When do you finally quit your day job and go all-in on your startup?
In this solo episode, Rob Walling answers listener questions about when it’s worth taking funding to speed up your path to full-time, how to think about equity when a co-founder joins late, and whether A.I. is shifting startup risk from market risk to feasibility risk. He also breaks down how to treat a low-priced, high-churn plan as “cheapium,” when to kill it, and how to test freemium without making a decision you can’t undo.
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Topics we cover:
- (2:48) – When is it time to quit your day job, and should you raise funding to do it faster?
- (4:35) – The “emotional runway” problem (and why bootstrappers burn out)
- (10:06) – Equity splits: when to talk about it, and what actually matters
- (13:57) – Late co-founder vs. business partner: how traction changes the %
- (18:34) – Is A.I. increasing feasibility risk (aka tech risk) for startups?
- (25:01) – Should a cheap, high-churn plan be treated like a marketing channel?
- (26:19) – “Cheapium” pricing: when to keep it, kill it, or test freemium
Links from the Show:
- Apply to TinySeed – Applications are until Feb 17th, 2026
- The SaaS Playbook by Rob Walling
- MicroConf – Community for SaaS Founders
- Slicing Pie by Mike Moyer
- Die With Zero by Bill Perkins
- Dharmesh Shah
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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Hiring engineers right now is noisy. You post a role and get flooded with AI polished resumes from people who’ve never actually shipped anything. G2I cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with over five years of experience, and they do live technical interviews with real humans checking for real skills. There’s no time wasters, no guesswork. Just candidates who can actually get the job done. Meta trusts them, Microsoft trusts them, and so do bootstrap founders who need to move fast without making expensive mistakes. Check them out at gt2i.co/rob. Get a seven-day free trial and $1,500 off when you mention startups for the rest of us. That’s g2i.co/rob. So if you can nights and weekends for the next couple years and get to the point where you’re supporting both you and your co-founder full-time, or you could sell 10% of your company, 12% of your company now, and you can get there way faster.
And whether that means you’re going to friends and family or to Angels or through an accelerator, I know which bet I would take. I would bet on myself and I’d want to get there faster.
Welcome back to another episode of Startups for the Rest of Us. I’m your host, Rob Walling. In this episode, I answer your listener questions on topics ranging from when do we leave our day jobs for our startup, questions about co-founders and late joining co-founders, how all that works, as well as a question about how AI might be impacting the viability of startups. And of course, I’ll cover another question or two depending on time. Before I dive into that, TinySeed applications close today. As a reminder, TinySeed is one of the best B2B SaaS accelerators in the world. It’s at tinySeed.com/apply if you are a SaaS founder doing at least $500 of MRR. We offer the right amount of funding for mostly bootstrap startups. We have an incredible roster of world-class SaaS mentors. We offer community with 325 other ambitious funded bootstrap SaaS founders, and we offer advice and guidance to get you to that next stage much, much faster.
If you’ve ever felt alone on the journey or like you just don’t have enough resources to move as fast as you’d like, and you’re looking for some guidance in community, head to tinySea.com/apply. And with that, let’s dive into my first listener question.
Speaker 2:
Hey, Rob, I’m Glenn. I’m the founder of 1020.IO. We’re a B2B SaaS that targets first responders. We provide location sharing between agencies. We launched in January. We’re growing quickly. We have 15 police and fire departments across two states currently using our platform. We do have revenue coming in, but it’s not enough for my founder and I to leave our full-time day-to-day jobs, which we’re dying to do. We’re so committed to our new startup that we just want to be doing this full-time right now. But reality is, is we do have families to take care of. We’re thinking about possibly taking on some type of angel investment or some seed round or possibly going through a startup accelerator, and just wanted to get your feedback on it, like we have families to provide for, but we’re also all in on our business. At what point do we just dive in 100% and say, “We’re doing this no matter what.
” Thank you.
Rob Walling:
This is a really good question. Thanks for asking, Glen. This is something that wouldn’t have been an issue 10 years ago because there was no funding for bootstrappers. And if you didn’t want to shoot for billion dollar or 10 billion dollar valuations, then you just ground it out. And these days, I think of it a bit as doing it on hard mode and doing it slowly and meticulously and capital efficiently. I’m really getting a lot of leads in here, but doing it in a capital efficient manner, but moving much slower. And there are obviously benefits to being capital efficient and moving slower, especially slower than say VC backed, right? But there’s an in between. I often say funded companies fail when they run out of money and bootstrap companies fail when they run out of motivation. And it’s true because you have an emotional runway.
We often talk about money, financial. Well, as a bootstrapper, you don’t have runway because you’re not burning anything, right? Maybe you’re taking money from your day job or whatever. But the company, since you’re doing it nights and weekends, you can keep doing this for 10 years financially, but can you do that emotionally? Most people cannot. And that emotional runway is different from person to person. It’s different based on how much traction you’re getting. As you grow, as your company hits these milestones and has successes, your emotional runway replenishes. And this is the thing that so many bootstrap founders don’t realize is some of them will say, “Well, I’m not going to sell because I just want to run this forever.” What they don’t realize is stuff Ruben and I talked about, I don’t know, four months ago, five months ago, about how once you plateau, your emotional runway starts to get drawn down.
And over time, it hits a point where you are unmotivated, uninspired, and it can be hard to keep going. So that’s the case of a company that was growing and plateaued. But in your case, the question that I pose is, how long can you keep doing this nights and weekends? And how long do you want to keep doing this nights and weekends? My guess is the want is no more, right? Like you’re already done and you wish you could have quit your day job months ago, but it’s purely a financial decision at this point. So what you’re trying to do is balance your financial runway and your emotional runway at this point, as well as a third component, which is your risk tolerance. Because if you have an infinite risk tolerance, whether that’s justified because you have wealthy parents who will backstop you or you have a million dollars in the bank, I’m sure if you had that, that you might already be all in on this.
But whether it’s justified or not, if you have infinite risk tolerance, meaning you can take risky bets, then realistically you just do it today, you’d go all in, right? And you might raise a bunch of money and be like, “Well, however it pans out is fine.” But for most of us, we are calculating like, “I have a day job. I have a family and you’re trying to balance your emotional and financial runway with that risk tolerance.” And it’s complex calculus and it’s different for every person. What I would say is if I was in a position like yours where I had early traction, and I mean, gosh, I don’t even know early traction. You have 15 companies paying you, that’s a sign, that’s a signal that something’s working, right? It’s not a guarantee that everything’s going to work and be amazing, but that’s not nothing.
And most SaaS founders that I know don’t get that far, especially with their early efforts. But if I had something that was working and I believed in it and I could raise a bit of funding to get me to focus on it earlier, I absolutely would. The thing that stands in most people’s way is that they don’t have a network. They don’t have anyone who will give them money. This was me. The first time I ever raised money was in 2018 when Ainar and I started TinySeat. Before that, I didn’t really know many people with money. I had no rich relatives. There were no entrepreneurs in the family. There were, they say friends and family around like none of my friends, none of my parents’ friends had any money. We were construction workers. We were a construction family, as you’ve heard on this show before.
And so I didn’t have the opportunity until Drip to be able to potentially raise money, and that would have been the time and decided to sell the company instead. So if you have friends and family who are willing to put in money at a reasonable valuation, do not value this company at 250 or $500,000 because you’re going to screw yourself for raising funds down the line. If you have that opportunity and your risk tolerance handles it, and you can look at if it’s you and a co-founder and you want to raise, I don’t know, 200,000, 300,000 and be like, “Well, if we grow, then this is runway for a couple years feasibly.” That’s a lot of time to make something work, especially if you’ve already done the grind of nights and weekends. So these days, knowing that we only have so many years in our lifetime and knowing how fleeting they are and how quickly they go, I am not going to spend time grinding on things that I can shortcut, that I can skip.
And I think funding is a way, again, if it lines up with your risk tolerance and your emotional runway and all this stuff, I think it’s a way to get there faster. Bill Perkins is the author of Die With Zero, and there’s a great quote from that book. He says, “We have two lives, and the second one begins when we realize we only have one.” So if you can nights and weekends for the next couple years and get to the point where you’re supporting both you and your co-founder full-time, or you could sell 10% of your company, 12% of your company now, and you can get there way faster. And whether that means you’re going to friends and family or to angels or through an accelerator, I know which bet I would take. I would bet on myself and I’d want to get there faster.
I’m not saying there’s no drawbacks to that approach. There are pros and cons to all of this. And I bootstrapped five companies and I’ve raised funding for one. And one of my companies was acquired by a venture back company that had raised $38 million. So I’ve been inside and outside of venture backed organizations and I know the trade offs. And these days, if I were in your shoes personally and I had the ability to raise funding and get there faster, that’s exactly what I’d be doing. So thanks again for that question, Glenn. I hope my thoughts were helpful. My next question comes from X Twitter, username Musings by Anjan. And Enjan asks, “How do founders think about equity and when do they start thinking about it? ” Also, how does this pan out if it’s an existing two year old single founder startup that’s bootstrapped and a co-founder is getting on board?
These are good questions. Founders should start thinking about equity pretty early on, but man, I know that sometimes if it’s just an idea and two people are kind of hashing it out and giving a little chat to it and figuring out if it’s even viable, I get it. At that point, do you want to say, “All right, are we fifty fifty? Are we 60 / 40? What do we each bring?” It’s not because it’s an awkward conversation, because you just don’t have any information. And so it’s this balance of doing it early where in a perfect world, you just decide on day one, but you have so little information that on the other side, you could wait six months or a year and then it becomes something and you’re applying to an accelerator or raising funding and you haven’t talked about equity and you have misaligned expectations of what you were thinking.
“Oh, I thought we were fifty fifty. What do you mean 75, 25?” And the other person says, “Well, I did a bunch more of the work or it was my idea, so I should get more of it. ” And it’s like, “Oof, if you haven’t had that conversation, that’s a tough one.” I know some folks talk about, “Well, if there’s two founders, you split it evenly by default, unless there’s a reason not to. ” And I mean, that’s certainly an easy way to do it, but I also think there needs to be a conversation around who’s bringing what to the company. The idea, I don’t really weigh it that much. I don’t think any idea is really worth equity, but what if someone brings a significant audience or they bring significant financial assets, some cash, or they have an amazing network, or they have something else that they’ve pre-sold it, or they’ve … I was going to say I already built half of it, but realistically, that’s going to happen anyway.
So I don’t know that’s a huge asset. It’s more of these unfair advantages. That’s what I’m thinking about is like, who brings more unfair advantages, if any? And if you’re all on the same playing field in terms of starting with nothing, well, then the default usually is a fifty fifty split. I’m not saying that’s the right way or the smart way, but it is given no other differences, it does feel like the most obvious way to do it. Now, there is a book called Slicing Pie, and it’s written by, I believe he’s a university professor, but it’s a way of, given the amount of work that each founder puts in, they kind of earn into their equity. And it’s not a terrible way to think about it. I think the thing that I struggle with though is what if you have someone who is later in their career and they have expertise and a network and skills that they are bringing that someone’s 45 years old and has built up a huge audience in a network and someone is 25 years old and they have, I mean, they’re full of motivation and they want to, let’s say, write a bunch of code, but the two skill sets aren’t equivalent and that’s where I think it requires conversations.
And in almost all cases, I think it would be helpful to have an unbiased third party, a UB3, as we used to say, an unbiased third party who can help give some guidance because I’ve had founders come to me and one founder will come and say, “Hey, we’re thinking about an equity split.” And usually I have a gut feeling having no dog in the race, usually I have a gut feeling of like, “Well, based on this and that, I think I’d probably go fifty fifty.” Or, “Yeah, you bring more.” It’s probably going to be, I’d say 60 / 40, give or take, a few. There are these ranges that are just kind of pattern matching and I think that’s a way to think about it. The second question on Sean asks is, how does this pan out if it’s an existing two year old single founder startup that’s bootstrapped and a co-founder’s getting on board?
So the two years old, that doesn’t matter much to me. It’s how much traction is there, how much progress has been made. If it’s still a pre-revenue company and you’ve written some code, you’re going to be doing this for years together. Oh, the other thing I forgot to mention actually about what people bring to the startup is like, what if one is able and willing to go full-time and the other is not? That’s another big factor, right? It’s not just about time, but it is about what you bring. So it’s another thing I wanted to throw in. But the idea of if you’re two years in, you’ve done it nights and weekends and you haven’t launched the product, I mean, you still have years and years of that journey ahead. Some are three, four, 10 years could literally be anywhere in there. And so does the two years you’ve spent nights and weekends equate at all to, if the two of you decide, “Hey, we’re going to go full time or whatever as soon as we can, raise funding and do all that still kind of feels fifty fifty-ish.” I guess someone’s put in some time, so maybe you could … I don’t know how you would offset that, but I certainly don’t think that for the rest of the life of the company, it should be some 60 40, 70, 30 split because someone spent nights and weekends building a product.
But with that said, now it depends to me on traction. What if that company, the two year company bootstrapped is doing 10K a month? Well, you’ve significantly de- risked that significantly. So it shouldn’t be anywhere near fifty fifty. And what if it’s doing 25 grand a month? Big difference, right? 50 grand a month. Each of these things, the company is just worth more. It’s just worth a lot more and the de- risking of it has a significant impact. And so there are no rules of thumb for this, but generally I have advised, I’ve had founders who are like, “Hey, I want to bring on a late stage co-founder.” And frankly, they shouldn’t be called a co-founder two years in. They’re not founding anything anymore. They are a business partner that is being added. And you can call them a founding engineer if they’re coming on as an engineer or founding whatever, founding employee, but are they a co-founder?
If you’ve been slogging for two years, that’s not what the term means. So I think be really careful or you can give them a title, right? They could be the director of blah, maybe a C level. I don’t like C level titles this early, but all that said, if I was doing 10K a month and someone wanted to join, oh man, they would need to brand … I mean, that’s a valuable business. Just think of what you could sell for that for through Quietlight Brokerage or acquirer.com. It’s worth hundreds of thousands of dollars. So if you give them whatever percentage that you give them, it’s a lot. So if you’re doing 10K, 20K a month, maybe they get 10 to 20%, 15 to 25, that just kind of feels right. I’m not saying this is like guaranteed that should be the number. If you’re going to become a billion dollar company and that’s the goal, that’s the other thing, I guess this all depends on goals, right?
If you’re going to become a billion dollar company, then you’re really still in the first, first inning, but if you are planning to maybe sell for … When you get to two million, then you’ve done a significant job of de- risking it. So I think there’s no right answer here. I think there’s a lot of this has to be a look at expectations. If you’ve raised funding, you said you’re bootstrap, but let’s say you’ve raised funding and you’re doing 25K a month, 50K a month, that number’s even smaller of what I think a kind of later stage person coming in, it starts to get in that three to 10% range pretty quickly. I think that founders often dismiss how much they de- risk a business by getting to revenue and by getting to, again, even small numbers like 10K, 15K, 20K a month is a signal, especially if churn’s low, like that’s a valuable business.
And you’ve done a lot to … You don’t just do that again, magically snap your fingers and have that again. Every time it’s a big risk to get there. And so I would just be very mindful with your equity. And of course it should always, I think, always vest. And it’s usually over four years with a one-year cliff. Those are just details, but you don’t want someone to come in, be able to work two or three months, get their equity, and then leave and take it all with them because that’s a catastrophic event and can help ensure that you can’t raise future funds, that when you exit, you’ve put a bunch of money in the pocket as someone who really didn’t work much on the product. So thanks for that question, Einjan. I hope my answer was helpful. My next question is also from X Twitter and it is Pablo Fernandez and Pablo was clarifying a question that he asked several episodes ago about feasibility risk and whether AI had changed the calculus of whether a business could be feasible.
And I didn’t fully understand his question and I think I misanswered it in that episode. I think that was with Ruben actually. So Pablo Chime did on Twitter and he said, “Hey, I just heard your answer to my question and start with the rest of us.” I think I didn’t phrase it correctly when I asked though. So maybe for a future podcast, here’s a reframing and I appreciate that. As a techie, so Pablo’s a developer, I get pitched ideas to join startups all the time and I’m seeing a shift. So I think this is where someone comes in and says, “I have an idea and I need a developer to build it. ” Okay. So in the past, they used to have market risk. So like Facebook for dogs, does anyone want this? Will there be any users? Where now I’m hearing a lot of, we’ll use AI to generate free money.
Of course, everyone wants that, but can AI generate free money? So that’s the idea that he’s saying the business idea is like, it’s a promise, like we’re going to use AI to do X, Y, Z. Sometimes these entrepreneurs do validation. I ask 10 people if they want free money and they all said, yes, this is a good example. Thanks Pablo. But that’s not the risky part. The risky part is that AI doesn’t magically solve problems, right? The risky part is, can you build this with AI? So that’s what I meant when I asked about feasibility risk and their validation should start at the lab and not the mom test. Is it just my bubble or is there industry wide shift here? By the way, I’m exaggerating. The problem is that many of those AI gifts for money looks impossible and then blame someone just makes it.
Yeah. So this is a really good question because, so there’s market risk, there’s technology risk and there’s execution risk, right? Those are the three risks in starting a startup. Execution is, can you get this done? Are you going to just stumble all over and not make any progress? Does your team suck or can they get it done if you have a good idea and a good market? So we’ll put that aside. Technology risk, we almost never talk about it on the show. And you’ll hear me mention it now and again, but I always dismiss it. I’m like, look, we’re not building Google. You’re not building an LLM, right? That’s what I’ll say on this show because if you’re listening here, that’s not what you’re thinking because we know you can build a credit app. We know you can build Basecamp. We know you can build drip.
We know you can build MailChimp, right? It might take you a while. These are certain things that will happen. There’s no technology risk, but it’s when you’re in biotech, med tech, you’re building drones, you’re trying to build a submersible that can go down and see the Titanic. You get it, right? That’s where there’s tech risk involved, but that’s not really, this podcast usually doesn’t cover much of that. But what you’re bringing up, Pablo, is that no, in this case, technology risk is a thing because if you promise I’m going to make AI that can replace, it can ingest your website and all of your knowledge base and it can just respond to all your support requests and it can decide what to build next in your product and it can … The question is, can it, does it actually do a good job of that?
And then of course the third risk is market risk and that’s where, am I going to be able to market it, find people? Does anyone want this? Can I find them at a cost that makes the business viable, blah, blah, blah. And market risk is usually the one that everyone trips on and everyone wants to avoid, right?That’s customer development. That’s where I talk about validation, landing pages, and talking to potential customers and all that. And that’s usually the riskiest piece of building a B2B SaaS. But in this case, Pablo, you’re pointing out something that is actually, I think, a very viable conversation and is the overpromising of AI. Acting like AI is magic and just does these things and just works and doesn’t change when they launch a new model that it’s going to work for the next six to 12 months and suddenly they launch a new model and it breaks everything.
So realistically, the idea is that feasibility risk is really a technology risk is what I’ve traditionally referred to it as. And to answer your question, yeah, there is, I wouldn’t say an industry wide shift, but it’s just the propensity to just think that AI can do everything, introduces this. And there’s a lot of disappointment. How many AI tools have you used that have promised something that then don’t deliver on that promise? I’ve experienced several, and I think most people have, and I think there’s maybe not a backlash, but a little bit of wariness around AI over promising for this stuff. And so that’s definitely something I think about. Market risk is still a very real thing. And I think having validation in a network and starting to build a launch list and all the stuff we talk about here is still super viable and something I would be doing.
But yes, if I were to have something I was going to build with AI, I would build a proof of concept in a weekend. Don’t you think you can do that? And if you can’t do it in a weekend, I would just build one before I started launching. These are the two risks that I would be trying to get over. I was talking with the founders of EMS SOAP. It’s a tinySeed company in the newest batch. And Raul, one of the co-founders is a fire chief in Florida, and he had an idea for paramedics using AI that it could transcribe their voices and put things in a medical report for insurance, basically. They have to document things in grim detail. And it would take 15 to 20 minutes after you do an emergency call to remember all the stuff you did and then write it all down and code it correctly.
And his hypothesis is, “I think AI can do this. ” Guess what he did? Did he go find a developer right away? No. He worked with, I believe it was ChatGPT, because you can just talk to ChatGPT and say, “I’m going to train you to do this. ” And you train a single GPT to do this. And that’s how he got this feasibility risk or technology risk out of the way where he was like, “Oh, this is good enough.” He proved it. That’s what a proof of concept, a POC is. And he proved that out as a non-technical founder. And then he went and found a developer to build this, to actually quote unquote build it right as a product. And that’s when he met his co-founder, who at first was just like a contractor or freelancer, and then became his co-founder of the product.
And so that’s what I would say is you’re right, the market is the risky part. And also there is feasibility or technology risk here. And so if I were non-technical, I would want to build this out in just a basic GPT first. And if I was a developer and someone was asking me to come on as a co-founder, I would say, “Have you built this in a GPT first?” And if not, let that be the first thing that we do if I’m going to agree to come on to get that risk out of the way. So thanks for rephrasing that question, Pablo. I hope that discussion was interesting. My last question of the day comes from Jacob about treating high churn plans as a marketing channel.
Speaker 3:
Hey, Rob, loving the podcast. You recommend sometimes dropping the lower priced, higher churn plan and focusing upstream. And you also say freemium products should treat the free users as a marketing channel. So I’m curious what your thoughts are on keeping a lower priced plan, but treating it as a marketing channel. They’re basically qualified leads already willing to pay who can grow into higher tiers. And if you kept it, should a founder track that plan separately from the core metrics, remove it from churn and MRR? Specifically, my software as a service company, DableWriter, is a B2C/prosumer product for novel writing. It’s got three plans from $9 to $29. The $9 plan accounts for only 15% of our subscribers and has the highest churn by one and a half percent. Should I drop it, keep it as a paying marketing channel, or convert it to a freemium plan if it meets the four criteria you and Ruben talk about, or just leave it alone?
How would you think about this idea generally and then specifically for my situation? Thanks. Appreciate it.
Rob Walling:
I like this question, Jacob, and I like the way you’re thinking about it. I do definitely have thoughts. This reminds me of Dharmesh Shah. He’s co-founder of HubSpot, which is what a many billion dollar company, and he gave a talk at business to software years ago and he talked about a cheapium plan. Well, I like that, right? So there’s freemium, which is free and there’s cheapium. And he said, you basically offer it at cost. So he’s like, “We might have a plan that you think about how expensive HubSpot is. ” And he’s like, “We might have a plan that’s $7.” And it basically pays for some very basic stuff. And he’s like, “We don’t make any money on that. We’re not building a great business on that, but you just make it something so there’s some kind of hurdle.” So this reminds me of that, and I always love that word cheapium because it was clever.
Realistically, the question that I’d be asking myself here is, do the people on that $9 plan actually upgrade to other plans? Every time I have advised a founder or at least brought up the idea of them canceling their cheapest plan, I always say, “But make sure people are not upgrading from that plan, that it’s not a funnel up into your more expensive plans, because if it is, then you should consider keeping it. ” That’s it. And I try to caveat … This is the thing with giving advice like this and kind of having rules of thumb is there’s always a caveat, right? When it comes to two-sided marketplaces, what I don’t say is never bootstrap a two-sided marketplace. What I say is don’t bootstrap a two-sided marketplace unless you already have access to one side. That’s actually what the full sentence is, right? It’s like the full quote of money is the root of all evil is actually the love of money is the root of all evil.
And that changes the meaning of it. So in this case, the full quote is, “I consider canceling my lowest plan if it’s high churn, as long as that’s not a feeder up into the other plans.” Now here’s the thing, even if it is a feeder, I still would be curious to see if I canceled it, if people would just bump to my middle plan, right? So that’s something I might want to test. But if you don’t see anyone going from that nine or very, very small amount upwards, then yeah, I would consider just removing it. The problem with having a plan that is high churn is it takes a toll on your support people. It is demoralizing to you as a founder to see your churn that high. And if you go to sell when you go to sell, because everyone sells, or if you were to go to raise money, your metrics will suck and it will negatively impact your valuations.
So sure, if you plan to keep it forever and never sell it, which again, you’re not going to do that, but if that’s your plan, then if you keep this lowest plan, I would absolutely exclude that plan from my churn. I mean, that’s really what you want to be doing because it muddies everything up. You have this 10, 12, 15% churn, but it’s all on the lowest plan. I’m sure it’s super high churn. It doesn’t help you actually see the business as it is, right? So yeah, you could exclude it in whatever reporting you’re using and then only worry about the higher churn. It’s fine. But if no one’s upgrading and it’s only 15% of your revenue, I don’t see why I would want that plan. That shows me that it’s broken. It’s like you could just eliminate that whole plan, eliminate all those churning customers who usually are higher maintenance.
In your case, they may or may not be, but why keep that around? That’s how I would think about it. And then the final part of your question is actually intriguing and it’s to just turn it into a freemium plan to stop charging for that $9. And since it’s only 15% of your revenue anyways, does that freemium plan get momentum and Become larger, and then you have that larger pool of people who can upgrade. My answer there, as you said, the four things that Ruben and I talk about, the biggest risk there is that it’s wrong, that you make it freemium and then you’re like, “Dang it. I would prefer it be $9 again.” Now, have you already downgraded all the people from the $9 plan to free and now you have this free plan with a bunch of people? Or is there a way you can test this just with new signups for now?
And what you do is whatever is in the $9 plan now, you have at least one or two features in that that you don’t put in the freemium plan. And then you add the free plan. That’s the only way I really know to test this stuff other than the rules of thumb we talk about here. So I have actually advised a couple TinySeed founders when they’re talking about this to just say, what would it … Let’s do a thought experiment of what would it look like to downgrade your plan instead of getting rid of it to a freemium plan and talk through it. And usually the answer is, “Oh, I don’t think that’s a good idea or I don’t think it’s worth the experiment.” But from there, it really is just an experiment of thinking about how can I do this in a way that … How do you do it in a way that’s easy to roll back is how I think about this stuff.
And usually grandfathering existing customers and whatever plan they are for now until you have more data is the way that I go. And then if I decide, “Oh, I’m pretty confident that freemium is the way.” Or, “Oof, pretty confident the $9 was the best.” Or, “Boy, freemium didn’t work, $9 didn’t work. I’m just going to cancel this whole thing altogether.” Or then you just remove it on the pricing page and just give yourself some time. You let the people churn out over time. And when that gets low enough, you figure out, do I want to bump people up or do I just let it ride? Just let it ride as it is until everybody churns out. So it’s definitely an interesting question. I like the way you’re thinking about this, Jacob, and I hope my thoughts on it were helpful. Thanks for sticking around through those listener questions.
There were some good questions today. I have a nice little backlog, but if you want your question answered on this very show, head to startupsfortherestofus.com, click ask a question in the top nav and you can record audio or video. It’ll go to the top of the stack. You can record it on your phone, on your computer, or you can send a text question and those go to the bottom of the stack, but I do eventually get to them. I only have about 15 text questions in the backlog right now. And of course, if you ask questions that are not early stage beginner idea stuff, those will also move ahead. If you’re doing 10K or a million a month, those are great questions to send in to the show so that I can keep the topics balanced and not only talk about early stage things. So thanks for joining me this week and every week.
This is Rob Walling signing off from episode 820.
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