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Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit

Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit



Podcast: Startups For the Rest of Us (LS 58 · TOP 0.5% what is this?)
Episode: Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit
Pub date: 2025-05-27

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What’s it take to bootstrap a niche SaaS to $90M without raising a dime?

In this episode, Kevin Wagstaff joins Rob Walling to share how he and his brother bootstrapped Spectora from a scrappy MVP to a $90M valuation. It’s a masterclass in finding traction in unsexy markets, building with empathy, and making smart bets like embedded payments.

Topics we cover: 

  • (4:39) – The surreal moment Kevin and his brother became multimillionaires
  • (9:14) – Why a mobile-first approach won in an outdated, overlooked niche
  • (17:39) – How adding payments created a second revenue stream and bigger valuation
  • (20:36) – The early hustle: trade shows, 6 AM demos, and Facebook group tactics

Links from the Show: 

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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The podcast and artwork embedded on this page are from Rob Walling, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.


Published on 7 months ago






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