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Rob Walling

๐Ÿ‘ค Speaker
3342 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

I want to ask you a question that I think some people are probably thinking right now, which is with an exit like this, you yourself took home a tremendous amount of money. Is it just shy of $100 million? Is that accurate?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

I want to ask you a question that I think some people are probably thinking right now, which is with an exit like this, you yourself took home a tremendous amount of money. Is it just shy of $100 million? Is that accurate?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

How do you keep going? Like, what do you do next? Like that money, I know it came in three chunks, but like, how do you think about how to stay busy? You're not going to, if I had that much money, I wouldn't go back and grind, right? I mean, hell, I have way less money than that. I'm not going to go back and grind. You know what I mean?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

How do you keep going? Like, what do you do next? Like that money, I know it came in three chunks, but like, how do you think about how to stay busy? You're not going to, if I had that much money, I wouldn't go back and grind, right? I mean, hell, I have way less money than that. I'm not going to go back and grind. You know what I mean?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

So it's like, how do you possibly think about what to do next to keep yourself happy, to have an impact, to keep learning, to stay sharp without maybe getting back in the game? Unless you, did you ever consider getting back in the game?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

So it's like, how do you possibly think about what to do next to keep yourself happy, to have an impact, to keep learning, to stay sharp without maybe getting back in the game? Unless you, did you ever consider getting back in the game?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Well, it's boring. I did it for six months. And again, my exit was much smaller than yours, but I took six months off after and I was like, this is, I was in my early 40s, like this is not what I'm doing forever because I need to learn, like me personally, right? I need to learn, I need to have an impact, I need to do all that.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Well, it's boring. I did it for six months. And again, my exit was much smaller than yours, but I took six months off after and I was like, this is, I was in my early 40s, like this is not what I'm doing forever because I need to learn, like me personally, right? I need to learn, I need to have an impact, I need to do all that.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

The thing I struggled with was my whole life, like growing up we didn't have much money so it was always a constraint. I had a very scarce mindset around money. And a big part of me for entrepreneurship was like, I want to have the freedom to work on interesting things that I want to, but I also want to be set for life at some point. That was a goal. And so I achieved that goal.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

The thing I struggled with was my whole life, like growing up we didn't have much money so it was always a constraint. I had a very scarce mindset around money. And a big part of me for entrepreneurship was like, I want to have the freedom to work on interesting things that I want to, but I also want to be set for life at some point. That was a goal. And so I achieved that goal.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

And then I was like, whoa, I'm like 40 years. That's been like the driving goal for me. My North Star was to have enough money in the bank and cash that I never had to work again. And then I was like, so what do I do now? And I had other, I had MicroConf, I had this podcast, I had stuff that I could work on and do, but I needed a new North Star.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

And then I was like, whoa, I'm like 40 years. That's been like the driving goal for me. My North Star was to have enough money in the bank and cash that I never had to work again. And then I was like, so what do I do now? And I had other, I had MicroConf, I had this podcast, I had stuff that I could work on and do, but I needed a new North Star.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

And my new North Star became to multiply the world's population of independent self-sustaining startups, right? That is now truly my North Star. Like everything I do with books, the podcast, YouTube, MicroConf, TinySeed, that's what I do. Because it brings me joy. And it is I view it now as my legacy.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

And my new North Star became to multiply the world's population of independent self-sustaining startups, right? That is now truly my North Star. Like everything I do with books, the podcast, YouTube, MicroConf, TinySeed, that's what I do. Because it brings me joy. And it is I view it now as my legacy.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Did you have a similar transition where you were like, my North Star is growing the company or wealth or whatever. And then you had to take I mean, it took me six plus months to figure mine out of like thinking about it a lot. I was actually kind of stressed about it. But did you reorient around something new?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Did you have a similar transition where you were like, my North Star is growing the company or wealth or whatever. And then you had to take I mean, it took me six plus months to figure mine out of like thinking about it a lot. I was actually kind of stressed about it. But did you reorient around something new?

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Yep, and that is a big mental shift that I think some people make and some people don't. And so I want to wrap the interview and give folks a few calls to action because you have several different things that you're working on. You already mentioned Beyond the Finish Line, which is btfl.org. And as you said, if someone is post-economic, they can hit you up there.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Yep, and that is a big mental shift that I think some people make and some people don't. And so I want to wrap the interview and give folks a few calls to action because you have several different things that you're working on. You already mentioned Beyond the Finish Line, which is btfl.org. And as you said, if someone is post-economic, they can hit you up there.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

In addition, you are at Retired Founder on Twitter and retiredfounder.com. And I wanted to read, not your H1, your H1 is hello, fellow founder, and you talk about your exit. But the second paragraph down is, this is not a pitch for anything. I have nothing to sell you. I have enough money. So I love that. I have enough money.

Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

In addition, you are at Retired Founder on Twitter and retiredfounder.com. And I wanted to read, not your H1, your H1 is hello, fellow founder, and you talk about your exit. But the second paragraph down is, this is not a pitch for anything. I have nothing to sell you. I have enough money. So I love that. I have enough money.