PodcastIntel
Sign in Get Started Free
The Startup CEO Show
The Startup CEO Show

300 Coffees, 12 Years, One Big Exit

Jan 5, 2026 · 01:03:36
AI Summary
  • Blair Livingston built Street Context, a vertical SaaS in capital markets, through 300 coffees over 12 years and relentless early hustle to open doors
  • Executed a painful 40% layoff to save the company and optimized for control (board and voting rights) to run the business strategically despite capital pressures
  • Delusional optimism is a founder superpower; delayed growth taught the importance of strategy-driven rather than capital-driven decisions

More from The Startup CEO Show

View all episodes →

Get AI Summaries for Every New Episode

Subscribe to The Startup CEO Show and get AI summaries, guest tracking, and email digests delivered automatically.

Sign Up Free →