10 Lessons From Building Two $10M Companies

I've taken two companies from zero to $10 million: Terminus, which raised over $100 million and exited to private equity for nine figures, and GTM Partners, a bootstrapped services business I'm running now. Same founder, completely different playbooks. In this video I share ten lessons from doing it twice, and the honest version of what building a business actually costs.

Some of it is counterintuitive: raising $100 million didn't put money in my pocket, but the bootstrapped company did. Most founders should never try to build a category. The better model in 2026 might be "service as a software," not software as a service. And the last three lessons are the ones nobody talks about: business nearly cost me my marriage, why faith and identity outside the company matter, and why growth never happens alone.

⏱ TIMESTAMPS
(00:00) Two ways to build a $10M company
(00:43) Lesson 1: business is hard, no matter what
(02:29) Lesson 2: raise money or bootstrap?
(05:11) Lesson 3: building in an up market vs a down market
(07:59) Lesson 4: software as a service vs service as a software
(08:33) Lesson 5: why 99% of founders should not build a category
(13:36) Lesson 6: thought leadership and owning the microphone
(14:57) Lesson 7: community, or you're just a commodity
(15:07) Your go-to-market motion: why events drove everything
(16:39) Lesson 8: a lean tech stack (and no CRM)
(17:35) Lesson 9: specialists over generalists
(19:00) Lesson 10: what outcome do you actually want?
(20:36) The hard truth: business nearly cost me my marriage
(22:04) Faith, identity, and not tying yourself to the company
(22:57) The co-founder relationship, and growing with someone

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