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

Startups For the Rest of Us

Rob Walling

Management, Entrepreneurship, Business, Marketing

4.8 • 792 Ratings

🗓️ 27 May 2025

⏱️ 51 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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– The surreal moment Kevin and his brother became multimillionaires (9:14) – Why a mobile-first approach won in an outdated, overlooked niche (17:39) – How adding payments created a second revenue stream and bigger valuation (20:36) – The early hustle: trade shows, 6 AM demos, and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: SaaS Launchpad Course MicroConf Kevin Wagstaff | LinkedIn Kevin Wagstaff (@KevinWagstaff3) | X Spectora Kevin’s Built to Sell Radio Episode 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

Transcript

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0:00.0	Welcome back to startups for the rest of us.
0:02.0	I'm your host, Rob Walling.
0:03.5	And in this episode, I talk with Kevin Wagstaff
0:07.0	about how he and his brother co-founded a SaaS company
0:11.5	and sold just under half of the company at a $90 million valuation.
0:17.0	Yeah, bootstrapped it to a $90 million partial exit and then sold another swath of the company a year later.
0:25.1	It's a pretty incredible story.
0:26.6	Kevin is a longtime listener of the podcast, a microcomf attendee, and you'll actually hear in the episode how he met the potential acquirer in the men's room at MicroConf in Denver, 2023.
0:40.7	It's a pretty incredible story.
0:42.5	And what's interesting is this podcast and MicroConf have now been around so long
0:47.7	that you are now hearing of folks who are the second or the third generation of founders,
0:55.7	even like Rubin, probably the fourth generation of founders that have come up listening to this podcast and reading the books and
1:00.4	going to microcomps and being part of this community.
1:04.0	And few things bring me more satisfaction and happiness in life than hearing these stories and hearing these stories directly from
1:13.4	the founders told straight from the heart like Kevin does in today's episode. It really is an
1:20.1	incredible story of how they bootstrapped and exited this company. And at the end, I ask for your
1:26.5	questions to bring Kevin back on the show.
1:29.9	So as you're listening, if you have questions for Kevin about anything,
1:33.0	about how they grew the business, why they sold, how they sold, just anything that you hear,
1:37.4	jot it down, send it to questions at startup to the rest of us.com
1:40.5	or at mention me at Rob Walling on X Twitter. And I'll bring Kevin back on.
1:45.3	He said he'd be game to answer some listener questions.
	...

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