Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Startups For the Rest of Us

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!

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