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.
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 SIG 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.
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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.
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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.
Kevin Hartz is the co-founder of Eventbrite, co-founder of Xoom, and General Partner at A* Capital. Over the past two decades, he’s taken two companies from idea to IPO, pioneered digital remittances, transformed the live events industry, and invested early in Airbnb, Pinterest, and Uber.
His career began in the early PayPal era, followed by founding Xoom and leading it to a public offering before its acquisition by PayPal, and later co-founding Eventbrite and scaling it into a global platform. In this episode, Kevin reflects on growing up between Miami and the Bay Area, how early political contrasts shaped his contrarian streak, and his time at Stanford — where he built an early social networking platform and connected with future PayPal leaders. He shares lessons from mentors like Pierre Lamond and Peter Thiel, the personal crisis that redirected his career, and what it was like to start Eventbrite with his wife.
We also explore his investment philosophy at A*, what he looks for in founders, and the industries he believes will define the next decade.
This week on Generating Alpha, I’m joined by Marty Chavez — computer scientist, Wall Street innovator, and one of the most influential technologists in modern finance. Trained as a physicist and doctor before pivoting to technology and markets, Marty has spent his career redefining how data, software, and capital intersect.
Best known for his time at Goldman Sachs, Marty served as CIO, CFO, and co-head of its Securities Division — pioneering the firm’s digital transformation and helping to build one of the most advanced trading architectures in the world. Today, he serves as Vice Chairman of Sixth Street and sits on the board of Alphabet, continuing to shape the future of finance and technology from both sides of the table.
In this conversation, we explore Marty’s path from early interest in coding to leadership on Wall Street, his experience applying machine learning in the ’90s, and the biggest lessons he’s learned about risk, systems, and human behavior. He shares thoughts on AI’s evolving role in finance, the importance of communication, and why being an outsider can be a superpower.
Marty’s perspective is invaluable because it bridges disciplines — offering rare clarity on how technology is reshaping markets, institutions, and the people who drive them.
This week on Generating Alpha I’m joined by Jim Chanos, legendary short seller, forensic investor, and one of the most iconic skeptics in modern financial history. For over four decades, Chanos has made a career out of going against the grain, identifying frauds, fads, and financial bubbles long before they unraveled.
He rose to national prominence for uncovering the accounting irregularities at Enron, shorting the company before its historic collapse. But that was far from his only call. Through his firm Kynikos Associates, Chanos has exposed some of the most high-profile corporate disasters of our time, from Baldwin-United to Wirecard, and developed a methodology for spotting systemic deception in markets.
In this conversation we trace Chanos’s early upbringing in Milwaukee and how his curiosity and contrarian streak led him from Wall Street to founding his own firm. We talk about his framework for detecting fraud, the behavioral patterns that repeat across financial history, and why some of the best short ideas are often hiding in plain sight. He shares lessons from past blow-ups, his thoughts on market cycles, and what it takes to stay disciplined in a world that rewards momentum.
Jim brings a level of intellectual honesty and rigor that is rare in today’s markets. His perspective is essential for anyone who wants to truly understand risk and uncover the stories that don’t make the headlines.
This week on Generating Alpha, I’m joined by Paul Krugman — Nobel Prize-winning economist, prolific writer, and one of the most influential economic thinkers of our time. Over the past five decades, Krugman has helped shape modern economics through both his academic work and his role as a leading public intellectual.
He first rose to prominence for his work on international trade and currency crises, which earned him the Nobel in 2008. But beyond academia, Krugman became a household name through his long-running New York Times column — which he concluded in 2024 — where he blended economic insight with sharp commentary on fiscal policy, globalization, inequality, and politics.
In this conversation, we talk about Krugman’s early life in Utica, the roots of his interest in economics, and the key — sometimes serendipitous — milestones in his career. We dive into his views on the global and U.S. economies, the evolution of trade policy, the rise of Wall Street’s influence, and the challenges of inequality and populism. He also shares what policymakers often get wrong, how he balances analysis with advocacy, and his advice for the next generation.
Paul brings a rare combination of clarity, experience, and conviction to economic issues that are often misunderstood. His perspective challenges assumptions and offers a powerful lens into how the world really works.
This week on Generating Alpha, I’m joined by Michael Rees — Co-President of Blue Owl Capital and the visionary founder behind Dyal Capital, the platform that pioneered GP stakes investing and reshaped the landscape of alternative asset management.
Michael launched Dyal Capital with a bold and unconventional insight: that owning minority stakes in leading asset managers could create durable, long-term value in a space historically focused on short-term performance. Over the past decade, under Michael’s leadership, Dyal has invested in some of the most elite and influential firms in alternatives—including Silver Lake, Sixth Street, Vista Equity Partners, H.I.G. Capital, and many others.
In 2021, Dyal merged with Owl Rock to form Blue Owl Capital, where Michael now helps lead one of the fastest-growing alternative investment platforms in the world—managing over $270 billion across private credit, GP stakes, and real estate strategies.
In this wide-ranging conversation, we talk about Michael’s early career at Lehman Brothers, the genesis of Dyal Capital, and how he built an institutional platform that redefined how investors think about the business of asset management itself. We also explore the key qualities that separate great firms from good ones, what he’s learned from working with some of the sharpest minds in finance, and how Blue Owl is positioning itself for the future of alternatives.
Michael’s story is one of innovation, resilience, and a relentless focus on building lasting value—offering powerful lessons for anyone navigating the evolving worlds of investing, entrepreneurship, and financial strategy.
This week on Generating Alpha, I’m joined by Annie Duke — a former professional poker player turned cognitive scientist, bestselling author, and one of the world’s foremost experts on decision-making under uncertainty. Over the course of her career, Annie has helped everyone from investors to CEOs to policymakers improve how they think about risk, probabilities, and knowing when to double down — and when to walk away.
Annie’s journey is anything but traditional. She left a PhD program in cognitive psychology at the University of Pennsylvania and went on to become one of the most successful poker players in the world, winning millions — including a World Series of Poker championship. After retiring from poker, she dedicated herself to teaching others how to make better decisions in environments where luck and skill collide.
She’s the author of multiple bestselling books, including Thinking in Bets, How to Decide, and Quit, which have become required reading for decision-makers in finance, business, and beyond. Her work sits at the intersection of psychology, game theory, and behavioral finance.
In this conversation, we explore how to make smarter decisions under uncertainty, the common mistakes even the smartest investors make, how to know when quitting is actually the most rational choice, and the frameworks she’s developed that anyone can apply — whether at the poker table, in markets, or in life.
This week on Generating Alpha, I’m joined by Joseph Edelman — founder and CEO of Perceptive Advisors, and arguably the most successful biotech investor of the past two decades. Over the last 25 years, Joe has built Perceptive into one of the most dominant and respected healthcare-focused investment firms in the world — with a track record that rivals the best human-managed funds in modern history.
Joe launched Perceptive in 1999 with a simple but highly differentiated insight: that deep scientific expertise, paired with bold and patient capital, could drive outsized returns in one of the most complex and volatile corners of financial markets. Since then, he’s backed some of the most transformative biotech and life sciences companies — businesses pioneering breakthroughs in gene therapy, rare diseases, oncology, and cutting-edge therapeutics.
In this rare conversation — his first-ever podcast appearance — we dive into his upbringing, how his passion for science shaped his worldview, the founding story of Perceptive, and how he navigates an industry defined by uncertainty, asymmetric outcomes, and extreme volatility. We also talk about what separates great investors in highly specialized spaces, how he thinks about risk, and the mindset that’s driven one of the most remarkable investing careers of the past quarter century.
Joe’s story is one of conviction, intellectual rigor, and staying true to a focused mission — offering a masterclass in long-term thinking for anyone in investing, entrepreneurship, or science-driven industries.
This week on Generating Alpha, I’m joined by Anthony Pompliano — a former soldier turned tech executive, investor, and one of the most influential voices in Bitcoin and digital finance. Known to millions simply as “Pomp,” Anthony has built a uniquely powerful presence at the intersection of technology, investing, and media.
After serving in the U.S. Army, Anthony transitioned into the private sector with roles at Facebook and Snapchat during periods of explosive growth. He later co-founded Morgan Creek Digital, an investment firm focused on blockchain technology and digital assets. Over the past several years, he’s become one of the most widely followed advocates for Bitcoin and decentralized systems — building an audience that spans Wall Street, Silicon Valley, and everyday retail investors. Through his daily newsletter and top-ranked podcast, he’s played a major role in shaping how a new generation understands money, innovation, and financial sovereignty.
In our conversation, we talk about how his upbringing and military background helped shape his work ethic and worldview, lessons he took from working directly with leaders like Mark Zuckerberg and Sheryl Sandberg, and how he came to see Bitcoin not just as technology, but as an ideology. We also explore what separates great founders and the mindset he uses to stay sharp in rapidly evolving markets.
Anthony’s journey is a testament to conviction, clarity of thought, and the power of building in public — and his perspective offers real value for anyone navigating the future of finance, media, or entrepreneurship.
This week, I had the honor of sitting down with Roger Altman—an icon of American finance whose influence spans Wall Street, Washington, and beyond. Roger began his career at Lehman Brothers, where he became the youngest-ever general partner in the firm’s history. In the 1980s, he played a key role in the founding chapter of Blackstone, working alongside Pete Peterson and Stephen Schwarzman as they shaped what would become one of the world’s largest alternative asset managers. But Roger’s contributions didn’t end in the private sector.
He twice served in the U.S. Treasury Department, including as Deputy Secretary under President Clinton, helping steer the country through critical fiscal and economic decisions. Then in 1995, he founded Evercore with a vision for a firm that would combine world-class financial advice with independence, integrity, and client-first values. Since then, Evercore has grown into a $10 billion company that has advised on over $5 trillion in transactions—earning a place among the most respected firms on Wall Street.
In our conversation, Roger shares reflections from a career that has intersected with nearly every major financial and political turning point of the last 50 years. We explore his early days at Lehman, his transition into public service, and the values that guided him as he built Evercore from scratch. He opens up about the lessons that skills that have aided him in the competitive enviornment of Wall Street, and the advice he’d give to a 15-year-old trying to make sense of the world today.
In this episode, I sat down with Tully Friedman—one of the true pioneers of private equity—for his first-ever podcast appearance. Tully co-founded Hellman & Friedman, a firm that helped define the modern buyout era, and later launched Friedman, Fleischer & Lowe, where he’s led investments in middle-market businesses with a highly focused and values-driven approach. Before that, he made his mark at Salomon Brothers during the firm’s golden age in the 1970s, gaining an early education in high-stakes finance at one of Wall Street’s most legendary institutions.
Over the course of our conversation, Tully shares how his early life and legal training shaped his worldview, the principles behind building two successful investment firms, and how he evaluates leadership and long-term value. We also discuss his partnership with the late Warren Hellman, his definition of a “great investment,” and the non-negotiable values he’s never sacrificed for returns.
This episode is full of timeless lessons on judgment, talent, integrity, and scale—told by someone who has quietly influenced generations of investors behind the scenes.
If you have not already, I urge you to subscribe or follow the podcast and share it if you enjoyed this conversation.
