From Amazon Exec to AI Strategist: John Rossman on Leading with Vision | Imagine AI Live 25 - E121

Imagine AI Podcast

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.” (0:00) Welcome & Introduction (0:22) Best Jeff Bezos Story (3:32) How Leaders Should Approach AI (4:36) How Leaders Should Use Tools like ChatGPT & Gemini (5:46) How to Level Up Your Prompting (7:17) Creating a Custom GPT with the Big Bets System (9:10) Data Security Concerns with Large Language Models (10:08) Example: Helping a Mid-Market Company Overcome a Low-Growth Mindset (12:51) Feedback on Imagine AI Live (13:51) How to Find John Rossman