Rob Walling

I mean, there's luck involved and there's all kinds of stuff. But it's crazy to see such an outsized outcome. There just aren't that many nine-figure bootstrapped exits like this. So I want to touch on something you've said a couple times now, and it's short-term generous, long-term greedy. Can you flesh that out, what you mean by that?

Yeah, I like that. It's really long-term thinking. And I like the way you say long-term greedy. It's intriguing to be thinking that way because so many folks don't think about running a company for 15 years, right? Myself included. Although I have run MicroConf now for 15 years, I think, 14. As you were going along, did it feel like 15 years?

Yeah, I like that. It's really long-term thinking. And I like the way you say long-term greedy. It's intriguing to be thinking that way because so many folks don't think about running a company for 15 years, right? Myself included. Although I have run MicroConf now for 15 years, I think, 14. As you were going along, did it feel like 15 years?

Or was it just something that you kind of, you didn't question and you just did every day? Similar to, I talk about why this podcast has shipped every week since 2010. People say, wow, that's a long time. It's like, doesn't feel like, I mean, when I look back, it's a long time, but like, I don't, this doesn't work for me. Like I do this because I love it.

Or was it just something that you kind of, you didn't question and you just did every day? Similar to, I talk about why this podcast has shipped every week since 2010. People say, wow, that's a long time. It's like, doesn't feel like, I mean, when I look back, it's a long time, but like, I don't, this doesn't work for me. Like I do this because I love it.

And frankly, microconf is just something, it's just part of me and it's what I do. My last SaaS company, Drip, was not. It was not an identity and I never thought I'd run that business for 15 years. So I'm just trying to give examples of like some of those really fit of like, I'm just going to do it. And it, you know, it did what it did and others, I keep going.

And frankly, microconf is just something, it's just part of me and it's what I do. My last SaaS company, Drip, was not. It was not an identity and I never thought I'd run that business for 15 years. So I'm just trying to give examples of like some of those really fit of like, I'm just going to do it. And it, you know, it did what it did and others, I keep going.

So I'm curious to hear what your feelings were during that 15 years of working on it.

So I'm curious to hear what your feelings were during that 15 years of working on it.

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?

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?

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?

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?

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?

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?

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.

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.

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.

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.

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.