Invest Like the Best with Patrick O'Shaughnessy

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.

Neil Mehta, founder of Greenoaks Capital and a savvy venture capitalist, discusses his journey in spotting future S&P 500 stars. He reflects on his bold 40% investment in Coupang, which paid off greatly. The conversation dives into his unique criteria for selecting visionary founders and creating unforgettable customer experiences. Neil emphasizes a hands-on approach to investment in an increasingly systematic world. Personal anecdotes highlight the evolution of technology and the meaningful bonds formed in his decade-long partnership.

In this intriguing conversation, Michael Ovitz, co-founder of CAA and a legendary talent agent, shares his insights on identifying exceptional talent across various fields. He discusses his unique 'pilot's checklist' for evaluating individuals and emphasizes the importance of time management as a crucial resource. Ovitz also dives into his transformative leadership at MoMA and the intersection of art and technology. He reflects on the pressures of success, the value of mentorship, and the evolving media landscape shaped by AI.

Darren Farber, Managing Partner of Albion River and former special advisor to the Deputy Undersecretary of Defense, dives deep into the world of defense investing. He discusses the evolving role of the U.S. in global defense and the technological innovations spurred by recent conflicts. Farber analyzes the situation in Taiwan and lessons learned from Ukraine, while unpacking the complexities of the U.S. defense budget. He emphasizes the importance of finding unique suppliers and maintaining technological superiority as America’s key advantage.

Josh Kushner, founder and managing partner of Thrive Capital, shares his insights from a decade of venture capital success. He discusses the importance of teamwork in investing and the power of creative thinking to challenge consumer norms. Kushner emphasizes the value of humility and listening in entrepreneurship, alongside the intrinsic motivation of founders. Additionally, he delves into the intricacies of evaluating talent in investment firms and navigating the ever-evolving tech landscape, all while advocating for adaptability and vision in business.

Gili Raanan, founder of Cyberstarts and a pioneer in cybersecurity investment, shares insights on the current landscape described as a "perfect storm" of global conflicts and AI advancements. He discusses his innovative "Sunrise" methodology for identifying customer pain points before solution development. The conversation highlights the necessity for resilient talent, personal adversity's role in entrepreneurship, and the significance of Google's acquisition of Wiz, showcasing trends that shape the future of cybersecurity and venture capital.