TIP715: Thinking in Bets by Annie Duke

TIP715: Thinking in Bets by Annie Duke

In this episode, Clay explores the book Thinking in Bets by Annie Duke, a guide to making better decisions under uncertainty. Drawing from her career as a professional poker player, Annie shares how to separate decision quality from outcomes and avoid the trap of “resulting.” Clay also discusses how our brains are wired for certainty, why embracing probabilistic thinking leads to better outcomes, and the value of building a truth-seeking support system. Additionally, he uncovers tools like backcasting, premortems, and kill criteria to improve long-term decision-making as investors. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 01:36 - What it means to “think in bets” and how poker can sharpen decision-making. 05:57 - The concept of “resulting” and how it distorts our ability to evaluate decisions. 08:17 - Why good decisions can still lead to bad outcomes—and vice versa. 09:41 - The role of System 1 vs. System 2 thinking in making better choices. 10:44 - How investing parallels poker with incomplete information and uncertainty. 26:29 - How to build a feedback loop that separates luck from skill. 34:03 - The importance of building a truth-seeking group or “buddy system.” 35:02 - The dangers of confirmation bias and how beliefs are often formed by default. 52:54 - How backcasting and premortems can help map out future decisions. 57:16 - The power of setting kill criteria to avoid emotional decision-making. And so much more! Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here. Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Annie Duke’s book: Thinking in Bets. Mentioned book: Big Mistakes. Related Episode: TIP623: The Art of Decision Making w/ Annie Duke. Related Episode: RWH015: Betting Better in Markets and Life w/ Annie Duke. Follow Clay on LinkedIn & X. Check out all the books mentioned and discussed in our podcast episodes here. Enjoy ad-free episodes when you subscribe to our Premium Feed. NEW TO THE SHOW? Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter. Check out our We Study Billionaires Starter Packs. Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORS Support our free podcast by supporting our sponsors: HardBlock Human Rights Foundation Vanta Plus500 Netsuite Shopify HELP US OUT! Help us reach new listeners by leaving us a rating and review on Spotify! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Episoder(1172)

TIP759: The Art of Spending Money w/ Morgan Housel

TIP759: The Art of Spending Money w/ Morgan Housel

On today’s episode, Clay is joined by Morgan Housel to discuss his newest book, The Art of Spending Money — Simple Choices for a Richer Life.  Morgan Housel is a partner at The Collaborative Fund. He...

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TECH004: Sam Altman & the Rise of OpenAI w/ Seb Bunney

TECH004: Sam Altman & the Rise of OpenAI w/ Seb Bunney

Seb and Preston analyze the book "Empire of AI," reflecting on Sam Altman’s rise and OpenAI’s transformation from a nonprofit into a powerhouse AI firm. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intr...

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RWH061: How To Thrive No Matter What w/ Arnold Van Den Berg

RWH061: How To Thrive No Matter What w/ Arnold Van Den Berg

In this episode, William Green chats with Arnold Van Den Berg, a revered investor whom he spotlighted in his book, Richer, Wiser, Happier. Against all odds, Arnold has run a highly successful investme...

5 Okt 20252h 20min

TIP758: Current Market Conditions & Investment Opportunities w/ Derek Pilecki

TIP758: Current Market Conditions & Investment Opportunities w/ Derek Pilecki

On today’s episode, Clay is joined by Derek Pilecki to discuss the current market conditions and the investment opportunities he’s finding in today’s chaotic environment. Derek is a managing member a...

3 Okt 20251h 2min

TECH003: Elon Musk's Tesla Robotaxi, Optimus, and more w/ Cern Basher (Tech Podcast)

TECH003: Elon Musk's Tesla Robotaxi, Optimus, and more w/ Cern Basher (Tech Podcast)

Cern Basher joins Preston Pysh to talk about robotaxi and robo-trucking economics, Optimus humanoid robots, and Wall Street’s short-term blind spots. Cern also unpacks Tesla’s Dojo shutdown, its tru...

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TIP757: Richer, Wiser, Happier Q3 2025 w/ Stig Brodersen & William Green

TIP757: Richer, Wiser, Happier Q3 2025 w/ Stig Brodersen & William Green

Each quarter, Stig Brodersen sits down with his friend and co-host William Green, author of Richer, Wiser, Happier. Together, they reflect on the lessons and stories that have made them Richer, Wiser,...

28 Sep 20252h 7min

TIP756: The Rise and Fall of Julian Robertson’s Tiger Fund w/ Kyle Grieve

TIP756: The Rise and Fall of Julian Robertson’s Tiger Fund w/ Kyle Grieve

Kyle Grieve discusses the rise and fall of legendary investor Julian Robertson, exploring how he built Tiger Fund into one of the most successful hedge funds of its era. You’ll learn about his investi...

26 Sep 20251h 2min

TECH002: Jensen Huang & NVIDIA w/ Seb Bunney - Review of The Thinking Machine by Stephen Witt

TECH002: Jensen Huang & NVIDIA w/ Seb Bunney - Review of The Thinking Machine by Stephen Witt

Preston and Seb launch their tech book review series with a deep dive into The Thinking Machine, a book about NVIDIA and its CEO Jensen Huang. They explore NVIDIA’s transformation from a gaming hard...

24 Sep 20251h 7min

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