Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Tue, 24 Sep 2024
In episode 732, Rob Walling interviews Jeff, a mostly anonymous and retired founder, about his mostly bootstrapped business and subsequent exits. Jeff shares how he started the company in 2003 and how he persevered in the early, lonely years to achieve traction in the business. They also discuss finding fulfillment after a huge, life-changing exit. Topics we cover: 2:17 – Jeff, the retired SaaS founder you haven’t heard of 3:32 – Refreshing the bank balance after multiple exits 5:26 – ARR multiples across several exits 8:11 – “Accidentally” SaaS, growing the business in the early days 11:35 – Getting through the toughest moments in the journey 16:31 – Why did the business work? 20:14 – “Short term generous, long term greedy” 24:32 – Staying busy after an exit 32:09 – Giving back to founders Links from the Show: Purchase The SaaS Launchpad before September 30th to get access to a live Q&A with Rob TinySeed Retired Founder (@RetiredFounder) | X Contact Retired Founder Beyond The Finish Line If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify
Full Episode
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?
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