Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
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You're traveling through another dimension. A dimension not only of sight and sound, but of mind. A journey into a wondrous land whose boundaries are that of imagination. That's a signpost ahead. Your next stop, startups for the rest of us. Welcome to this week's episode. I am Rob Walling, And you might recognize that intro from the amazing and talented Rod Serling, who created and wrote so many episodes of one of my favorite series, The Twilight Zone. But this is not The Twilight Zone. This is Startups for the Rest of Us, where every week since 2010, I've shipped an episode focused on helping bootstrapped and mostly bootstrap startup founders. We're founders who seek freedom, purpose, and relationships, and we don't want to sacrifice our life in order to build our startup. But we want our startup to change our life for the better. Today's conversation is pretty incredible. It's a founder who effectively bootstrapped. He uses the word bootstrap because they raised a couple hundred thousand dollars.
And if you're in venture capital land, that is bootstrap. Usually it's anything less than a million is considered bootstrap. built his company with a co-founder for 15 years, and had three subsequent exits to private equity, where he sold a portion of his equity in each one. The last exit was for $615 million. It's an incredible story, and my guest today is extremely knowledgeable and extremely accomplished. Before we dive into my conversation, the SaaS Launchpad is live. It is the best course I have ever created. It is the most comprehensive. There are reviews coming in already of people who are blown away by the depth and the quality and the quantity of the content. It's at saslaunchpad.co if you're interested. And as of the day this episode goes live, if you buy the course in the next six days before September 30th, you're going to be able to get on a live Q&A call with me where we're going to do a group call, talk about questions people have from the course, or probably about anything else, to be honest. saslaunchpad.co. I'm so confident in this course.
We have a 30-day, no-questions-asked money-back guarantee, so really there is no risk for you to check it out. That's saslaunchpad.co. And with that, let's dive into my conversation. Jeff, thanks so much for joining me on Startups for the Rest of Us.
Hey, Rob. Thanks for having me.
So as background for folks, you are at Retired Founder on Twitter. And your story is pretty incredible. I'll call it your personal H1, which is your Twitter bio. It says, Retired SaaS Founder sold the business for more than $600 million. seeking purpose and community post exit. You bootstrapped a company and sold it for a crazy amount of money. So why hasn't everyone heard of you? 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?
I guess the obvious answer would be I must not be that interesting. But perhaps beneath that is I like to keep a low profile just for my own safety and security. And by being anonymous, it also helps me be completely authentic with anything I have to talk about.
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. 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?
Oh man, the first word that comes to mind is relief. And following that, probably enthusiasm. As a bootstrap founder, it's very difficult to take a lot of risk.
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