Generating Alpha Podcast

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

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

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

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

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

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

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

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 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

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 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 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 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.