Imagine AI Podcast
Join Chris Madden in exploring the latest in artificial intelligence with insightful interviews with CEOs and top executives from AI startups and industry leaders. A must-listen for anyone interested in AI news and the minds driving its innovation.
From Amazon Exec to AI Strategist: John Rossman on Leading with Vision | Imagine AI Live 25 - E121
John Rossman, former Amazon exec and author of Big Bet Leadership, shares what it takes to make bold, high-impact decisions in the AI era. In this pop-up podcast recorded live at Imagine AI Live 2025 at the Fontainebleau in Las Vegas, John joins host Chris Madden to explore how frameworks, engineered prompting, and customer obsession can help leaders build competitive moats. Rossman unpacks the "active skeptic" mindset, the role of experimentation in transformation, and why leaders must act now—not when it’s too late. Plus: the Bezos story that shaped his thinking, and how the Big Bet System is changing how companies solve “wicked problems.”
Key Points
- Thinking like an owner and avoiding organizational constraints can drive extraordinary results in business.
- Combining great frameworks with AI and engineered prompts can provide powerful, rapid solutions to complex business problems.
- Leaders should engage as active skeptics with AI, proactively exploring and testing new use cases to maintain a competitive edge.
Chapters
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Transcript
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