Episode 819 | QSBS, Exit Multiples, How to Learn Marketing, and More Listener Questions (Rob Solo)

Rob Walling:
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Visit mercury.com to apply online in minutes. Mercury is a FinTech company, not an FDIC, insured bank banking services provided through Choice Financial Group and column NA members FDIC. And so to take two businesses at the same a RR and say they’re going to be growing the same amount while one is more profitable, the one that’s more profitable could actually be growing faster if you weren’t putting all that money in the bank. Profitability is a drain on growth and since growth is what drives exit multiples, that’s the thing that I personally would be looking at if I wanted an amazing life-changing exit. 

Welcome to another episode of Startups For the Rest Of Us, I’m your host, Rob Walling, and in this episode I answer listener questions on topics ranging from A-Q-S-B-S exit multiples when they move from profit to a RR, why people talk about a RR multiples with SaaS, how to learn marketing as a developer and more listener questions before we dive in to that tasty goodness TinySeed applications are open. So I run one of the best startup accelerators in the world for SaaS companies. It’s called TinySeed, and we open applications twice a year. You can add to TinySeed dot com slash apply if you’re interested if you’re a B2B SaaS founder doing at least $500 in MRR. And if you have questions for the TinySeed team, we’re doing a live stream on February 11th, 10:00 AM Eastern. We’ll leave a link in the description of this show so you can get notified when we go live. 

And if you want to know what it’s really like to go through the TinySeed Accelerator, you should check out TinySeed Tails season five with Harris Kenny that show aired on this very podcast feed just because it was four months ago, five months ago. If you scroll back, you’ll see the episodes marked with a title and it saw Harris reach half a million dollars in a RR after joining the accelerator. It wasn’t an easy journey, and if you go to TinySeed dot com slash bonus, you can access a private coaching call that I did with him as he was making some really hard growth decisions. So TinySeed dot com slash apply if you’re interested in applying. I hope to see there. And with that, let’s dive into my first listener question.  

Speaker 2:
Hey Rob, thanks for all that you do with startups. For the Rest Of Us, it’s meant a lot to me and my business. My question is about business entities. We are looking at changing to an S corp because we have positive revenue and I think it would be financially make a lot of sense, but it makes me wonder whether I should be thinking a lot more about becoming a C Corp for the specific reason of the Qs, bs, the qualified small business stock and the potential tax benefits upon an exit. What is your latest thinking as the background? Our business is entirely bootstrapped and we’re not looking for outside funding. So really it would just be for the QSBS, taking double taxation hit along the way, pencilling it out. I guess there’s a few ways it could go. I’m curious what the latest thinking is that from the bootstrappers perspective. Thanks so much. I look forward to hearing your response.  

Rob Walling:
For those who aren’t familiar, QSBS is a US tax benefit that applies to eligible shareholders of a qualified small business. So it’s qualified small business stock, and this is a United States IRS exclusion or whatever, a federal government exclusion from taxes. And I’m not a lawyer nor an accountant. So Google this or ask Chad GBT. But the general idea is if you own shares in a company and that includes founders and you sell for less than a certain amount and you hold those shares for five years or longer, you pay no federal income tax on that sale. And the limit used to be really low, it used to be $10 million and in July of 2025 it was raised to I believe $15 million and you have to hold it for five years or longer. But if you only hold it three years, you get a 50% exclusion. 

If you hold it for four years, you get a 75% exclusion five years gives you the a hundred percent. So the idea here is taxes in the US are not great and even long-term capital gains taxes can hit you for 20%. If you sell millions of dollars plus there’s a 3% this and then you have state taxes and you have all this stuff. But to be able to sell a company and to not pay federal capital gains tax is a big deal and it’ll save you money. Now the question is about whether Ryan and his co-founders should go with a C corp or NAS corp because you only get the exclusion if you are a C corp. And the answer really truly is, it depends. Do you think you’re going to hold the company for at least three years because even that 50% exclusion, imagine sell for 10 million bucks and not paying federal tax on 5 million of that. 

It’s a huge deal. It’s at least a million dollars in your pocket that would otherwise go to the federal government. And it’s actually more because there’s a 3% affordable Care Act thing. Again, I’m not an accountant, I just know what I’ve seen happen to my money, what I sold and then other founders. So it’s a significant amount of money. The big question is do you think you’ll hold for three years and do you think you’ll sell your stock versus an asset purchase? So when an acquirer buys you, sometimes they buy the stock that gives them the liability they have to take on the liability then of your company. If they only buy the assets, then you retain the liabilities and there’s no hard and fast rule. But I do know generally the smaller the acquisition, the more likely it is to be an asset purchase. 

What I don’t know is where I’d say that line is 5 million and below asset purchase probably more common, 8 million, 10 million and below asset purchase. Is it more common? I don’t know. I should probably ask a r vol set. I have seen acquisitions in the eight to 10 million range that were stock purchase agreements, especially when the company was a C corp and they said, I’m only going to sell shares because I get this tax-free status. And so that then is a signal to an acquirer that if you are not willing to buy the stock, you want to buy the assets, then don’t make me an offer because I’m not going to entertain it because of this significant tax savings that I’m going to get if I sell shares. So all that to say today, if I were starting a startup, knowing what I know now, knowing that everyone sells, having seen folks, some folks qualify for QSBS and other folks, not because they started an LLC or an S corp. 

I personally would do the C corp and I would take the double tax hit in the short term and I would be looking to sell for assuming I’m looking to sell for 10 to 30 million, 10 to 40 million somewhere in there. That’s kind of seems to be a reasonable target number for a lot of TinySeed folks and that’s the tact I would take. Now, is that the right answer? No, there is no right answer for this one. This is not even a rule of thumb. You know how I give guidance, don’t do B2C two set of marketplaces, they take a percentage of GMB, all that stuff. This is not that. This truly is. If you want to start a lifestyle business and you think you might just take out dividends over the long term or you’re not going to keep it for at least three years or your exit’s going to be small enough that it’s an asset purchase agreement, there’s all these things that could go the other way that will make maintaining a C corp a pain in the ass for you, then you shouldn’t do it. 

And that’s I think really what it comes down to. But the majority of companies we back with TinySeed are C corps. And in fact, with our latest fund that we raised that we just closed, that fund only invests in C Corps and there’s a bunch of reasons for that. It actually makes everything simpler for us. We have invested in LLCs and entities from other countries and it is a significant burden financially and time-wise to do that. Now we know why venture capitalists don’t do that, but realistically, if you want to raise additional funding later or if you want to have a significant exit, it’s certainly a decent signal to have that C corp. So thanks for that question Ryan. Hope it was helpful. My next question is from Alan Reed. The subject is exit multiples based on top line revenue. When people talk about exit multiples, they usually focus on top line revenue, especially a RR. 

There seems to be much less emphasis on EBITDA or free cashflow. Why is that? All else being equal is a company with higher a RR but lower free cashflow really worth more than a company with lower a RR, but stronger free cashflow. I’ve heard that exit multiples typically range from four to seven XARR. Does that range factor in differences in profitability? This is a good question, Alan. People talk about exit multiples, including me in terms of a RR only when we’re talking about SaaS, because SaaS is the best business model in the world. So you don’t talk about a RR or even just top line revenue exit multiples with e-commerce, with agencies, with content sites, with other types of online businesses because they just don’t sell for that. Those are sold like more traditional businesses. And the reason we talk about it on this show as a RR is because SaaS is one of the only businesses that sells for top line revenue multiples. 

Because SaaS is such an incredible recurring business model and especially if you achieve net negative churn, you can really have incredible multiples on that. A RR, when you sell a SaaS company for let’s say it’s around 2 million is where the crossover point is 2 million and up and that used to be lower. It used to be about a million, but then times change. Inflation. It’s inflation and different economic times. If you sell for 2 million and up, you should be, I’ll say thinking in terms of an A RR multiple, even if you’re not growing quickly, let’s say you’re flat or just growing 10% a year or something and you’re at 2 million, I would be looking at a one to two XARR multiple as a loose rule of thumb. And there is no other business type that that’s really a thing. It’s just so often talked about as an EBITDA multiple and if you’re at two or 3 million or 5 million, it doesn’t really matter and you’ve doubled in the last year. 

Let’s say you grew a hundred percent, yeah, you’re talking five to 10 x or four to eight x somewhere in that range, and it can be higher than that. I’ve seen a 15 x error or a multiple on a business doing several million because it hadn’t negative return and it just was an intense bidding war. It’s it’s a marketplace that’s an auction, right? So when we give these multiples, think of them like a bell curve and I can say, well, the smallest one I’ve ever seen is a 0.5 XARR and the highest one I’ve ever seen is a 20 XARR. And those are factual statements, but if you look across a hundred sales, the big bell in the middle is probably at five x or something and then it goes out from there and gets smaller on each side to the point where, oh, there’s 10 in the middle and then there’s eight and eight on each side, and then there’s six and six and it just kind of slopes down until you have I seen one that’s sold for 0.5 x and one that’s old for 20. 

Sure. That doesn’t mean that that’s the range. I’m not going to say it’s 0.5 x to 20 because that’s not helpful for anyone. It’s just how narrow do you want the part of the bell curve to be? How directed do you want it to be? And so I can say five to 10 or four to eight, but it is somewhere in there. The thing is, is acquirers in that range tend to be strategics or they tend to be private equity, and what they really care about is growth. The top three things they look at are growth, growth and growth, and then churn is the next one and the absolute revenue amount, like if it’s 2 million versus 5 million versus 10 million also matters and intervals that can come on here. And he’s done a whole talk on this topic that’s really good, but growth is what matters and that’s what will drive growth and churn and that’s what will drive that a RR multiple up. 

So your question of all else being equal is a company with higher a RR, but lower free cashflow really worth more than a company with lower a RR, but stronger free cashflow. The answer is yeah, it can be for sure because think of it, free cashflow is a short-term thing. Free cashflow is now I want to take out cash out of the business now and if I’m buying a two or $3 million business, a RR SaaS company that has 10% net negative churn and I’m going to pump millions of dollars into growth and I can then grow this thing to 10 or 20 million a RR and I can sell it for a four to eight x multiple. Let’s say I get it to 20 million, doesn’t really matter if it’s profitable. Let’s say I sell for a hundred million at that point, it doesn’t matter that it was profitable. 

No, because making the money on the exit and so therefore the profitability doesn’t matter because you are truly looking at the future and what you can get for the business down the line. And even if, let’s say, well, so you’re only looking to sell it. Let’s say you grew it to 20 million a RR and it truly is net negative turn 10%. You could cut back on staff and at scale a SaaS company can have gross margins of 80 to 90% and net margins of let’s say 30 to 50%. And for easy math, let’s just say you can get that $20 million SaaS company to a 50% net margin. You are throwing off 10 million a year at that point in free cash flow. And that’s a number that matters, not the, oh, I’m doing 2 million a year and I’m going to try to crank out 750 grand and profit this year, a million dollars a year. 

That sounds like a lot to us. It just doesn’t move the needle of these acquirers. And so no, they don’t care about cashflow in the short term. It doesn’t really matter nearly as much as the fundamentals of the business and how they see they can grow it and growth and momentum and churn or retention. Those are just opposite sides of the same coin. Those are the things that are really intriguing because when you look, what am I going to do with this business in the next three to five years, which is how private equity thinks about it and probably how strategics think about it as well, that’s what matters. So your last question is, I’ve heard exit multiples typically range for four to seven XARR. Does that range factor in differences in profitability? If you’re growing, they don’t care if you’re growing, they don’t care. 

And if I were to sell business doing $3 million a year and it was profitable versus 3 million a year and it was breakeven and they were both growing as fast, yeah, I guess maybe the profitable one would get a slight, maybe slight bump. But you know what? If you are profitable, you’re not investing in growth, you’re putting cash in the bank and so you’re not going to be growing as fast almost inevitably. And so to take two businesses at the same a RR and say they’re going to be growing the same amount while one is more profitable, the one that’s more profitable could actually be growing faster if you weren’t putting all that money in the bank. Profitability is a drain on growth and since growth is what drives exit multiples, that’s the thing that I personally would be looking at if I wanted an amazing life-changing exit. So thanks for that question, Alan. I hope it was helpful. My next question is from Andrew Miller on the interaction between co-founders and mastermind groups.  

Speaker 3:
Hey Rob, long time listener for about five years now. First time question asker. I am getting way ahead of myself and I’ve been reading your exit strategy book, excellent read. We’re nowhere near Exit, but you mentioned masterminds and Masterminds have been mentioned plenty of times at all stages of the business, and I just wondered what your opinion on when you have co-founders, should you be in the same mastermind group as your co-founders or should you be seeking out separate mastermind groups each? Thanks for all you do. Thanks for the community. It’s  

Rob Walling:
Amazing. This is a great question Andrew, and I wanted to answer it really quickly here on the show. I would not want to be in a mastermind with my co-founder because I think it’s a waste of time to have two high functioning co-founders getting the same information and spending that same time in a group. You want a myriad of opinions, you want different inputs, different smart people thinking through the problems that you have. So I have never been in a mastermind with a co-founder and I think that’s a good thing. In addition, what if you start having trouble with your co-founder, you want to talk to your mastermind about it, how you should handle this tricky situation with a co-founder, which definitely happens. I don’t feel like there’s a hundred percent right and wrong answer, but I’m probably 95%. I personally would not want to be in a mastermind with my co-founder, and I think that’s probably the general advice that I would give to founders who ask me this exact question. 

Thanks for that question. I hope it was helpful. And my next question is from sebastian@stack.io. Sebastian asks, do you have any thoughts on SaaS that earns additional revenue through transaction fees based on customer GMV or gross merchant value? Do you see this type of revenue the same way as usage-based fees or is it higher or lower quality? This is a really good question. So if I was starting a bootstrapped or mostly bootstrap SaaS today, I would not make it solely based on customer GMV, but Sebastian specifically asked thoughts on a SaaS that earns additional revenue, meaning you are charging a monthly fee just monthly or annual, just like any other SaaS, additional revenue through GMVI think is a great idea. If I had any way to do this that made sense in my SaaS, I would 100% do it. I see the GMV being higher quality than usage-based fees because it tends to be, it depends on the business, but it tends to grow over time in a way that usage can be spiky and not grow as smoothly. 

In addition with GMV, as you charge them a percentage, you can also lower your credit card processing fee by switching away from, there are providers that are really easy to get set up on that are 2.9%, but you can find processors that do, I think it’s 1.5 or 1.9, it’s somewhere in there. And so you could still charge a totally reasonable fee. Let’s say it’s 1.9. I don’t actually remember that. The bottom, bottom man that I’ve seen Tiny C Company gets to, but it’s somewhere in the one points. So if you get to 1.9 and you’re charging 2.9, you’re taking a percentage 1% of GMB. If you charge that 3.9, 4.9, which is pretty reasonable in a lot of contexts, you are taking a significant amount of customer revenue, not a significant amount of their revenue, but it adds up across your customer base of a hundred, 500 or a thousand customers. 

So do I think this is as good as MRR? Probably slightly less, but man, it really depends on the curve. It depends on how smooth it is and if it’s truly going up over time as your MRR is, I think you can make the argument. You’re certainly going to try to make the argument during an acquisition that this is high, super high quality revenue. I have seen businesses acquired, we have 234 investments I’m in, and I would say there’s at least it’s more than 10% have a GMV component. 20% feels high to me. So let’s just say 15 is going to put you at what, like 35, 38 companies and it’s good revenue usage based is different, right? I see. We have folks who have SMS, they charge for SMS or charge for emails sent or charge for whatever, and you’ll see it’s super spiky even if the trend is that it grows over time, it’s not nearly as smooth as customer GMV. So think about my last SaaS company I did, which was drip email service provider marketing automation. We didn’t process payments, so there was just no real opportunity to do a percentage of GMV and so we didn’t charge it, but if I had the opportunity, the option and it made sense, given my product category a hundred percent, I would have that as a component of my pricing. So thanks for that question. I hope my thoughts were helpful and my last question of the day comes from Sean.  

Speaker 4:
Hey Rob, my name’s Sean, and I hear you mentioning that it’s very important to have a founder who does sales and marketing on the team. And I think that sounds like a very reasonable suggestion. If I’m a developer and I want to learn this stuff myself, it’s so hard to learn about marketing because there’s just so much garbage out there. There’s so many self-promoting marketing gurus, it’s 80 to 20 fluff to actual content or sometimes worse. So my question for you is where can a developer who wants to do a single founder bootstrapped SaaS go to learn really basic marketing techniques without all of the fluff? Any pointers you have for me would be greatly appreciated. Thanks so much for the podcast. Keep it up.  

Rob Walling:
Thanks for this question, Sean. This is a lot harder than one might think. Back in the day when I was learning marketing, I would read marketing tactic books specifically like SEO for Dummies, literally ad Words for Dummies, idiots Guide to Ad Words to try to learn it or I’d go on, and there was a guy named I think Perry Marshall who it was all info marketing. There was people who talked about copywriting. This is like 2000 6, 7 8. Dan Kennedy had a series of books about marketing. That’s how I learned copywriting and direct response. And then I would go get these subject matter specific books. I remember when I started doing Facebook ads with Hit Tail, I bought every Kindle book, all three of them that had been written about Facebook ads, no joke. And I read all of ’em and just took notes and then tried things. 

And so that’s how it was back then. There were no people talking about startup marketing. And that is why I started talking a lot about startup marketing because when I looked around on how to market a startup, it really was a bunch of venture capitalists talking about virality and billboards and brand advertising and banner advertising. And I don’t know, man, it was brutal. And so that’s the thing. Let’s break down marketing really quick. Marketing is strategy, marketing strategy, and then marketing project management, which you don’t really need to learn. It’s just keeping on top of people to get done. And then there’s the marketing tactics. There’s individual things like AdWords and partnerships and integrations and content and SEO and even the cold outreach, which isn’t marketing, it’s more lead gen, but you get the idea. It’s all just getting new people to hear about your product. 

So marketing tactics. Once you have an idea of what you should try in what order for those, I will go seek out someone who is talking about them. So I know that Selli FTE and Daniel Ebert, who both are TinySeed mentors actually, they talk about sales and cold outreach, and there are several, honestly, go to TinySeed dot com slash mentors and look for any sales mentors like Ben Hynek, anybody who’s doing sales mentorship for us is going to be extremely well vetted for B2B SaaS. And if they’re on this list, me or someone on my team have personally vetted them. And so if you’re looking for content on sales, just go command F on that page and look for sales. And if they are putting out content, I would say it’s probably quite good. Jen Abel also from jellyfish the sales content. If I was thinking about marketing strategy and growth, I would be looking, trying to follow Heat and Shaw, Mark Thomas, dev Basu. 

Again, these are TinySeed mentors, and I’m not saying them to say, oh, push TinySeed mentors on you. It’s the idea is that I hand pick the best people in B2B SaaS to be our mentors. So it’s an instant filtering. It’s a nice filtering for you to say, well, at least these people know what they’re doing now. Then the next question is, is everyone on the mentor list putting out content? And no, a lot of them, so you’ll have to see which of them have a podcast, which of them have a blog, which of them have written a book and give some thought from there. But the idea is thinking about marketing strategy is a lot harder than tactics. And I have an entire chapter in the SaaS playbook if you haven’t read it, and it’s just about marketing, and most of it is talking about how to do marketing strategy, which is like, what should I work on next? 

Should I do SEO? Should I do AdWords? Should I do pay-per-click ads? Should I do other things? And I outline a framework there. It’s not the only framework for deciding what to do next. Again, you can follow, I talked about three growth folks earlier, Mark Thomas Heaton and Dev Vasu. You can listen to stuff by Ruben Gomez when he comes on this show. He doesn’t put out content on his own. He’s too busy growing a company, but these are folks that are thinking about growth. Brian Balfour is amazing for high level growth stuff. Now, Brian Balfour is not going to teach you how to click in the AdWords interface, but he’s going to teach you how he thinks about growing companies. And so that’s the first step I’d be thinking about is as a developer, a single founder, how do I think about even how to prioritize marketing approaches? 

And that is why the SaaS Playbook has a chapter on it. Again, I’m not saying it’s the only framework, but I have the three factor framework in there for thinking about it. Now, once I’ve picked a marketing approach or two that are my next things that I’m going to experiment with, that’s when I’m going to go deep on a particular topic. And so for Facebook ads, am I going to go look at Growth Ninja, which is run by a longtime friend of mine and someone who ran Facebook ads for Drip and who has recently run them for my wife, Dr. Sherry Walling? If they put out content on Facebook ads, I’m probably going to look at it. And if I’m going to hire somebody to do Facebook ads, it’s probably going to be them. And if I want to do content and SEO, am I probably going to look at the content that Ross Hudgins is putting out. 

He runs an agency of, I don’t even know, a hundred, 120 people that is just a content marketing agency. Yeah, I’m going to look at Ross Hudgins. I like Ross Simmons. Why does everyone name Ross? Ross Simmons is great and puts out quite a bit of content for on content marketing and SEO. And of course, I’m going to be looking at anything Asia iRANO puts out and everything that Corey Haynes puts out. Cory Haynes has several sites including swipe file and Conversion Factory, and he is putting out AI skills. Even like last week, he put something out that’s getting popular. And so these are folks that are legitimate. And what it really depends on the challenge is you can say, well, does Rob Walling know SaaS marketing? And I’d be like, yeah, I do. I’m not the number one expert on it, but I generally know how I would market a SaaS. 

But if you ask me, okay, so in meta ads, should I use retargeting or should I do the lookalike audience and which button should I click? It’s like, I don’t do that anymore. I did used to, but I haven’t done that in 10 or 12 years. And so it depends on what layer you’re trying to get to. If you really decide, Hey, I’m going to try Facebook or Instagram ads, then you have to go deep. You have to find someone that’s reasonable that you don’t feel like is a bunch of fluff, and then you go deep on that particular topic to learn it well enough to implement it yourself. Or you spend some budget to hire someone who you get a recommendation for or who you believe is reliable and you pay them to run those campaigns for you. So that’s kind of it. I know I’ve thrown out a lot of names here, and some of them are more high level strategy folks and growth folks, and then other people specialize in a particular topic. 

But that’s the key, right? That’s why marketing is so complicated, is that you can’t just usually find or hire one person to do all of this stuff. No one knows all of this to the degree that you want. And there’s going to be no single source for all of the content across all the 20 B2B marketing approaches that I include in the SaaS playbook. I don’t know a single individual, including myself, that is actually good at all 20 of those. And so the thing to ask yourself is, well, which ones will reach my customers? Where are my customers? Where do they exist? How can I reach them with marketing? I narrow that list down to the top two, three or four, and I kind of do that in the SaaS playbook. I say, look, these are the big five, the most common five for Bootstrap SaaS. 

And then I say, these are the next five, and these are the most common ones that I see across our types of companies. And then you kind of hand pick, well, I know the competitors are doing this, so it probably works. And I know that my folks are actually in Hangouts and SEO is a big channel, and I think they’re on Instagram. If I’m marketing to realtors or artists like tattoo artists, Instagram’s going to be a big deal. And if I’m marketing to hardcore B2B SaaS founders, Instagram is probably not the best place to find them, right? There are better places like LinkedIn or X Twitter. So I totally hear you on this. There are so many people out there. The fluff content bugs the out of me, and it is one of the reasons that I started writing books is I was infuriated by not being able to just find legitimate content on marketing my companies in the 2005 to 2010 range. 

It’s why I wrote Start Small, stay Small, and Why So much Emphasis in that book is on marketing, and it’s about changing your mindset as a developer to think more like an entrepreneur and thinking an entrepreneur requires thinking much more about marketing and sales than we typically would as developers. So I hear you and I empathize with your struggle of like, where do I go to learn this? And the answer of course is these days, it depends. Back in the day, it really was like, well, there’s kind of one person talking about this, especially in bootstrapped the bootstrap circles. It’s like Pel was talking about more like word of mouth stuff and content, and Patrick McKenzie was talking just purely about SEO and dabbled in AdWords, and I was doing SEO AdWords and some content marketing, and then we all branched out from there. But that gives you an idea. 

The hard part is figuring out, well, which one, two or three approaches do I want to dive into? And then finding reliable sources for each of those. So thanks for that question, Sean. I appreciate it. I hope it was helpful. And that wraps up my listener questions for the day. Thanks so much for joining me today, this week and every week. I am doing okay on listener questions. I wouldn’t say running low, but I could certainly use some more, especially audio video questions, especially questions that are not for beginners that are in. You’ve launched and you have five 10 K of MRR. You have five 10 million of a RR would love questions on those kinds of topics. Thanks for listening this week and spending another 30 minutes with me. If you keep coming back, I’ll keep recording. This is Rob Walling signing off from episode 819.