We Study Billionaires - The Investors Podcast

Becca and Rob from AnchorWatch join Preston to unpack the future of Bitcoin custody and insurance. They explore multisig security, time-locked vaults, inheritance planning, insured yield products, and how institutional players like banks and insurers are adopting crypto through innovative custody models, convertible debt strategies, and reinsurance collaborations. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 09:26 - How AnchorWatch uses Miniscript and multisig for Bitcoin custody 15:20 - Why Bitcoin is gaining traction in institutional asset management 19:07 - AnchorWatch’s approach to inheritance and asset protection 27:05 - What Fannie Mae and Freddie Mac's crypto guidance means for lending 39:51 - How Bitcoin custody is evolving to resemble traditional banking 40:28 - How insurance firms are gaining Bitcoin exposure via convertible debt 45:22 - The potential for Bitcoin-denominated insurance products 46:05 - AnchorWatch's collaboration with institutional partners like Allianz 47:07 - Yield opp

In this episode, Stig Brodersen speaks with David Fagan, a successful entrepreneur and investor, about the powerful overlap between building businesses and investing in public markets. They explore why business owners often think differently about diversification, dividends, and risk—and how habits, friendships, and clarity of purpose shape long-term success in both business and life. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 05:35 – Why some business owners often become better investors through firsthand experience with risk, volatility, and capital allocation. 14:57 – The blind spots business owners have when they enter the world of investing. 23:09 – Why you might shift your attitude toward dividends after experiencing firsthand how brutal capitalism is. 28:30 – David shares the daily habits that help him stay grounded, including exercise, reading, and reflection. 35:49 – A different take on “you are the average of the five people you spend the most time with”—and the tradeoffs of seeking higher

On today's episode, Clay is joined by Shawn O'Malley to discuss his work on The Intrinsic Value Podcast and two key holdings from The Intrinsic Value Portfolio. Shawn recently launched The Intrinsic Value Podcast alongside co-host Daniel Mahncke, where they conduct weekly deep dives into companies while building their own concentrated portfolio of 20 holdings.  In this conversation, they explore Reddit's transformation from an unprofitable tech IPO to a rapidly growing, cash flow positive business, and examine Uber's dominant market position and diversified revenue streams. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 02:01 - Shawn's process for conducting weekly company deep dives on The Intrinsic Value Podcast. 16:14 - How Reddit transformed from an unprofitable IPO to a rapidly growing cash flow positive business. 29:27 - How Reddit’s user base presents unique challenges for its advertising business. 44:11 - Why Bill Ackman invested $2 billion in Uber’s stock. 52:29 - Why Uber is well-positioned to be

Andrew and Jesse join Preston to discuss Smarter Web’s transformation into a major Bitcoin Treasury firm, UK market dynamics, valuation strategies, and future growth plans, including preferred shares. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 14:02 - What is MNAV and why is it a crucial metric for valuing Bitcoin Treasury firms? 35:20 - How does Smarter Web plan to maintain its lead in the UK Bitcoin market amid rising competition? 49:52 - What are the benefits and risks of investing in a Bitcoin Treasury company versus Bitcoin directly? Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Slides presented (Part 1). Slides presented (Part 2).  Smarter Web Company's Website. Smarter Web Company's X Account. Andrew’s X Account. Jesse'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. N

On today’s episode, Kyle Grieve discusses the power of mental models, how they sharpen our thinking, and how they improve our decision-making in investing and everyday life. He explores various key concepts in general thinking, including the circle of competence, inversion, first-principles thinking, probabilistic thinking, and more. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 02:01 - What exactly are mental models? 04:37 - The three failures people have with interacting with reality. 08:43 - A simple 6-step framework for making mentals into a habit. 17:45 - How to utilize what you already know to gain an edge. 29:40 - The importance of thinking in first principles to improve your ability to innovate and simplify. 36:10 - How to use thought experiments to analyze a business. 41:14 - Why using second-order thinking can rapidly enhance your quality of thinking. 49:46 - How probabilistic thinking helps make sense of a dynamic world. 58:54 - Why spending time thinking about a problem backwards can improve your

On today’s episode, Kyle Grieve discusses Charlie Munger’s legendary speech, The Psychology of Human Misjudgment, and unpacks all 25 of his cognitive biases that often lead even the most intelligent people to make poor decisions. Drawing from Poor Charlie’s Almanack, Kyle explores how these psychological tendencies—like incentive-caused bias, social proof, and inconsistency avoidance—can distort our thinking in business, investing, and everyday life. He blends Munger’s timeless wisdom with real-world investing examples, personal experiences, and practical strategies to help listeners make better, more rational decisions. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:02 - Why incentives quietly override moral behavior. 06:32 - Why liking and disliking an investing thesis can distort reality. 09:54 - Why doubt avoidance cause investors to take significant risks in things like IPOs. 12:07 - How inconsistency avoidance causes a lazy creep into our thinking processes. 24:38 - How to avoid the destructive effec

Bitcoin market insights, Treasury trends, stablecoin regulation, and bold predictions for Bitcoin's future. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:21 - How global liquidity and leverage affect Bitcoin's market performance 08:56 - The evolving role and risks of Bitcoin Treasury companies 17:26 - Why stablecoin regulations are reshaping digital finance 18:35 - What the Genius Act means for bank and non-bank stablecoin issuers 21:03 - How Tether and JPM are responding with gold tokens and Layer 2 solutions 24:50 - Why the Base network's centralization raises concerns 27:45 - Differing views on the US dollar's future amid AI-driven economic shifts 35:30 - Long-term predictions for Bitcoin and gold prices 40:33 - The strategic role of Bitcoin options trades 48:06 - Legal strategies for enforcing advertising contract disputes Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Related Episode: ⁠Bitcoin Mastermind 1st Q

In this unusually personal and candid episode, William Green answers a wide range of probing questions posed by listeners to his podcast and readers of his book, “Richer, Wiser, Happier: How the World’s Greatest Investors Win in Markets & Life.” Here, William discusses the key qualities, principles, and practices he’s observed in the best investors; how they handle adversity; what he’s learned from his own setbacks, failures, and mistakes; and how he’d invest if he were starting over. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 01:19 - What were the three best decisions William Green ever made? 17:04 - What Charlie Munger and Bill Miller can teach us about handling adversity. 23:40 - Why he views indomitable perseverance as the key to success. 34:52 - What drives investing stars like Bill Ackman, Will Danoff, and Mario Gabelli. 48:19 - Why the best investors focus on reducing complexity. 01:03:58 - How to succeed while constructing a calmer, more spacious life. 01:12:50 - How William approaches the art

In this episode, Clay dives deep into the remarkable story of Heico — a quiet compounder that’s delivered over 22% annual returns for more than three decades. While aerospace may seem like a commoditized or slow-moving industry, Heico flips that assumption on its head.  Clay breaks down how the Mendelson family transformed a struggling parts supplier into a $38 billion industry leader through exceptional capital allocation, a culture of ownership, and a nearly unbreakable moat built on regulatory mastery and being a partner that customers can trust. Whether you're an investor, entrepreneur, or business strategist, this episode offers timeless lessons on how to build and sustain a truly durable business. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 01:27 - The story of how the Mendelsons took a tiny parts supplier and turned it into a $38B aerospace powerhouse. 06:47 - How Heico turned strict FAA regulations into its biggest competitive advantage. 10:10 - Why airlines prefer Heico parts over the OEM alternati

Jim Chanos and Pierre Rochard face off on Bitcoin-native corporates, debating governance, valuation models, capital structure, and whether BTC on the balance sheet adds value or risk. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro  02:27 - Why Jim Chanos is short BTC companies but long Bitcoin itself 05:44 - Pierre Rochard's view on using corporate debt/equity to acquire BTC 13:03 - Capital structure tools best suited for BTC-native companies 14:12 - Whether BTC treasuries offer more than just bull-market beta 19:23 - The risks of NAV premiums and misaligned management incentives 20:16 - Debate over proper valuation frameworks: NAV vs. cash flow 24:30 - Could BTC treasuries evolve into financial infrastructure—or stay niche? 26:25 - The systemic implications of too many firms holding BTC on balance sheets 36:22 - 2030 predictions: spot BTC vs. BTC-native equities vs. ETFs 40:17 - What a “responsible” BTC treasury strategy could look like Disclaimer: Slight discrepancies in the timestamps may occ

On today’s episode, Kyle Grieve discusses the principles of value investing, including how to distinguish between speculation and true investing, the dangers of Wall Street's incentive structures, and the importance of prioritizing downside protection over upside potential. We’ll also delve into discipline for value investing, how to develop a margin of safety mindset, and how to build a risk-averse strategy and portfolio. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 05:04 - Why most investors speculate rather than invest—and how to tell the difference 11:01 - Why fund managers have structural weaknesses that require them to prioritize the wrong things 13:26 - Why EBITDA can mislead—and how it hides a business’s actual condition 16:46 - Why value investors focus more on downside protection than upside potential 18:47 - How to think about margin of safety when constructing a portfolio 31:51 - The three temperamental traits most critical to successful value investing 36:38 - Why value invest

In this episode, Clay reviews Lee Freeman-Shor's book — The Art of Execution. Freeman-Shor studied 45 of the world's top investors over seven years, revealing why investment success depends far more on execution than stock picking. Through analysis of nearly 1,000 investments, he discovered that even the best investors are wrong half the time, but their success comes from how they handle both winners and losers.  This episode provides essential lessons on the execution strategies that determine long-term investment success. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 06:07 - The three types of investor behaviors when facing losing positions and their outcomes. 08:37 - The psychological biases that trap investors in losing positions for years. 11:48 - Why even the world's best investors are wrong 51% of the time. 38:17 - Why selling winners early is more damaging than holding losers too long. 56:25 - How concentration beats diversification for generating superior long-term returns. 58:42 - Why execution mat

Preston Pysh welcomes back NVK, renowned Bitcoin expert and founder of Coinkite, for an in-depth conversation on the future of Bitcoin, the evolving dynamics of its core development, and the promising rise of decentralized platforms like Nostr. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro  02:01 - How Bitcoin's increasing price may sustain mining incentives post-halving 09:37 - The evolution from Satoshi’s original code to the current Bitcoin Core 14:15 - Insights into Bitcoin Knots and the separation of wallet and consensus code 19:41 - Critiques of Bitcoin’s development scene and current conference culture 20:09 - The controversy surrounding Bitcoin Core’s GitHub governance 24:22 - Debates around removing the OP_RETURN 83-byte limit 32:23 - Nostr’s potential to revolutionize identity and AI communication 35:45 - Key adoption challenges facing Nostr and possible solutions 44:44 - The philosophy and features behind Coinkite’s hardware wallets Disclaimer: Slight discrepancies in the timestamps ma

In this episode, Stig Brodersen speaks with Guy Spier who has outperformed the S&P 500 since 1997, with a 9.6% vs. 8.8% CAGR. They explore why Guy invested in The Economist, and how friendships, service, and living by an inner scorecard guide his life and investment philosophy. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 02:27 - Why Guy Spier decided to invest in The Economist. 13:16 - How Guy is living by his inner scorecard. 55:16 - Why friendships are there for a reason, a season, or a lifetime. 55:16 - How does Guy invest in friendships? 01:09:03 - How to facilitate thoughtful conversations with friends. 01:22:03 - How do you seek wisdom? 01:44:04 - How do you identify how to best be of service? 01:57:43 - What money can and can’t buy you. 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

In this episode, Clay shares the key principles behind his personal investment approach. His approach has been shaped by over a decade of experience and lessons from great investors like Charlie Munger, Nick Sleep, and Chris Mayer. He explains how he builds a portfolio focused on high-quality businesses and long-term compounding. It’s a candid look at how he filters out the noise and plays the game on his own terms. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:19 - How Clay defines and pursues financial independence through investing. 05:22 - The lessons Clay learned from Charlie Munger, Nick Sleep, and Chris Mayer. 08:35 - How Clay constructs and thinks about his personal portfolio. 16:22 - Why great businesses often beat cheap stocks over the long run. 27:05 - What “sidecar investing” means and how to apply it. 58:08 - The importance of simplicity and ignoring market noise. 01:04:26 - Why patience may be the biggest edge in investing. Disclaimer: Slight discrepancies in the timestamps may occ

James and Preston dissect the evolving cryptocurrency landscape—from market structure transitions and on-chain data missteps to Bitcoin mining incentives and the cutting-edge strategies behind Bitcoin Treasury companies. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro  02:47 - Lessons learned from the 2020-2021 crypto cycle 04:59 - Why the crypto market is shifting from spot to leverage-driven models 05:54 - The role of futures and ETFs in today’s low-activity network 10:42 - How mining subsidies influence innovation and decentralization 14:08 - Why fees are crucial for protecting Bitcoin from censorship 19:32 - How Bitcoin’s dominance affects altcoin cycles 26:35 - Insights into tokenized sovereign debt and blockchain scalability 32:15 - The potential long-term shift in global KYC regulations 33:13 - The rise and risks of Bitcoin Treasury companies 38:53 - Key differences between MicroStrategy and competitors Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform di

On today’s episode, Kyle Grieve discusses how Warren Buffett evolved from a young entrepreneur with an intense fascination for numbers into one of history’s most disciplined and independent investors. The episode explores the key influences, early lessons, and defining choices that shaped his unique approach to business and capital allocation. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:04 - How Buffett showed business instincts as a young boy 03:44 - How Buffett used scuttlebutt early in his career 04:26 - The influence Buffett’s father had on his mindset 11:06 - Three timeless principles Buffett learned from Ben Graham 19:11 - The period Buffett compounded at over 50% annually 23:49 - How a “cigar butt” taught Buffett pricing power 29:33 - Why Buffett embraced concentrated investing from the start 45:14 - Why Buffett saw media companies as modern-day toll bridges 54:02 - Buffett’s core disagreement with efficient market theory 1:00:00 - What Buffett learned while rescuing

On today’s episode, Kyle Grieve chats with Ian Cassel about what separates good, great, and GOAT investors by breaking down the five core skills of stock picking. We'll also explore how elite investors evolve, avoid common traps, and develop underappreciated edges that compound into long-term outperformance. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 02:30 - What sparked Ian’s obsession with investor greatness. 07:41 - The two metrics that reveal actual investing skill. 13:07 - Why radical self-honesty drives long-term improvement. 16:41 - The track records that define good, great, and GOAT investors. 19:09 - What a jiu-jitsu legend taught Ian about mastery. 19:09 - Five core skills every top investor must develop. 36:19 - Why staying the same means falling behind. 44:16 - Hidden skills that give GOATs an unfair edge. 01:08:16 - The rare skill Ian leverages for outperformance. 01:11:15 - Offense vs. defense: applying it to your portfolio. Disclaimer: Slight discrepancies in the timestamps ma

Preston sits down with Chris and Joe to explore how Bitcoin is changing the way we think about corporate treasuries, asset valuation, and investment risk. They dive into the STRIVE report, debate traditional financial models, and propose new frameworks for evaluating assets in a Bitcoin-denominated world. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 01:58 - How Bitcoin reshapes asset valuation and opportunity cost analysis 10:23 - Why Internal Rate of Return (IRR) is crucial for comparing investments in a Bitcoin world 13:05 - The challenges of applying traditional DCF models to Bitcoin 20:45 - The concept and implications of the equity stability premium 22:59 - How Bitcoin’s volatility can be reframed as an asset rather than a liability 26:19 - Why volatility perceptions differ between traditional finance and Bitcoin maximalists 31:08 - How Bitcoin adoption trends impact valuation and investment strategy 08:29 - Preston’s personal journey in reevaluating valuation models using Bitcoin 40:46 -

In this episode, William Green chats with investing legend Bill Nygren, who oversees about $25 billion at Harris Associates. Bill is the firm’s Chief Investment Officer for US Equities & co-manages two flagship mutual funds: Oakmark Select & Oakmark Fund. Here, he discusses the processes, principles, habits & mindset that have enabled him to beat the market over three decades. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 05:32 - How Bill Nygren became a contrarian bargain hunter. 18:05 - Why sports gambling companies often refuse to take his bets. 47:56 - What three qualities he seeks in any company. 01:00:05 - How he scored big on Amazon, Google, Apple & Netflix. 01:11:11 - Why he never relaxes his disciplined focus on valuation. 01:16:04 - What he learned from hedge fund star Michael Steinhardt. 01:24:47 - How Bill’s team performs “Devil’s Advocate Reviews” for each stock. 01:33:55 - Why he developed his “Mistake Management Protocol.” 01:46:51 - How to succeed without ruining your health or yo