We Study Billionaires - The Investor’s Podcast Network

TIP773: How Systems and Simple Math Shape Better Investing w/ Kyle Grieve

Host Kyle shares mental models from systems thinking and mathematics that shape his personal investing approach. He explains concepts like feedback loops, kill criteria, cone of uncertainty, scale, algorithms, critical mass, compounding, power laws, randomness, and regression to the mean, grounding each in concrete investing examples. Throughout, he emphasizes structuring decisions to favor long-term cash flow compounding while surviving volatility and avoiding portfolio blowups.

Nov 30, 2025

TIP772: How Great Compounders Turn Time Into a Superpower w/ Kyle Grieve

Host Kyle Grieve analyzes the book "The Compounders" and explores why a small group of exceptional businesses can compound capital at high rates for decades. He explains the central importance of maintaining returns on invested capital above the cost of capital, sustaining high reinvestment rates, and leveraging time, while highlighting the roles of decentralization, culture, incentives, and working capital discipline. The episode walks through multiple case studies, including Nvidia, Lifco, Indutrade, Bergman & Beving, AdTech, Constellation Software, Heico, Ametek, and Judges Scientific, to illustrate how great compounders turn time into a superpower.

Nov 28, 2025

BTC255: Bitcoin Is For Everyone w/ Natalie Brunell (Bitcoin Podcast)

Host Preston Pysh interviews journalist and educator Natalie Brunel about her book "Bitcoin Is for Everyone" and how her immigrant family's experience with the American dream and the 2008 financial crisis shaped her worldview. They discuss why the current fiat-based financial system feels broken, how inflation and debt erode savings and opportunity, and why Natalie believes Bitcoin is a hopeful, apolitical form of money that can restore property rights, enable low time preference, and counter systemic wealth concentration. The conversation also covers the challenge of explaining Bitcoin simply, its relationship to energy and human rights, and broader geopolitical and industrial vulnerabilities in the US.

Nov 26, 2025

TIP770: Mastering the Markets w/ Andrew Brenton

Host Clay Fink interviews Andrew Brenton of Turtle Creek Asset Management about why he believes public markets have become less efficient and how that shapes his value-oriented investing approach. They discuss Cliff Asness's "The Less Efficient Market Hypothesis," behavioral biases, bubbles, and the impact of passive flows and short-termism. Brenton then walks through Turtle Creek's investment theses and valuation approach for Floor & Decor and Kinsale Capital, and explains how he thinks about cyclicality, intrinsic value, portfolio optimization, and sticking with a high-active-share strategy through periods of underperformance.

Nov 21, 2025

BTC254: Bitcoin & Macro Overview w/ Luke Gromen Q4 2025 (Bitcoin Podcast)

Host Preston Pysh interviews macro analyst Luke Gromen about growing financial stress in the U.S. and globally, focusing on the Treasury's heavy reliance on short‑term funding, strain in repo and funding markets, and the fiscal math of interest plus entitlements nearly consuming all tax receipts. They discuss how Bitcoin acts as an early warning signal for tightening liquidity, why gold is increasingly favored by sovereigns, the contradictory policy push around stablecoins, and how AI capex, energy constraints, geopolitical shifts, and rare earth dependencies further complicate the outlook. Gromen argues policymakers are trapped between preserving the bond market and reindustrializing the U.S., and that some form of sharp market "whoosh down" may be needed before large‑scale liquidity support returns.

Nov 19, 2025

TIP769: How Home Depot's Founders Built a $300 Billion Company from the Ground Up w/ Kyle Grieve

Host Kyle Grieve provides a narrative deep dive into the origins and growth of Home Depot, drawing heavily from the founders' book "Built from Scratch". He traces Bernie Marcus and Arthur Blank's early careers, their firing from Handy Dan, the creation of the Home Depot concept, the role of key partners like Ken Langone and Pat Farah, and the company's early financing and expansion challenges. The episode then examines Home Depot's competitive strategy, supplier relationships, management philosophy, and long-term performance, extracting lessons for entrepreneurs and investors about culture, pricing, competition, and disciplined growth.

Nov 16, 2025

TIP768: Best Quality Stock Idea Q4 2025 w/ Clay Finck

Host Clay Finck presents Interactive Brokers (IBKR) as his quarterly best quality stock idea, analyzing its business model, economics, and long‑term growth prospects. He covers the firm's history and founder Thomas Pederphy's automation-focused culture, its revenue drivers like commissions and net interest income, and its unique low-cost, tech-heavy positioning versus competitors such as Charles Schwab and Robinhood. The episode also explores IBKR's competitive advantages, management incentives, valuation, key risks, and why Clay holds a 2% personal position in the stock.

Nov 14, 2025

BTC253: Quantum Computing and Bitcoin w/ Charles Edwards (Bitcoin Podcast)

Host Preston Pysh speaks with Charles Edwards about what quantum computing is, how it works at a high level, and why it matters for Bitcoin's security. They distinguish physical from logical qubits, review industry forecasts for when quantum computers could break current cryptography, and examine Bitcoin's specific vulnerabilities and proposed upgrades like BIP360. The conversation also covers migration logistics, governance challenges for the Bitcoin community, and how to think about investing in quantum technologies as both an opportunity and a hedge.

Nov 12, 2025

TIP767: Mastermind Discussion Q4 2025: Sanofi, Remitly & Crocs w/ Stig Brodersen, Tobias Carlisle, and Hari Ramachandra

The episode is a quarterly mastermind discussion where Stig Brodersen, Tobias Carlisle, and Hari Ramachandra each pitch an investment idea and stress-test each other's theses. Hari presents Sanofi as a relatively cheap, dividend-paying global biopharma with durable vaccine and immunology franchises that he views as a "T-bill with growth" type holding. Stig analyzes Remitly, a fast-growing digital remittance platform, weighing its strong unit economics and underbanked niche against strategic drift, intense competition, and heavy stock-based compensation, while Toby pitches Crocs as a deeply undervalued, cash-generative footwear brand facing fashion, tariff, and acquisition risks but offering significant upside if issues are managed.

Nov 9, 2025

TIP766: Intelligent Fanatics: How Great Business Leaders Win w/ Clay Finck

Host Clay Fink summarizes the book "Intelligent Fanatics" by Ian Cassel and Sean Iddings, explaining how extraordinary business leaders build durable competitive advantages through culture, incentives, and long-term thinking. He dives into case studies of Herb Kelleher at Southwest Airlines, Les Schwab at Les Schwab Tire Centers, and Chester Cajot at QuickTrip, highlighting their unconventional strategies and employee-first philosophies. The episode distills common traits of intelligent fanatics and connects them to how investors can better evaluate management teams and business quality.

Nov 7, 2025

TIP765: What the World's Great Philosophers Can Still Teach Us About Wealth and Wisdom w/ Kyle Grieve

Host Kyle Grieve explores how ideas from major philosophers can improve investing decisions, emotional control, and definitions of success. Drawing on Ethan Everett's book 'The Investment Philosophers', he connects thinkers like Spinoza, Nietzsche, Hume, Voltaire, Pascal, William James, Baudrillard, Schopenhauer, Montaigne, Kierkegaard, Camus, Martin Buber, and Bruce Lee to practical investing mindsets and behaviors. The episode blends philosophical concepts with real investing examples from Kyle and well-known investors such as Warren Buffett, Howard Marks, George Soros, and David Einhorn.

Nov 2, 2025

TECH006: Open-Source AI That Protects Your Privacy w/ Mark Suman (Tech Podcast)

Host Preston Pysh interviews Maple AI founder Mark Suman about building privacy-preserving, verifiable AI using trusted execution environments and secure enclaves. They discuss the cultural importance of privacy at Apple, the risks of feeding proprietary AI systems with intimate personal data, and how verifiable, open-weight models can mitigate manipulation and data leakage. The conversation also covers Maple's architecture, AI memory, the open-source vs proprietary model race, AI-assisted software development, and the potential future of running personal AI servers at home.

Oct 29, 2025

TIP763: Investing Lessons for My 18-Year-Old Self w/ Clay Finck

Host Clay Finck delivers a solo episode structured as a letter to his 18-year-old self, sharing 12 key lessons from his investing journey, including starting early, using index funds, focusing on great businesses, and managing emotions. He explains why beating the market is difficult but possible, how patience and time horizons create an edge, and why moats, management quality, and megatrends matter more than simple valuation metrics like P/E. The episode also covers investor psychology, avoiding unnecessary complexity, building a peer network, and developing an independent, process-driven investment philosophy that fits one's personality and goals.

Oct 24, 2025

BTC252: Bitcoin Mastermind Q3 2025 w/ Joe Carlasare, Jeff Ross, and American HODL (Bitcoin Podcast)

Preston Pysh hosts a quarterly Bitcoin mastermind with Jeff Ross, American Hodl, and Joe Carlisari focused on current Bitcoin sentiment, macroeconomic conditions, and how hard assets like gold and Bitcoin fit into the evolving global landscape. They argue the traditional four-year Bitcoin cycle is breaking down, discuss golds recent outperformance versus both stocks and Bitcoin, and explore implications of liquidity trends, Fed policy, and a potential long period of hard-asset outperformance. The conversation also covers the US strategic Bitcoin reserve, AI and robotics as economic forces, the state of Bitcoin treasury companies and miners, and rising geopolitical tensions with China and the BRICS bloc.

Oct 22, 2025

TIP761: Tesla Stock Deep Dive w/ Clay Finck

Host Clay Finck delivers a solo deep dive on Tesla, examining its evolution from a misunderstood EV startup into a trillion‑dollar company and a potential AI, robotics, and energy powerhouse. He covers disruptive innovation, Elon Musk's leadership and controversial compensation plan, Tesla's automotive and energy businesses, emerging bets like Optimus and robo‑taxis, intensifying global competition (especially from BYD), and both the bullish optionality and key bear risks around execution, governance, and valuation.

Oct 17, 2025

TECH005: What Tech Is Doing to Us with Justin Evidon (Tech Podcast)

Host Preston Pysh and guest Justin Evidon discuss how modern technology can be a double-edged sword, offering huge benefits while quietly reshaping behavior, privacy, and health. They cover social media recommendation algorithms, data sovereignty, decentralized protocols like Nostr, and emerging privacy-preserving AI tools. The conversation also explores physical impacts of technology such as LED light flicker, blue light, and electromagnetic exposure, along with practical strategies to protect circadian rhythms and use tech more intentionally.

Oct 15, 2025

TIP759: The Art of Spending Money w/ Morgan Housel

Host Clay Fink interviews author Morgan Housel about his book "The Art of Spending Money, Simple Choices for a Richer Life," focusing on how money intersects with happiness, expectations, and independence. They discuss why more money only increases happiness under certain psychological conditions, the dangers of status-driven spending and social debt, and why contentment and autonomy matter more than sheer net worth. In a closing segment, Clay shares his own biggest lessons from the book, including using savings to buy optionality, the power of contrast, and the hidden costs of tying identity to possessions.

Oct 10, 2025

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

Host Preston Pysh and guest Seb Bunney discuss Karen Howe's book "Empire of AI: Dreams and Nightmares of Sam Altman's OpenAI," using it as a springboard to explore Sam Altman's biography, the founding and evolution of OpenAI, and the opaque 2023 boardroom crisis that briefly ousted Altman. They examine OpenAI's unusual nonprofit/for‑profit hybrid structure, its partnership with Microsoft, tensions between AI safety and competitive speed, and the hidden labor and economic costs of training large AI models. The conversation also touches on AGI definitions, human-AI interaction, other labs like Anthropic and DeepMind, NVIDIA's role in AI, and briefly previews their next book on longevity.

Oct 8, 2025

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

Host William interviews investor Arnold Vandenberg about his decades-long exploration of the subconscious mind, one-pointed attention, and flow states, drawing on examples from yogic practices, neuroscience, and extreme situations like concentration camps. Arnold explains how he has used focus, breathwork, self-hypnosis, affirmations, and character development to transform his health, athletic performance, investing career, and resilience in the face of adversity. He also shares his current investment positioning in an overvalued market, emphasizing commodities and capital preservation, and concludes with reflections on happiness, love, and overcoming selfishness.

Oct 5, 2025

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

Host Clay Fink interviews hedge fund manager Derek Pilecki about his recent performance and how he is navigating current market conditions in the financial sector. Pilecki explains his process of targeting ideas with potential to double in three years, combining value investing with an awareness of momentum and technicals, and selectively using leverage at both the company and portfolio level. He discusses opportunities in regional and European banks, beaten-down fintech names, case studies in Robinhood and WEX, and his views on interest rate cuts, inflation, and the real estate market.

Oct 3, 2025

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

Host Preston Pysh interviews investor and technologist Cern Basher about Elon Musk's ecosystem of companies, focusing on Tesla's pivot away from the Dojo training supercomputer toward custom inference chips, and how this underpins autonomous vehicles and humanoid robots. They explore the economics and deflationary impact of Tesla RoboTaxis and autonomous trucking, the massive potential of the Optimus robot to transform labor and corporate balance sheets, the role of Tesla Energy in enabling abundant power, and how these automation trends connect to Bitcoin as a long-term treasury asset in an AI-driven world.

Oct 1, 2025

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

Host Stig Brodersen and co-host William Green have a wide-ranging quarterly Richer, Wiser, Happier discussion on universal truths, money and happiness, and the role of books and teachers in living well. They explore epistemic humility, cultural and psychological differences in values, and how these insights apply to investing decisions. They also examine research on income and happiness, how wealth can and cannot improve life, and share their own reading habits and spiritual influences that shape their thinking about how to live.

Sep 28, 2025

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

Host Kyle Grieve presents a solo deep dive into the career of hedge fund legend Julian Robertson and the rise and fall of his Tiger Fund. He covers Robertson's background, investment philosophy, famous trades such as the mid-1990s copper short, his use of networks and sentiment to find mispricings, and his seven core stock-picking themes. The episode also examines how leverage, fund size, market bubbles, and centralized decision-making contributed to Tiger's eventual closure during the dot-com era.

Sep 26, 2025

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

The episode is a book-club style discussion of Stephen Witt's "The Thinking Machine," focusing on how NVIDIA evolved from a niche gaming graphics company into a central player in the AI revolution. Preston and Seb trace the technical and strategic milestones behind NVIDIA's rise-parallel processing, GPUs, CUDA, and neural networks-while examining Jensen Huang's leadership style, culture-building, and obsession with speed and iteration. They also touch on the implications and risks of AI, Huang's reluctance to address them directly, and preview their next book on OpenAI and Sam Altman.

Sep 24, 2025

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

Host Kyle Grieve shares his personal investing philosophy, tracing how early speculative losses in cryptocurrencies led him toward disciplined value investing in equities. He explains his return goals, focus on absolute rather than relative performance, a two-bucket framework (quality compounders and microcap inflection-point stocks), detailed criteria for evaluating management and capital efficiency, and his sell and portfolio management rules. Kyle also covers concepts like circle of competence, behavioral biases, environment design for inaction, and reflects candidly on mistakes of commission and omission to illustrate how he continues refining his process.

Sep 21, 2025

TIP754: Rule Breaker Investing w/ David Gardner

Host Clay interviews David Gardner, co-founder of The Motley Fool, about his new book "Rule Breaker Investing" and the distinctive growth-oriented philosophy that produced multiple 100-bagger stock picks like Amazon, Netflix, and NVIDIA. Gardner explains why he diverged from Warren Buffett-style value investing, embraces losses as part of a venture-capital-like approach, and focuses on qualitative factors such as leadership, culture, and brand that traditional valuation metrics ignore. The conversation also covers his six traits of Rule Breaker stocks, six habits of Rule Breaker investors, conscious capitalism, the importance of optimism, and several current companies he believes embody his framework.

Sep 19, 2025