

Invest Like the Best with Patrick O'Shaughnessy
Colossus | Investing & Business Podcasts
Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com
Episodes
Mentioned books

9 snips
Sep 5, 2025 • 1h 48min
Sean Feeney - Reinventing the Restaurant Business - [Invest Like the Best, CLASSICS]
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.

304 snips
Sep 2, 2025 • 1h 14min
Justin Ishbia - Lessons from Acquiring 586 Companies [Invest Like the Best, REPLAY]
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.

1,614 snips
Aug 26, 2025 • 2h 27min
Joe Liemandt - Building Alpha School, and The Future of Education - [Invest Like the Best, EP.439]
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.

560 snips
Aug 19, 2025 • 1h 38min
Mark Bertolini - Performance During Pain - [Invest Like the Best, EP.438]
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.

365 snips
Aug 12, 2025 • 1h 30min
Peter Lacaillade - Backing The Best Managers In Private Markets - [Invest Like the Best, EP.437]
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.

388 snips
Aug 5, 2025 • 1h 33min
Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]
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.

355 snips
Jul 29, 2025 • 1h 53min
Ramtin Naimi - Building Abstract - [Invest Like the Best, EP.435]
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.

933 snips
Jul 25, 2025 • 1h 25min
Brad Jacobs - Think Big and Move Fast - [Invest Like the Best, CLASSICS]
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.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
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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

567 snips
Jul 22, 2025 • 1h 23min
Zach Dell - Powering the Future - [Invest Like the Best, EP.434]
Zach Dell, co-founder and CEO of Base Power Company, dives into the complexities of the electrical grid and the urgent need for updates to meet rising demand from AI and electric vehicles. He introduces innovative solutions like distributed home batteries that not only offer backup power but also support the grid. Dell emphasizes the pivotal role of affordable energy in driving human progress, discusses the evolution and financing of battery technologies, and outlines Base's unique approach to energy management for Texas homeowners.

696 snips
Jul 15, 2025 • 1h 14min
Alan Waxman - Building Sixth Street - [Invest Like the Best, EP.433]
Alan Waxman, co-founder and CEO of Sixth Street, takes listeners on a captivating journey through innovative investing. He shares insights from his days at Goldman Sachs and how they shape Sixth Street's unique strategies. Waxman discusses significant investments in Spotify and Airbnb during tough times, and the exciting sports partnerships with Real Madrid and FC Barcelona. He emphasizes the importance of an ego-less hiring approach and Sixth Street's 'face the tiger' philosophy, which encourages a culture of collaboration and adaptability in dynamic market landscapes.