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 Unchained Netsuite Shopify Fundrise 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 Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

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TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

Kyle Grieve discusses how a series of unforgettable real-world stories reveal the hidden psychological traps that derail investors. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:03:07 - How Ro...

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TIP791: Best Quality Stock Idea Q1 2026 w/ Clay Finck

Clay breaks down his best quality stock idea for Q1 2026: Visa. Visa is a global payments network that operates as a toll booth on commerce. Visa is one of the most durable and capital-light business...

13 Feb 1h

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Jeff Booth, Jack, and Nick explore a year-long paper linking Bitcoin to fundamental physics, framing Bitcoin blocks as discrete, quantized units of time. They connect concepts from quantum mechanics a...

11 Feb 1h 16min

TIP790: Wealth Beyond Money w/ Thomas Mueller-Borja

TIP790: Wealth Beyond Money w/ Thomas Mueller-Borja

In this episode, Stig Brodersen speaks with Thomas Mueller-Borja, the Global Co-Head of Real Estate and Global CIO for Value-Add Real Estate at BlackRock. They explore how great investors define games...

8 Feb 1h 19min

TIP789: The Story of Uber w/ Clay Finck

TIP789: The Story of Uber w/ Clay Finck

In this episode, Clay tells the story of Uber. Uber started as a simple idea, and evolved into one of the most disruptive companies of the modern era. Drawing from Brad Stone’s The Upstarts, the episo...

6 Feb 1h 16min

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TECH014: Is AGI Here? Clawdbot, Local AI Agent Swarms w/ Pablo Fernandez & Trey Sellers (Tech Podcast)

Preston, Trey, and Pablo unpack the evolution of AI from agentic capabilities and decentralized systems to practical open-source tools like Clawdbot. They examine AI’s potential, security risks, per...

4 Feb 1h 10min

TIP788: Simple Investing w/ David Fagan

TIP788: Simple Investing w/ David Fagan

Stig Brodersen speaks with David Fagan about the case for indexing and what most investors get wrong about performance, financial advisors, and risk. They explore why missing a few percentage points c...

1 Feb 1h 6min

TIP787: The 5 Types Of Wealth w/ Kyle Grieve

TIP787: The 5 Types Of Wealth w/ Kyle Grieve

Kyle Grieve discusses a refreshingly different take on wealth inspired by The Five Types of Wealth by Sahil Bloom. Rather than focusing solely on money, the conversation explores a more holistic frame...

30 Jan 1h 7min

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