Generating Alpha Podcast

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.

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

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.

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

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.

This week on Generating Alpha, I’m joined by Larry Silverstein, one of New York’s most influential real estate developers and the Chairman of Silverstein Properties. Over the course of his career, Larry has transformed the skyline of Manhattan, developing and managing some of the city’s most iconic office and residential towers. He is best known for his pivotal role in rebuilding the World Trade Center after 9/11 — a project that became both a personal mission and a symbol of resilience for New York City.Larry’s journey is a story of perseverance and vision. From modest beginnings in Brooklyn, he built a career marked by bold deals, steady leadership, and an unwavering commitment to New York. His story spans the purchase of his very first building, the challenges and triumphs of his early ventures, and the defining moment of taking on the responsibility to rebuild Lower Manhattan in the wake of tragedy.In this conversation, we dive into Larry’s early life and career, the lessons he learned from his first projects, and the vision that has guided him for decades in real estate. We also explore how he navigated the extraordinary challenge of leading the World Trade Center redevelopment, his philosophy on resilience and leadership, and the wisdom he has drawn from a lifetime shaping the future of New York City.

This week on Generating Alpha, I’m joined by Michael Chu — Global Co-CEO of L Catterton, the world’s largest consumer-focused private equity firm with more than $35 billion under management. Over three decades, Michael has helped transform L Catterton from a boutique investor into a global powerhouse with offices across North America, Europe, Asia, and Latin America. Known for his deep understanding of consumer behavior and brand equity, he has built a reputation as one of the foremost thinkers on what makes businesses not just succeed, but endure.At L Catterton, Michael has overseen investments in some of the world’s most iconic consumer brands, including Restoration Hardware, Birkenstock, Equinox, Peloton, and Vitamin Water. His career reflects a unique blend of financial expertise and behavioral insight, giving him a front-row seat to how timeless brands are built, scaled, and kept relevant across generations.In this conversation, we explore the principles that separate enduring brands from fleeting trends, the lessons Michael has learned from scaling L Catterton into a global leader, and the challenges of maintaining cultural relevance over time. We dive into his perspective on the future of consumer investing, what he believes defines the next wave of iconic brands, and the timeless insights he’s gained about growth, resilience, and long-term success in the consumer space.

This week on Generating Alpha, I’m joined by Barry Sternlicht — founder, chairman, and CEO of Starwood Capital Group, and one of the most accomplished real estate investors ever. Since founding the firm in 1991, Barry has grown Starwood into a global powerhouse with over $100 billion in assets under management, investing across every major real estate class. He has created and managed more than 80,000 hotels, multifamily, and residential units worldwide, while launching iconic hospitality brands like W Hotels, St. Regis, and 1 Hotels, redefining the way design and brand intersect with real estate.Barry’s accomplishments extend far beyond hospitality. Under his leadership, Starwood has executed transactions totaling hundreds of billions of dollars, spanning hotels, residential, office, retail, and industrial properties. He has been recognized repeatedly as one of the most influential figures in real estate, known for his contrarian eye, his ability to anticipate market cycles, and his pioneering focus on sustainable development years before it became mainstream.In our conversation, Barry reflects on a childhood shaped by resilience and early entrepreneurial ventures, the pivotal lessons he learned working under Neil Bluhm at JMB, and the rise of Starwood Hotels. We also dive into the biggest risks and near misses of his career, his philosophy on evaluating deals and negotiation, and the timeless advice he’d give to the next generation of leaders and entrepreneurs.