Rich Williams on Hypergrowth, Product Obsession, and CEO DNA

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CEO Tradecraft

Jason Radisson

4 episodes

3 days ago

CEO Tradecraft is a podcast about the work behind the title. What it really means to lead a company when the stakes are high and the answers aren’t obvious. Each episode, your host, Jason Radisson, talks with CEOs and senior operators about how they make decisions under pressure, scale teams, and navigate power, performance, and politics. You’ll hear real stories, not the official narrative. The wins, losses, pivots, and all the messy parts in between. The plays that really matter in business, as in life, they rarely get talked about, or passed down. That's what this show is for.

Management

Business

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All content for CEO Tradecraft is the property of Jason Radisson and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Management

Business

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Rich Williams on Hypergrowth, Product Obsession, and CEO DNA

CEO Tradecraft

44 minutes 40 seconds

5 months ago

Rich Williams on Hypergrowth, Product Obsession, and CEO DNA

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.🔗 Links📺 Subscribe for new episodes: https://www.youtube.com/@ceotradecraft🔗 Follow us on LinkedIn: https://www.linkedin.com/company/ceotradecraft/🎧 Listen on Spotify: [your link]📱 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 tactics. No fluff.