Invest Like the Best with Patrick O'Shaughnessy

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.

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Brad Jacob's simple principle of "think big, move fast" is one I think about often. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions and raised $30 billion of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 2011 and has grown into one of the largest logistics businesses in the world. He is a true force of nature, and I hope you enjoy his episode. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠⁠⁠WorkOS⁠⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠⁠WorkOS.com⁠⁠⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit ⁠⁠joincolossus.com/episodes⁠⁠.  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up ⁠⁠here⁠⁠. Follow us on Twitter: ⁠⁠@patrick_oshag⁠⁠ | ⁠⁠@JoinColossus⁠ Show Notes (00:00:00) Welcome to Invest Like the Best (00:02:11) Identifying key factors in a market before investing (00:05:07) Gleaning insights from early acquisition experiences (00:08:43) Delving into the seller's mindset during a business sale (00:12:51) Weighing pre-built against organic growth strategies in acquisitions (00:17:20) Defining the elements of an ideal business (00:22:49) Engaging constructively with Wall Street (00:24:36) Discussing the substantial buyback of XPO shares (00:28:16) Ambition as a recurring theme in entrepreneurial success (00:30:17) Emphasizing the need to facilitate team agility (00:32:35) Highlighting the joys of post-acquisition integration (00:36:09) Drawing lessons from Ludwig Jesselson's principles (00:40:34) Comparing the risks and rewards of early versus late adoption (00:44:09) Reflecting on errors made in trend analysis (00:48:59) Strategies for implementing new technologies in enterprises (00:51:59) The significance of thought experiments in strategic decision-making (00:56:00) Recalling transformative events from his early years (00: 57:22) Outlining what makes a meeting 'electric' (01: 01:53) Sharing experiences with exemplary leadership (01:05:02) Strategies for maximizing team potential (01:07:37) Deciding the right time to step away from a business (01:08:58) Unveiling unexpected challenges in entrepreneurship (01:18:45) Philosophies for leading a fulfilling life (01:21:04) Finishing How To Make A Few Billion Dollars (01:22:53) The kindest thing anyone has ever done for Brad