Unicorn Leaders · 2026-02-19 · 1h 8m
Samuel Witherspoon was a lawyer who walked away from a safe career to co-found a tech company. The first thing he built? A platform for selling divorces online. He was ashamed to tell people what he did for a living. So he sat in a boardroom with his co-founders and asked a dangerous question: what if we burned it all down and started over? That question launched a 12-year grind into one of the most guarded industries on Earth - Canadian defense intelligence. Someone told Sam that no one ever makes the transition from services to product, especially selling into government. His response? "Watch me." Today, Anvil's software runs on active military operations. Their unofficial company patch is a cockroach. The motto: Hard to Kill. In this episode, Samuel shares how a team of 30 competes against billion-dollar American defense contractors, why Canada's sovereignty moment is opening doors that didn't exist two years ago, and what it really takes to outlast giants when you can't outspend them.
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