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

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Manage episode 519867929 series 3298391
Content provided by Mistral.vc. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Mistral.vc or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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!

  continue reading

Chapters

1. Intro (00:00:00)

2. The Flight to Vegas that Sparked a $120M Insurance Company (00:01:48)

3. Building a Fake Insurance Product in One Weekend to Test Demand (00:03:03)

4. Working Solo for a Year While Burning Through Savings (00:11:00)

5. Flying to South Africa for 7 weeks to Land First Insurance Partner (00:14:43)

6. Convincing 5 Friends to Quit their Jobs (00:19:58)

7. Pivoting from Mobile App to Embedded Insurance (00:27:56)

8. Elon's Tweet Creates Rocket Ship Growh Overnight (00:46:03)

239 episodes

Artwork
iconShare
 
Manage episode 519867929 series 3298391
Content provided by Mistral.vc. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Mistral.vc or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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!

  continue reading

Chapters

1. Intro (00:00:00)

2. The Flight to Vegas that Sparked a $120M Insurance Company (00:01:48)

3. Building a Fake Insurance Product in One Weekend to Test Demand (00:03:03)

4. Working Solo for a Year While Burning Through Savings (00:11:00)

5. Flying to South Africa for 7 weeks to Land First Insurance Partner (00:14:43)

6. Convincing 5 Friends to Quit their Jobs (00:19:58)

7. Pivoting from Mobile App to Embedded Insurance (00:27:56)

8. Elon's Tweet Creates Rocket Ship Growh Overnight (00:46:03)

239 episodes

All episodes

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