Jason Strasser

How a $4M poker champion turned every decision you make into a bet — and why that changes everything Annie Duke, Ph.D. (@AnnieDuke — WSOP bracelet winner, $4M in tournament winnings, national bestselling author of Thinking in Bets, Special Partner @ First Round Capital, PhD in Cognitive Psychology from Penn) "A good bet is one that carries positive expectancy. What a good bet is NOT — is one that wins." We cover: - Why every decision you've ever made is a bet (even ordering off a menu) - The green light vs. red light rule for separating outcomes from decisions - How to build an EV calculation for something as messy as choosing a career - Why loss aversion is secretly an uncertainty problem — and how great risk takers solve it - When to trust your gut vs. when gut feel is just bias in disguise - The pre-mortem framework — how to find your blind spots before it's too late - Mental time travel: the parenting tool Annie uses to raise better decision-makers - How she explained luck, hard work & probability to her 4 kids at the dinner table Thanks for making time, Annie. Been a fan of yours for a while. Timestamps: 00:00 Intro 01:12 Defining bets as resource allocation under uncertainty 04:52 Positive expectancy vs. outcome-based evaluation 06:11 Resulting: Why outcomes are not proxies for decision quality 15:19 Calculating expected value in high-variance career paths 18:55 Moving from implicit intuition to explicit decision modeling 24:27 Using base rates and reference classes for startups 30:26 Psychological traits of elite risk takers and traders 31:33 How prospect theory and loss aversion distort risk 45:12 Deconstructing gut feel and the role of intuition 49:36 Evaluating optionality and impact in fast-moving environments 57:13 Mental time travel: Tools for managing temporal discounting 01:01:31 Quantifying the intersection of luck and hard work 01:04:43 Internalizing a probabilistic worldview for long-term edge