Invest Like the Best with Patrick O'Shaughnessy

Ben Gilbert and David Rosenthal, co-hosts of the Acquired podcast, share insights from their investment journeys. They analyze legendary corporate acquisitions, spotlighting the dynamics of high-value tech deals like Instagram's. The duo discusses the intricacies of startup competition and community-building while emphasizing the critical role of mentorship in overcoming career hurdles. Tune in for a blend of historical context and practical investing lessons, making it a must-listen for aspiring investors!

Leore Avidar, co-founder and CEO of Lob, shares his entrepreneurial journey in simplifying direct mail through technology. He delves into his passion for sports card collectibles and the evolving market dynamics. Leore discusses the challenges of running dual ventures and the importance of strategic partnerships. His insights on creating and selling 'superpowers' reveal how entrepreneurs can innovate and scale effectively. The conversation inspires budding entrepreneurs to embrace risks and cultivate a mindset for aggressive growth.

Jacqueline Novogratz, Founder and CEO of Acumen, shares her inspiring journey from Wall Street to launching a microfinance bank in Rwanda. She discusses the importance of investing in character and how dignity shapes her investment strategies. The conversation delves into the power of moral imagination and empathy in addressing poverty. Jacqueline highlights examples of entrepreneurs in marginalized communities and advocates for collaboration between businesses and governments to tackle pressing global issues. A thoughtful exploration of redefining success through generosity and community empowerment.

Justin Singer, founder and CEO of Caliper Foods and Stillwater Brands, dives into the transformative power of regulations in the cannabis industry. He discusses how regulatory changes shape market opportunities and the importance of understanding shifting landscapes. Justin shares his journey into cannabis, tackling misconceptions about success and the unique dynamics of THC versus CBD markets. He also reflects on the potential for federal regulation and its implications for social justice, while emphasizing the need for integrity in business practices.

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.