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 📌 Subscribe for daily GTM OS strategy and leadership frameworks: https://www.youtube.com/@SangramHere?sub_confirmation=1