He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure

Episode notes

Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insurance for Tesla, Toyota, and MasterCard. But the journey was brutal. Wayne worked solo for a year, burning through savings in San Francisco. Flew to South Africa for 7 weeks to land his first insurance partner. The real breakthrough came 4 years later, in 2019, when Elon tweeted about Tesla insurance—instant rocket ship growth. Today Sure is the rails for embedded insurance, like Visa for credit cards. They raised $120M but haven't needed money since 2021 because they've been profitable since their Series B. Why You Should Listen: How to validate an entire business in a weekend. Why he worked solo for a year before raising money or hiring anyone. The exact playbook for pivoting while keeping your old product alive. How one Elon Musk tweet created instant product-market fit.