millions of dollars a year that still have almost no social media presence. So it is not only possible to get there. I would say it is easier to get there if you’re not focused on that distraction. And lastly, the thing that you’re going to have to weigh as a bootstrap founder is the next sentence I’m going to say, which is, I know some devs and I was in this spot where I regretted continuing to write all the code. 

Now, some devs bootstrapped because they want to write all the code, realize that will probably hamper your growth. But if you’re okay with that, that’s why you’ve bootstrapped. So you can be in charge of this and you can dictate the limits or the constraints that you’re willing to put into your business. But I believe that code is usually a certainty. Code is something you can hire someone to do because that next feature does not have any risk versus marketing. And sales usually have a ton of the risk as well as product like deciding what to build, how to take feedback in, how to find product-market fit, all those things are very risky. Those are things that founders should be focused on. I do know some developer founders who continue to write code well into the millions of a RR and even tens of millions for that matter. 

But usually, inevitably they do step away from it because they realize at a certain point it’s just not the best use of their time, even though they love doing it. And to cap this off, Tobe didn’t ask this question, but things that I never regretted doing or spending time on and I never regretted keeping under my purview and not outsourcing, we’re talking to customers constantly. We’re designing the product, and I don’t mean visual design, but deciding what to build, how it was going to operate, how are we going to architect this? What’s the API going to be like the real nitty gritty decisions around building the product. And the third is marketing and sales. I don’t know of a seven or eight figure TinySeed founder that has outsourced or delegated their marketing and sales before they hit a few million in a r. Now, a lot of folks may hire ahead of growth or ahead of marketing, but it’s to take over an effort that’s already in play. 

You’ve heard me talk a lot on this podcast about zero to one and how hard that is as a marketer or as a salesperson and as the founder, I’m a staunch believer that you need to keep that under your own purview until you’ve proven it out and you’ve built it into a process that can be handed off to someone else. So thanks for that question Tobe. I hope it was helpful. My next question is from Miguel Sarena. And Miguel asks, how do you decide to do it yourself versus hire a growth agency to do paid ads, SEO partnerships, et cetera? So this actually piggybacks really well on the last point that I was making is that in general, there are a few roles in a SaaS marketing department, right? There’s marketing strategy, which is deciding, I dunno, what do we try next? What do we do next? 

Where do we put our efforts? So it’s very strategic thinking. High level. There is marketing implementation, which is where you’re an individual contributor and you are clicking the buttons in the Google AdWords console. You are writing the articles or editing the articles and building links and doing that work of SEO or in terms of partnerships, you are going out and building the relationships yourself and getting all that done. So those are individual contributor roles or folks who are actually boots on the ground. And then the third role really is project management, which is kind of making sure everything gets done and there’s more nuance than this, but fundamentally, that’s how I think about a SaaS marketing department, especially in the early stage. So the question of how do you decide to DIY versus hire a growth agency is that as the founder, I would not try to outsource marketing strategy and frankly, project management, maybe I would hire somebody to do it, but realistically, marketing strategy, deciding what to do in what order, how many resources to put behind it, that’s something that me as the founder, I would want to learn how to do. 

In the old days when I was truly, truly bootstrapping and had almost no money, I then had to go learn the marketing approaches. So I also was the Google Ads person. I was the person doing SEO, I was the person doing partnerships. That’s what I had to do. Now, if I’d had any funding, I would’ve hired out those individual roles. And so these days, if you have any modicum of money and you can pay someone who really knows Facebook ads or really knows Instagram ads or really knows Google ads or LinkedIn ads or Twitter ads, I like coming up with the strategy and then hiring someone to implement that specific approach. And the reason is is that if you try to learn it and you try LinkedIn ads and they don’t work, you don’t know if you’re not good at them or if they don’t work for your business or your customer type. 

But if you hire someone who you think is pretty good and you get references and you pay them a couple grand a month for three months and they run ’em and it just doesn’t work, you at least have some modicum of confidence that LinkedIn ads for now probably aren’t the best fit for your business. And so individual contributor marketing roles and sales roles, frankly, like S-D-R-B-D-R stuff are things that I consider hiring out before a million, 2 million, 3 million. And when you’re on a budget, let’s say you’re doing 20 KA month, you don’t have the money to hire an amazing growth marketer, but you might have the ability to hire a freelancer who’s good at SEO or a small micro agency who knows how to do Google ads or LinkedIn ads, or you could hire a part-time biz dev person, which is a head of partnerships to handle those for 10 hours a week of work where they’re focusing on doing that. 

Now, that still means that you are saddled with the strategy and potentially the project management, but that’s the way that I see it working, trying to outsource marketing strategy when you haven’t gone from zero to one yet. I mean, you’ve heard us talk on this podcast. I’ve talked with Derek Rimer, I’ve talked with Ruben Ga as I’ve talked with Craig Hewitt, I’ve talked endlessly on this podcast solo, and it’s just the pattern that I see. People aren’t able to hire out sales and marketing before they get to a repeatable process. And usually that’s when you’re in seven figures of a RR. So thanks for that question, Miguel. I hope that was helpful. Are you drowning in challenging tech decisions? You should check out today’s sponsor tech stack. Unlike typical staffing agencies, these folks are startup specialists. With over a decade of experience in startup software development, tech stack can help your startup build an MVP that’s designed for explosive growth, rapidly expand your team for new features or optimize your existing code base for peak performance. 

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My next question is from Casper Vaughn Reed. Casper indicated their SaaS is doing $17,000 in MRR and asks. I have a product that caters to one-time events. It allows you to create scoreboards and leaderboards and often gets used for seasonal sports and corporate events. Revenue growth has been good around five to 10% month over month, but it’s mainly come from one time transactions. My question is how do I build up a healthy subscription business? I used to have a monthly subscription, but MRR peaked just below 10 K, 90% of my subscriptions churned giving one-time use as a reason. Can I fix it? Do I even need to fix it? Hope this question is an interesting one. I like this question because it really does call out the thought that not every business should be a subscription business. And there are some businesses or some apps or tools or utilities that people may only need to do once or once integrate while maybe it’s once a quarter, once a year. 

And those types of businesses are much more difficult to turn into subscription companies for obvious reasons. So one option is to just not worry about it and to take your 17 KA month. And I guess I said at the beginning of this question that it was 70 KMRR, and that’s not true. He wrote it’s 17 K of monthly revenue. And so I said MRR, because of course I think in SaaS and everything’s MRR, but in this case it is monthly revenue. Take your 17 K and enjoy it and use that to stair step your way up to recurring revenue. That is one option. Another option is to do what a lot of SEO keyword tools have done. When you think about people doing SEO keyword research, if you’re not an agency and you have one website, you often need to do keyword research infrequently. Maybe it’s once a year, maybe it’s once a quarter, maybe it’s once every six months. 

And so churn in those tools can be high. So what have those tools done? Well, they’ve built in things that you would use on a weekly or monthly basis, rank tracking to see where you rank for the keywords that you’re trying to rank for website quality monitors or the SEO monitoring of your site to say, oh, you have broken links, you’re missing these tags to keep everything up to date and in sync and operating well, any type of thing that someone might want a recurring use out of or that they might want to monitor or use on an ongoing basis is one approach to trying to become a subscription tool when you’re currently a one-time use tool. Another way that I see bigger companies doing this is they say, you can only pay annually and you get a year subscription for X amount of dollars. 

And that’s really a tactic that you can use for this. Personally, I don’t love it. It just feels a little like Verizon making their pricing impossible to figure out so that you can’t actually price compare between their own plans and the plans of their competitors. But that certainly is one way that people fight churn is to only sell annual subscriptions. And the problem is there’s problems with it, right? Your customers might get a little miffed if there are other options that are one-time use that are cheaper, they’ll go use them. They will often complain, oh, I used it once and then maybe potentially do a chargeback, ask for a refund. There’s a bunch of challenges with that, but it is an option that I wanted to throw out in the spirit of brainstorming and getting all the ideas out there. And I think from a high level, those are probably the three things that I would consider. 

And probably in your shoes, I would try to make this subscription by building other stuff and seeing if it works. If I had the energy and the excitement and the motivation to do it. And if it doesn’t work, then I would do plan A, which is just leave it as one time and use that to stair step your way up. I don’t know if it’ll work or not. I don’t know if there are other features, other things you can cater to that these folks are trying to do on an ongoing basis. I just don’t understand the business well enough. And if you have absolutely no ideas for how to do that and you’ve asked your customers and they have no ideas for you and you ask your mastermind or a co-founder or an advisor or your spouse or a good friend or this podcast and no one has any ideas, then yeah, there are tools that really just shouldn’t be subscription. 

And that may be the case. I of course, always like to at least try to invest some elbow grease into it. First, I actually did this with T net invoice back in, I dunno, whatever, 2005 or six where it had peaked. It was a one time sale as well, $300 one time with like 20% maintenance a year, and it had peaked between three and 5,000 a month. And so in any given month it was great. It was making my house payment plus a car payment, which I didn’t have because I had big cash for the car. But you get the idea. It was just a nice side income. As I worked full-time during the day and I really tried to grow that business, I was like, I want to get it to 10 K, 12 KA month so that I can quit my day job. 

And I spent about a year nights and weekends trying to do that before I realized this is a step one business. Now that term didn’t exist then hadn’t come up with the STA step method. That would be what, seven years later maybe. But in retrospect, it was something that I never regretted putting that time in and trying to grow it. I learned a lot during that time about what worked, what didn’t work. And when I got to the point where I was out of ideas and out of motivation, then I put it on autopilot and autopilot’s not real realize every 18 months Google would slap it. A competitor would come up, something I’d need to update the code. There were all these things that would happen, but as autopilot as you can make it. And then I moved on to my next thing, and that is actually when I built out a portfolio of products. 

Now with a portfolio of products, never try to grow more than one at a time. You focus on one, you get it to grow, and you get basically that recurring traffic that then builds hopefully recurring revenue and then get it to the point where it’s stable and maybe you autopilot that one too. And so I stacked a bunch of step one businesses to get myself to step two, to buy out my own time, quit the day job, and then I moved on to true recurring revenue with step three. That tends to be my approach is to try things that I think could work that I have the motivation to do and that I think I can learn from whether they work or not, whether they fail or succeed. At least I’ve learned to something from that. So that would tend to be the approach I would take. 

But you of course can look at your own personality and say, do I want to do that? Do I want to try to make it subscription? Or do I just want to take this amazing revenue that is generating and use it to build that standalone SaaS or true recurring revenue? Thanks for that question, Casper. I hope it was helpful. My next question is from Benjamin Hoy on X Twitter, how do I decide whether a customer type is worth selling to or targeting? I have consumers buying my SaaS, but also schools contacting me and occasionally small businesses. How do I decide whether targeting one or the other is worth it? In my experience, you just have to try. So first of all, there’s a difference between selling to and targeting, selling to if they’re approaching you inbound, what’s the real risk there? The risk is a school approaches you says, we want to buy it. 

And you say, great, it’s $500 a month or a thousand dollars a month. Make sure that you charge enough, by the way. And if it’s a school actually charge per year. So 6,000, 12,000, 25,000 a year, whatever you’re going to charge, charge enough to make it worthwhile. And you send them this quote and you can read founding sales by Pete Kanji or you can follow Jen Abel, Matt Ock, Stelli fte, some of the sales folks in the SaaS space and learn, Hey, how do I kind of navigate this? And if the school comes back and says, well, we need you to sign a big security checklist or fill out this 30 page doc to close the deal, then depending on what you’ve charged, do you know if you’ve undercharged and you need to turn down the deal, or if you’ve charged what 30 grand a year, then it becomes worth your time to fill out all of that and deal with procurement. 

So that’s the real danger is that you get into a sales cycle or a sales process and you realize it’s more headache than is worth it. And frankly, it’s going to be hard to know until you try it. The biggest thing though, whether it’s schools or small businesses, is charge enough to make it worthwhile. So charge a little more, especially if you’re resistant to doing it, charge a little more, charge a lot more than you think you need to. And if they say no, what are you out? Nothing. A conversation. And if they say yes, make sure it’s worth it. My dad, who was an electrician for 42 years and became a project manager, used to say, there are no bad jobs. There are only jobs without enough money in them. And what that meant is no matter how grindy a project was, if you had enough profit in that, then it was worth it. 

Similarly, when you’re selling to schools or businesses or enterprises, there are no bad deals. There are only deals that aren’t worth it. You didn’t charge enough. I will tell you that most small businesses what they have a single decision maker, they’re relatively easy to sell to, but if they’re non-technical, I dunno what your product is, if they’re non-technical, then there can be the onboarding headaches, right? This is customer pain versus competitor pain. And so you get to decide. But if you have consumers buying this, you probably already have that. I can’t imagine selling to a small business, that process is going to be very different than selling to an individual. Schools might be different, although private schools and language schools in that tend to operate like small businesses where they are a for-profit and certain people, managers or whatever have credit cards and they often buy a small business. 

If you get into public schools, K through 12 universities, the procurement and all that can be an annual seasonal budgetary cycles. There’s several TinySeed companies that deal with this, and it is a bit more of a pain. But for me, if I were trying to decide whether to sell to them, if they’re already approaching me, I would give it a shot a few times and see what it’s like. Targeting them is another question. Targeting them implies you maybe update your positioning, your H one or you at least add some landing pages. You start doing some SEO for the terms they’re searching for. Do you buy ads? You start marketing to these as an additional ICP. Right? Now, your ideal customer persona or ideal customer profile is consumers. Adding schools and small businesses as additional ICPs can be good. It can be good, especially if you can charge more, right? 

What if you have a personal plan and you have your small business plan and you have your academic plan and whatever. They have different pricing and they have different features, and they have different amounts of the value metric that you’re using if you have one. And that does allow you to segment your users and segment that process. And then maybe schools get a demo, and if they’re a one call close and they pay you enough, it’s worth it. And maybe consumers and small businesses don’t. There can be some benefit to it. Now, the flip side of that is, well, don’t you want to focus on a single ICP? There’s arguments on both sides. I have had businesses where there’s one, and I’ve had businesses where there were three or four drip actually launched with four different ICPs and we actually narrowed over time. So I can see it both ways. 

And again, in your shoes, I would ask myself, am I interested in potentially making more money and learning more about how to deal with other audiences and other ICPs potentially growing this business, making it a better business? Because certainly consumers are not going to pay as much as schools and small businesses. I’d ask myself, do I want to do that? Do I want to learn it? And my answer of course would be yes, because I like trying new things. I’m a maximizer and I’m someone who likes to learn things. So that’s my take Benjamin. Hope it was helpful. And with that, this episode will come to a close. Thanks so much for joining me this week and every week. It’s always great to be on the mic with you. If we’re not connected on X Twitter, which is where I asked for these later stage questions. Let’s connect. I’m at Rob Walling and of course if you have later stage questions, feel free to ping me on Twitter or send them to questions at startups For the Rest Of Us dot com. If you have early stage questions, feel free to send them there as well. I have a decent backlog of those and someday I will get back to them. Thanks for joining me again this week. This is Rob Walling signing off from episode 736.