Generating Alpha Podcast

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.

In a rare interview, Jeff Yass, founder of Susquehanna International Group and former professional poker player, delves into the transformative potential of prediction markets. He discusses how these markets can improve decision-making and expose political falsehoods, while also predicting their future role in reducing costs for insurance and hedging. Jeff highlights the psychological barriers to adoption and emphasizes the need for strong probability skills in education. With insights into market manipulation and operational decisions, his views meld finance with the art of gambling.

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

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 Mike Anders, co-founder and General Partner at ICONIQ Capital — the discreet wealth manager and investment platform behind some of the world’s most influential leaders, including Mark Zuckerberg, Sheryl Sandberg, and Dustin Moskovitz. Often described as part family office, part venture powerhouse, and part philanthropic partner, ICONIQ now oversees more than $100 billion in assets while maintaining a remarkably low profile outside of Silicon Valley.In our conversation, Mike reflects on his unique upbringing as the son of two professors, splitting his childhood between Rhode Island and Palo Alto, and the early role models and experiences that shaped his worldview. We trace his path from politics to Wall Street, through the early scars of traditional wealth management, and into the partnership with Divesh Makan that became the foundation of ICONIQ.Mike shares his philosophy on building an organization that listens more than it speaks, curates collective intelligence, and acts as a “world-class caddy” for some of the most important entrepreneurs of our time. Along the way, he offers insights on what he’s learned from advising the visionaries shaping the future, how he filters signal from noise, and the advice he’d give to a 16-year-old navigating today’s world.

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 Thomas Kaplan, one of the most successful commodities investors of our time, renowned for his rare ability to pair historical perspective with bold conviction in the markets. Over the course of his career, Thomas has made some of the most significant calls in silver, gold, and natural gas — building multibillion-dollar ventures like Leor Exploration and Electrum Group — while also emerging as the world’s largest private collector of Rembrandts and a passionate advocate for wildlife conservation through Panthera, the global wild cat conservation organization he founded.Thomas’s journey is anything but conventional. With a BA and PhD in Modern History from Oxford, he began as a historian before turning to the markets, where he quickly distinguished himself through contrarian bets that few others dared to make. His story spans silver discoveries in Idaho and South America, pioneering work in natural gas exploration, and his enduring commitment to gold as a store of value and strategic asset. Beyond investing, his pursuits reflect his deepest passions: from art and history to preserving the world’s most endangered species.In this conversation, we dive into how Thomas’s early passions for history, art, and wild cats shaped his worldview, how his background as a historian influences his investment philosophy, and the principles that guided his most audacious calls in the commodities markets. We also explore his partnership with John Paulson on Donlin Gold, his journey as a collector and custodian of Rembrandt’s legacy, and the timeless lessons he has drawn about human nature from decades navigating fear and greed.

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 Alan Zafran — co-founder and managing partner of IEQ Capital, the $41.7 billion wealth management firm advising some of the most successful entrepreneurs, executives, and families in the world. Over more than three decades in the business, Alan has built a reputation for pairing sophisticated investment expertise with a deeply personal, relationship-driven approach to serving clients. Known for his ability to navigate both complex markets and complex family dynamics, he’s become a trusted advisor to those managing generational wealth.Before launching IEQ in 2019, Alan co-founded Luminous Capital, growing it into one of the largest independent advisory firms in the country before selling to First Republic. His career has also included leadership roles at Goldman Sachs and Merrill Lynch, giving him a rare vantage point on how wealth management has transformed over the years—from a largely product-driven sales model to one centered on fiduciary advice, customized strategies, and holistic planning.In this conversation, we explore Alan’s upbringing, his unconventional path into finance, and the lessons learned from advising clients with $10 million and $1 billion alike. We dive into his philosophy on risk, the opportunities and pitfalls of investing’s democratization, and the ways families can instill both drive and grounded values in the next generation. We also discuss the principles that have guided his career, how he thinks about building trust at the highest levels, and the single piece of advice he would give to a 15-year-old looking to make their mark in the world today.

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.