Building and Selling in "Impossible" Markets with WePay's Bill Clerico

Founders in Arms

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 opportunities

The unconventional partnership strategy that led to WePay's $400M JPMorgan acquisition

How to position strategic partnerships as pathways to acquisition rather than just revenue

Why WePay's delayed pivot from consumer to developer APIs cost them market leadership

The specific tactics for getting enterprise buyers excited about acquisition vs. partnerships

How to navigate the early fintech landscape without established banking infrastructure

Why timing strategic decisions matters more than perfecting the original plan

The 12-18 month timeline required for enterprise acquisition conversations

How crisis-driven industries create first-time openings for technology adoption

Bill's contrarian thesis on investing in utilities, insurance, and government sectors

In 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