Stephen J. Dubner
Journalist and Host, Freakonomics Radio
This episode will premiere August 20, 2026 at 7:00pm ET
“Everybody who does something great fails a lot on the way there.”
Summary
In this episode of Leadership Matters, I had the honor of being joined by journalist, author, and fellow SiriusXM radio host Stephen J. Dubner. Stephen is the co-author of Freakonomics, one of the most acclaimed works of nonfiction in the twentieth century. The book recently received a twentieth anniversary reprint, helping a new generation foster an economist’s perspective on topics ranging from crime rates to sumo wrestling. Stephen also hosts Freakonomics Radio, which reaches some 2.5 million listeners a month, and has recently turned his attention to a new talk show, Better in Person, in which he invites remarkable people into his living room and follows them out into the world.
Our conversation traced the full arc of Stephen’s life, including his childhood in Duanesburg, NY, signing a record deal with Clive Davis, and the New York Times Magazine profile of a young University of Chicago economist named Steven Levitt that eventually evolved into Freakonomics.
Along the way, Stephen makes a case for what we might call a Freakonomics mindset: fostering curiosity as a discipline to be practiced, entertaining every alternative explanation before defending your own, and appreciating luck as a far larger factor in any success story than most people care to admit. He closes on an argument worth hearing at this moment in history: that we too easily mistake a period of disruption for a bad time to be alive, and that skepticism should not be confused with cynicism.
Mentions & Resources in this Episode
Freakonomics Twentieth Anniversary Edition: A Rogue Economist Explores the Hidden Side of Everything — by Steven D. Levitt and Stephen J. Dubner
Choosing My Religion: A Memoir of a Family Beyond Belief – by Stephen J. Dubner
“How to Host a Talk Show, with Dick Cavett,” Freakonomics Radio
Guest Bio
Stephen Dubner is co-author of the Freakonomics book series, host of Freakonomics Radio, and host of the new TV talk show Better in Person, which you can watch on the Freakonomics YouTube channel, on Apple Podcasts, and elsewhere.
The eighth and last child of an upstate New York newspaperman, Stephen has been writing since he was a child. (His first published work appeared in Highlights magazine.) As an undergraduate at Appalachian State University, he started a rock band (The Right Profile), which Clive Davis signed to Arista Records. This brought Stephen to New York City, but he ultimately quit music and earned an M.F.A. in writing at Columbia University, where he also taught in the English Department. He was an editor and writer at New York magazine and The New York Times before quitting to write books. He is happy he did so. In addition to the Freakonomics series, he is the author of Turbulent Souls (Choosing My Religion), Confessions of a Hero-Worshiper, and the children’s book The Boy With Two Belly Buttons. He and his family still live in New York, and Better in Person is to some degree a love letter to that great city.