Invest Like the Best with Patrick O'Shaughnessy

Jesse Zhang, co-founder and CEO of Decagon, delves into the world of AI customer service. He discusses the importance of understanding customer willingness to pay, revealing insights that shaped Decagon's direction. The conversation highlights the intense competition in AI, the need for continuous improvement loops in product development, and the critical nature of data as a competitive edge. Jesse also shares his thoughts on the dynamics of fundraising in the AI space and the importance of hiring the right talent in a competitive market.

In this discussion, Dylan Patel, founder and CEO of SemiAnalysis, dives into the intricacies of the semiconductor supply chain and AI infrastructure. He analyzes the interconnected strategies among OpenAI, Nvidia, and Oracle, highlighting how compute capacity drives their deals. Dylan shares insights on current high-value AI applications, the significance of reinforcement learning, and the implications of supply chain bottlenecks. He also contrasts US and Chinese approaches to AI, offering a comprehensive view of the industry's landscape and future opportunities.

In this engaging discussion, Ben Clymer, founder of Hodinkee and luxury watch expert, shares his passion for Rolex, especially the iconic Daytona. He dives into the watch's motorsport roots and sentimental value. Ben explains the shifting dynamics of the luxury watch market, including Rolex's strategic focus and manufacturing innovations. He also unpacks the impacts of rarity and distribution on customer experiences. Listeners will gain insights into Rolex's meticulous craftsmanship and the brand's enduring legacy in horology.

Barry Diller, a veteran media executive and founder of IAC, dives into his transformative career that shaped modern entertainment. He shares his 'creative conflict' philosophy, emphasizing the power of pushing boundaries for innovation. Diller recounts engaging tales of collaboration with icons like Rupert Murdoch and Bill Gates, discusses the risks behind pioneering the Movie of the Week, and explores how personal struggles can empower professional success. Get insights into his experience with 150 internet deals and his current media portfolio strategies.

Jeff Horing, Cofounder and Managing Director of Insight Partners, dives into the inner workings of one of the largest tech investment firms with over $100 billion in assets. He shares insights on their unique sourcing strategy involving 60-80 global analysts and the advantages of a contrarian ‘one fund’ approach. Horing discusses the evolution of investment strategies, the transformative role of AI in accelerating growth, and the importance of strong relationships with founders. This conversation offers a fascinating glimpse into the world of tech investing and mentorship.

Sam Hinkie, a venture capitalist at 87 Capital and former NBA executive, shares his unique insights on building trust and relationships in business. He emphasizes the value of studying the 'breadcrumbs' individuals leave behind, which can reveal much about their trajectory. The conversation highlights unconventional interview techniques focused on curiosity, attracting top talent, and the importance of genuine connections. Hinkie draws parallels between sports leadership and business dynamics, offering a fresh perspective on team building and success.

Sean Feeney, co-founder of Grove House Hospitality Group and owner of acclaimed NYC restaurants Lilia and Misi, shares his inspiring journey from finance to culinary success. He reveals how he disrupted traditional norms in the restaurant industry, focusing on authenticity and community engagement. Feeney discusses the immersive dining experience, the power of storytelling, and the importance of nurturing customer connections. Tune in for a fascinating look at how his passion for food transformed into a thriving business built on innovation and strong relationships.

Justin Ishbia, Founding Partner of Shore Capital, shares his insights on acquiring nearly 600 companies in three years. He discusses the importance of operational excellence and structured systems in private equity, especially in microcap investments. Ishbia emphasizes nurturing young talent and building effective boards, while also exploring negotiation tactics in private finance. He reflects on the value of strong personal relationships and how innovation stacking can create competitive advantages in diverse sectors, particularly healthcare and real estate.

In a fascinating conversation, Joe Liemandt, Principal at Alpha School and founder of Trilogy Software, discusses his ambitious vision to revolutionize education using AI. He shares how his tutoring system enables students to achieve 2x learning outcomes and begs to stay engaged even during summer breaks. Joe critiques traditional education, emphasizing the need for personalized learning and adaptive teaching methods. He also explores the intersection of AI and human psychology, making a compelling case for the future of education and investment in this transformative sector.

Mark Bertolini, former CEO of Aetna and current CEO of Oscar Health, shares his remarkable journey of overcoming a severe skiing accident while leading significant healthcare innovations. He discusses his transformation from personal pain to championing employee welfare, implementing groundbreaking policies that generated massive shareholder returns. Bertolini argues for a consumer-centric model in health insurance and emphasizes the importance of empathy and servant leadership in healthcare. His insights on resilience and community impact provide a powerful perspective on navigating challenges.