Explore every episode of the podcast Generating Alpha Podcast

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

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 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.

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.

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

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

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.

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.

This week, I had the rare opportunity to sit down with Asher Edelman—one of the most legendary and unconventional figures to ever emerge from Wall Street. A pioneer of corporate raiding in the 1980s and widely recognized as one of the real-life inspirations for Gordon Gekko, Asher built a reputation for bold, high-stakes takeovers that redefined the balance of power between shareholders and management. After founding Edelman & Co., he became known not just for his financial acumen, but for the psychological precision with which he approached every deal—often guided by his monthly reading of The Art of War.

Beyond finance, Asher has had an extraordinary second act in the art world, where he's become a prominent dealer, collector, and curator with a keen eye for value and authenticity. He recorded this conversation in his Switzerland office, surrounded by pieces from his personal art collection, which he graciously walked me through.In this episode, we explored his early days on Wall Street in the 1950s, his most memorable corporate battles, and the traits that separated survivors from legends. He also shared insights on the current state of activism, including his candid take on an investor he believes doesn’t live up to the title. Asher’s perspective is sharp, original, and completely unfiltered—this is a rare glimpse into a mind that has shaped both markets and culture for over half a century.

P.S. I apologize for the choppiness at some parts of the interview, I had some technical difficulties on my end.

This week, I had the pleasure of sitting down with Scott Bok—a deeply thoughtful leader whose journey from Grand Rapids, Michigan to the top of Wall Street reflects quiet determination, intellectual rigor, and a deep commitment to principled leadership.

Best known for his long tenure as CEO of Greenhill & Co., Scott has helped shape the modern M&A landscape.Scott’s story is one of steady ascent. After earning his law degree from Penn, he began his career at Wachtell, Lipton, Rosen & Katz before moving to Morgan Stanley, where he spent over a decade navigating the fast-evolving world of investment banking. He later joined Greenhill in its early years and eventually led the firm through its IPO, the global financial crisis, and its recent sale to Mizuho—all while fostering a culture that prioritized independence, trust, and long-term thinking.

Our conversation touched on his early influences, the defining moments of his career, and the lessons he's drawn from decades of advising CEOs and boards on high-stakes decisions. Scott brings a rare blend of humility and insight, and his reflections offer valuable guidance not only for those in finance, but for anyone striving to lead with clarity and integrity.I hope you enjoy this episode as much as I did.

This week, I had the pleasure of sitting down with Dan Ariely, one of the most influential voices in behavioral economics and a pioneer in understanding the irrational forces that drive human behavior. A bestselling author whose books—including Predictably Irrational, The Honest Truth About Dishonesty, and Dollars and Sense—have sold millions of copies worldwide, Dan has helped reshape how leaders across business, healthcare, and policy think about decision-making. His TED Talks have garnered over 10 million views, and his research at Duke University continues to inspire both academic and corporate communities around the globe.Dan’s personal story is as powerful as his professional work. After surviving a traumatic accident as a teen in Israel, he became deeply fascinated by how people experience pain, make choices, and navigate complexity—insights that fuel his mission to design systems that support better, more human decisions.While this podcast usually features financial leaders, I knew I had to bring Dan on because understanding the why behind decisions is just as critical as the strategies themselves. In our conversation, we explored his early life, the behavioral patterns that shape utility and trust, and what it takes to create environments where both employees and ideas can thrive.Dan’s blend of scientific insight, practical wisdom, and human empathy makes this episode uniquely powerful—and one I believe every leader should hear.

This week, I had the pleasure of sitting down with Anthony Scaramucci, a true embodiment of resilience, reinvention, and grit. Best known as the founder and managing partner of SkyBridge Capital, Anthony’s journey has taken him from humble beginnings in Long Island to the highest levels of Wall Street and a brief but unforgettable turn in Washington, D.C.

Anthony’s story is one of constant evolution. After starting his career at Goldman Sachs, he took the leap to build his own firm, navigating market cycles, public scrutiny, and personal setbacks along the way. What stands out most about Anthony is his unwavering belief in the power of authenticity. Whether in finance, politics, or media, he’s never been afraid to speak his mind or challenge the status quo—and he’s built a business culture at SkyBridge that reflects those same values.

Our conversation touched on his upbringing, his biggest wins and losses, and the philosophy that’s kept him grounded through it all. We talked about what it really means to be an outsider, how to cultivate courage and curiosity throughout your life, and why staying true to yourself is the ultimate competitive edge.

Anthony’s energy, self-awareness, and candor make him a rare figure in any industry—and his ability to keep pushing forward, no matter the obstacles, is both inspiring and instructive.

I hope you enjoy this episode as much as I did.

This week, I had the distinct honor of speaking with Howard Marks, one of the most respected and insightful investors of our time, and the co-founder and co-chairman of Oaktree Capital Management. Known for his deeply analytical memos and disciplined approach to risk, Howard has helped shape the landscape of investing.

Howard’s career began in equity research at Citibank in 1968, where he witnessed firsthand the boom and bust of the Nifty Fifty era. He later transitioned into high-yield and distressed debt, eventually co-founding one of the first distressed debt funds at TCW in 1988 with Bruce Karsh. In 1995, the two left to launch Oaktree Capital Management, which has since grown into one of the world’s leading alternative asset managers—with a distinct culture focused on risk control, intellectual honesty, and long-term thinking.

In our conversation, we explored the defining chapters of Howard’s career—from building conviction around a then-niche strategy, to the building of Oaktree. Along the way, we discussed what makes a great investor, the importance of price, and how Howard and Bruce Karsh built one of the most effective partnerships in modern finance.

And on a more personal level, we reflected on his childhood, the influence of the late Charlie Munger, and what advice he’d give to a 15-year-old navigating the world today.

Howard’s clarity of thought, long-term orientation, and humility make him a rare voice in the industry—and I came away from this conversation with a deeper appreciation for the philosophy behind Oaktree and Howard's success.

I hope you enjoy this episode as much as I did.

This week, I had the distinct honor of speaking with Barry Ritholtz, one of the most original and influential voices in modern finance, and the co-founder, chairman, and CIO of Ritholtz Wealth Management. With a career that has spanned law, trading, strategy, and media, Barry’s unique path has given him a perspective that few in the industry can match.

After beginning his professional life as a lawyer, Barry made the unconventional leap into finance—first as a trader, then as a strategist, and ultimately as the architect of one of the fastest-growing wealth management firms in the U.S. Alongside Josh Brown, he built Ritholtz Wealth Management on the foundation of transparency, evidence-based investing, and a deep respect for behavioral finance.

Barry’s latest book, How Not to Invest, is a culmination of decades of experience studying markets, investor psychology, and systemic failures. Rather than offering yet another formula for beating the market, the book takes a different approach—highlighting the most common mistakes investors make and the thinking traps that lead to underperformance. Organized into three categories—bad ideas, bad numbers, and bad behavior—it’s a guide for avoiding the pitfalls that derail so many investment journeys.

In our conversation, we covered Barry’s unconventional upbringing, the twists and turns of his career, and the mental models that have shaped his approach to investing and decision-making. We also dug into the principles behind his book, his thoughts on media consumption, and how young people can navigate their own paths in an increasingly noisy world.

I hope you enjoy this episode as much as I did.

This week, I had the distinct honor of speaking with Felix Zulauf, a legendary figure in the world of macro investing and the founder of Zulauf Consulting. With over four decades of experience navigating the complexities of global markets, Felix has cemented his place as one of the most insightful and influential voices in finance.He began his career at Swiss Bank before joining UBS, where he rose to become Head of Global Asset Management. In 1990, he struck out on his own to launch Zulauf Asset Management, a fund that managed billions and delivered consistent, long-term outperformance. A longtime member of the Barron’s Roundtable, Felix is known for his sharp macro insights, contrarian thinking, and ability to anticipate major turning points in markets well before they occur.Beyond his impressive track record, what sets Felix apart is his global mindset and philosophical approach to investing. Over the years, he's cultivated a deep understanding of how politics, economics, and psychology intersect to drive market behavior. His insights have shaped how many professionals view the world.In this episode, we spoke about his early years growing up in Switzerland, his path from commercial banking to global strategist, and the motivations behind founding his own firm. We explored how he developed his mental framework and the evolution of his investing process.We also discussed the unique challenges and advantages of managing money independently versus within large institutions, the key geopolitical forces driving markets today, and how he continues to stay sharp after 40+ years in the business.Hope you enjoy this conversation as much as I did.

Felix's YouTube: @zulaufconsulting

Felix's LinkedIn: https://www.linkedin.com/company/27109806/admin/dashboard/

This week, I had the honor of speaking with Annie Lamont, one of the most respected investors in healthcare and fintech. As the Co-Founder and Managing Partner of Oak HC/FT, Annie has built a reputation for identifying and backing transformative companies that have reshaped industries. With over 30 years in venture capital, she has led investments in some of the most innovative companies in healthcare, financial services, and technology. Annie’s journey began with a strong foundation—after attending Stanford, she started her career at Hambrecht & Quist, where she gained exposure to high-growth technology and healthcare companies. She later joined Oak Investment Partners, where she spent decades honing her investment philosophy before co-founding Oak HC/FT, a firm dedicated to healthcare and fintech innovation. In this conversation, we dive into Annie’s early career, the lessons she learned navigating venture capital as a young investor, and the turning points that led her to build Oak HC/FT. She shares how she evaluates new industries, her approach to investing in cutting-edge fintech and healthcare startups, and how the increasing overlap between these sectors is shaping the future. We also discuss the principles that guide her investments, the biggest changes in venture capital over the last two decades, and the qualities that define great entrepreneurs. Finally, Annie offers invaluable advice on breaking into venture capital, navigating market cycles, and the lessons she would share with her younger self. This episode is packed with insights from one of the most influential investors in the industry—I hope you enjoy it!

This week, I had the privilege of sitting down with Tim Draper, a legendary venture capitalist, entrepreneur, and advocate for innovation and freedom. As the founder of Draper Fisher Jurvetson (DFJ), Draper Associates, and Draper University, Tim has played a pivotal role in shaping the startup ecosystem, backing companies like Tesla, SpaceX, Baidu, Coinbase, Robinhood, Skype, and Twitch.

Coming from a long line of investors—his grandfather was the first venture capitalist in Silicon Valley—Tim has spent decades pushing boundaries in finance, technology, and education. He was an early advocate for Bitcoin, making headlines in 2014 when he purchased 29,656 BTC in a U.S. Marshals auction.

Beyond investing, Tim has championed entrepreneurial education through Draper University, where he helps young founders develop real-world skills. He is also known for his bold ideas, including his controversial proposal to split California into multiple states, and his strong views on decentralization and the future of innovation.

In our conversation, we dive into his upbringing, how he built his venture capital empire, and the big bets he believes will shape the future. Tim shares his insights on Bitcoin, AI, and investing in transformative technologies, as well as his advice for young entrepreneurs looking to break into the world of business and venture capital.

This episode is packed with incredible stories, valuable lessons, and bold ideas—I hope you enjoy it!

This Wednesday, I had the privilege of speaking with Bob Prince, one of the most influential macro investors of our time. As Co-Chief Investment Officer at Bridgewater Associates, the world’s largest hedge fund, Bob has spent decades refining the firm’s systematic approach to global markets, risk management, and economic forecasting.

Bob joined Bridgewater in the 1980s, working alongside Ray Dalio to develop the firm’s renowned All Weather strategy—a risk-balanced investment approach designed to perform across economic cycles. Over the years, he has been a key architect of Bridgewater’s macroeconomic insights and portfolio construction methods, helping institutions and governments navigate volatile markets. His ability to bridge economic theory with practical investing has made him one of the most respected voices in finance.

In our longest episode yet, we dive deep into Bob’s journey—from his early career and formative experiences to the evolution of Bridgewater and the principles behind its success. He shares insights on leadership, decision-making, and the role of humility in investing, along with lessons learned from working with some of the greatest minds in finance.

We also discuss what he’s watching in today’s macro environment, and his advice for the next generation. Thanks for tuning in and I hope you enjoy!

This Tuesday, I had the privilege of sitting down with Glenn Dubin, someone I consider a friend and mentor. Glenn is a legendary investor and entrepreneur who built one of the most successful hedge funds of this era. As the co-founder of Highbridge Capital Management, Glenn played a pivotal role in shaping the modern hedge fund industry, pioneering a multi-strategy investment approach that set new standards for risk management and performance. Glenn began his career after graduating from Stony Brook University, starting out as a floor broker before venturing into proprietary trading. In 1992, he co-founded Highbridge Capital Management with childhood friend Henry Swieca, growing it into a global powerhouse. The firm was later acquired by JPMorgan Chase, marking one of the most significant deals in hedge fund history. Glenn currently runs his family office, Dubin & Co, building and investing in the most innovative and interesting businesses across industries in the 21st century. Beyond investing, Glenn has been deeply involved in philanthropy and healthcare innovation, supporting medical research and education through the Dubin Family Foundation. He is heavily involved in Modern Art, serving as a trustee of the MOMA alongside our former guest Steve Cohen. His disciplined approach to markets, leadership, and risk-taking has made him a widely respected figure in finance. In this episode, we explored Glenn’s journey from the Washington Heights to leading a billion-dollar fund, his views on leadership, economic tailwinds, and building a durable business, as well as his advice for those looking to succeed in today’s financial landscape. Here are links to materials mentioned in the podcast: Highbridge HBS Case Study: https://hbsp.harvard.edu/product/OB77-PDF-ENG Invest Like The Best with Alex and Matt: https://podcasts.apple.com/us/podcast/matt-perelman-alex-sloane-the-art-of-franchise-investing/id1154105909?i=1000673134417 Acquiring Minds with Jordan Dubin: https://acquiringminds.co/articles/jordan-dubin-guild-garage-group

Today, I had the honor of sitting down with Alan Schwartz, a distinguished leader in finance and investment banking. Best known for his tenure as the CEO of Bear Stearns, Alan has had a remarkable career at the highest levels of Wall Street, navigating some of the most challenging moments in financial history.

Alan began his career after earning his degree from Duke University, joining First Boston before moving to Bear Stearns in 1976. Over the next three decades, he rose through the ranks, eventually becoming CEO in 2007, just months before the 2008 financial crisis. As the firm faced unprecedented turmoil, Alan played a critical role in its final days, ultimately overseeing its sale to JPMorgan Chase.

Following his time at Bear Stearns, Alan transitioned to Guggenheim Partners, where he currently serves as Executive Chairman, helping to build one of the most respected financial services firms in the world.

In this episode, we discuss Alan’s journey, his perspectives on leadership, connecting the dots, and the lessons he’s learned from navigating crises. He also shares invaluable insights on the evolution of investment banking, and advice for those looking to build lasting careers in finance.

Today, we had the privilege of speaking with Michael Mauboussin, one of the most respected minds in value investing. With a career spanning decades in finance, Michael has been at the forefront of applying behavioral science, probability, and market efficiency to investment strategy.

Michael began his career after earning his degree from Georgetown University, later becoming a longtime Chief Investment Strategist at Legg Mason Capital Management. He has since held senior roles at Credit Suisse and Morgan Stanley, where he has shaped investment thinking with his deep research into expected value, skill vs. luck, and the psychology of markets.

Beyond his professional work, Michael is a prolific author, having written several essential books, including The Success Equation and More Than You Know, which explore how to make better decisions in uncertain environments. He also serves as an adjunct professor at Columbia Business School, where he teaches and mentors the next generation of investors.

In this episode, we dive into Michael’s journey, his perspectives, and his advice for investors at every level. Whether you’re a professional or just starting out, this conversation is packed with insights that will change how you approach investing. We hope you enjoy!

Today, we had the honor of sitting down with Alan Patricof, a true pioneer in the world of venture capital. Widely credited as one of the first VCs in history, Alan has played a pivotal role in shaping the industry over the past five decades.

Alan began his career after earning degrees from Ohio State University and Columbia Business School, and in 1969, he founded Alan Patricof Associates, one of the first venture capital firms in the U.S. That firm later evolved into APAX Partners, which became one of the largest private equity funds in the world. Through APAX, Alan was an early investor in game-changing companies like Apple, AOL, and Office Depot.

In 2006, he co-founded Greycroft alongside Dana Settle and Ian Sigalow, focusing on early-stage media investments in companies such as Huffington Post and Venmo. Then, at age 85, he launched Primetime Partners with Abby Levy, a fund dedicated to investing in businesses that serve the aging population.

Now, at 90 years old, Alan remains incredibly sharp and engaged, continuing to push boundaries in both business and life. In this episode, we dive deep into his remarkable career, his insights on venture capital, advice for entrepreneurs, and his perspectives on longevity. Thanks for listenings.