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  1. A Product Market Fit Show | Startup Podcast for Founders
  2. He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure
He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure

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

A Product Market Fit Show | Startup Podcast for Founders · Nov 17, 2025

From a weekend prototype for flight insurance to powering Tesla, Sure's 10-year journey reveals the power of pivoting to an embedded, B2B model.

Product-Market Fit is a Spectrum, Not a Switch

Sure's journey shows that PMF is not binary. The company achieved initial PMF with its prototype, then again with its first product, and again after its pivot. However, launching auto insurance with a major EV brand created a "literal rocket ship" moment that represented a completely different order of magnitude of PMF.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago

Sure's Founder Worked Solo For a Year to Land an Enterprise Partner Before Hiring

Instead of immediately hiring after validating his idea, the founder of Sure worked alone for a year. He used this time to secure the company's first critical insurance partner, ensuring the business was on stable footing before asking anyone else to leave their job and join the venture.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago

Sure Raised Its Series C While Profitable with All Series B Cash in the Bank

Counter to the 2021 venture climate of growth-at-all-costs, Sure operated with a private equity-like discipline. They raised a $100M Series C when they were already profitable and hadn't spent any of their Series B funds. This capital efficiency provided the freedom to control their own destiny and make long-term decisions.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago

Sure Pivoted by Validating its New B2B Model Before Sunsetting its Original B2C App

Rather than making an abrupt turn, Sure managed its pivot from a B2C app to a B2B platform gradually. They kept the original mobile app running while they built and validated the new B2B distribution model, only sunsetting the app once the new strategy proved viable and began to ramp up.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago

To Enter the US Insurance Market, Sure First Launched in South Africa

Faced with complex U.S. regulations, Sure's founder went to South Africa. He leveraged its single-regulator system and his personal roots to land his first insurance partner. This validation then served as crucial social proof to sign the same company's U.S. division, de-risking a much larger market entry.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago

Sure's Founder Validated His Insurance Idea with a Fake-Door MVP in One Weekend

Before securing an insurance partner, Sure's founder built a prototype, spent a few thousand on ads, and achieved a 15.9% conversion rate. A fake payment error revealed intense user demand when people tried to buy up to seven times, confirming the idea's viability before building the real product.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago

Sure's First Enterprise Launch Failed When Its Partner Went Bankrupt a Week Prior

Startups pursuing an enterprise model face extreme external risks. After months of work, Sure's pivotal first B2B launch partner went out of business just one week before the go-live date. This highlights the fragility of relying on a single large partner and the resilience required to overcome setbacks outside your control.

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

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

A Product Market Fit Show | Startup Podcast for Founders·5 months ago