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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

Why does it, why is it in your name across the marquee? You know, there's people with huge YouTube followings that have like done a fraction of what you've done. What is the, what's going on there?

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

Why does it, why is it in your name across the marquee? You know, there's people with huge YouTube followings that have like done a fraction of what you've done. What is the, what's going on there?

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

And then we'll dig into that today. You're willing to talk numbers and all this stuff you were telling me in the pre-interview. I was like, whoa, okay, that's great. And so that is, you're anonymous, but I have vetted that you, in fact, have done these things. And so folks listening, as the first anonymous guest, it's kind of neat to have someone who has had... such an incredible journey.

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

And then we'll dig into that today. You're willing to talk numbers and all this stuff you were telling me in the pre-interview. I was like, whoa, okay, that's great. And so that is, you're anonymous, but I have vetted that you, in fact, have done these things. And so folks listening, as the first anonymous guest, it's kind of neat to have someone who has had... such an incredible journey.

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

I want to start by taking us to the end, so to speak, the exit, and you can explain how it's actually exits. But what I really want to go to is that moment that you refresh that bank balance and you realize I never have to work again. Like I'm all set. What was that emotion? What was that feeling?

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

I want to start by taking us to the end, so to speak, the exit, and you can explain how it's actually exits. But what I really want to go to is that moment that you refresh that bank balance and you realize I never have to work again. Like I'm all set. What was that emotion? What was that feeling?

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

The biggest perk, yeah. And to give folks an idea of the timeline real quick, we'll talk through this in more detail, but you co-founded the business in 2003. You sold a majority share of it to private equity in 2017, so 14 years ago.

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

The biggest perk, yeah. And to give folks an idea of the timeline real quick, we'll talk through this in more detail, but you co-founded the business in 2003. You sold a majority share of it to private equity in 2017, so 14 years ago.

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

But then you got what they call a second bite at the apple and a third bite at the apple, meaning you rolled equity and you had another exit in 2020 and then you had a final exit in 2022. That's the $615 million exit. And it was 14 times ARR. So that's an interesting thing.

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

But then you got what they call a second bite at the apple and a third bite at the apple, meaning you rolled equity and you had another exit in 2020 and then you had a final exit in 2022. That's the $615 million exit. And it was 14 times ARR. So that's an interesting thing.

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

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.

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

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.

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

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

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

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

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

Why was that the case?

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

Why was that the case?

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

It's unbelievable.

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

It's unbelievable.

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

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?

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

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?