Invest Like the Best with Patrick O'Shaughnessy

Jeremy Giffon, a general partner at Tiny and co-founder of MediaCore, dives into the world of private markets. He discusses identifying unique investment opportunities stemming from misaligned incentives. The conversation covers the challenges faced by founders in a saturated market and the need for clear communication. Giffon shares insights on simplicity in investment strategies, the power of passion in professional life, and the significance of personal resilience. He emphasizes the value of uncovering hidden insights and maintaining open dialogue in business partnerships for lasting success.

David Senra, a historian of founders and entrepreneurs, shares profound insights from his extensive research on iconic figures like Estée Lauder and John Rockefeller. He discusses how obsession and childhood experiences fuel entrepreneurial success. The conversation explores the delicate balance of ego in business, emphasizing humility and continuous learning. Senra highlights the personal connection founders have with their creations and how passion, intertwined with pain, impacts their journeys. His reflections inspire a deeper understanding of the entrepreneurial spirit.

Martin Casado, a partner at Andreessen Horowitz and pioneer in software-defined networking, returns to discuss the AI revolution. He shares insights on AI's impact on creativity and policymaking, while addressing emerging challenges in investment and innovation. Casado emphasizes the need for sustainable business models in a rapidly evolving landscape and highlights the intricate dynamics of unstructured data management in AI startups. He balances optimism and skepticism regarding AI's future, exploring its profound effects on social interactions and digital infrastructure.

In this insightful conversation, Modest Proposal, an anonymous investor with a keen eye on public and private markets, delves into the complexities of today's economic landscape. He discusses the difference between frontier and open-source AI models, emphasizing the AI commoditization shift. The talk also covers overcapacity issues in transportation post-COVID and the economic implications of GLP-1 drugs for managing health conditions. Modest articulates the nuances of capital market dynamics, illustrating the challenges and opportunities investors face today.

In this engaging conversation, Robert Greene, renowned author of "48 Laws of Power" and "Mastery," shares deep insights into human behavior and the quest for purpose. He discusses the importance of unmasking authenticity and navigating social dynamics in a world dominated by social media. Greene emphasizes the long, transformative journey to mastery, weaving lessons from historical figures into practical advice for today. He also highlights the power of nonverbal communication and the impact of observation and encouragement in achieving success.

Pat Grady, a seasoned growth investor at Sequoia Capital, shares insights from his extensive portfolio, including giants like Snowflake and Zoom. He discusses the unique culture of 'healthy peer pressure' at Sequoia, emphasizing relationship-building with founders. Grady also highlights the importance of clarity over perfection in investment evaluation, using vivid examples. The conversation delves into the role of AI in transforming investing and ends with reflections on mentorship, kindness, and the pursuit of excellence in business.

Frank Blake, former chairman and CEO of Home Depot, shares his insights on leadership and organizational culture. He discusses the inverted pyramid model, focusing on prioritizing customers and employees to drive growth. Blake emphasizes the importance of personal connections through gestures like handwritten notes and the value of employee stories in shaping company culture. He also reflects on empathy in leadership during crises and how kindness can transform workplace dynamics, ultimately creating a more engaged and productive environment.

Adam Sandow, the chairman and CEO of SANDOW Companies and founder of Material Bank, revolutionizes the print media landscape with innovative business models. He shares his journey of transforming beauty magazine subscriptions and redesigning the sample request process for designers. Sandow emphasizes understanding customer pain points and the unique advantages of print in a digital era. Their conversation also delves into navigating media evolution, the balance of credibility, and the immersive experience offered by print, advocating for quality content amid digital distractions.

Howie Liu, co-founder and CEO of Airtable, leads a no-code app platform revolutionizing workflows for over 300,000 organizations. He discusses key growth decisions influenced by the COVID-19 pandemic, emphasizing the agility needed for sustained success. Liu delves into integrating AI into customizable workflows while contrasting horizontal and vertical software solutions. He reflects on the evolution of product philosophy and the potential for technology to reshape industries. His entrepreneurial journey offers insights into balancing innovation with strategic operations.

Mark Groden, Founder and CEO of Skyryse, is on a mission to make general aviation as safe as commercial aviation. He shares insights on the safety challenges uniquely faced by helicopters and advances in technology aimed at reducing accidents. Groden discusses his innovative SkyOS and the role of automation in making flying more accessible. He also reflects on the potential for increased public confidence in air travel as safety measures improve, ultimately striving to transform personal air travel into a routine experience.