Generating Alpha Podcast

In this conversation, Keith Rabois, Managing Director at Khosla Ventures and a tech industry titan, shares insights from his remarkable career. He discusses the unique culture at PayPal that cultivated future founders and emphasizes the importance of identifying exceptional talent with world-changing potential. Keith reveals his rapid decision-making process for investments and highlights the importance of building a strong talent density in startups. He also reflects on his move to Miami for a better quality of life, and offers advice for aspiring entrepreneurs.

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

Ryan Tolkin, CEO and CIO of Schonfeld Strategic Advisors, transformed the firm into a global hedge fund powerhouse after starting as an intern. He discusses his early investment experiences and the pivotal shift to accepting outside capital for expansion. Tolkin shares insights on attracting talent, maintaining a strong culture, and navigating market complexities to enhance portfolio management. He emphasizes the importance of identifying true signals amid noise and his daily routine that balances professional demands with personal life.

Collin Roche, Co-CEO of private equity firm GTCR, discusses his unique Leaders Strategy, which focuses on identifying world-class leaders before they even start companies. He shares insights on what differentiates top operators, the importance of storytelling in investment, and the keys to long-term success: leadership, data use, and teamwork. Collin also reflects on his upbringing, the value of a liberal arts education, and the lessons he's learned from his experiences at Goldman Sachs and throughout his career.

Antonio Gracias, Founder and CEO of Valor Equity Partners, is an influential investor-operator known for early investments in Tesla and SpaceX. In this conversation, he shares insights on using first-principles thinking and non-linear reasoning to make counterintuitive investment choices. Gracias discusses the challenges of scaling technology businesses, the importance of aligning values in teams, and how disruption can create opportunities. He also reflects on lessons learned from his experiences with entrepreneurs like Elon Musk and offers advice on prioritizing core values over rigid plans.

This week on Generating Alpha, I sat down with Thomas Peterffy — founder of Interactive Brokers, one of the most profitable and technologically advanced trading platforms in the world, used by nearly every professional trader.Born in post–WWII Hungary, Peterffy grew up under communist rule before escaping the Soviet Bloc and arriving in New York in 1965 with no money and no ability to speak English. He started as a draftsman, taught himself to code, and eventually found his way onto Wall Street — where he revolutionized finance by bringing computers to options trading decades before it became the norm.Over time, Peterffy built Interactive Brokers into a $120 billion global powerhouse with profit margins higher than Visa’s. His relentless focus on automation, transparency, and efficiency helped define the modern era of electronic trading and made IBKR the go-to platform for professionals around the world.In our conversation, we spoke about his early life behind the Iron Curtain, how he built one of the most advanced trading systems ever created, his philosophy on risk and innovation, and what continues to drive him even after becoming the 22nd richest person in the world.It’s a story of grit, intellect, and visionary ambition — from a refugee who transformed the very structure of global markets.

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

This week on Generating Alpha, I’m joined once again by Mickey Drexler—the legendary “Merchant Prince” who reshaped modern retail through his leadership at Gap and J.Crew.In part two of our conversation, Mickey shares his unfiltered perspective on why he’s always had a distaste for corporate America, and how bureaucracy, complacency, and ego often kill creativity. We dive into his definition of good taste—how intuition, curiosity, and emotional intelligence drive product decisions—and the mindset that helped him scale Gap from $400 million to $14 billion while turning it into one of the most recognizable brands in the world.Mickey also opens up about his leadership philosophy—why he values brutal honesty, how he quickly reads people to know if they’re the right fit, and what it really takes to build an organization fueled by passion and excellence.It’s a candid, wide-ranging conversation that goes beyond fashion—about culture, leadership, and the relentless pursuit of quality. Few people see the world like Mickey Drexler, and his lessons resonate with anyone building something meant to last.Generating Alpha Rho Offer: rho.co/generatingalpha

This week on Generating Alpha, I’m joined by Mickey Drexler — one of the most legendary figures in modern retail. Best known for transforming Gap into a global powerhouse and later reinventing J.Crew into a cultural phenomenon, Drexler has earned the nickname “The Merchant Prince” for his unparalleled ability to read consumers, build brands, and shape culture. Over decades, his vision has not only changed how America shops, but also redefined what it means to lead with instinct and creativity in business.In this first part of our conversation, Mickey reflects on his childhood in the Bronx, including his tough relationship with his father and the values that came from growing up in a working-class family. He shares how those early struggles instilled resilience, independence, and a relentless drive to prove himself — qualities that became central to his career.We trace his unlikely entry into retail, beginning with his very first job at a department store, where he developed a fascination with customers and the details of the shopping experience. From there, Mickey rose through the ranks of the fashion world, eventually becoming CEO of Ann Taylor, where he sharpened the instincts and discipline that would later serve as the foundation for his industry-defining work at Gap and J.Crew.We also dive into Mickey’s people philosophy — why he believes in being brutally honest, how he quickly assesses whether someone is the right fit, and why it rarely takes him more than a few minutes to form a judgment. His candid perspective on leadership and human behavior offers timeless lessons for anyone navigating business, management, or life.

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