Invest Like the Best with Patrick O'Shaughnessy

Hamilton Helmer, Co-founder and Chief Investment Officer of Strategy Capital, shares his profound insights as an expert in business strategy and author of "Seven Powers." He dives into the seven strategic powers companies can leverage for competitive advantage, discussing the importance of counter-positioning and cornered resources. Helmer illustrates how early-stage firms can navigate barriers as they evolve, emphasizing operational excellence and the significance of network effects in tech. He also highlights the artistic side of strategy and the value of mentorship in business.

Tobi Lutke, co-founder and CEO of Shopify, shares insights on navigating the digital commerce landscape. He discusses Shopify's shift to direct consumer engagement, emphasizing the importance of supporting local businesses. Lutke delves into decision-making as a CEO, exploring the balance between delegation and personal involvement. He reflects on transforming workplace culture through intuitive design and personality typing frameworks. Additionally, he highlights the value of kindness and personal growth, especially during challenging times.

Ali Hamed, a private credit expert, returns with insights on current market dynamics and opportunities. He discusses the impact of COVID on private credit, highlighting which areas have stalled and where investors can find growth. Hamed emphasizes the importance of focusing on quality over returns amid uncertainty and explores the rise of digital business models. He also dives into the complexities of junior versus senior debt, and how evolving online platforms are redefining small businesses and investment strategies.

Chris Bloomstran, Founder and CIO of Semper Augustus, shares his insights on the public equity market and investment strategies. He discusses the challenges of achieving high returns in the next decade compared to the last. Bloomstran explores the current state of the energy sector and its return potential. He emphasizes the importance of identifying resilient businesses with pricing power and capital efficiency. The conversation also touches on market dynamics influenced by government interventions and the implications of deflation versus inflation.

In this engaging conversation, Josh Kopelman, founder of First Round Capital, shares insights from his venture capital journey and entrepreneurial background. He discusses the evolution of startup culture, emphasizing the importance of founder character and adaptability in today's landscape. Josh also draws an intriguing analogy between navigators and cartographers in investment strategies. He highlights how First Round builds supportive platforms for entrepreneurs, illustrating the changing dynamics in seed investing amidst today's challenges.

Manny Stotz, founder of Kingsway Capital and an expert in frontier markets, shares his insights on investing in emerging economies like Egypt, Bangladesh, and Pakistan. He discusses the unique demographics and market dynamics that create opportunities for growth. Manny dives into the importance of strong brand building and the critical role of distribution networks in these regions. He emphasizes the potential of high-quality businesses and the value of understanding local conditions for successful investing, even amid market challenges.

Sarah Tavel, a general partner at Benchmark and former product leader at Pinterest, dives into the dynamics of consumer technology and marketplaces. She shares valuable insights on the food delivery market's evolution, emphasizing DoorDash's strategy over Grubhub. Tavel discusses the importance of reputation scores within networks and the unique challenges of building niche marketplaces. Additionally, she explores how effective user engagement can drive marketplace success, leveraging data and community to enhance experiences.

Boyd Varty, a seasoned wilderness adventurer, shares his journey of spending 40 days in the African wild. He dives into the emotional and psychological transformations sparked by solitude in nature. Varty recounts thrilling moments, including tracking lions, and reflects on the challenges of isolation. He discusses the significance of mental preparation for such a journey and how this experience could change his perspective on life and connection with others. His insights promise a deeply introspective adventure for listeners.

In this conversation, Gavin Baker, Founder and CIO of Atreides Management, shares insights on navigating investing during bear markets and the COVID-19 impact. He discusses adapting strategies amid volatility and the importance of cash flow metrics. Baker explores the evolving tech landscape, particularly concerns for software companies and recurring revenue. He highlights 'space as a service' and its rising relevance, along with investment opportunities in the metaverse. The discussion touches on embracing chaos as a unique path for opportunity and growth in the market.

D.A. Wallach, former lead singer of Chester French and artist-in-residence at Spotify, shares his journey from music to healthcare investing. He discusses how advancements in personalized medicine and genetic therapies are revolutionizing treatment options. Wallach dives into the potential of CRISPR technology and the ethics surrounding gene editing, as well as the complexities of drug pricing in today's healthcare system. He emphasizes the importance of informed choices in healthcare investments and the transformative role of technology in personal health.