Generating Alpha Podcast

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.

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