Generating Alpha Podcast

Ian Livingstone, co-founder of London Regional Properties and longtime private investor known for buying distressed assets and owning hotels like the Fairmont Monte Carlo. He tells the story of moving from optometry to building a global real estate and operating portfolio. Conversation covers buying during crashes, refurbishing iconic hotels, family-controlled capital, and opportunistic cross-sector investing.

Yoni Assia, co-founder and CEO of eToro and veteran fintech entrepreneur, reflects on building a social investing platform that popularized CopyTrader. He discusses starting during the 2008 crisis, early crypto work with Vitalik, scaling a retail investing network, co-founder dynamics with his brother, risk controls through crypto winters, and the future of tokenization and AI in finance.

Dmitry Balyasny, founder and CIO of Balyasny Asset Management, a multi-strategy hedge fund leader. He talks about building a multi-manager platform, rigorous risk management, and creating a culture that attracts and develops top investment talent. Short stories cover his trading origins, capital allocation approach, and how open communication and training sustain long-term edge.

Pete Muller, founder and CEO of PDT Partners and a mathematician-turned-musician, built a secretive, high-performing quant firm and also writes music and crosswords. Conversation covers building durable models, shaping a collaborative culture that avoids burnout, navigating the 2007 quant crisis, limits to scaling strategies, and how music and diverse interests inform creative problem-solving.

Larry Connor, founder of The Connor Group and record-setting adventurer, built a contrarian real-estate firm focused on operating apartments as businesses. He discusses counter-cyclical buying, an operational playbook that hires outsiders, a culture of extreme accountability, lessons from failure, and how exploration fuels purpose and disciplined risk-taking.

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.