Invest Like the Best with Patrick O'Shaughnessy

Zack Kanter, the Founder and CEO of Stedi, shares insights on the evolution of business, contrasting Walmart's traditional retail practices with Amazon's digital innovation. They discuss the OODA loop's relevance in agile environments and draw parallels between military strategies and modern business models. Kanter emphasizes the importance of navigating 'build vs. buy' decisions, while exploring learning frameworks like 'just-in-time' vs. 'just-in-case.' Finally, he highlights the necessity of addressing unvoiced concerns to foster healthy team dynamics.

Chris Bloomstran, president and CIO of Semper Augustus Investments Group, shares his expertise on what defines a quality business. He dives into the importance of unique business models and customer relationships, with companies like Richemont and Disney illustrating current market trends. Bloomstran also reflects on his investment missteps and the key role of management quality in successful companies. His insights into growth versus value investing reveal the subtle nuances investors must consider in today’s dynamic market.

Brian Christian, author of "Algorithms to Live By", dives into the fascinating interplay between computers and humanity. He discusses the evolving nature of intelligence, including the pursuit of Artificial General Intelligence (AGI) and the implications it has on our understanding of what it means to be human. The conversation touches on career strategies in the age of automation, decision-making principles like the 37% rule, and the ethical considerations surrounding AI technology. Christian's insights provoke thought about our future with machines.

In this conversation, Eric Sorensen, CEO of Panagora Asset Management and a veteran of quantitative research, shares insights drawn from his diverse background, including a stint as a fighter pilot. He discusses the evolution of quantitative equity research and its increasing significance in financial markets. Eric also delves into the role of natural language processing in finance and the importance of creativity and innovation in research. Additionally, he highlights how risk premia impacts investment strategies and the necessity of adapting to a rapidly changing landscape.

Jane McGonigal, a world-renowned game designer and author of "Reality is Broken," discusses the transformative power of games. She explains how gaming fosters personal growth and collaboration, shifting focus away from competition. McGonigal shares her journey creating SuperBetter, a game that aids health recovery, emphasizing the role of play in overcoming challenges. The conversation encourages parents to engage in gaming with their kids and explores the psychological effects of design, aiming to harness games for real-world problem-solving.

In this insightful discussion, Bill Gurley, a general partner at Benchmark Capital known for his sharp investment acumen, delves into the power of network effects in business. He explores how increasing returns reshape traditional investment strategies and highlights the importance of team dynamics in fostering these effects. Gurley also shares his fascination with user-generated content platforms and the evolving landscape of marketplaces, emphasizing their potential for growth and the significance of adapting revenue models in a rapidly changing market.

Jesse Livermore, an anonymous thought leader on financial Twitter, dives deep into his unconventional investment strategies and unique research methodologies. He discusses the art of blending intuition with analytical thinking, highlighting the role of simplicity in decision-making. From his military background to navigating market complexities, Jesse emphasizes the importance of humility and the search for truth in investing. His insights into the dynamics of market valuation challenge traditional methods and advocate for cultivating constructive dissent in investment environments.

In this episode, Chuck Akre, founder of Akre Capital Management and a seasoned investor managing $10 billion, unveils his unique 'three-legged stool' framework for evaluating companies. He emphasizes the importance of imagination over mere knowledge in investing. Chuck shares insights on identifying extraordinary businesses, effective leadership traits, and the critical role of capital allocation. He also illustrates his investment philosophy with real-world examples like Bandag and shares thoughts on the significance of reinvestment in long-term success.

In this engaging discussion, Jerry Neumann, a thoughtful early-stage investor known for his structured insights on venture capital, shares his views on the pitfalls of gut-based investing. He delves into the risk misalignment in the VC space, the diminishing returns on popular edges like network effects, and emphasizes the importance of understanding value chains and IP protection. Jerry also critiques the influx of new VC firms and the implications of short-term thinking. His data-driven approach offers listeners a fresh perspective on navigating the complex landscape of venture investments.

In this engaging discussion, Sam Hinkie, the former President and GM of the Philadelphia 76ers, delves into his innovative, data-driven approach to basketball management. He shares how adopting a long-term perspective can minimize competitive pressure and foster success. Hinkie also highlights the thrilling early days of basketball analytics at the Houston Rockets and the importance of courage in navigating asymmetric outcomes. With insights on decision-making and team building, he explores the challenges and triumphs of integrating data in sports.