TIP714: Bet Big, Bet Rarely: The Dhandho Investing Playbook w/ Kyle Grieve

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: SimpleMining Hardblock Found AnchorWatch DeleteMe Fundrise CFI Education Indeed Vanta Shopify The Bitcoin Way Onramp 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 Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Perianne Boring and Brian Estes join the show to break down today’s most pressing crypto issues—from rising tariffs and DOJ coin audits to the White House Digital Asset Summit. They share insights on the evolving market structure, the future of stablecoin legislation, and how Washington is shaping the next phase of digital finance. Plus, a look at Bitbonds, Thank God For Bitcoin, and the under-the-radar trends that could define the next cycle. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:29 - Key takeaways from the White House Digital Asset Summit 05:48 - Where the stablecoin bill stands and what’s holding it up 04:12 - Senator Moreno's legislative roadmap on digital assets 10:27 - Why tariffs are making headlines again and how they affect digital assets 15:17 - Market trends that may be flying under the radar 19:54 - What the DOJ coin audits mean for the crypto industry 28:10 - How the market structure is evolving with increased regulation 35:58 - The future of banking post-stablecoin legislation 43:05 - How Bitbonds could play a role in the next wave of crypto innovation 52:20 - Insights from the film Thank God For Bitcoin Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Related episode: Making THE Bitcoin Movie w/ Kelly and Brian Estes. Link to the movie: God Bless Bitcoin. The Digital Chamber’s Website. Perianne's X Account. Brian’s X Account. 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? Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Follow our official social media accounts: X (Twitter) | LinkedIn | | Instagram | Facebook | TikTok. Check out our Bitcoin Fundamentals Starter Packs. 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. Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORS Support our free podcast by supporting our sponsors: SimpleMining Hardblock Found AnchorWatch DeleteMe Fundrise CFI Education Indeed Vanta Shopify The Bitcoin Way Onramp Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

On today’s episode, Clay is joined by Niklas Sävås to discuss the business model of serial acquirers.  A serial acquirer is a company that grows primarily by repeatedly acquiring other businesses as a core part of its strategy. Over the past two decades, many serial acquirers have proven to be profitable investments in the stock market including Constellation Software and Lifco AB. In this episode, Clay and Niklas break down the most important factors to understanding the business model as investors. Niklas Sävås is a senior equity analyst at Redeye AB where he does extensive research on serial acquirers in the Nordics. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 01:55 - What a serial acquirer is and why serial acquirers are able to buck conventional thinking on making acquisitions. 08:54 - What the return profile is for serial acquirers in making private acquisitions. 10:35 - Best practices used by successful serial acquirers. 24:49 - Why it’s important to be the buyer of choice as a serial acquirer. 40:18 - The most common challenges that serial acquirers face. 49:01 - The importance of organic growth for serial acquirers. 54:41 - An overview of the Roko IPO. 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. Check out Redeye. Investing by the Books Podcast. REQ Capital Report. Follow Niklas on LinkedIn & X. 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: SimpleMining Hardblock Found AnchorWatch DeleteMe Fundrise CFI Education Indeed Vanta Shopify The Bitcoin Way Onramp 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 Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

 Wall Street veteran and macro expert, James Lavish, and Preston Pysh have a candid back and forth about the Trump tariffs and what the impact in game theory looks like moving forward. They also talk about how it's impacting fixed income, equities, and Bitcoin. Plus how the U.S. might navigate things from here and what's expected ahead. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 04:14 - How MAG 7 dynamics differ from MAGA trade policies 04:48 - Insights from the Street on where equities and crypto are headed 14:07 - How the U.S. dollar contributed to structural trade imbalances 14:49 - Why China's bond selloff may be a response to U.S. tariffs 15:56 - The potential size of the “boggie” in market selloffs and debt 16:23 - Ray Dalio’s framework for understanding today’s deeper economic shifts 16:41 - The case for the end of globalism and what replaces it 23:42 - Why Elon Musk might be at odds with his economic circle 28:02 - What tariffs mean for inflation and the bond market 36:19 - The role of Dollar Stablecoins in the evolving financial system Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES James’ X Account. James’ The Informationist Newsletter. James’ Bitcoin Opportunity VC Fund. 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? Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Follow our official social media accounts: X (Twitter) | LinkedIn | | Instagram | Facebook | TikTok. Check out our Bitcoin Fundamentals Starter Packs. 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. Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORS Support our free podcast by supporting our sponsors: SimpleMining Hardblock Found AnchorWatch DeleteMe Fundrise CFI Education Indeed Vanta Shopify The Bitcoin Way Onramp 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

In today's episode, Stig Brodersen shares 20 pieces of advice with his 20-year-old self. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 02:02 - Why the limits of your language are the limits of your world 06:35 - Why you need to leave your comfort zone 09:05 - Why you can grow from making yourself vulnerable 21:29 - Why you can have anything but not everything 33:29 - Why you should do what you say and say what you do 53:02 - Why you should be intentional with your relationships - but not too much 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. Stig’s blog post on his portfolio and track record since 2014. Stig’s podcast on his journey into financial independence.  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: SimpleMining Hardblock Found AnchorWatch DeleteMe Fundrise CFI Education Indeed Vanta Shopify The Bitcoin Way Onramp 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 Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm