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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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.