Invest Like the Best with Patrick O'Shaughnessy

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.

Peter Lacaillade, Chief Investment Officer at SCS Financial, oversees a massive $50 billion in private investments for ultra-high-net-worth families. He discusses the advantages of SCS's pooled vehicle structure that competes with institutional giants, highlighting how proper vetting and character assessment are crucial in private equity. Lacaillade also dives into the rise of independent sponsors, AI's role in investment strategies, and how exceptional managers set themselves apart. Explore the dynamics of private markets shifting toward a more engaged approach with strong partner relationships.

Andrew Milgram, founder of Marblegate Asset Management, dives into the nuances of distressed investing in the middle market. He discusses the consequences of the K-shaped economy, where small firms struggle as larger entities thrive. Milgram shares his fascinating journey with NYC taxi medallions and stresses the importance of active engagement and negotiation in distressed assets. He also sheds light on niche investments, the emotional challenges of investing, and the need for transparency in the industry, emphasizing collective responsibility in addressing economic disparities.

Join Ramtin Naimi, founder of Abstract Ventures, as he shares his incredible journey from running a hedge fund as a teen to building a successful $2 billion venture firm. He draws fascinating parallels between the art world and venture capital, revealing how insights from art collecting can enhance investment strategies. Ramtin discusses his unique approach to early-stage investing, focusing on building relationships and a keen understanding of market dynamics. With Abstract's impressive track record, he highlights what sets his firm apart in the competitive landscape of Silicon Valley.