Bill Clerico is the founder and former CEO of WePay, which he sold to JPMorgan Chase for $400 million, and is now founding managing partner of Convective Capital, investing in wildfire risk management and physical resilience technologies. Starting WePay during the 2008 financial crisis when VCs said "no one makes money in payments except PayPal," Bill built one of the pioneering fintech companies alongside Stripe and Square.What you'll learn:Why VCs avoiding entire sectors often signals the biggest opportunitiesThe unconventional partnership strategy that led to WePay's $400M JPMorgan acquisitionHow to position strategic partnerships as pathways to acquisition rather than just revenueWhy WePay's delayed pivot from consumer to developer APIs cost them market leadershipThe specific tactics for getting enterprise buyers excited about acquisition vs. partnershipsHow to navigate the early fintech landscape without established banking infrastructureWhy timing strategic decisions matters more than perfecting the original planThe 12-18 month timeline required for enterprise acquisition conversationsHow crisis-driven industries create first-time openings for technology adoptionBill's contrarian thesis on investing in utilities, insurance, and government sectorsIn this episode, we cover:(00:00) Introduction and Bill's journey from investment banking to entrepreneurship(08:13) Starting WePay during the 2008 financial crisis in Boston(12:00) Getting into Y Combinator and the early pivot struggles(17:37) The acquisition strategy and JPMorgan partnership approach(24:38) Lessons on founder burnout and sustainable company building(36:19) Convective Capital's thesis on physical risk management(42:38) Building an insurance company for high-risk California properties(46:35) The future of wildfire risk and climate resilience investing

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