Episode 780 | “I’ll Never Sell My Company” and Other Myths Founders Tell Themselves

Rob Walling:
Welcome to this episode of Startups For the Rest Of Us. I’m your host, Rob Walling, and in this episode I sit down with fan favorite Ruben Gamez. He’s the founder of Sewell 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. Do I use that clickbait word infiltrating? Realistically, these are things that we hear enough that we realize folks are buying into ideas that could be harmful to their business or their career. One of them the thought that I will never sell my company. I am happy to just run it forever. There is a conversation 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 three. 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 that go through our world class accelerator called TinySeed, you should head to TinySeed dot com slash invest. You can read it more about our thesis there. Our minimum for the remaining portion of this fund is lower than it has been in the past, 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, tiny c.com/invest. And with that, let’s dive into this amazing conversation with Ruben Gomez. Ruben Reuben, ga, 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.  

Ruben Gamez:
Yeah, I don’t know. Five-ish or something. Somewhere around there.  

Rob Walling:
No, I think five within the last 18 months.  

Ruben Gamez:
No,  

Rob Walling:
Not either. I’m always trolling you with that stuff. Anyways, great to have you back on the show. You’re the founder of Sewell, as many people know, and you are also founder of Bid Sketch and you’ve been doing SaaS for 16 years, I think, man, I think since oh nine. You’re like one of the bootstrap SaaS OGs and you’re also where I steal all of my good ideas.  

Ruben Gamez:
Cool. 15. I always say 15 years, but yeah, I guess it’s 16 now, huh? I  

Rob Walling:
Think it is. It’s time  

Ruben Gamez:
To oh 9 0 8, something like that. Yeah, yeah,  

Rob Walling:
It might be oh eight. Yeah. And this episode I think has come about because you and I often text about things that we see online here on podcasts see on X Twitter, and sometimes it’s like, wow, this is a great idea, Jason Cohen’s tweet on X, Y, Z, so on point. And other times we see a tweet and we’re like, wow, this is catastrophically bad, misguided so bad that we 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? 

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, this makes no sense. So we wanted to call it out. The first one is kind of a combination. I think there are think quite a few bootstrappers and whether they’re indie hackers or they’re more the ambitious bootstrappers who want to get to a million, 5 million, 10 million a RR. 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, everyone sells. I mean, they really do. All the examples I always throw out of like, Hey, I never thought MailChimp would sell. I never thought, I didn’t think Baremetrics would sell. 

It was just, I dunno 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 probably the one that may never sell. But I guess to throw it to you, what is the danger of a bootstrap founder starting a company and let’s say this is not a little indie hacker project. This is not something, ooh, it’s a step one, step two, business, 5K, 10 K, it’s going to plateau great. I’m never going to sell that. It’s like, fine, whatever. That doesn’t matter. But what if you’re growing when you’re at a half a million or a million or 2 million a RR and you’re growing well, 20 to a hundred percent a year and it’s going well, and you’re like, well, I’m just never going to sell. I like being bootstrapped. I don’t know what I would do next. All the objections. What’s the issue that you see with that?  

Ruben Gamez:
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 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 be like, oh yeah, we’re just kicking back. I can see this going for, of course I can see it going forever when something is growing. Amazing. Yeah, yeah, life is good. Then it slows down and that feeling just sucks. They don’t like that feeling. They work on it and then we’ve seen this so many times, then they can’t change the growth, they can’t improve that. So then they want out, they start a new thing and they figure 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, 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.  

Rob Walling:
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 four to five X revenue multiple an A RR 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. Well, on this show maybe we say four to seven or four to six, five to seven a or multiple, but that is if you are doing, let’s say 2 million bucks a year and you’re growing at 40, 50 or more percent per year, if you do not have that, let’s say you’re flat, let’s see at 2 million and you’ve grown less than 10% say in the last year, which is effectively as flat odds are, you’re going to get a one to two XARR multiple. 

If you get an a RR multiple, they might look, people might say, well, I’m buying on profit, and then we’re talking again that four to six, five to seven, 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 to for profit. So that’s the difference is we’re talking, let’s just throw a couple numbers at, let’s say you’re doing 2 million and you get five x six x, you get 10 12,000,001 to two x is like 2 million bucks about the revenue you’ll do this year, and two x is obviously 4 million. That is, we get these numbers in our head when they’re growing and I don’t know, I remember being calculating my net worth in my head as the MRR would tick up. Ooh, that’s 5K of MRR this month that we went up. So that’s times 12 is 60 K of a RR. 

And let’s say we sold for five x, 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 five KA month every month or whatever percentages, 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 we want to be for people to be aware of the reality of it, but they might say, so then, so should I just sell the moment I hit a million or 2 million? Should I sell then? Is that what we’re saying?  

Ruben Gamez:
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. And that makes it harder and harder to stay at the same growth rate. We’re not even talking about increasing it, just staying growing 50% or that’s hard. The more you make the harder it is.  

Rob Walling:
Absolutely. Yeah. And I did a talk on plateaus 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. The folks want to see it right now. They can go to microcomp.com and you can buy the videos. But I think in two, three months we’re going to have just that video up on YouTube. And one of the things I talk about in that talk was the math for calculating your plateau, 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 10 K and you have a 2% churn rate, then you divide 10,000 by 0.02 and you will plateau at 500,000 of MRR. That’s not too bad. That’s 6 million bucks. Most people aren’t adding 10 K-M-R-R-A month, and most people don’t have a 2% churn rate. That’s the challenge In the talk I gave the example of adding 5K MRR and having a three or 4% turn rate, and in which case you’ll plateau much earlier than that.  

Ruben Gamez:
Yeah. I think part of it is staying ahead 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 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, 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 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 finding new growth, is that you get to pull another rabbit out of the hat,  

Rob Walling:
Which is hard.  

Ruben Gamez:
Yes, it’s  

Rob Walling:
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 this integrations and whatever else was going on, 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 finding that first marketing approach is hard enough, adding new ones is just like that. Or like Robert said, rabbit out of a hat. So their headwinds there. And I think what you keep saying, and you’ve said this on the podcast in the past, is getting ahead of it. How do you get ahead of it? How do you think about, well, I’ve calculated that I’m going to, let’s say I’m at a million a RR right now, 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 Sowell.  

Ruben Gamez:
So for me, I am always trying to experiment a little bit of our time and budget on other stuff and maybe some of that hits and shows promise, but a lot of times it just doesn’t. So it really requires 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 engine. And in fact, 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 using spreadsheets or anything like that. You’re really just thinking through, I’m doing a little bit of research of 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 based off of some rough estimates of what we think we can do there.  

Rob Walling:
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. 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 SaaS app in our ecosystem that is in between let’s say one and 20 million a RR 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, or 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. And I saw that and then I was like, how are we going to get past that? Plateau is coming. It wasn’t months away, but 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. I was a little burned out and I was getting a little tired of the email space with blacklists, 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 bus past that, cool, I’m invested in this for another two to three years, probably should raise some funding. Frankly, at the time we were cash strapped and that was hampering growth in hiring and stuff. Or I could consider taking these offers that are coming in. And for me and Derek, Eric, 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 or multiple, because we did get a nice a RR multiple, and if we ran it over the top, which I say more folks do than probably should, 

That would’ve been tough. It would’ve been tough.  

Ruben Gamez:
So this is something that I’ve seen 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? 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,  

Rob Walling:
Right? Get to two, 3 million, whatever. And yeah, no, that’s a great question. So there’s a couple of things. 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, I know a lot of founders that are running or have run flat businesses and it’s so boring. Super. Yeah, it’s rough. It is. As founders, we are naturally designed to see some number go up into 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 could 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 I would just would get bored. And I don’t know that most founders think about that.  

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

Rob Walling:
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 5 million, it doesn’t matter. It doesn’t matter. It’s boring. And this is one of the reasons Basecamp, I don’t know if they’re growing or flat or we don’t know. We know they’re super profitable, but there is a reason that they rewrite their entire code base every four or five years because they think DHH gets bored and then they launch other products because they get bored  

Ruben Gamez:
Email products.  

Rob Walling:
Totally. And look power to them. They can do whatever they want, but realize that their business, again, Jason Fried 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 Fried and DHH. Those dudes are raking an 8 million, I’m sorry, 8 million, eight figures a year of net profit. So on the outside 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.  

Ruben Gamez:
Even them pulling in all that cash, they’re still looking for other stuff.  

Rob Walling:
So that was one big thing that I think founders should be aware of is flat businesses are not only boring, they’re demoralizing too. 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, what do we think? I could 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 at 3 million a year, if I’m growing and I am not selling that thing for 10 million at 3 million a year, I’m going to get 15, 20, 20 5 million. Basically you’re going to get a lot of cash upfront 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, is why would I sell it for two x or three x? 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?  

Ruben Gamez:
Even if it’s three x, which is a lower multiple for business, 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 that if you make it super profitable, that probably means you’re the one grinding doing most of the work 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. So it just takes longer. Plus as you go along, it’s harder and harder to keep up with the growth we just talked about. 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.  

Rob Walling:
And I’ve known a few founders who have said, Hey, I’m going to get this business. It’s growing fast and I think I can get it to 3 million a RR in that range, let’s say two to four. But 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 this really good multiple and I want to be growing like crazy. And I remember being like, why not keep running it? Why don’t you keep running, running it? And he said, because at that point I have generational wealth 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 five Xs or 10 Xs in the next couple years, do you regret it? I don’t. Drip has more than 10 XD since we sold it. In fact it 10 XD within probably two years, maybe three. And there were a bunch of factors at play there. There’s a bunch of venture capitally invested in it. I mean, we grew the team from 10 to 125 by the time I left. There’s a lot of things, but did I ever think to myself, man, I really wish I hadn’t sold and I still owned it. Not once. Yeah, not once,  

Ruben Gamez:
Right.  

Rob Walling:
Alright, 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 people are built differently, we’re wired differently. And it specifically applies to, it’s usually an excuse of 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, 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. I don’t know how to do outbound sales or how to do X, Y, Z 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? 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 you sent me a tweet the other day, someone’s going to build, said they build 60 apps, 60,  

Ruben Gamez:
60  

Rob Walling:
Apps that each going to make $500 a month. They want 30 K of above the recurring revenue. And I was like, oh my lord, good luck. The logistics of just managing the domains in the payment accounts alone. But if you and I chimed in on that, they’d probably say, well, I’m just bill different and I’m not going to put all my eggs in one basket or whatever. So tell me, am I summarizing it well, and what are your thoughts on this? What am I missing on this topic of being built different?  

Ruben Gamez:
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 see it come down to because where’s the growth in that? Right? This is a very static sort of self-identity type of thing. So even 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, right? And 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 those other things, the things that you, you’re great at now. So we’re always learning new things, always having to figure stuff out and things get difficult and it’s not always easy, but that’s how you get good at stuff or 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, 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.  

Rob Walling:
Yeah, it is. 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 X 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 them on the podcast that I won’t say 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, but this fits my personality. And I chimed in one time and I said, it 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 have anything to do. My personality or my desire doesn’t have anything to do with what gets results.  

Ruben Gamez:
Playing video games is really fun for me. And easy comes easy. It does come easy. It just comes easy to you. It does. I’m built for it, but that’s not going to help me get customers. 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 I could say I like doing podcasts, I like talking, so I’m going to do podcasts to get customers, but 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 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 and connections and everything else. 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.  

Rob Walling:
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 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. 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,  

Ruben Gamez:
Yeah, I remember, yes. Remember when we were doing Facebook ads? You were doing like hit tail, remember?  

Rob Walling:
Oh my God,  

Ruben Gamez:
The grind.  

Rob Walling:
Yes, I do. I remember.  

Ruben Gamez:
Yeah, man.  

Rob Walling:
Yes. It’s crazy. Multiple days a week in that ad thing, getting images generated.  

Ruben Gamez:
It’s not the most exciting or most fun thing, but no did the work  

Rob Walling:
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 cajillion dollars in funding, can you hire someone to do sales? I’m like, maybe. But if you don’t and you’re bootstrapping, you have to do it all. And I think if you have 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? And they said for that, but basically they were saying, because you were suggesting some marketing approaches, you should do this, this, that, and this. Do what it takes, not what you want to do. 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?  

Ruben Gamez:
I don’t know. I feel like for a lot of this stuff, I don’t think in those terms. 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, 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. 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 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.  

Rob Walling:
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 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 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.  

Ruben Gamez:
Yes, but there is a fun to a lot of these things, even the grindings to some of it, right? I don’t know. Can you go 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 have some stuff that I have to do with the state of Delaware today. I’m doing that stuff yet I’m not thinking about like, oh, this is super fun, or Oh, this is terrible, whatever. I know it’s not something that I would choose to do or enjoy, but it doesn’t mean business is 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.  

Rob Walling:
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 am 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 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 hundred million sent a millionaire without working if you get really, really lucky.  

Ruben Gamez:
Yeah, no, it’s a lot like that. I was literally thinking about this with a lot of that goes around with especially the 60 apps type mentality, right? It’s like going to the convenience store and getting a bunch of lottery tickets and scratching them off and hoping that one of them is a big winner  

Rob Walling:
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 this 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 into my mind. It’s something we see frequently people talking about, but the excuse to be 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 10 KA 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 3 million in a market and someone else is doing five KA month and that five KA month is like, yeah, this market’s just too hard. SaaS stuff doesn’t work anymore. SEO doesn’t work. AdWords don’t work all the market. It’s different in 2025. 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 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. I was like, we have to talk about this. Expand on your thinking there.  

Ruben Gamez:
It actually happens often where you have the same apps being launched at the same time and even if it’s 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 won billions, and if it’s all luck, he must be super, the luckiest person ever, right?  

Rob Walling:
Really lucky. Yes. David Cancel has had five exits for cash heat, and Shaw has had, I don’t know, four successful SaaS companies. We could name a lot of people. It’s not luck.  

Ruben Gamez:
No,  

Rob Walling:
It’s not luck. There’s some luck involved in all of it, but it’s  

Ruben Gamez:
Right, not as much as, yeah, I think it makes people, 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. It doesn’t necessarily mean that it is their fault unless they’re off playing video games or doing something else or avoiding the things that work, a lot of the stuff that we talked about to make progress. But it makes it so that they don’t have to assume responsibility for any of it, and they don’t have to feel bad.  

Rob Walling:
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 it and throw it out there and I shouldn’t grind and I shouldn’t do. 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.  

Ruben Gamez:
Sure, there’s always some element of luck, but even that you can increase, right? You can create more luck by 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. But if you are building a product and you never show it to anyone, you never talk to anybody in related industry, 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 from the activities that they’re doing, but also they’re just going to have more luck that’s going to help them along.  

Rob Walling:
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 something there. And even I say on this podcast, doing things in public creates opportunity or creates luck to be honest. 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 that my sentence kind of breaks down is you can’t, 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 alright, maybe that doesn’t work. But if you want to see examples, if folks want to hear examples of people who stories of them kind of grinding and doing stuff. 

Number one, you do a lot of marketing that is not social media. In fact, you don’t do any social media marketing for Sewell, right? It’s all these other channels and we can probably dive into ’em someday, but I interviewed Kevin Wag, staff of Spector, I believe it was the home improvement or no, it was SaaS for home inspectors, I’m sorry. And how he and his brother bootstrapped and sold half the company for 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 he did get up at 6:00 AM on a Sunday to do a demo to close a deal, and they did a bunch of Facebook group stuff, which is not the funnest thing,  

Ruben Gamez:
And consistently over a period of time I heard that it’s great if you listen to that 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 is probably offput to some people who think about the amount of work required to get to that point.  

Rob Walling:
It’s a lot. That was episode 776 if folks want to check it out, two episodes before that was a Noah Tucker who runs Social Snowball that 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. This is the thing I want to drive home. Again, it’s not that these guys hated their life the whole time. This is 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 ’em could do it again because they don’t rely on luck. 

Luck is just a small piece of the puzzle. Just like you had bid sketch, which you still run Sewell, and if you were like, I’m going to start another SaaS, right? Well, first I’d tell you, you know what? Maybe exit Sewell first so you’re not running three companies. That would be my first. That’s not going to happen, but, but if a few years from now, 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 because you’ve learned so much and haven’t relied on luck.  

Ruben Gamez:
Yeah, 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 guarantee that that’s going to work, but chances are pretty damn good.  

Rob Walling:
Rubin, 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 sewell.com and if they want to follow you on X Twitter, you are at Earthling Works. Thanks again for coming on.  

Ruben Gamez:
Thanks for the invite.  

Rob Walling:
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 Reuben 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, jaded 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 X 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.