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Rob Walling

πŸ‘€ Speaker
4164 total appearances

Appearances Over Time

Podcast Appearances

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

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?

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

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.

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

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.

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

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.

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

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.

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

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?

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

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?

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

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?

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

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?

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

Feel free to talk about you and your co-founder that you executed well because I think the founders themselves have to be pretty instrumental in any business like this working. But people say, well, it's the market or the idea was the right time. We got a little lucky with timing. How do you think about why this business works so well?

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

Feel free to talk about you and your co-founder that you executed well because I think the founders themselves have to be pretty instrumental in any business like this working. But people say, well, it's the market or the idea was the right time. We got a little lucky with timing. How do you think about why this business works so well?

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

Yeah, that's a big thing. I mean, there's so many directions I want to take that. I've talked a lot lately about how, or a bit lately about how I think success of when I look at tiny C companies are the founders multiplied by the market or the opportunity.

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

Yeah, that's a big thing. I mean, there's so many directions I want to take that. I've talked a lot lately about how, or a bit lately about how I think success of when I look at tiny C companies are the founders multiplied by the market or the opportunity.

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

And the reason it's multiplied is let's say you have a founder who's a, you know, one out of 10, if we're just going to have a numerical rating scale, but it's like a great market opportunity.

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

And the reason it's multiplied is let's say you have a founder who's a, you know, one out of 10, if we're just going to have a numerical rating scale, but it's like a great market opportunity.

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

they will execute mediocre and you know they may have a middling success but if you have a founder who's a nine and they have a real market or it's a market that they don't get a little bit lucky with or they don't hit at the right time or whatever then it's similar it's middling and we see a few tiny seed founders just like you are such a good founder and i'm so sorry that you

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

they will execute mediocre and you know they may have a middling success but if you have a founder who's a nine and they have a real market or it's a market that they don't get a little bit lucky with or they don't hit at the right time or whatever then it's similar it's middling and we see a few tiny seed founders just like you are such a good founder and i'm so sorry that you

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

They're just not getting the traction. This sucks. But it sounds like between you and your co-founder, that division of labor, and it sounds like both of you really executed well. And then you have that market and you multiply the nine by nine or the 10 by 10. Suddenly you're at 100 versus these are all contrived. But you get the idea of what I'm saying. And there are more factors in that, right?

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

They're just not getting the traction. This sucks. But it sounds like between you and your co-founder, that division of labor, and it sounds like both of you really executed well. And then you have that market and you multiply the nine by nine or the 10 by 10. Suddenly you're at 100 versus these are all contrived. But you get the idea of what I'm saying. And there are more factors in that, right?

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

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?