Invest Like the Best with Patrick O'Shaughnessy

Patrick O'Shaughnessy runs Positive Sum, an investment firm, and his podcast reflects someone who's genuinely curious about how the best investors and business builders think. Each week he sits down with one guest for a long-form conversation that usually runs 60 to 90 minutes. The guest list reads like a who's who of institutional investing, venture capital, and business strategy -- fund managers running billions, CEOs of public companies, founders building something unusual, and occasionally an academic or author who's rethinking conventional wisdom. What makes the show work is Patrick's interviewing style. He does his homework, asks specific questions, and then gets out of the way. There's no grandstanding, no interrupting to show how much he knows. He lets his guests build their arguments fully, which means you get the kind of depth you'd normally only find in a private meeting or an investor letter. Topics range widely: capital allocation frameworks, how to evaluate management teams, the economics of specific industries, what separates good businesses from great ones, how technology reshapes competitive advantages. A single episode might cover everything from supply chain logistics to the psychology of decision-making under uncertainty. The show skews toward a more sophisticated investing audience. If you're looking for stock tips or basic portfolio advice, this isn't it. But if you want to understand how professional allocators think about deploying capital and evaluating opportunities, there's nothing quite like it in podcast form. The production is minimal -- just two people talking -- and that simplicity is a feature. With a 4.7-star rating from over 2,000 reviews, the quality speaks for itself.