Invest Like the Best with Patrick O'Shaughnessy

Patrick O'Shaughnessy runs O'Shaughnessy Asset Management and uses this podcast to have long, unhurried conversations with the best investors, founders, and business leaders in the world. With 565 episodes and a 4.7 star rating from 2,250 reviews, Invest Like the Best has earned a reputation as one of the most intellectually rigorous investing shows available. Recent guests include Josh Kushner of Thrive Capital, Reed Hastings discussing the Netflix business model years after stepping down, and Ben Horowitz on venture capital decision-making at scale. Episodes typically run 60-90 minutes and go deep -- Patrick is not interested in surface-level takes or sound bites. He asks follow-up questions that push conversations into territory most interviewers never reach. The show skews more intermediate than pure beginner, but it belongs on this list because the best way to learn investing is to hear how the people who do it for a living actually think. Patrick has a talent for making complex investment frameworks understandable without oversimplifying them. You will hear discussions about how to evaluate businesses, what makes certain competitive advantages durable, how to think about valuation across different market environments, and why some investors consistently outperform while others do not. The production quality is outstanding, and full transcripts and show notes are available at joincolossus.com. Treat this one as the podcast you graduate into once the basics are solid.