Rob Walling

Let's talk about that real quick because people ask all the time, like if I'm doing 2 million and growing at blah, what's my revenue multiple? And it's always like, it just depends. You know, I can do a bell curve of like of the past, 20 exits that I know of. I can give you the range, but I know a friend of mine who is a M&A advisor and he got someone a 23X ARR offer.

And then I heard someone three days ago who got a 2X ARR. So is that the range? It's two to 23. It just depends, right? It depends on the space and the market and the growth and this and that. The most common parts of the bell curve for SaaS tend to be in that, what is it? Four to, it's about five to seven, but you see five to eight and it depends on the market. So

And then I heard someone three days ago who got a 2X ARR. So is that the range? It's two to 23. It just depends, right? It depends on the space and the market and the growth and this and that. The most common parts of the bell curve for SaaS tend to be in that, what is it? Four to, it's about five to seven, but you see five to eight and it depends on the market. So

Why was that the case?

Why was that the case?

It's unbelievable.

It's unbelievable.

And let's give folks an idea of what the business was. We're not going to name the business because very quickly someone could find your identity, but it was a bootstrapped SaaS company. And what industry did you operate in?

And let's give folks an idea of what the business was. We're not going to name the business because very quickly someone could find your identity, but it was a bootstrapped SaaS company. And what industry did you operate in?

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?