20VC: Annie Duke on Reversible vs Irreversible Decisions, How To Evaluate Risk, The Theory of Sunk Cost in Venture & How to Optimise Both the Discussion and Quality of Investment Decisions

Annie Duke joins us on 20VC

Annie Duke made her name as a professional poker player. She won a World Series of Poker bracelet winner at the 2004 Tournament of Champions. And, she is the only woman to win the NBC National Poker Heads Up Championship. Annie has authored two National Bestsellers “Thinking in Bets” & “How To Decide”.

“What good poker players and good decision-makers have in common is their comfort with the world being an uncertain and unpredictable place.”

Annie Duke, Thinking in Bets

Today, Annie is also the founder of the non-profit How I Decide. They develop curricula and tools to improve decision making and critical thinking skills for under-served middle schoolers.


In Today’s Episode You Will Learn:

1.) How did Annie go from poker to Bestselling author and coach of the world’s leading investors?

2.) How does Annie Duke check the nature of risk? What is good risk vs bad risk? How does Annie think through reversible vs irreversible decisions? What is her framework? Why does Annie believe most irreversible decisions are actually reversible? How does it change your thinking?

3.) How does effective solo-decision-making differ from effective group decision-making? What decision-making biases does Annie often see venture being guilty of making? What 3 things can one do to improve the decision-making of the collective group?

4.) How does Annie Duke think about sunk cost? When is enough, enough and you should walk away? Does this tie into Annie’s thinking on portfolio theory? How does Annie think about pre-mortems? What is their ideal structure? What does she include?

5.) How does Annie define critical thinking? What tips would Annie give to someone to advance their level of critical thinking? What behaviours can one install to seek to protect critical thinking? How does this differ in team environments?

“We don’t win bets by being in love with our own ideas. We win bets by relentlessly striving to calibrate our beliefs and predictions about the future to more accurately represent the world. In the long run, the more objective person will win against the more biased person. In that way, betting is a form of accountability to accuracy.”

Annie Duke

Item’s Mentioned In Today’s Episode

Annie’s Favourite Book: The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing

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