300 Coffees, 12 Years, One Big Exit

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What does it really take for a finance guy to become a startup founder and build all the way to a meaningful exit?In this episode of the Start Up CEO Show, I sit down with Blair Livingston, founder of Street Context, to unpack the real story behind building a vertical SaaS business inside one of the hardest enterprise markets on earth: capital markets. Blair shares how 300 coffees and relentless hustle opened doors early, why “delusional optimism” is a founder superpower, and what it felt like to spend nearly a decade “crossing the desert” before growth finally took off.We also get into the gritty stuff most founders avoid: when raising money becomes a trap, why strategy can’t be driven by capital, how Blair executed a painful 40% layoff to save the company, and why he optimized for control (board + voting) so he could run the business with clarity and transparency. Finally, Blair opens up about the emotional whiplash of selling, post-exit identity shifts, and why he’s now focused on AI + tokenization as the next major wave in finance.

Blair Livingston

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