Founders in Arms Building and Selling in "Impossible" Markets with WePay's Bill Clerico
Sep 5, 2025
Bill Clerico, the founder of WePay and now managing partner at Convective Capital, shares his journey from building a pioneering fintech startup during the 2008 financial crisis to selling it for $400 million. He discusses why avoiding certain sectors can reveal hidden opportunities and highlights the unconventional partnerships that led to WePay's acquisition by JPMorgan. Clerico also reflects on the importance of timing in strategic decisions and explores innovative solutions for high-fire risk insurance, revealing insights on navigating challenges in crisis-driven industries.
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Contrarian Signal In Investor Pessimism
- When investors say a sector is broken, that can signal a massive opportunity if you can solve its structural challenges.
- Bill uses fintech as an example where regulation and oligopoly made entry hard but created durable payoffs for successful innovators.
From Couch Hack To YC In 2008
- Bill and cofounder Rich built WePay from a college roommate couch and a bachelor-party problem in 2008.
- They shipped a product, joined Y Combinator, and used Demo Day funding to move to Silicon Valley.
Pivot Fast To Where Growth Lives
- If a third-party integration grows faster than your consumer product, pivot decisively toward the scalable business model.
- Avoid running both models in parallel for years because it delays leadership and destroys team alignment.