Invest Like the Best with Patrick O'Shaughnessy

Alan Waxman, co-founder and CEO of Sixth Street, takes listeners on a captivating journey through innovative investing. He shares insights from his days at Goldman Sachs and how they shape Sixth Street's unique strategies. Waxman discusses significant investments in Spotify and Airbnb during tough times, and the exciting sports partnerships with Real Madrid and FC Barcelona. He emphasizes the importance of an ego-less hiring approach and Sixth Street's 'face the tiger' philosophy, which encourages a culture of collaboration and adaptability in dynamic market landscapes.

Caryn Seidman-Becker, Chairman and CEO of Clear, transformed a bankrupt company into a leading secure identity platform. She recalls the early gritty days of sourcing hardware and rebuilding the business. Caryn shares insights on evolving identity verification, emphasizing innovation's role. She discusses balancing decisive actions with reflective leadership, tackling challenges in the travel industry, and embracing technology. With a vision for the future, she believes your face will soon become the key to everything, revolutionizing how we interact with security.

Jens Grede, co-founder and CEO of Skims, dives into the captivating intersection of pop culture and commerce. He argues that understanding consumer behavior is crucial in today's fragmented media landscape, noting how cultural shifts demand comfort and authenticity. Grede discusses the resurgence of brands like Abercrombie & Fitch and the importance of adapting to market changes. He highlights the unique challenges of scaling a fashion label while maintaining cultural relevance and emphasizes the evolving trust dynamics in digital media, where individual influencers are gaining prominence.

Charlie Songhurst, former head of strategy at Microsoft and prolific angel investor, shares invaluable investing insights from his experience with nearly 500 companies. He discusses the contrasting investment philosophies of the East and West coasts, emphasizing the importance of balancing quant and qual strategies. The conversation delves into navigating remote work while exploring cryptocurrencies like Bitcoin and Ethereum. Additionally, Songhurst highlights the complexities of investing, the influence of strong mentorship, and how hiring dynamics shape startup success.

In this engaging discussion, Alex Pall and Drew Taggart, the duo behind The Chainsmokers, unveil their transition from music superstars to insightful venture capitalists with their fund, Mantis. They explore the parallels between creativity in music and investing, advocating for authenticity and the importance of taste. The pair shares their personal journeys, emphasizing the significance of resilience through failure and maintaining intentionality in an oversaturated market. Their insights into building connections and navigating the business landscape remind us that passion and people drive both music and investment.

In this engaging discussion, Jay Hoag, co-founder of Technology Crossover Ventures, shares his pioneering insights into growth investing. He emphasizes the importance of macroeconomic factors affecting technology investments and presents a contrarian view that consumer internet holds significant potential over the trending SaaS and AI sectors. Jay reveals how TCV has evolved from traditional cold-calling to AI-driven sourcing, and he dives into the unique structure of their three-person investment committee, showcasing the balance between aggressive and conservative investment strategies.

Dinakar Singh, founder and CEO of Axon, shares a heartfelt journey marked by his child's battle with spinal muscular atrophy (SMA). He explores the emotional and financial motivations behind his commitment to developing life-saving drugs. Discussing the challenges of gene therapy and the pressing need for innovative treatments, he highlights grassroots efforts and collaboration in the biotech industry. Singh emphasizes the importance of community support and reforms to improve access to essential medications for families facing rare diseases.

Bill Gurley, a general partner at Benchmark Capital, shares his in-depth market analysis, focusing on the often-overlooked issues in venture capital as companies remain private longer. He discusses the misaligned incentives among GPs, LPs, and founders, leading to valuation challenges. The conversation also delves into the transformative impact of AI, likening it to past technology revolutions, and examines its implications for investment strategies. Gurley offers vital insights on adapting to the shifting investment landscape.

Kevin Taweel, Co-founder of Asurion, and Irv Grousbeck, Lead Director on its board, share fascinating insights into the company's evolution. They discuss the importance of frugality and cost management that propelled Asurion's impressive growth. Listeners will learn about strategies that foster a high-performance culture and the significance of effective communication within teams. The duo also explores the challenges of entrepreneurship, board dynamics, and the transformative power of strategic investments, providing lessons for future leaders.

John Zito, Co-President of Apollo Global Management, shares insights on the evolution of capital markets and Apollo's pivotal role. He discusses the convergence of private and public markets and their strategy to capture full client portfolios. Zito highlights Apollo's innovative approaches to investment during challenging times, like their turnaround of Hertz. He also explores the impact of AI on finance and the importance of adaptability in this dynamic landscape, making for a fascinating conversation on the future of investing.