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!
