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

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.

Keywords:

startup podcast, startup podcast for founders, Sure, Wayne Slavin, embedded insurance, InsurTech, product validation, bootstrap to profitable, Tesla insurance, B2B pivot

00:00:00 Intro

00:01:48 The flight to Vegas that sparked a $120M insurance company

00:03:03 Building a fake insurance product in one weekend to test demand

00:11:00 Working solo for a year while burning through savings

00:14:43 Flying to South Africa for 7 weeks to land first insurance partner

00:19:58 Convincing 5 friends to quit their jobs

00:27:56 Pivoting from mobile app to embedded insurance

00:46:03 Elon's tweet creates rocket ship growth overnight

Send me a message to let me know what you think!