Rob Walling

Got it. And starting in 2003, there really wasn't, I put in quotes, there wasn't SaaS. Constant Contact was around and MailChimp was just, and Basecamp was a couple years later. But were you charging a subscription when you launched it in 2003 or was it one time back then and then you migrated to subscription later? Yeah.

Got it. And starting in 2003, there really wasn't, I put in quotes, there wasn't SaaS. Constant Contact was around and MailChimp was just, and Basecamp was a couple years later. But were you charging a subscription when you launched it in 2003 or was it one time back then and then you migrated to subscription later? Yeah.

Ben Chestnut, co-founder of MailChimp, I interviewed him at MicroConf, and he basically said the same thing. He was like, we were just charging one time because that's what we thought software was. And then suddenly we realized we need to, I don't remember why they switched to subscriptions, but it was very much an accident for them as well.

Ben Chestnut, co-founder of MailChimp, I interviewed him at MicroConf, and he basically said the same thing. He was like, we were just charging one time because that's what we thought software was. And then suddenly we realized we need to, I don't remember why they switched to subscriptions, but it was very much an accident for them as well.

So talk to me, you told me offline that you started in 03, you became profitable in 07. So four years of what I would call grinding. Were you working a day job at the same time? Because how can you be an unprofitable bootstrapped company? Those two things aren't, you don't have burn rate because you don't have cash in the bank.

So talk to me, you told me offline that you started in 03, you became profitable in 07. So four years of what I would call grinding. Were you working a day job at the same time? Because how can you be an unprofitable bootstrapped company? Those two things aren't, you don't have burn rate because you don't have cash in the bank.

And was it so mostly bootstrapped is obviously what I refer to that as. So as you hit profitability in 07, what did the company look like? Was it still small? Was it you and your co-founder? Did you have much of a team?

And was it so mostly bootstrapped is obviously what I refer to that as. So as you hit profitability in 07, what did the company look like? Was it still small? Was it you and your co-founder? Did you have much of a team?

In the journey between 03 and 18, which is 15 years, that's when you retired. You did the first part of your exit, partial exit in 17, then you retired in 18, and then you had these other exits afterwards because you just owned shares, right? What I want to find out is... Do you have a memory of, I guess, one of the hardest time periods or one of the hardest moments?

In the journey between 03 and 18, which is 15 years, that's when you retired. You did the first part of your exit, partial exit in 17, then you retired in 18, and then you had these other exits afterwards because you just owned shares, right? What I want to find out is... Do you have a memory of, I guess, one of the hardest time periods or one of the hardest moments?

A time where you kind of said, well, this might be it. This isn't going to work. Or maybe it was months of stress fighting spammer. Every entrepreneur has many of these stories, but do you have any go-to story of like, this was terrible?

A time where you kind of said, well, this might be it. This isn't going to work. Or maybe it was months of stress fighting spammer. Every entrepreneur has many of these stories, but do you have any go-to story of like, this was terrible?

Yeah, that sounds terrifying. And that, you know, the longer you do this, I've seen so many founders now get hacked, get cease and desist, have employees embezzle. You know, it's just these edge case things you hear about. You're like, well, that's such an edge. That'll never happen. But it's like, no, it's either I have view across 191 companies. So that's a law of large numbers.

Yeah, that sounds terrifying. And that, you know, the longer you do this, I've seen so many founders now get hacked, get cease and desist, have employees embezzle. You know, it's just these edge case things you hear about. You're like, well, that's such an edge. That'll never happen. But it's like, no, it's either I have view across 191 companies. So that's a law of large numbers.

It's going to happen to some of them. Or, you know, you had your one company, but you did it for 15 years. And so the odds of something happening in that timeframe is, and it's terrifying. How did you handle it in the moment? Some people completely like freeze up and like, don't know what to do and panic. And that's like a there's fight, flight or freeze, I think are the reactions.

It's going to happen to some of them. Or, you know, you had your one company, but you did it for 15 years. And so the odds of something happening in that timeframe is, and it's terrifying. How did you handle it in the moment? Some people completely like freeze up and like, don't know what to do and panic. And that's like a there's fight, flight or freeze, I think are the reactions.

Do you remember panicking and then calming down and saying, well, we just got to fix this? Or what was you know, kind of what was your, your mo there?

Do you remember panicking and then calming down and saying, well, we just got to fix this? Or what was you know, kind of what was your, your mo there?

This is going to be a tricky question, or maybe you've already thought about this, but why did the business work? Why did it work so well that it was obviously a massive success for you and your co-founder and even the private equity firms that bought it and resold it? What is at that core?

This is going to be a tricky question, or maybe you've already thought about this, but why did the business work? Why did it work so well that it was obviously a massive success for you and your co-founder and even the private equity firms that bought it and resold it? What is at that core?