Patrick O’Shaughnessy is the CEO of O’Shaughnessy Asset Management, the host of the Invest Like the Best podcast, and a great friend.  Patrick’s podcast and widely read monthly mailing list of books, available at investorfieldguide.com, have made him a celebrity of sorts in the investing world. Those familiar with his voice will already know how wide his curious mind travels, but I image far fewer know much about his daily investing activities.

Our conversation begins with Patrick’s early start in the business and discovered passion for research. We turn to investing at OSAM, covering four core quantitative factors, how those factors work, the research process to dive deeper into each factor and explore new ones, machine learning, differentiated portfolio construction, and the impact of quants on the market.  We then turn to Patrick’s experience as a podcaster, discussing his conceptual learning loop, lessons from interviewing, and the ways he has applied lessons from the podcast to OSAM’s asset management business.  We close by discussing investing in external managers, including a great nugget on probing quantitative strategies.

Patrick and I both finished this conversation feeling that we had just scratched the surface, which might be fodder for a Part B down the road.  Regardless, I’m indebted to Patrick for being the catalyst behind the creation of Capital Allocators two years ago, and it was my great pleasure to get him on the other side of the microphone.