Invest Like the Best with Patrick O'Shaughnessy

Jesse Livermore, a research partner at O’Shaughnessy Asset Management, dives into the complexities of today's 'upside down markets.' He unpacks how fiscal policy can create surprising effects on stock performance despite challenging economic conditions. Livermore explains the evolving role of the Federal Reserve and its impact on market dynamics, particularly post-COVID-19. He also discusses the intricate balance between cash, bonds, and equities amid government stimulus, shedding light on the paradox of strong stock markets amidst economic struggles.

Rahul Vohra, Founder and CEO of Superhuman, and Evan Reiser, CEO of Abnormal Security, dive into the emotional aspects of product design. Vohra shares how game design principles can convert mundane software into engaging experiences, while discussing the balance between innovation and strategy in product development. They explore the importance of brand strength for investment success and the evolving landscape of email security. Together, they illustrate how understanding customer emotions can lead to impactful solutions and successful business strategies.

Modest Proposal, a well-respected thinker on financial Twitter, dives into investment strategies for today's dynamic market. He discusses the shift towards prioritizing future potential over historical performance. The conversation also highlights how reducing friction can enhance consumer engagement, with examples like Uber and Zillow. Additionally, Modest delves into the evolution of seemingly trivial business ideas and the complexities of navigating online marketplaces. His insights on monopoly dynamics and valuation challenges provide a fresh perspective on investing.

Lauren Taylor Wolfe, co-founder and Managing Partner of Impactive Capital, discusses the modern activist investor playbook. She delves into how strategies have evolved, favoring collaboration over the traditional adversarial approach. Wolfe emphasizes the importance of ESG integration and long-term value creation. The conversation also touches on the growing impact of employee activism post-COVID and the need for diverse leadership in corporate governance. Additionally, they introduce Positive Sum, a new initiative focused on early-stage equity investing.

Rory Sutherland, Vice Chairman of Ogilvy & Mather Group and author of "Alchemy," shares his unconventional marketing insights. He argues that spreadsheets can stifle creativity and explores the difference between product delivery and emotional impact. The effectiveness of direct mail in a digital world surprises many, especially younger consumers. Rory also discusses how asking simple questions can uncover deeper truths in customer experience, emphasizing that innovative solutions often stem from recognizing psychological nuances.

Michael Seibel, Partner at Y Combinator and former CEO of Justin.tv and Socialcam, shares insights gained from reviewing thousands of startup applications. He discusses the evolving landscape of entrepreneurship, particularly post-COVID, and emphasizes the importance of adaptability and strong co-founder relationships. Michael delves into the significance of understanding customer dynamics and product-market fit, highlighting innovative approaches founders are taking to tackle social issues. His keen perspective makes for a thought-provoking conversation on the future of startups.

Michael Mauboussin, head of Consilient Research at Counterpoint Global, discusses the notable shift from public to private equity markets. He explores the declining IPO landscape, the importance of intangible assets, and their impact on investment strategies. Michael emphasizes the need for better investment valuation in light of intangible assets and outlines the challenges of navigating private equity amidst increasing liabilities. He also provides guidance for young investors seeking unique opportunities and dives into the role of cognitive diversity in investment decision-making.

Jeremiah Lowin, founder of Prefect.io, and Chetan Puttagunta, partner at Benchmark Capital, delve deep into the fascinating open-source software business model. They explain how companies can give away valuable tools for free while monetizing additional features, fostering community trust, and reshaping development approaches. The discussion covers the shift to cloud-based models, community engagement, and the potential of API-first strategies that democratize innovation. Their insights reveal how these principles can transcend software, offering lessons for various industries.

Katrina Lake, co-founder and CEO of Stitch Fix, shares her journey of revolutionizing retail through data science and personalized styling. She discusses the evolution of e-commerce in apparel and how the pandemic accelerated shifts in consumer behavior. Katrina highlights the importance of combining data-driven strategies with human creativity. The conversation also touches on the emotional challenges she faced during Stitch Fix's IPO and the significance of building strong partnerships with suppliers in the era of stakeholder capitalism.

In this discussion, Brian Armstrong, co-founder and CEO of Coinbase, delves into the future of cryptocurrency and decentralized finance. He highlights significant developments and infrastructure established over the past decade, and shares his vision for the 2020s. Armstrong emphasizes the promise of a modern financial system, the challenges of scalability, and regulatory hurdles facing the crypto world. He also reflects on the lessons learned from building Coinbase and the importance of mentorship in fostering innovation and confidence.