Episode 780 | "I'll Never Sell My Company" and Other Myths Founders Tell Themselves
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Welcome to this episode of Startups for the Rest of Us. I am your host, Rob Walling. And in this episode, I sit down with fan favorite Ruben Gomez. He's the founder of SignWell

and an oracle of SaaS bootstrapping. And he and I talk through a couple of myths or misunderstandings that we see infiltrating the bootstrapper community. You like the way I use that clickbait word, infiltrating? Realistically, these are things that we hear enough that we realize folks are buying in to ideas that could be harmful to their business or their career. One of them, the thought that I will never sell my company, I'm happy to just run it forever.

There is a conversation about around being built differently because you don't like to market and so you're just going to not market and expect your business to be successful as well as some other topics that we dive into. It's a great show. It's conversational back and forth and Ruben and I are speaking from our experiences growing our own software companies as well as the SaaS founders that we've been surrounded by for 15 to 20 years at this point.

Before we dive into our conversation, if you are interested in indexing across hundreds of B2B SaaS companies and you're an accredited investor, we are raising TinySeed Fund 3. There's only a bit more room in this fund. And so if you've been on the fence and you're interested in investing in early stage B2B SaaS ambitious founders,

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And we are seeing great results from Fund One, which has been around for about six years. So our thesis is holding so far, and we would love for you to be part of it. TinySea.com slash invest. And with that, let's dive into this amazing conversation with Ruben Gomez. Ruben Gomez, welcome back to the show. Hey, good to be here.

for your 432nd appearance on Startups for the Rest of Us. Dude, I've lost count. I just don't even know. Yeah, I don't know. Like five-ish or something. Somewhere around there. No, I think five within the last like 18 months. No, not even. I'm always trolling you with that stuff. Anyways, great to have you back on the show. You're the founder of SignWell, as many people know. And you are

You're also founder of Bidsketch, and you've been doing SaaS for 16 years, I think, man. I think since 2009, you're like one of the bootstrap SaaS OGs, and you're also where I steal all of my good ideas. Oh, 15. I always say 15 years, but yeah, I guess it's 16 now, huh? I think it is. It's time. 2009, 2008, something like that. Yeah, it might be 2008, yeah. Yeah.

And this episode I think has come about because you and I often text about things that we see online, hear on podcasts, see on ex-Twitter. And sometimes it's like, wow, there's a great idea. Isn't Jason Cohen's tweet on XYZ so on point, right? And other times it's, we see a tweet and we're like, wow, this is catastrophically bad.

Misguided. So bad that we like need to rant about it. And then this episode came about because there were a couple of things that are not just...

I think bad advice or bad ideas, but we've seen them kind of spreading or we hear folks saying them a lot, right? Right. And so at a certain point I said this would make a great podcast episode and we just plunked things. So I don't know if these are quite three myths or maybe just three sentiments that we've heard founders say.

that were like, question mark? Like what? This makes no sense, right? And so we wanted to call it out. The first one is kind of a combination, I think. It's, there are, I think, quite a few bootstrappers and whether they're indie hackers or whether they're more kind of the ambitious, you know, bootstrappers who want to get to a million, 5 million, 10 million ARR. There are folks who believe they will never sell.

And I know I always say everyone sells and people nod their head. I mean that when I say it, like everyone sells. I mean, they really do. You know, I, all the examples I always throw out of like, Hey, I never thought MailChimp would sell. I never thought, I didn't think barometrics would sell. It was just, I don't know why I never thought that. I was like, Josh is just going to run it forever. I didn't know I was going to sell drip, whatever. Everyone sells eventually, except for Basecamp. That's them. That's probably the, you know, the, the one that, that may never sell. But,

I guess to throw it to you, what is the danger of

of a bootstrap founder starting a company and let's say this is not like a little indie hacker project this is not something oh it's a it's a step one step two business 5k 10k it's gonna plateau great I'm never gonna sell that it's like fine whatever like that doesn't matter but what if you're growing you know when you're at a half million or a million or two million ARR and you're growing well 20 to 100% a year and it's going well and you're like well I'm just never gonna sell I like being bootstrapped I don't know what I would do next you know all the objections what what's the issue that you see with that

I think there comes a point where growth slows. It either slows so much that it basically is a plateau or it just is a legit plateau. And at that point...

founders go for a very long time trying to change it they don't feel like just that contrast between when they're growing and that feels great super easy when things are feeling really good growth is going well to just you know just be like oh yeah we're just you know kicking back I can see this going for of course I can see it going forever when something is growing

Amazing. Yeah. Yeah. It's life is good. Then it slows down and that feeling just sucks. They don't, they don't like that feeling to work on it. And then we've seen this so many times. Then they can't change the growth. You know, they can't improve that. So then they want out, they start a new thing and they figured they're going to sell. And then they find out that they can't sell the business for very much.

A lot of founders don't understand that growth multiples on exits have a huge impact. It's everything. There's such a big difference between selling when things are good and when you're like, okay, I tried everything. It's been flat for a couple of years. I just can't get, you know, it just kind of sucks. I want out. It's like, okay, well, now you're going to be very disappointed with what you're going to get. So I think that's one of the bigger dangers in my opinion. Yeah.

Yeah, and to put some ranges to that, and I was throwing these out on Twitter the other day because someone said that they were trying to get a 4 to 5x revenue multiple, an ARR multiple on their SaaS, and they didn't get that so they weren't going to sell.

And I chimed in just saying, hey, that is not a default. We throw out ranges on this show. Maybe we say four to seven or four to six, five to seven ARR multiple. But that is if you are doing, let's say, two million bucks a year and you're going at 40, 50 or more percent per year. If you do not have that...

Let's say you're flat. Let's say you're at 2 million and you've grown less than 10%, say, in the last year, which effectively is flat. Odds are you're going to get a 1 to 2x ARR multiple. If you get an ARR multiple, people might say, well, I'm buying on profit. And then we're talking, again, that 4 to 6, 5 to 7, but it's profit. And most of us don't run our businesses. It depends, right? If you're growing fast, you don't run it for profit. So that's the difference is...

is we're talking, let's just throw a couple numbers out. Let's say you're doing 2 million and you get 5x, 6x, you get 10, 12 million. And 1 to 2x is like 2 million bucks, about the revenue you'll do this year. And 2x is obviously 4 million. That is, we get these numbers in our head when they're growing, right?

And I don't know, I remember being calculating my net worth in my head as the MRR would tick up, you know, ooh, that's 5K of MRR this month that we went up. So that's, you know, times 12 is 60K of ARR. And let's say we sold for 5X, that's $300,000 in net worth or in business enterprise value that we've created. But what that leaves out is that's only if we keep growing 5K a month, every month, you know, or whatever percentages, right? And that's...

We don't want to be curmudgeons and people who are like, you should sell now. I guess that's the next question is like, we want to be for people to be aware of the reality of it, but they might say, so what then? So should I just sell? Like the moment I hit a million or two million, should I sell then? Is that what we're saying?

I think you just have to stay ahead of it and be mindful. So if you're going to go for five more years, 10 more years, if that's what you see, then just be aware that businesses don't just grow forever in the way that they're growing, especially at the earlier stages.

And that plateaus are always coming and you can calculate that. It's just math, right? Because the more you grow, even if your churn stays the same, which typically it does, like you have 2% churn, 3%, 5%, whatever it is, that means you have more customers, more revenue coming in and you're churning. Basically, you need more new, fresh revenue and customers to make up for the additional churn as you grow. Right.

And that makes it harder and harder to have, to stay at the same growth rate. We're not even talking about increasing it, just staying growing 50%. That's hard. The more you make, the harder it is. Absolutely. Yeah. And I did a talk on

that you reviewed for me and helped me improve it from the time I did it in Europe last year until I did it here in New Orleans a couple months ago. And we are going to be pulling that video and putting it on our YouTube channel. If folks want to see it right now, they can go to microconf.com and you can buy the videos. But I think in like two or three months, we're going to have just that video up on YouTube. And one of the things I talk about in that talk is

the math for calculating your plateau, you know, which is the new MRR in a given month divided by your churn rate. So if you're adding $10,000 of MRR each month, relatively consistently, look, I know it's not to the penny, give or take on average over the past, whatever, it's 10K and you have a 2% churn rate, then you divide 10,000 by 0.02 and you will plateau at 500,000 of

of MRR. That's not too bad. That's 6 million bucks. Most people aren't adding 10K MRR a month and most people don't have a 2% churn rate. You know, that's the challenge, right? In the talk, I gave the example of like adding 5K MRR and having a 3% or 4% churn rate, in which case you'll plateau much earlier than that.

Yeah, I think part of it is staying ahead, like knowing when that happens. And what I mean by when I say staying ahead of it is that means that you have to do new things or, you know, more of what you're doing if there's a lot to be done there to grow more. You have to stay ahead of it. Both of our friends, Robert Graham, who runs a he's the CEO of a YC company.

doing many, many millions of dollars. I like how he put it pretty recently when we were talking about this. He said something like, you know, the prize that you get, and it can start to feel this way, the prize that you get for pulling a rabbit out of your hat, and that's kind of like finding new growth, right, is that you get to pull another rabbit out of the hat. Which

Which is hard. Yes, it's not. Which is hard. Yeah, that's the thing. If you have an existing marketing approach or two that are working or five like we did with Drip, none of which were these big stellar things, but each one was 10, 15% of our new trials. We had all the integrations and whatever else was going on. A, each of those will plateau naturally. Some of them will kind of stop working at a certain point.

And then you have to think about how big is my market? How much market share can I actually get? So adding new marketing approaches as we all finding that first marketing approach is hard enough. Like adding new ones is just like that. Or like Robert said, rabbit out of a hat. So there are headwinds there. And I think what you keep saying, and you've said this on the podcast in the past, it's like getting ahead of it. How do you get ahead of it? How do you think about, well, I've calculated that I'm gonna, you know, let's say I'm at a million ARR right now.

And given what we're doing right now, I'm going to plateau at about 1.5, 1.6, and that is six or eight months out. So I have some time to think about it. How do you, Ruben, think about this with your own businesses? Because I know you've gone through the process with Sunwell. Yeah.

So for me, I am always trying to experiment a little bit of, you know, of our time and budget on other stuff. And maybe that some of that hits and, you know, shows promise, but a lot of times it just doesn't. So it really requires like a ton of energy and time to find a new channel, just like when you did it the first time. It requires a ton of activation energy. And in fact, it's

sometimes it's harder than finding that first channel because the first channel that you find is probably the easier thing, the more obvious thing. And now you have to do something new. So for me, it's really just similar process of experimenting, thinking through where there is enough. And a lot of it is just kind of

being systematic and using math. And it's not like this complicated thing to where I'm, you know, I'm using spreadsheets or anything like that. You're really just thinking through and doing a little bit of research of like, how does this market work? Every market works a certain way. Where are the opportunities still in this market? Competitors that are bigger, what's working for them? What haven't we done? And then prioritizing those, you know, based off of like some rough estimates of, you know, what we think we can do there. Yeah.

Yeah, and I think the key takeaway, if someone's listening to this, it's not to be scared all the time and be like, oh my God, I'm going to plateau. I should sell now. I should panic. And that's not what we're saying. Like we are saying, be aware that you will naturally plateau if you do not bring more to the game. I don't know that I can think of a single thing

SaaS app in our ecosystem that is in between, let's say, one and 20 million ARR that has just continued to grow and grow and grow and grow based on something they did in the early days. It always requires some type of additional, as you said, activation energy, some zero to one energy of bringing in a new marketing approach or a new expansion or a new product. There's something there. And so if you're listening to this, I mean, I remember thinking about this with Trip. And one of the reasons that we sold was I was like,

How far can we take this before we plateau? I don't know. I mean, I could do some math on it, but it, and I saw that. And then I was like, how are we going to get past that plateau that is coming? It wasn't, it wasn't months away, but it was, it was definitely out there. And I didn't have a strong sense of how to do that. And I didn't know if I had the activation energy to continue doing that. You know, I was a little burned out and I was getting a little tired of,

So the email space with blacklist, you know, there are certain things that just pull on you and you're like, how? And I kept asking myself if I'm going to get the activation energy to bust past that. Cool. I mean, I'm invested in this for another two to three years. Probably should raise some funding, frankly, at the time because we were cash strapped and that was that was hampering growth and hiring and stuff. Or I could consider taking these offers that are coming in. Right. And for me and Derek, like that was I've never regretted it. So I'll just say it was the right decision for us.

It's not that everyone has to do that, but I made a calculated decision to take money off the table instead of putting at risk our multiple because we did get a nice error, our multiple. And, you know, if we ran it over the top, which, which...

I say more folks do than probably should. Right. That would have been tough. It would have been tough. So this is something that I've seen, like when talking over this topic, people reply, which is, I'll just run it as a profitable business for X number of years. So why didn't you do that? Like, what was your thinking for exiting Drip instead of just running it for a few more years and just taking the cash out of it? Right. Get to two, three million, whatever. And yeah, no, that's a great question. So there's a couple of things. Yeah.

Number one is, it is so demoralizing running a flat business or running a slow growing business. It gets so boring. I know several founders, you know, I know a lot of founders that are running or have run flat businesses and it's just, it's so boring. It's rough. It is. As founders, we are naturally designed to see some number go up and to the right.

How do you get your energy? You don't get your energy punching a clock and showing up to keep something flat. You have to see, usually it's MRR. If you're running a SaaS, that's the number. We can say, well, maybe it's your YouTube channel followers for your SaaS or your email subscription. No, you don't care. The scorecard is MRR. So that was a big one of like, I would just get, I would get bored. And I think, I don't know that most founders think about that.

No, I like the nine to five phrase that you use there because it kind of like for some reason people have a really easy time thinking about how difficult it would be to just like do a nine to five, just zone out and just run through the motions day in, day out. For some reason, they have a tough time equating that to that's exactly what happens in a flat business. Yeah.

Yep. You're responding to support tickets, you're shipping features, you're making product decisions, you're still doing the marketing, you're doing all the sales calls, you're doing it all. And it's kind of for, it's to tread water.

And again, if it's two or three or four or five million, it doesn't matter. It doesn't matter. It's boring. And this is one of the reasons like Basecamp, I don't know if they're growing or flat or like, we don't know. We know they're super profitable. But there is a reason that they like rewrite their entire code base every four or five years because they think DHH gets bored, you know, and then they launch other products because they get bored. Email products. Totally. And I'm not, look, power to them. They can do whatever they want, but realize that their business is,

Again, Jason Freed confirmed this on stage at MicroConf. Basecamp throws off tens of millions of dollars a year in net profit. And for all intents, it's basically Jason Freed and DHH. Those dudes are raking in eight million, I'm sorry, eight million, eight figures a year of net profit. So on the outside, why don't we all say, well, they're just living the dream. They're living the dream. And it's like, yeah, that is cool. But they are bored with the core product. Yes. Even them pulling in all that cash, they're still right. Yep.

looking for other stuff. Right. So that was the big, that was one big thing that I think founders should be aware of is like flat businesses are not only boring, they're demoralizing too at both of those things. The other thing was I looked at the numbers and I thought no matter how profitable I make this, let's say I get to 3 million and I'm making, I'm like, what do we think? I can make a million dollars a year? Sure. Make a million dollars a year.

But if I can sell this thing now for $10 million and I get long-term cap gains on it instead of income tax, and I draw 10 years and $3 million a year if I'm growing, and I say, I'm not selling that thing for $10 million. At $3 million a year, I'm going to get $15, $20, $25 million. Basically, you're going to get a lot of cash up front in a way that accelerates all that earnings and then allows you to do your next thing or to do whatever you want, frankly, for the rest of your life rather than

Because this is the other thing we hear, right? It's like, well, why would I sell it for 2x or 3x? Why would I sell it for such a low multiple? I should just run it and pull out the profit. We often hear that. Why wouldn't you do that?

Even if it's 3x, which, you know, is a lower multiple for a business that that means it's not growing that fast usually or there's some risk or whatever. I think people are thinking that they're going to run it for three years and they get that cash in three years. It's not three years, not even close because.

We're talking about profit, whatever's left over in the business. If you make it super profitable, that probably means you're the one grinding, doing most of the work, right, during that time. So it's a tougher amount of time, tougher number of years. And then besides that, whatever the profit, even if it's really high, you're taxed more on it usually, right? So it just takes longer. Plus, as you go along, it's harder and harder to keep up with the growth like we just talked about. Like all these things come together into...

It being a longer period of time than people think and it being a harder sort of slog during that time. And just they're having significant risk versus getting the cash up front, freeing you up to work and do on whatever you want to do next.

Yeah, and I've known a few founders who have said like, hey, I'm going to get this business because it's growing fast and I think I can get it to 3 million ARR in that range, let's say two to four. But like some specific folks have said, hey, I want to get to 3 million and then I want to sell. And I want to sell for like this really good multiple and I want to be growing like crazy. And I remember being like, why not keep running it? You know, why don't you keep running it? And he said, because at that point I have like generational wealth and

And why would I keep pushing it? And he said, and I see some headwinds. And he had done the analysis. And did he know for sure? Of course not. Hard decisions, incomplete information. But he walked away with a really nice eight-figure payday. And so if the business 5Xs or 10Xs in the next couple years, do you regret it? I don't. Like Drip has more than 10Xed since we sold it. In fact, it 10Xed within...

probably two years, maybe three. And there were a bunch of factors at play there. There's a bunch of venture capital invested in it. I mean, you know, we grew the team from 10 to 125 by the time I left. There's a lot of things. But did I ever think that

To myself, man, I really wish I hadn't sold and I still owned it. You know, not once. Yeah, not once. Right. All right, let's move on to the second topic. It kind of ties in, but it's crazy how often I'm seeing this quote or this sentiment that like people are quote unquote built differently, rewired differently. And it specifically applies to, it's usually an excuse of like you and I are like do the hard things.

do what it takes to succeed. And that usually means launching something, focusing on it, figuring out marketing approaches, you know, whatever the approach that we talk about on this podcast. But there are other schools of thought that it's like, well, that doesn't fit with my personality. Like I don't know how to do outbound sales or how to do XYZ marketing or sales approach. I don't know how to do that. Or it's outside my comfort zone. I've seen all these phrases. So I'm not going to do that. I'm going to do what I know. I know content marketing. So I'm going to do that.

And specifically with an example like that, it's like, shouldn't the first question be where are my customers and what's going to be the most successful rather than my comfort zone, right? So that's a little thing there. But this idea that we're built different and there are just certain people who, I don't know, they're just wired to build 27 apps or as you sent me a tweet the other day, someone's going to build, said they build 60 apps. 60, yeah. 60 apps that each going to make $500 a month because they want 30K of revenue. And I was like, oh my Lord, good Lord.

luck, like the logistics of just managing the domains and the payment accounts alone. So, but, but, you know, if we, if you and I chimed in on that, they'd probably say like, well, I'm just built a friend and I, I'm not going to put all my eggs in one basket or whatever it is. So tell me, am I summarizing it well? And like, what, what are your thoughts on this? What am I missing on this topic of being quote built?

different? Yeah. I usually just see it as an excuse for people to sort of do things that they're comfortable with and not the uncomfortable stuff is really mostly what I, what I see it come down to because, um, where's the growth in that, right? This is a very static sort of self-identity type of thing. So like even the things that they say that they're good at,

How did you get good at those things? What if before you got good at those, you just stuck with what you knew and didn't write? You're like, oh, well, I'm just going to stick with the things that I know and I'm good at. You would never have gotten good at that.

those other things, the things that you you're great at now. Right. So we're always learning new things, always having to figure stuff out and yeah, things get difficult and it's not always easy, but that's, that's how you get good at stuff or, you know, that's how you learn. That's how you grow as a person. You find what things you enjoy, what things you'd rather have other people do for you or whatever, however you want to manage all that. It's like,

Without experimenting, like it really is just this mindset that's the opposite of a sort of experimentation sort of mindset. It's tough to grow that way. Yeah, it is. It's the fixed versus growth mindset is a piece of it. Although that usually is I believe that I can change versus I'm willing to do things that are uncomfortable that make me change.

But I've equated this to folks, and I've stopped chiming in on this on ex-Twitter because I just get tired of saying the same thing over and over. But I've equated it to saying, because I would say, hey, don't launch 20 things and see what sticks. You've heard me rant about this on the podcast. I won't say, you know, again, why I believe that. But I'll chime in with my reasoning of like, hey, here's why I think that's a bad idea. And someone will say, well, I'm just built differently. Or like, well, this fits my personality.

And I chimed in one time and I said, you know what fits my personality? Not working out and eating right to lose weight. What fits my personality is eating ice cream. I love eating ice cream. It's my favorite dessert, actually. And so that fits my personality. The fallacy is like, but that doesn't, like what, that doesn't have anything to do, my personality or my desire doesn't have anything to do with what gets results.

Yeah. Like playing video games is really fun for me and easy. It comes easy. It does come easy. It does. I'm built for it, but that's not going to help me get customers. Right. Uh,

It really comes down to where the people that I think are going make up our ideal customer, where can I find them, and what type of marketing activities will best work to get distribution and get customers for a product. And, you know, I could say I like doing podcasts, I like talking, so I'm going to do podcasts to get customers, but that's

That's probably, for most SaaS, that is not an effective channel. That's usually not good.

And I don't want to say that it doesn't matter at all what you're good at, because you can look at a market and, you know, a customer type and say, well, these two or three things seem to be effective in this market or seem like there would be good ways to reach these customers. And if one of those works best with the things I like, then, of course, I'm going to prioritize that. So use your strengths effectively.

and connections and everything else. It doesn't mean you don't look at that. But first you work backwards from where do I get customers? And then if there's some overlap with the things that you're good at, then great, use that. That's where it is. And if I was really good at building a personal brand and building audiences and going on podcasts, I wouldn't start a SaaS. I would start an info product and course business. That's what you do. And guess what? That's actually what I do. I don't run a SaaS anymore because I enjoy...

What I do, audience building and putting out podcasts, I like that better. And so I was under no illusion after building a few SaaS companies that I wanted to keep grinding on that type of stuff. I just didn't enjoy it as much as writing books and being in a personal brand, you know, influencer, whatever it is someone wants to call me.

I enjoy that more. It's just more fun for me. Maybe because I'm wired differently. No, but here's the thing. But I was willing to grind and do whatever it took to grow the businesses back in the day, right? I was willing to. I remember. I remember, yes, you remember when we were doing Facebook ads and you were doing like Hytale?

Remember? Oh, my gosh. The grind. Yes, I know. The constant iteration. Yeah, man. Yes. It's crazy. Multiple days a week in that ad thing getting images generated. It's not the most exciting or most fun thing, but no, it did the work.

And that, exactly. And I did it because I wanted to be a successful entrepreneur. I think that folks who are builders, product people, developers, makers, I don't think you're an entrepreneur until you take on the full role, a full scope of running a business. And look, if you have a kajillion dollars in funding, can you hire someone to do sales? I'm like, maybe. Maybe.

But if you don't and you're bootstrapping, you have to do it all. And I think if you have a kind of a hobby project that maybe you get lucky and takes off if you're not someone who's willing to really look at what are the marketing and sales approaches that it takes to grow this thing. And someone asked you, I won't say their name on X Twitter, but they said to you, they said, Earthling Works, I'm genuinely intrigued. Do you think you're wired differently to have the desire or patience to

to, and they said for that, but basically they were saying like to Greg, cause you were suggesting some marketing approaches, right? I'm going to, you should do this, this, that, and this, these are do what it takes, not what you want to do. Right? So this person was saying, do you think you're wired differently, Ruben, or that you're just more disciplined? What do you say to that?

I don't know. I feel like for a lot of this stuff, I don't think in those terms. Like I feel like people spend too much time thinking about whether something's difficult, whether they can do it, whether I spend more time just trying to figure it's not really a thing, like a way that I'm built or anything like this. It's just where I put my focus and attention.

If my focus and attention is on how difficult something is, how big of an obstacle I see, then yeah, it's going to feel really hard. And that doesn't feel good. Like, why, why am I going to, you know, how am I going to bring out the energy in me and get started? If that's the case, I'm just looking at, okay, what's the first thing? What's the, you know, first step? What's the next thing that I need to do? And that's where I put my time and attention.

focus on. So it's almost like just not overthinking it, not spending a lot of time in my head about it. If I really simplify it, I think that you value success more than you value your constant carefree enjoyment of every minute growing your business. You value success more than wanting to have fun growing

eight hours a day, five, six days a week, whatever it is that you're working on. And I think some other people think, I mean, maybe this is a controversial take.

Maybe they think, no, this should be fun all the time. I shouldn't do anything I don't want to do. Sorry, I laugh because you know how much, how many things have you done in your professional career as an entrepreneur that you don't want to do? I've done so many things. And I believe that is one of the reasons why I'm successful. There's just no chance that I would be who I am or have the success I've had without the willingness to do that.

Yes. But there is a fun to a lot of these things, even the kind of the grindiness to some of it, right? Like, I don't know, can you go long term without finding some enjoyment to this? It's kind of like, or framing it in a way. I think a lot of it really just comes down to framing. And sure, I can, you know, I have some stuff that I have to do with the state of Delaware today.

And I'm doing that stuff. Yes. I'm not thinking about like, oh, this is super fun. And, you know, or like, oh, this is terrible or whatever. Like, I know it's not something that I would choose to do or enjoy, but I'm

It doesn't mean business is sh**ty or that it sucks or that my day sucks. I still really enjoy what I'm doing and this is just part of what I need to do to move forward and make progress. That's it. You have to enjoy some of it. You have to enjoy maybe the majority. Who knows what percentage it is, but you have to enjoy a significant amount or you'll burn out. You will. So you have to find that balance. But I'm under no illusion and I don't know...

Do I know a single entrepreneur who didn't do anything grindy that they didn't want to do and got success? Yeah, and they got really, really lucky that one time. So if you want to bet your entrepreneurial success on getting lucky that way, you're the one in a thousand. I mean, of course it happens. It's just very, very, very rare. It's way more rare than people. I guess it's a little bit of the lottery ticket mentality of like, hey, you can become a centimillionaire without working.

If you get really, really lucky. Yeah, no, it's a lot like that. I was literally thinking about this with a lot of that goes around with the, especially the 60 apps type mentality, right? Like it's like going to the convenience store and getting a bunch of lottery tickets, scratching them off and hoping that one of them is a big winner. Yeah.

And I like things that are repeatable and that I think give me a higher chance of success than a lottery ticket over many years. The last topic I kind of want to transition us to, but we've already started talking a little bit about it, is it's kind of around getting really lucky. It's all just luck. No one knows what they're doing. And it ties in with people having excuses of why their app didn't work, why their business doesn't work. And frankly, this got sparked recently

Into my mind, it's something we see frequently people talking about. But the excuse to speak specifically is I've now seen several founders start effectively the same business, the same SaaS serving the same market with same ideas. And one of them was incredibly successful.

and sold for tens of millions of dollars completely bootstrapped and walked away with generational wealth. And other folks plateau at 10K a month. And we've seen this multiple times. You and I, again, we're not going to name names, but we see this in, it's multiple apps across different markets, across things that we see where it's like someone's doing two, three million in a market and someone else is doing 5K a month. And that 5K a month is like, yeah, this market's just too hard. SaaS stuff doesn't work anymore. Like SEO doesn't work. AdWords don't work. All the market, it's different in 2025. You know, there's,

It's a list of excuses, frankly. And you and I were texting back and forth as we often do. And we were saying, isn't it stark that these two products, starting at relatively the same timeframe, had such different outcomes? And people don't look at that often because they want to blame things. And to quote you, you said, people love excuses. What do you think...

I mean, aside from that just being very poignant and I was like, yeah, I just screenshotted that and put it in this outline because I was like, we have to talk about this. Expand on your thinking there. It actually happens often where you have the same apps being launched at the same time. And even if it's like a completely new category, how often do we see that? All the time. And a lot of times you'll see most of the people just have really just...

The amount of success that they have is just very small. They shut down the apps and they never really get anywhere. And there are people who make it work. Not just that, but then we also see people who make one thing work after another, like Jason Cohen, right? He did four, has done four startups in the millions of dollars, the latest one billions, right?

And if it's all luck, he must be super, like the luckiest person ever, right? Really lucky. Yes. David Cancel has had five exits for cash. Heaton Shaw has had, I don't know, four successful SaaS companies. We could name a lot of people. It's not luck. No. It's not luck. There's some luck involved in all of it, but it's... Right. Not as much as, yeah. I think it makes people feel...

some people feel better about when they don't have success with what they're doing. Because then if it's luck, it's not their fault. And I think this is their framing. Like it doesn't necessarily mean that

It is their fault unless they're off playing video games or, you know, doing something else or avoiding the things that work to, you know, a lot of the stuff that we talked about to make progress. But it makes it so that they don't, you know, have to assume responsibility for any of it and they don't have to feel bad.

Yep. They don't have to assume responsibility and they don't have to do anything they don't want to do. Because if it's luck, I should just build and throw it out there and I shouldn't grind and I shouldn't do, you know, referring back to the past 25 minutes of this show of like, no, you probably have to grind because luck is usually a very small component of the success. Yeah.

Sure, there's always some element of luck, but even that you can increase, right? You can create more luck by, you know, creating more opportunities, more of the right type of opportunities. And it's not just like any activity, it's the right type of activity that will help create some additional luck.

Like if you're building a product and you never show it to anyone, you never talk to anybody and relate it, you're just going to have less luck than someone who's out there promoting the product, talking about it, showing it to the right people and doing a lot of work around customers and potential partners. And that person is going to have not just better results, just straight up direct, like from the activities that they're doing, but also they're just going to have more luck.

that's going to help them along. Yeah, there's a quote. I think it's attributed to Thomas Jefferson. I don't know if he said it or not, but it's like, the harder I work, the luckier I get. Luck is when preparation meets opportunity. It's always like something there. Oh, and even I say on this podcast, like doing things in public creates success.

Or creates luck, to be honest, right? Doing things in public, publishing blog posts and launching SaaS. And as you're saying, you can't just do any random thing. This is maybe where my sentence kind of breaks down. Because I guess someone could then say, well, I launched my SaaS and my doing things in public is posting to Twitter. And it's like, well, that, all right, maybe that doesn't work.

But if you want to see examples, like if folks want to hear examples of people who, stories of them kind of grinding and doing stuff, number one, you, you do a lot of marketing that is not social media. In fact, you don't do any social media marketing for Seinwell, right? It's all these other channels and we can probably dive into them someday. But I interviewed Kevin Wagstaff of Seinwell

I believe it was the home improvement, or no, it was SAS for home inspectors, I'm sorry, and how he and his brother bootstrapped and sold half the company for, you know, at a $90 million valuation. Listening to that episode, I was struck. Actually, it was such a good story, and there was so much...

Of the, we just did what it took. We didn't care. And I don't mean working 90 hour weeks. Some people will be like, oh, so you just got to grind. You just got to be a Silicon Valley bear. I say, no, no, no, no, no. That's not what I mean. I mean, working on things that are hard or maybe you don't want to do, or that he did get up at 6am on a Sunday to do a demo to close a deal. And he, they did a bunch of Facebook group stuff, which is not the funnest thing. And consistently over, over a period of time, I heard that. And it's, it's great. If you listen to that and you,

And you hear about all of the stuff that he did for as long as he did, then it's like, oh, okay, I can see it sort of come together. And it also like is probably off-putting to some people who think about the amount of work required to, you know, get to that point.

It's a lot. That was episode 776, if folks want to check it out. Two episodes before that was Noah Tucker, who runs socialsnowball.io. The title of that episode was How a Non-Technical Founder Bootstrapped to Millions in Revenue. His story was very similar. He's a single non-technical founder. He now runs a team of 24. It's completely bootstrapped and is wildly successful. And everything you heard him talk about was...

doing what it took, not what he wanted to do. And he does enjoy it day to day. You know, this is the thing. I want to drive home again. It's not that these guys hated their life the whole time. That's not it. This is not delayed gratification, grinding for years to get there. Man, I know these guys now. They could do it again. Either of them could do it again, right? Because they don't rely on luck.

luck is just a small piece of the puzzle. Just like you, you know, you had BidSketch, which you still run, SignWell. And if you were like, I'm going to start another SaaS, right? Well, first I'd tell you, you know what? Maybe exit SignWell first so you're not running three companies. That's not going to happen. But, you know, if a few years from now, you know, if you were to be like, I'm going to start another one, it's like, well, that's going to be great and it's going to succeed or have a high likelihood of success, right? Because you've learned so much and haven't relied on luck.

There are no guarantees, of course, but there are some people that do the work and if they're starting something new, it would not be a problem for me to put my money on them. And yeah, I wouldn't expect a guarantee that it's going to work, but chances are pretty damn good.

Ruben, thanks so much for joining me once again on Startups for the Rest of Us. If folks want to use the best electronic signature app on the internet, it's at signwell.com. And if they want to follow you on XTwitter, you are at EarthlingWorks. Thanks again for coming on. Thanks for the invite.

Thanks again to Ruben for coming on the show. And after we hit stop on the record button, we came up with two or three more myths right at the end. And so I put it into a new outline and maybe I can convince Ruben to come back on the show here in a month or two and we can keep this type of format going. If you enjoyed the conversation of this episode in particular, because it's a little different than a lot of startups for the rest of us, right? It's a conversation between two grizzled, shaded SaaS founders.

talking through thoughts and ideas that we agree with and don't agree with. And if you felt this was interesting, you can at mention us on ex Twitter. I'm at Rob Walling and Ruben is at Earthling Works. Thank you for listening this week and every week. This is Rob Walling signing off from episode 780.