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In this episode, Vlad Tenev reflects on Robinhood’s transformation from a three-product platform to a diversified ecosystem with 11 significant revenue-generating lines, including prediction markets, a card program, and a growing interest in global expansion. He explains how shifting macro conditions—rising interest rates and a tougher trading environment—pushed Robinhood to pivot toward a broader, all-weather business model, focusing on wallet share, assets under custody, and higher-value subscription offerings like Robin Hood Gold. He articulates a multi-arc strategy: to dominate active trading, to become the go-to wallet for the next generation’s financial needs, and to scale into business and institutional services, potentially outside the United States. The discussion then moves to recent product launches: an expanded, web-accessible prediction markets with sports and the ability to trade individual actions, a Cortex AI assistant integrated into trading workflows, and tokenization initiatives that aim to unlock illiquid assets by enabling 24/7 trading and DeFi-style capabilities. Vlad emphasizes the practical goals of technology to reduce costs and improve user experiences, while maintaining market integrity and compliance as cornerstone challenges for broader adoption. A recurring theme is the balance between growth and ensuring accessibility for both new and seasoned investors, with an emphasis on not merely attracting traders but embedding Robinhood in people’s broader financial lives. The conversation also touches on the evolving relationship between public markets and retail investors, noting how openness to retail participation has shifted in IPOs and private company financing, partly driven by Peter’s and OpenDoor’s experiences. Vlad also shares aspirational discussions about Harmonic, his mathematics-focused AI venture, and stories about how advances in AI could eventually influence finance, physics, and beyond. The episode closes with reflections on staying engaging during earnings communications, the potential for retail investors to influence AI policy, and a light note on snow in California as a playful glimpse of the 2026 outlook.

In early 2021, a viral battle erupted in the stock market, primarily between internet investors and large hedge funds, sparked by Reddit user Keith Gill's observations about GameStop. Gill believed the company was undervalued despite its struggles, investing $53,000 in its stock. Meanwhile, hedge funds had shorted 130% of GameStop's stock, betting on its decline. This created an opportunity for Redditors to drive up the stock price, leading to a "short squeeze" that forced hedge funds to cover their losses, resulting in massive financial turmoil for them. By January 26, GameStop became the most traded stock in the U.S., skyrocketing from a few dollars to over $490, with hedge funds losing $70 billion. The movement gained momentum, with billboards urging the public to buy GameStop stock. However, Robinhood restricted buying, leading to public outrage and accusations of market manipulation. The SEC launched an investigation, and the situation raised questions about the financial system's integrity. The GameStop rebellion highlighted the intersection of social media and finance, revealing widespread discontent with the financial system and prompting discussions on potential regulations. This event marked a cultural shift in how the financial market is perceived, with implications for the future of investing.

In this episode, Patrick Bet-David interviews Michael Saylor, CEO of MicroStrategy, who recently made headlines by purchasing $4.6 billion worth of Bitcoin, marking it as the largest single Bitcoin purchase ever. Saylor reflects on his previous appearances on the podcast, noting the fluctuating stock value of MicroStrategy and the company's ongoing strategy of acquiring Bitcoin without selling it. He emphasizes that Bitcoin represents a digital form of real estate, akin to owning Manhattan in cyberspace, and believes that its value will continue to grow significantly over the coming years. Saylor discusses MicroStrategy's financial strategy, including raising $21 billion in equity and fixed income securities to fund Bitcoin purchases. He explains that the company has consistently bought Bitcoin since August 2020, with a total investment of $6.6 billion. He asserts that Bitcoin is a superior asset class compared to traditional investments like bonds and equities, which he views as toxic capital that erodes value over time. Throughout the conversation, Saylor addresses concerns about volatility and margin calls, stating that MicroStrategy's debt structure, primarily consisting of convertible debt, protects the company from margin calls. He highlights the unique position of MicroStrategy as a public company with a focus on Bitcoin, attracting both Bitcoin enthusiasts and institutional investors who cannot directly invest in Bitcoin due to regulatory constraints. Saylor expresses confidence in Bitcoin's future, predicting that its market capitalization will grow from $1.8 trillion to $240 trillion over the next two decades, with each Bitcoin potentially reaching a value of $13 million. He argues that Bitcoin is a revolutionary form of money that will empower individuals and businesses globally, and he encourages listeners to adopt a long-term investment strategy focused on Bitcoin. The discussion also touches on the regulatory landscape, with Saylor criticizing the current SEC leadership for being unconstructive toward the digital asset industry. He believes that a more supportive regulatory framework could facilitate the growth of digital assets and improve access to capital markets for a broader range of companies. Saylor concludes by reiterating his commitment to Bitcoin, emphasizing its role as a non-toxic store of value and a means of economic empowerment. He encourages investors to buy and hold Bitcoin for the long term, positioning it as a critical asset for future wealth generation.

In this episode, Anthony Pompliano interviews Evgeny Gaevoy, founder and CEO of Wintermute, a major player in the crypto market with daily trading volumes between $5 to $10 billion. Gaevoy discusses how traditional financial institutions, like BlackRock and Fidelity, are driving Bitcoin demand, rather than retail investors. He notes that while crypto-native firms are reducing their Bitcoin exposure, traditional firms are increasingly interested in derivatives and complex trading strategies. Wintermute aims to expand into traditional finance, leveraging its expertise in both crypto and traditional markets. Gaevoy emphasizes the importance of OTC desks for discreet trading, especially for altcoins, and highlights the growing interest in Ethereum due to its potential upside. He believes that crypto will merge with traditional finance, particularly through tokenized securities. Gaevoy's competitive spirit drives his ambition to be among the wealthiest, viewing investing as a strategic game. Wintermute's unique position allows it to navigate both crypto and traditional markets effectively.

Ken Griffin’s hunger for information and speed almost reads like a playbook for ruthless learning. Fresh from Enron’s bankruptcy, he watched Citadel pursue him with relentless interviews, eventually meeting him in Aspen and Houston after a jet-ride recruitment sprint. Griffin describes Citadel’s practice of interviewing hundreds of Enron traders to reverse engineer the business and map its profit engine. The Yale talk later frames this mindset as the founder’s habit of seeking maximum risk opportunities aligned with his obsession, choosing Citadel’s niche path, and eventually building one of the world’s largest funds from a dorm-room start in Chicago in 1990. Griffin’s core thesis surfaces in Ed Thorp’s stories—the idea that the best entrepreneurs assemble the right toolkit at the right time and then relentlessly apply quantitative analytics to beat the market. He recounts meeting Thorp, hearing about the Princeton Newport model, and how a 19-year-old Griffin was backed by two mentors who believed in him. Citadel began with a million-dollar seed and explosive returns, then shifted from pure research to a trading framework, rooted in the motto that the glory lies in research and trading monetizes it. The firm’s early edge, like convert ARB, was eventually commoditized, pushing continuous learning. Adversity is Griffin’s constant teacher. He details Citadel’s near-collapse during the 2007-08 crisis, the Long-Term Capital Management lessons he studied in 1998, and how those episodes trained him to build a ‘risk wall’ and to hire and retain talent who stay in the game. He quotes Buffett on tides and naked swimmers and stresses that leadership emerges most clearly when markets turn, forcing decisions under uncertainty. The mantra emerges: time is the filter; the ability to adapt, both psychologically and financially, determines who survives and who thrives after the storm. Beyond crisis and edge-building, Griffin emphasizes education and culture: seek mentors, hire relentlessly, and push others to improve. He foregrounds the importance of decision repetition—‘reps matter’—and of lifelong learning, arguing that the vast majority of what matters in a career has yet to be learned. He urges embracing risk now, choosing ventures with large total addressable markets, and selling relentlessly as a founder’s job. He invites listeners to study great businesses outside finance, to build a personal mission, and to stay relentlessly curious about the next frontier.

In this podcast, hosts Saam Paar and Shaan Puri discuss the recent resurgence of GameStop stock and the figure behind it, Keith Gill, known as Roaring Kitty. Gill, who initially invested $56,000 in GameStop during the 2020-2021 stock market frenzy, became a symbol of the retail investor movement against hedge funds that were shorting the stock. His charismatic online presence on platforms like Reddit and YouTube helped rally support, leading to a massive short squeeze that made him $30 million. After a period of silence, Gill returned to social media with cryptic posts that sparked renewed interest in GameStop, causing the stock to triple in value. The hosts explore the dynamics of short selling, the impact of social media on stock prices, and the potential ethical implications of Gill's actions. They highlight the David versus Goliath narrative of retail investors challenging Wall Street, particularly in light of accusations against platforms like Robinhood for halting trading during the stock's peak. They also discuss the role of Ryan Cohen, the CEO of GameStop, who has become an activist investor and is seen as a key player in the company's future. The conversation touches on the broader implications of this phenomenon for the creator economy, with Gill monetizing his influence without traditional business models. The hosts express curiosity about the future of GameStop and Gill's strategies, while reflecting on their own experiences with investing and the emotional rollercoaster of the stock market. The episode concludes with a discussion on the importance of feedback and personal growth, inspired by a call from Scott Harrison, founder of Charity Water.

Michael Saylor, CEO of MicroStrategy, shares his journey from an Air Force upbringing and MIT education to leading a pioneering tech company. He founded MicroStrategy at 24, initially focusing on business intelligence software. Over the years, he navigated multiple market cycles, adapting to technological changes and competition, ultimately taking the company public in 1998. Saylor discusses his early skepticism towards Bitcoin, recalling a 2012 tweet criticizing it. However, after witnessing the economic impacts of COVID-19 and the diminishing value of cash, he began exploring Bitcoin as a potential hedge against inflation. He emphasized the importance of understanding macroeconomic trends and the need for companies to protect their cash reserves. In 2020, Saylor led MicroStrategy to invest heavily in Bitcoin, purchasing $250 million worth initially, followed by additional investments. He meticulously prepared his board by sharing educational resources and engaging in discussions about Bitcoin's value proposition. Saylor highlighted the importance of strategic buying to avoid market disruption, stating that they acquired Bitcoin without affecting its price. He believes that the volatility of Bitcoin will decrease as institutional investment increases, and he sees Bitcoin as a superior asset compared to gold and traditional cash. Saylor encourages other CEOs to consider Bitcoin for their treasuries, likening the situation to breaking the four-minute mile barrier, where once one company invests, others will follow. Saylor concludes by expressing admiration for the Bitcoin community and its ethos, stating that their support has been instrumental in MicroStrategy's decision to adopt Bitcoin as a key asset. He invites others to learn more about MicroStrategy and his insights on Twitter.

Bitcoin’s treasury arms race kicked into high gear when Semilar announced an all-stock acquisition of Strive, signaling a drive to scale by consolidating Bitcoin on a single balance sheet. The move underscores a race to build war chests, with the premium around 210% and an arbitrage dynamic linked to MNAV pricing that hinges on deal certainty. Strive, which spans asset management and a medical business, will spin out the latter, and the combined group soon crosses 10,000 Bitcoin. The rapid public debut and deal structure illustrate a broader push toward large, industry-changing treasury activity. Bitcoin’s latest price action involved a sizable liquidation, with price dropping from around 117–118k to about 112k, described as the largest year-to-date move at roughly two billion dollars. The move increased volatility after a period of calm, and CME options open interest reached about six billion dollars—a record level that signals active hedging and speculation. The discussion ties the sell-off to Federal Reserve signals: Powell framed the drop as risk management rather than a rate-cut cue, while Moran advocated a lower neutral rate. Gold demand and cross-asset dynamics were also highlighted. On the ecosystem side, the conversation covers Tether’s moves toward a 500 billion valuation and the emergence of USAT as a US-compliant stablecoin, distinct from USDT. Plasma is preparing a mainnet launch backed by Tether, aiming to anchor final settlement on Bitcoin and reinforce Bitcoin’s role as a permanent ledger. The discussion frames Tether as a powerful player with both inside and outside money, shaping future liquidity and cross-border finance, while user growth and network effects are cited as reasons to maintain a bullish stance into year-end.

In this conversation, Lex Fridman speaks with Richard Craib, founder of Numerai, a crowdsourced hedge fund that utilizes machine learning models submitted by users. Numerai aims to democratize stock trading by providing anonymized data for users to develop AI-driven trading strategies. Craib highlights the potential of this model to disrupt traditional finance, similar to the decentralized coordination seen in the GameStop saga and Wall Street Bets, where ordinary people collectively influenced stock prices against hedge funds. Craib admires the decentralized nature of Wall Street Bets, noting how users built credibility through past performance and community engagement. He explains that the GameStop phenomenon was unique because users targeted a heavily shorted stock to create a short squeeze, demonstrating the power of collective action. He emphasizes that while shorting can be seen as unethical, it serves a purpose in market efficiency. The discussion touches on the implications of anonymity in online communities and the potential for manipulation by charismatic leaders. Craib expresses concern about the chaotic nature of decentralized power but also acknowledges its potential for positive change. He believes that Numerai's staking mechanism, which aligns user incentives with model performance, could be a solution to credibility issues in online platforms. Craib describes Numerai's approach to data, emphasizing the importance of obfuscation to protect proprietary information while allowing users to find patterns. He discusses the challenges of financial modeling, particularly the non-stationary nature of market data, and the need for diverse strategies to avoid overexposure to specific risks. The conversation also explores the future of finance, with Craib envisioning a world where AI systems, guided by human oversight, dominate trading. He reflects on the philosophical aspects of money and finance, suggesting that finance empowers innovation and societal progress. The discussion concludes with Craib sharing insights on entrepreneurship, emphasizing the importance of passion and commitment in building successful startups.

Robin Hood now has eight lines generating 100 million a year or more, up from three, and it's stronger in a declining rate environment than in a rising one. Vlad recalls, 'Being an immigrant, moving from Eastern Europe to the US,' and describes early separation and adapting to new schools. He notes, 'the single biggest commonality in the most successful founders is a high frequency of moving in childhood,' and says America remains the land of opportunity. Leadership is a conductor balancing inspiration with feedback. During the GameStop era, he describes rapid growth, the fear of what could go wrong, and the push to communicate early: 'the full play by play on a Clubhouse being interviewed by Elon Musk.' After lawsuits, he notes a broader network with Musk, Benioff, and others. He recalls the shift to remote work: 'we were a remote first company' after ambiguity, followed by a large hiring surge and a later pullback to stabilize culture and operations. He outlines diversification: eight nine‑figure revenue lines, margin improvements, and 24‑hour market access, plus institutional opportunities in advisory and retirement products. Crypto growth includes the Bitstamp acquisition and Robin Hood Gold from X1. He says AI will be a huge technology shift that could change financial services and assist advisors while automating routine work. He envisions two routes to a $100B company: lead in active trading and capture assets from Millennials and Gen Z globally, including Europe and the UK.

The episode explores the theme of whether wealthy individuals are "crazy or genius," featuring stories about John Collins Black's $2 million treasure hunt and Michael Saylor's Bitcoin strategy. Black has hidden treasure worth $2-3 million across America, including rare artifacts, and released a book with clues for treasure seekers. His journey began as a musician, transitioning to a tech entrepreneur and Bitcoin investor, inspired by the Fenn treasure hunt. Saylor, CEO of MicroStrategy, has controversially converted his company's cash reserves into Bitcoin, amassing $37 billion worth. His strategy involves issuing corporate bonds to finance Bitcoin purchases, effectively detaching the company's stock value from its declining software business. Despite skepticism about his approach, Saylor's aggressive investment has significantly increased MicroStrategy's stock price. The discussion highlights the allure of treasure hunting and the risks associated with high-stakes investments. The hosts reflect on the potential dangers of Saylor's strategy, noting that past cycles have seen similar aggressive investors face downfall. They emphasize the importance of understanding the risks involved in such ventures, with Saylor's unwavering confidence raising red flags. The episode concludes with a commitment to seek clarity on Saylor's strategy and the broader implications of Bitcoin investment.

In this episode, hosts Saam Paar and Shaan Puri welcome Andrew Wilkinson, founder of Tiny, a company that has acquired around 20 businesses and recently went public with a market cap of approximately $600 million. Andrew shares insights on the "Profit First" mentality, emphasizing how businesses can improve profitability by managing cash flow differently. He discusses his experiences with various companies, highlighting that often, the most effective strategies are not flashy but rather simple adjustments, such as raising prices or optimizing operations. Andrew reflects on the contrast between "sexy" businesses, like his bakery and deli, and more straightforward, profitable ventures like We Work Remotely, a job board that significantly increased profits through basic marketing and pricing strategies. He notes that many entrepreneurs chase glamorous projects, while the real gains often come from mundane improvements. The conversation also touches on networking, with Andrew sharing anecdotes about how he successfully connected with influential figures like Bill Ackman and Charlie Munger. He emphasizes the importance of being proactive and finding common ground when reaching out to potential contacts. Andrew discusses the psychological aspects of business management, particularly how the "Profit First" approach can create a sense of urgency and discipline in spending. He suggests that by limiting available cash, businesses can become more thoughtful about expenses, ultimately leading to better financial health. The episode concludes with reflections on personal growth and the challenges of changing human behavior. Andrew shares his belief that while people can change, it often requires hitting a low point first. The hosts express appreciation for Andrew's insights, particularly regarding practical business strategies and the importance of awareness in financial management.

Bitcoin and gold sit at opposite ends of a currency-debasement debate, with gold continuing to hit new highs while Bitcoin has paused recently. Gold is up about 42% year-to-date, and the hosts note that gold holders and Bitcoiners are like brothers in arms against currency debasement. They explain that gold often leads and Bitcoin follows, yet both assets tend to rise when macro conditions favor easy money. Deutsche Bank recently suggested that central banks will include both gold and Bitcoin in portfolios by 2030, underscoring a broader shift among retail, institutions, and funds toward these stores of value. Over longer horizons, Bitcoin is seen as having a structural edge because large pools of capital still lack exposure, a dynamic that could push prices higher over time. The conversation then turns to a recent Bitcoin Treasury M&A deal: Strive Asset Management announced a merger with Similar Scientific, paying roughly two times the market price while Similar traded near NAV. Strive’s offer would move about 5,000 Bitcoin onto its balance sheet, aiming to accrete value for shareholders as the premium mathematics reflect premium to NAV and the strategic logic of consolidation. The discussion expands to the integration of crypto into traditional finance. BlackRock is described as a Bitcoin-focused powerhouse given the profitability of its Bitcoin ETF, and Bitwise is praised for educating advisers and pushing crypto into mainstream awareness. The speakers argue that the line between crypto and conventional finance is blurring: exchanges now offer stocks, Bitcoin, and crypto; custody providers pursue bank licenses; and even fintechs blend crypto into their offerings. The idea of Bitcoin as Bitcoin per share in treasury strategies is used to illustrate how growth expectations translate into valuation premia. Premiums to MNAV reflect beliefs about future purchases and balance-sheet expansion, and participants note that markets could compress or expand these premia as capital raises or acquisitions occur. The four-year cycle remains a debated topic, with some awaiting clarity while others favor a straightforward, buy-and-hold approach. On AI and monetary policy, the hosts contend that AI could replace the Fed because a computer can ingest data, synthesize it, and apply programmatic rules, whereas the Fed is described as reactive and political. They argue programmatic policy could fix forecasting errors and give clearer planning for capital costs.

Bitcoin could surge to 150,000 faster than many expect, Jordy Visser argues, driven by a convergence of artificial intelligence and massive financial markets expansion. He points to the Mag 7’s ascent from one trillion to fifteen trillion and suggests Bitcoin’s market might chase a similar scale as AI accelerates efficiency and capital investment. The conversation opens with the bad jobs report, the inflation picture, and a Fed that Visser says is behind the curve. Tariffs, AI-driven productivity, and energy costs shape how markets are pricing risk and growth today. Visser frames the economy as sprinting into a headwind: a powerful deflationary force from tariffs and AI, with inflation measured around 1.98% and jobless claims stubbornly flat. He notes housing is holding up while rates are expected to fall, and PMIs are drifting higher globally. Despite strong earnings, a cautious narrative persists about payrolls and the trajectory of demand. The stock market’s all-time highs and gold and Bitcoin’s outperformance are presented as forward-looking signals, underpinned by anticipated monetary easing and continued corporate capital expenditure in AI. On Bitcoin, Visser revisits his own forecast and acknowledges being wrong about timing. He describes a framework where Bitcoin is a risk asset tightly linked to global liquidity and the digital economy. If the MAG7 stop outperforming, Bitcoin could catch a bid as institutions, and perhaps governments, increase exposure. He argues the next phase may involve more adoption by public companies and large investors, with a potential move toward multi-hundred-thousand-dollar prices and eventually higher targets as the macro environment remains favorable for asset prices. The discussion shifts to technology and energy. Visser highlights Tesla’s robo-taxis and the race in vision-based AI for autonomous systems, arguing that ‘eyes on the car’ and on-device data centers could drive explosive growth. He notes AI-driven efficiency will rewrite business competition, and he returns to the policy playbook—probing narratives, signaling a possible national emergency—while underscoring rising electricity prices and the demand surge for batteries and transformers. The overall tone is that rapid AI adoption and policy signals will continue to reshape markets, with Bitcoin and crypto as part of the new macro landscape.

Jim Simons built what many call the greatest money-making machine by treating markets as a solvable, data-driven system rather than a battlefield of hunches. A mathematician and codebreaker, he believed markets move in orderly patterns that only data can reveal. In a Long Island office, he assembled mathematicians, physicists, and computer scientists to collect historic records and develop algorithms. Early moves included trading commodities at Meil Lynch while in grad school, showing a hunger for wealth and a preference for thinking over conventional careers. He studied at MIT, earned his PhD at Berkeley, and soon joined the Institute for Defense Analysis, where he learned to think in problems rather than disciplines. This narrative draws on The Man Who Solved the Market by Gregory Zuckerman. At 26, he left academia to trade currency and, after a decade of experiments and near misses, launched Renaissance Technologies with a group and conviction: finance could be modeled like a scientific problem. The early fund grew from a $4 million seed to tens of millions as it rode currency moves, but the experiment sputtered. A pivotal split with partner Leonard Bomb in 1984 after a drawdown taught him the fragility of collaboration. In 1988 the Medallion Fund began its long, money-making run, powered by a data-centric approach that would outpace intuition and become legendary. Behind the systems was a focus on data. Simons gathered prices back to the 1800s, collected Federal Reserve data by hand, and hired Strauss to clean sources into a searchable database. He recruited from IBM's computational linguistics group, bringing Peter Brown and Mercer, and he insisted that the best minds work with the best tools. When a market move did not fit a model, their instinct was to test, not abandon. Axecom formed with James Axe and Sandor Strauss, building the data backbone that would support Medallion, while Burl Camp pushed for shorter holding periods to amplify edge. By 1990, after trials with partners, Simons reorganized Medallion around short-term edge. Burl Camp's push for frequent turnover yielded gains, and Axe exited with a payout as Simons bought out his stake. The fund grew, but secrecy intensified: by the early 1990s Renaissance was private, with profits distributed to employees rather than outside investors. Simons articulated five guiding principles in later years: do something new; surround yourself with the smartest people; be guided by beauty; don't give up easily; hope for good luck.

In this episode of the "Into the Impossible" podcast, host Brian Keating interviews author Greg Zuckerman about his book, "The Man Who Solved the Market: How Jim Simons Launched the Quant Revolution." Zuckerman discusses Jim Simons' multifaceted career as a mathematician, hedge fund titan, and philanthropist, emphasizing his unique approach to quantitative trading through mathematical models rather than intuition. Simons, who has a background in code-breaking, founded Renaissance Technologies, which revolutionized trading by using data analysis and algorithms. Zuckerman highlights Simons' relentless curiosity and leadership style, which fosters collaboration among talented individuals. The conversation touches on Simons' philanthropic efforts, particularly in pure scientific research, and his personal experiences with luck and loss. Zuckerman notes that Simons' approach to leadership and management can provide valuable lessons beyond finance, making the book relevant to various fields. The discussion concludes with Zuckerman expressing interest in writing about the scientific advancements related to COVID-19, reflecting on the potential for breakthroughs in biology and medicine.