Rich Williams (former CEO of Groupon) joins Jason Radisson to talk about the realities of hypergrowth, what it takes to become a product-driven CEO, and why curiosity, conflict, and decision speed are non-negotiables in leadership.

This episode of CEO Tradecraft breaks down what most leadership conversations gloss over—operational scars, inflection points, and the actual skill set behind the title.

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Connect with Jason: https://www.linkedin.com/in/jason-radisson/

Chapters:00:00

- Intro01:44 - Welcome + Why Groupon Was a Hot Mess (in a Good Way)06:46

- Inside the Founding Team: Andrew, Eric, and the Samwers08:32

- IPO, Chaos, and the Three-Legged Stool Problem11:28

- Is Hypergrowth Just What Tech Does?14:56

- Operational Rigor, Manual Systems, and Scaling Pain17:56

- Forward-Deployed Teams and the Future of Work23:05

- Reflections on the CEO Skillset Groupon Built25:36

- Seeking Out the Hard Stuff: Intentional CEO Pathing28:28

- Becoming a Product Leader (Even If You Start in Marketing)31:33

- What Great Product Managers Actually Do34:34

- From Technical Co-Founder to CEO: The Next Generation37:36

- CEO DNA: Curiosity, Conflict, and Rapid Decisions43:40 - Outro

CEO Tradecraft goes deep with founders, operators, and executive decision-makers.

Real stories. Real strategies. Real tactics.