Generating Alpha Podcast

Epizodes

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  Episode 56: Gavin Baker - Managing Partner of Atreides Management 08.07.2026 1h 15min

  This week on Generating Alpha, I sat down with Gavin Baker, founder and CIO of Atreides Management, one of the most respected technology-focused investment firms in the market today.Gavin grew up in Houston, Texas, the son of two attorneys, with an early obsession with history, books, and games of skill and chance. He arrived at investing almost by accident — a college internship at Donaldson, Lufkin & Jenrette introduced him to equity research, and he never looked back. After graduating from Dartmouth, he joined Fidelity Investments, where he would spend over a decade covering semiconductors, pharma, telecom, and retail before rising to manage the $17 billion OTC fund.It was at Fidelity where Gavin developed the convictions that would define his career. As a young semiconductor analyst, he was among the first to identify the inventory buildup that preceded the dot-com crash. He built early, high-conviction positions in NVIDIA and Tesla, and was an early institutional investor in SpaceX. After leaving Fidelity, he founded Atreides Management, where he has continued to focus on deep tech, semiconductors, and the infrastructure underpinning artificial intelligence.In our conversation, we explored Gavin's unlikely path from aspiring rock climber to one of the sharpest technology investors of his generation, the frameworks he built covering commodities and semiconductors early in his career, what makes Jensen Huang and Elon Musk generationally exceptional, how he thinks about the AI buildout relative to every prior technology cycle, the psychology of navigating drawdowns, and the advice he gives to young investors starting out today.It's a rare look inside one of the most rigorous and historically grounded investment minds in public markets — and a masterclass in finding conviction at the earliest stages of transformative technology.This was filmed in February 2026
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  Episode 55: Economic Myths with Jeff Yass - Co-Founder and Managing Director of Susquehanna 22.06.2026 19min

  This week on Generating Alpha, I sat down with Jeff Yass — co-founder and managing director of Susquehanna, one of the largest trading and quantitative finance firms in the world — and the first repeat guest in the history of the show.This one is different. The first time around, we walked through prediction markets. This time we skipped that entirely and went straight at the ideas — the economic myths Jeff thinks the majority of people get backwards.We covered a lot of ground: why comparing the national debt to GDP is the wrong way to think about whether America owes too much, why consumer surplus means the people we vilify as billionaires may be the ones giving society the most value, what's actually broken about the progressive tax system, and why he believes school choice and vouchers are one of the most underrated ideas in the country.It's a fast, contrarian tour through the things Jeff believes most people get wrong about taxes, markets, and value creation — and a rare chance to hear one of the sharpest probabilistic thinkers alive lay out his first principles.
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  Episode 54: Michael Shvo - Chairman and CEO of SHVO 20.05.2026 32min

  This week on Generating Alpha, I sat down with Michael Shvo — real estate developer, art collector, and founder of SHVO, one of the most distinctive luxury development firms in the world.Michael grew up in Arsuf, Israel, the son of two organic chemistry professors. As a teenager he taught himself to trade oil and gas stocks, made millions, and lost it all before finishing school. He completed his military service, moved to New York at 23 with $3,000 to his name, and talked his way into a job at Douglas Elliman — where he invented the concept of the real estate team, building a group of 27 people around him and doing over $300 million in sales to become the firm's top broker.He left in 2004 to found SHVO, and within four years had done $15 billion in transactions worldwide. But what set him apart wasn't the volume — it was the vision. Michael pioneered the marriage of fashion and real estate, bringing Armani into residential development before anyone else thought to, and went on to build a firm defined as much by art and culture as by architecture and capital. Today SHVO oversees more than $8 billion in assets across five major American markets, with properties that include 711 Fifth Avenue, the Crown Building, and Big Red in Chicago.In our conversation, we talked about growing up between two worlds, building one of the most recognized names in luxury real estate from nothing, what he actually means when he talks about luxury, and how he keeps spotting iconic properties before the rest of the market catches on.It's a rare look inside the mind of a developer who has never once built anything ordinary.
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  Episode 53: Christian Angermayer - Founder of Apeiron Investment Group 11.05.2026 51min

  This week on Generating Alpha, I sat down with Christian Angermayer — serial entrepreneur, biotech pioneer, and founder of Apeiron Investment Group, one of the most unconventional private investment firms in the world.Christian grew up in a small town in Bavaria and dropped out of university at 20 to co-found Ribopharma, a biotech built on groundbreaking RNA interference technology. He sold it to Alnylam Pharmaceuticals before turning 25, and has spent the two decades since founding three unicorns, backing four more, and completing over 50 IPOs and M&A transactions across life sciences, fintech, crypto, and frontier technology.His most defining chapter has been psychedelics. At a time when psilocybin was still considered fringe science, Christian seed-funded Compass Pathways and founded atai Life Sciences — taking it public on Nasdaq at a $3.2 billion valuation — almost single-handedly transforming psychedelic medicine from a relic of the 1960s into one of the most compelling frontiers in modern psychiatry.His latest bet is just as bold. This past Friday, Enhanced Games — his performance-enhancing-drug-permitted alternative to the Olympics that doubles as a performance medicine and telehealth platform — debuted on the NYSE at a $1.2 billion valuation.In our conversation, we talked about betting on ideas before the world is ready, building and IPOing companies across entirely different industries, the science and philosophy behind the psychedelic renaissance, and what Enhanced Games is actually building beyond the headlines.It's a rare look inside the mind of a builder who keeps finding the future before anyone else does.
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  Episode 52: Michael Paulus - Founder of PCM Encore 04.05.2026 42min

  This week on Generating Alpha, I sat down with Michael Paulus — serial entrepreneur, fintech pioneer, and founder of PCM Encore, one of the fastest-growing fiduciary wealth management firms in the country.Michael earned his undergraduate degree in Economics and a Master's in Management Science and Engineering from Stanford, where he helped manage a portion of the university's endowment through the student-run Blyth Fund. He went on to consult at Boston Consulting Group and became a Partner at Andreessen Horowitz before co-founding Assurance IQ — an insurance technology platform he bootstrapped to a billion-dollar exit to Prudential Financial, making him one of the youngest self-made billionaires in the country. He also helped build Addepar, a financial analytics platform now reporting on trillions in assets.But PCM Encore is his most personal bet. Frustrated that no wealth manager could deliver the conflict-free, sophisticated solutions his own family needed, he built the platform himself — then opened it to the world. The firm crossed $1.2 billion in AUM within six months of launching to outside families, operating as a 100% employee-owned fiduciary with no commissions, no hidden fees, and no products to push.In our conversation, we talked about the lessons from bootstrapping and exiting a billion-dollar business, why he believes wealth management is fundamentally broken, what it really means to be a fiduciary, and how he thinks about portfolio construction for high-net-worth families.It's a rare look inside the mind of a builder who keeps finding new industries to reinvent — and winning.Presented by: rho.co/generatingalpha
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  Episode 51: Fabrice Grinda - Founding Partner of FJ Labs 01.04.2026 35min

  This week on Generating Alpha, I sat down with Fabrice Grinda — serial entrepreneur, prolific angel investor, and founding partner of FJ Labs, one of the most active venture funds in the world with over 1,100 investments across six continents.Fabrice grew up in Nice, France, the son of a doctor. He arrived at Princeton, graduated summa cum laude in economics, and was already running his first business — Princeton International Computers, exporting hardware to Europe — before he had his degree. He spent a matter of months at McKinsey before walking away at 23 to launch Aucland, a direct eBay competitor in France that became one of Europe's largest auction sites. From there he built Zingy, a mobile media company he scaled to $200 million in revenue in four years, before founding OLX in 2006 — a classified ads marketplace that grew to 350 million monthly users across 40 countries and became one of the most trafficked websites on the internet.Along the way, he tried to buy the Alibaba.com domain from an unknown Jack Ma — and ended up an early investor in Alibaba instead. Forbes later named him the #1 angel investor in the world. Today, through FJ Labs, he has made over 1,100 investments and seen more than 300 exits — backing companies like Coupang, Delivery Hero, and Rappi — all without leading rounds, taking board seats, or spending more than two calls on a decision.But what makes Fabrice genuinely singular isn't just the track record. It's the intentionality behind it. In 2012, he gave away all his possessions. He's designed his life around Turks & Caicos, New York, and Revelstoke, optimizing not for accumulation but for happiness on his own terms.In our conversation, we talked about growing up in France and catching the entrepreneurship bug early, what he learned from nearly going bankrupt and borrowing on credit cards to make payroll, the contrarian logic behind launching OLX in over 100 countries simultaneously, his pattern recognition for great marketplace businesses at the seed stage, why his two-call investment model is a feature and not a bug, and how he thinks about designing a life most people never consider.It's a rare look inside one of the most prolific and unconventional investing minds of his generation — and a masterclass in building wealth, companies, and a life entirely on your own terms.Presented by: ⁠rho.co/generatingalpha⁠
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  Episode 50: Ian Livingstone - Co-Founder of London Regional Properties 24.02.2026 31min

  This week on Generating Alpha, I sat down with Ian Livingstone, co-founder of London Regional Properties, one of Europe's most successful and enduring private investment firms — with over $30 billion deployed across four decades and approximately $10 billion in assets under management today.Ian's journey began in Ealing, London, where he grew up the son of a dentist. After qualifying as an optometrist in 1984, he opened his first eyewear store in 1989. Within three years he'd acquired the David Clulow chain, growing it to 170 stores across the UK including concessions in Harrods and Selfridges. He served as chairman of the Optika Clulow Group for two decades, building it into one of the leading optical retail businesses in Europe, before selling to Luxottica in 2011.But the business that would define his career began in 1987, when Ian and his brother Richard founded London Regional Properties at the height of a commercial property crash — buying distressed assets at half price while every institution in the market was running for the exits. That contrarian bet became the foundation of a portfolio that today spans David Lloyd Leisure, Hilton hotels in London, the leasehold on Cliveden House, a $2 billion development in Panama City, and the Fairmont Monte Carlo — one of the most iconic hotel addresses in the world, which Ian acquired in 2007 and spent nearly two decades transforming. Along the way, they provided seed funding for Evolution Gaming, a Swedish online gambling company whose 8.6% stake grew into a position worth nearly $3 billion. Through it all, Ian and his brother have retained full family control — no outside capital, no institutional partners, no compromise.In our conversation, we explored Ian's unlikely path from optometrist to entrepreneur, the philosophy behind buying aggressively when everyone else was selling, how he thinks about opportunity across wildly different asset classes, the story behind the Fairmont Monte Carlo, what nearly four decades of family control actually looks like, and where he sees the market today.It's a rare look inside one of the most deliberate and disciplined investing minds in Europe and across global markets — and a masterclass in building lasting private wealth on your own terms.Presented by: rho.co/generatingalpha
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  Episode 49: Yoni Assia - Co-Founder and CEO of eToro 18.02.2026 50min

  This week on Generating Alpha, I sat down with Yoni Assia, co-founder and CEO of eToro, the platform that has fundamentally changed how a generation approaches investing.Yoni's story begins in Savyon, Israel, where finance was in the air from childhood — his father founded Magic Software and would pull over the car to read stock quotes with his kids, while his mother ran a copyright law firm. After serving as a programmer in the IDF and earning dual degrees in Management and Computer Science, he got his first taste of product-building with CDRide, selling on-ride videos to people coming off roller coasters. In 2007, he co-founded eToro with his brother Ronen and friend David Ring. Then 2008 hit — and watching the global financial system freeze in real time only sharpened his conviction that markets needed to be opened up for everyone.What emerged was revolutionary. In 2010, eToro launched CopyTrader, allowing everyday investors to automatically replicate the strategies of the world's best traders. The idea helped define an entirely new category — social investing — and the platform has since grown to over 40 million registered users across more than 100 countries, going public on Nasdaq in May 2025 at a valuation of $5.64 billion. Along the way, Yoni collaborated with a young Vitalik Buterin on the Colored Coins project in 2012, years before Ethereum existed, and spent three hours at dinner with Warren Buffett in 2020 making the case for the future of finance.In our conversation, we explored that journey in full — the crises navigated, the breakthroughs earned, and what nearly two decades of building alongside his brother actually looks like. We also discussed how eToro has survived crypto winters, regulatory battles, and multiple market crashes, what Yoni took away from his dinner with Buffett, and the advice he'd give to a 16-year-old who wants to make their mark on the world.Presented by: rho.co/generatingalpha
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  Episode 48: Dmitry Balyasny - Managing Partner and CIO of Balyasny Asset Management 05.02.2026 52min

  This week on Generating Alpha, I sat down with Dmitry Balyasny, Founder and Chief Investment Officer of Balyasny Asset Management (BAM), one of the world's most successful multi-strategy hedge funds with over $30 billion in assets under management.Dmitry's journey began in 1992 when he joined Schonfeld Securities as a proprietary trader straight out of Loyola University Chicago. Over nine years, he honed his craft in volatility arbitrage and options trading, eventually becoming Head of the Volatility Arbitrage Group. In 2001, he founded Balyasny Asset Management with a clear vision: build a best-in-class platform that attracts and retains exceptional investment talent across multiple strategies.Under Dmitry's leadership, BAM has become known for its rigorous risk management, disciplined capital allocation, and ability to generate consistent alpha across market cycles. The firm operates dozens of portfolio management teams spanning equities, quantitative strategies, commodities, and credit, unified by a culture of intellectual rigor and accountability. Dmitry built one of the industry's most sophisticated infrastructures for portfolio management, combining centralized risk oversight with decentralized decision-making that empowers talented investors.In our conversation, we explored how Dmitry thinks about talent evaluation and building high-performance investment teams. We discussed his framework for risk management at scale, the evolution of multi-strategy investing over two decades, and how BAM has maintained its edge as the industry has become increasingly competitive. We also talked about his philosophy on capital allocation, learning from losses, and creating a culture where the best investors want to build their careers.It's a rare look inside one of hedge fund investing's most disciplined minds and a masterclass in building institutional excellence.Presented by: rho.co/generatingalpha
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  Episode 47: Pete Muller - Founder of PDT Partners 03.02.2026 35min

  This week on Generating Alpha, I sat down with Peter Muller, founder and CEO of PDT Partners, one of the most successful and secretive quantitative trading firms in modern finance.Pete's journey is unlike any other on Wall Street. After graduating with honors in mathematics from Princeton, he moved to California to compose music for rhythmic gymnastics teams before landing at BARRA, where he discovered his passion for quantitative finance. In 1993, he pitched Morgan Stanley with a radical idea: using quantitative models rather than human traders to manage portfolios. They gave him two years to make it work. He founded Process Driven Trading (PDT) and built it into a legendary operation that reportedly generated over $20 billion in cumulative profits before spinning out as an independent firm in 2012.What made PDT extraordinary wasn't just the returns—reportedly averaging over 20% annually through 2010—it was the culture. Pete recruited physicists, mathematicians, and unconventional thinkers who thrived in an environment valuing precision and innovation, maintaining consistent performance through multiple market cycles while staying almost entirely out of the public eye.Beyond finance, Pete is an accomplished singer-songwriter and pianist who has released six albums, performed at the Montreux Jazz Festival, and famously busked in New York City subways. He creates crossword puzzles for The New York Times, serves as a trustee of Berklee College of Music, and co-founded Math for America.In our conversation, we explored how Pete builds models that actually work, manages risk through volatile markets, and created a culture that attracts the brightest minds in finance. We also discussed the parallels between music and quantitative trading, and why the best strategies come from asking better questions.It's an extraordinary window into one of finance's most brilliant and enigmatic minds.Presented by: rho.co/generatingalpha
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  Episode 46: Larry Connor - Founder of the Connor Group 30.01.2026 43min

  This week on Generating Alpha, I sat down with Larry Connor, founder and managing partner of The Connor Group and one of the most successful real estate investors of the past three decades.Larry's path was unconventional. After graduating summa cum laude from Ohio University with degrees in English and history, he started a painting business in high school, built and sold a tavern with a 300% return, then spent nine years running Orlando Computer Corporation before it failed. That failure became his "PhD in the Hard Knocks of business" and the foundation for an extraordinary career.In 1991, Larry founded what would become The Connor Group with just $400,000 and one investor to buy three apartment communities in Dayton, Ohio. He built the firm on a contrarian thesis: treat apartments not as passive real estate investments, but as operating businesses with dramatic margin improvement potential. Over 32 years, The Connor Group has delivered over 30% average annual IRR to investors—outpacing firms like Brookfield and Blackstone. Out of 241 acquisitions, they've lost money on only eight. Today, the firm manages $5 billion in assets across 18 markets.Beyond business, Larry is one of the world's most accomplished adventurers. In 2021-2022, he became the first person in history to dive to the deepest part of the ocean—the Mariana Trench—and travel to the International Space Station in the same year. He's won national racing championships, competed at Le Mans, flies F-5 fighter jets, and is planning to dive to the Titanic wreckage to prove deep-sea exploration can be done safely.In our conversation, we explored how Larry thinks about counter-cyclical investing and building a culture of extreme accountability. We also discussed his philosophy on hiring people with no industry experience, why failure is the greatest teacher, and what connects exceptional entrepreneurship with pushing the limits of human exploration.It's a rare look at one of America's most distinctive investors and a masterclass in contrarian thinking, operational excellence, and living without limits.Presented by: rho.co/generatingalpha
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  Episode 45: Keith Rabois - Managing Director at Khosla Ventures 10.01.2026 40min

  This week on Generating Alpha, I sat down with Keith Rabois, Managing Director at Khosla Ventures and one of the most accomplished operators and investors in Silicon Valley history.Keith's path was unconventional. After studying political science at Stanford, where he met Peter Thiel and worked on The Stanford Review, he graduated from Harvard Law School, clerked for the U.S. Court of Appeals for the Fifth Circuit, and practiced as a litigator at Sullivan & Cromwell. That legal foundation became the bedrock for an exceptional career at the intersection of building and investing.Keith started in tech as an executive at PayPal, then moved to LinkedIn as VP of Business and Corporate Development before becoming COO of Square, helping scale the company through its critical growth years. His operating experience is matched by an extraordinary investing track record. At Khosla Ventures, he led the first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. At Founders Fund, he led investments in Ramp, Trade Republic, and Aven, and made early personal investments in YouTube, Airbnb, Palantir, Lyft, and Eventbrite. He has ranked as high as number four on the Forbes Midas list in the U.S. and number eight globally. In 2021, he co-founded OpenStore, and recently returned to Opendoor's board as Chairman.In our conversation, we explored how Keith thinks about identifying asymmetric opportunities and how he evaluates talent at the earliest stages. We also discussed his framework for being a great seed investor and why the best people frame themselves as not just the best, but the only.It's a rare look at one of Silicon Valley's most influential builders and a masterclass in execution, leverage, and long-term value creation.Presented by: rho.co/generatingalpha
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  Episode 44: Paul Wachter - Founder and CEO of Main Street Advisors 18.12.2025 45min

  This week on Generating Alpha, I sat down with Paul Wachter — founder and CEO of Main Street Advisors, the firm that has quietly become one of the most influential strategic advisory platforms in entertainment, sports, and culture.Paul’s path to building MSA was anything but conventional. After studying at Wharton and Columbia Law School, he began his career in law before moving into senior roles in investment banking at firms like Kidder Peabody and Schroder & Co. That blend of legal rigor, financial sophistication, and strategic thinking would later become the foundation for a new kind of advisory model — one built not just around deals, but around long-term partnership.MSA was born with its first client, Arnold Schwarzenegger, and grew alongside a generation of iconic talent. Under Paul’s leadership, the firm helped redefine what it means to represent creators and athletes — not just as earners, but as owners, builders, and partners. From negotiating LeBron James’s lifetime deal with Nike, to architecting Beats by Dre from idea to its landmark sale to Apple, Paul has been at the center of some of the most consequential transactions in modern culture.In our conversation, we explored how MSA thinks about authenticity and trust when building brands, how Paul evaluates talent early in their careers, and what separates enduring businesses from short-lived influence. We also discussed what great negotiation really looks like at the highest level.It’s a rare, inside look at the strategist behind some of the most powerful figures in music, sports, and entertainment — and a masterclass in building long-term value at the intersection of culture and capital.Presented by: rho.co/generatingalpha
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  Episode 43: Ryan Tolkin - CEO and CIO of Schonfeld Strategic Advisors 12.12.2025 44min

  This week on Generating Alpha, I sat down with Ryan Tolkin — CEO of Schonfeld, a multi-billion dollar alternative asset manager that has quietly become one of the most powerful and consistent forces in the hedge fund industry.Ryan's history with the firm dates back to a high school internship, where his analytical talent was first spotted. He joined the firm as Chief Investment Officer at 27, a role he ascended to just a few years out of college, demonstrating a precocious understanding of risk and capital markets. It was under his leadership that Schonfeld transitioned from a proprietary family office to a major global player, making the pivotal decision to accept outside, third-party capital in 2016 and build the multi-strategy platform we know today.We discussed how his early experiences—from trading (perhaps even starting with baseball cards) to managing risk at a young age—shaped his systematic approach to portfolio management.In our conversation, we spoke about how Schonfeld designs its platform to maximize manager performance and minimize drawdowns, what it takes to seperate signal from noise in todays age, and the habits and mindset required to compound advantage over decades in a highly competitive industry.It’s a rare look inside the thinking of a modern hedge fund leader helping shape the next generation of top portfolio managers—and the quiet architecture behind enduring success.Presented by: rho.co/generatingalpha
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  Episode 42: Collin Roche - Co-CEO and Managing Partner of GTCR 08.12.2025 40min

  This week on Generating Alpha, I sat down with Collin Roche — Co-CEO of GTCR, one of the most influential and consistently successful private equity firms of the modern era.GTCR is widely known for pioneering the Leaders Strategy — a model that flips traditional private equity on its head by first identifying world-class executives, then building companies around them. Under Collin’s leadership, the firm has continued to scale and shape category-defining businesses across healthcare, software, and financial services, quietly creating billions in value behind the scenes.Collin’s approach sits at the intersection of strategy, psychology, and long-term thinking. Rather than chasing trends, he focuses on people, structure, and disciplined execution — the unglamorous but decisive work that turns good ideas into great enterprises.In our conversation, we spoke about what separates elite operators from average ones, how GTCR identifies leaders before companies even exist, and the habits and mindset required to compound advantage over decades.It’s a rare look inside the thinking of a modern private equity leader helping shape the next generation of great companies — and the quiet architecture behind enduring success.Presented by: rho.co/generatingalpha
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  Episode 41: Antonio Gracias - Founder and CEO of Valor Equity Partners 27.11.2025 40min

  This week on Generating Alpha, I sat down with Antonio Gracias — one of the few true first-principles thinkers in modern business and a key architect behind some of the most transformative companies of the 21st century.A student of physics and the human brain, Gracias began his career as an operator — stepping into distressed and underperforming businesses and engineering turnarounds through discipline, systems thinking, and relentless execution. He eventually founded Valor Equity Partners, which became one of the earliest and most influential growth investors in America.At Valor, Gracias backed a generation-defining wave of companies long before they were obvious — including Tesla, SpaceX, and other frontier-technology firms that now shape global industry. Beyond capital, he played hands-on operational roles inside several of these businesses, guiding teams through scaling challenges, manufacturing complexity, and strategic inflection points.In our conversation, we spoke about his analytical approach to problem-solving, what he learned from years spent fixing broken companies, the mental models he relies on when backing founders like Elon Musk, and how he evaluates technologies that could define the next several decades.It’s a rare look inside the mindset of an investor-operator who has quietly influenced industries from electric vehicles to space exploration — and whose first-principles approach continues to shape some of the most ambitious companies on the planet.
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  Episode 40: Thomas Peterffy - Founder and Chairman of Interactive Brokers 30.10.2025 33min

  This week on Generating Alpha, I sat down with Thomas Peterffy — founder of Interactive Brokers, one of the most profitable and technologically advanced trading platforms in the world, used by nearly every professional trader.Born in post–WWII Hungary, Peterffy grew up under communist rule before escaping the Soviet Bloc and arriving in New York in 1965 with no money and no ability to speak English. He started as a draftsman, taught himself to code, and eventually found his way onto Wall Street — where he revolutionized finance by bringing computers to options trading decades before it became the norm.Over time, Peterffy built Interactive Brokers into a $120 billion global powerhouse with profit margins higher than Visa’s. His relentless focus on automation, transparency, and efficiency helped define the modern era of electronic trading and made IBKR the go-to platform for professionals around the world.In our conversation, we spoke about his early life behind the Iron Curtain, how he built one of the most advanced trading systems ever created, his philosophy on risk and innovation, and what continues to drive him even after becoming the 22nd richest person in the world.It’s a story of grit, intellect, and visionary ambition — from a refugee who transformed the very structure of global markets.
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  Episode 39: Jeff Yass - Founder and Managing Director of Susquehanna International Group 23.10.2025 25min

  This week on Generating Alpha, I’m joined by Jeff Yass — founder of Susquehanna International Group, one of the most successful trading firms in the world.Jeff is a former professional poker player and horse bettor turned options trader. In 1987, he founded Susquehanna with five friends, and today it stands as one of Wall Street’s largest and most influential firms. Thanks to Susquehanna’s success and its early stake in ByteDance, Jeff is now the 26th wealthiest person in the world — yet remains one of the most private figures in finance.In one of his first-ever podcast interviews, we spent 25 minutes focused entirely on prediction markets — why Jeff believes they represent the future of truth-seeking, how firms like Susquehanna will shape their evolution, and what obstacles still stand in the way of mass participation.We also discussed whether some decisions shouldn’t be quantified, how to protect markets from manipulation, and Jeff’s advice for students on what to study in 2025.Presented By: Rho.co/generatingalpha
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  Episode 38 (Part 2): Mickey Drexler - Former CEO of The GAP and J.Crew 14.10.2025 1h 6min

  This week on Generating Alpha, I’m joined once again by Mickey Drexler—the legendary “Merchant Prince” who reshaped modern retail through his leadership at Gap and J.Crew.In part two of our conversation, Mickey shares his unfiltered perspective on why he’s always had a distaste for corporate America, and how bureaucracy, complacency, and ego often kill creativity. We dive into his definition of good taste—how intuition, curiosity, and emotional intelligence drive product decisions—and the mindset that helped him scale Gap from $400 million to $14 billion while turning it into one of the most recognizable brands in the world.Mickey also opens up about his leadership philosophy—why he values brutal honesty, how he quickly reads people to know if they’re the right fit, and what it really takes to build an organization fueled by passion and excellence.It’s a candid, wide-ranging conversation that goes beyond fashion—about culture, leadership, and the relentless pursuit of quality. Few people see the world like Mickey Drexler, and his lessons resonate with anyone building something meant to last.Generating Alpha Rho Offer: rho.co/generatingalpha
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  Episode 38 (Part 1): Mickey Drexler - Former CEO of The GAP & J. Crew 04.10.2025 37min

  This week on Generating Alpha, I’m joined by Mickey Drexler — one of the most legendary figures in modern retail. Best known for transforming Gap into a global powerhouse and later reinventing J.Crew into a cultural phenomenon, Drexler has earned the nickname “The Merchant Prince” for his unparalleled ability to read consumers, build brands, and shape culture. Over decades, his vision has not only changed how America shops, but also redefined what it means to lead with instinct and creativity in business.In this first part of our conversation, Mickey reflects on his childhood in the Bronx, including his tough relationship with his father and the values that came from growing up in a working-class family. He shares how those early struggles instilled resilience, independence, and a relentless drive to prove himself — qualities that became central to his career.We trace his unlikely entry into retail, beginning with his very first job at a department store, where he developed a fascination with customers and the details of the shopping experience. From there, Mickey rose through the ranks of the fashion world, eventually becoming CEO of Ann Taylor, where he sharpened the instincts and discipline that would later serve as the foundation for his industry-defining work at Gap and J.Crew.We also dive into Mickey’s people philosophy — why he believes in being brutally honest, how he quickly assesses whether someone is the right fit, and why it rarely takes him more than a few minutes to form a judgment. His candid perspective on leadership and human behavior offers timeless lessons for anyone navigating business, management, or life.