Charley Ellis is an investment luminary, founder of Greenwich Associates, author of seventeen investment books, longtime member of Yale’s Investment Committee, and regular guest on the show. At the tender age of 85, Charley has published two books this year: Figuring It Out, an annotated compilation of some of his best investment writing over fifty years, and Inside Vanguard, a history of the index juggernaut. We sat down to discuss both of his latest works.

Our conversation covers common characteristics of the best professional services firms and selections from Figuring It Out and Inside Vanguard. From Figuring It Out, we discuss the challenges of professional investment management, investment committees, and analogies to investing from tennis, baseball, golf, and running. From Inside Vanguard, we cover the rocky early days of Bogle’s folly, the firm’s on again/off again relationship with Wellington, its growth under Jack Brennan, compensation model, recent initiatives, and future prospects.