This week on Generating Alpha, I’m joined by Annie Duke — a former professional poker player turned cognitive scientist, bestselling author, and one of the world’s foremost experts on decision-making under uncertainty. Over the course of her career, Annie has helped everyone from investors to CEOs to policymakers improve how they think about risk, probabilities, and knowing when to double down — and when to walk away.

Annie’s journey is anything but traditional. She left a PhD program in cognitive psychology at the University of Pennsylvania and went on to become one of the most successful poker players in the world, winning millions — including a World Series of Poker championship. After retiring from poker, she dedicated herself to teaching others how to make better decisions in environments where luck and skill collide.

She’s the author of multiple bestselling books, including Thinking in Bets, How to Decide, and Quit, which have become required reading for decision-makers in finance, business, and beyond. Her work sits at the intersection of psychology, game theory, and behavioral finance.

In this conversation, we explore how to make smarter decisions under uncertainty, the common mistakes even the smartest investors make, how to know when quitting is actually the most rational choice, and the frameworks she’s developed that anyone can apply — whether at the poker table, in markets, or in life.