Invest Like the Best with Patrick O'Shaughnessy

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.

Fidji Simo, former CEO of Instacart and board member at Shopify, shares her journey from leading Facebook to transforming grocery retail. She discusses the impact of digital transformation in grocery shopping and the unique role of Instacart shoppers. Fidji emphasizes the importance of data and AI in enhancing customer experiences, along with her management philosophy that focuses on harnessing individual strengths. She also explores how generative AI is redefining online shopping, offering personalized meal suggestions to delight consumers.

Graham Weaver, founder of Alpine Investors and lecturer at Stanford Business School, discusses a unique private equity model targeting $20 million revenue businesses. He shares how Alpine places military veterans and top MBAs as CEOs, capitalizing on succession challenges faced by baby boomer owners. The conversation delves into leadership development, emphasizing resilience, emotional intelligence, and employee satisfaction as key to business success. Weaver also reflects on the importance of passion in the investment landscape and his personal journey of overcoming challenges.

Gustav Söderström, Co-President and Chief Technology Officer at Spotify, shares insights from the forefront of audio and video innovation. He discusses Spotify's evolution from a music platform to a multimedia giant, serving over 650 million users. Gustav reveals how the integration of AI is transforming user interaction and decision-making. He highlights Spotify's unique 'bets board' for resource allocation and the lessons learned from leadership challenges, including a notable interface failure. This candid conversation is packed with strategies for navigating the rapid tech landscape.

Rick Ruback and Royce Yudkoff, Harvard Business School professors, dive into entrepreneurship through acquisition. They discuss the evolution of the search-fund ecosystem, highlighting the differences between funded and self-funded models. Insights on finding ideal acquisition targets emphasize the importance of aligning personal strengths with business choices. The duo also addresses the impact of government-backed loans, niche service industries, and the challenges of transitioning ownership, offering a treasure trove of wisdom for aspiring entrepreneurs.

David Senra, host of the Founders podcast, shares insights gleaned from 400 entrepreneur biographies. He emphasizes the remarkable power of focus found in exceptional builders like Todd Graves and James Dyson, who thrive by honing in on simple ideas. Senra advocates for pursuing passions beyond profit, critiquing consumerism in favor of craftsmanship. He highlights the importance of resilience, talent cultivation, and a long-term commitment to one’s mission, inspiring listeners to discover their true calling and embrace the journey of authentic entrepreneurship.

In this engaging conversation, Cliff Sosin, founder of CAS Investment Partners, shares his unique investment journey from engineering to hedge funds. He dives deep into his substantial investment in Carvana, detailing its market cap rollercoaster from $60 billion to a 99% drop, and back towards $50 billion. The discussion offers insightful reflections on investing with intention, the complexities of logistics in Carvana’s operations, and the evolving role of AI in investment strategies. Cliff's experience sheds light on the delicate balance between concentration and diversification in today's market.

Cyan Banister, an angel investor at Long Journey Ventures and the first female partner at Peter Thiel's Founders Fund, shares her incredible journey from homelessness to investing in major companies like SpaceX and Uber. She discusses the intersection of spirituality and investment, emphasizing the need for purpose-driven investing. Cyan also delves into contrarian thinking, the challenges of navigating different investment stages, and meaningful life encounters, including a memorable interaction with Bill Murray that teaches the value of authenticity and joy.

Matt Huang, co-founder of Paradigm and former Sequoia Capital partner, brings profound insights into the crypto investment landscape. He discusses his transformative experiences, including a remarkable $10,000 return on his ByteDance investment. Matt shares frameworks for navigating the complexities of crypto and the importance of diverse teams in venture capital. He also addresses the potential of cryptocurrencies to enhance economic freedom and the challenges of regulation while advocating for a nuanced understanding of investment opportunities.