Malcolm Gladwell and Kenya Barris on The Unusual Suspects, Improbable Careers, and Why Curiosity Wins

According to Malcolm Gladwell and Kenya Barris, curiosity is what they have most in common. Malcolm is a bestselling author and journalist, known for his books The Tipping Point, Outliers and more. Kenya is a Hollywood writer, producer, and actor known for creating the TV series Black-ish, Mixed-ish, Grown-ish and Black AF.

Together, they host the Audible Original show The Unusual Suspects (audible.com/podcast/The-Unusual-Suspects-with-…), now in its second season, where they bring that curiosity to conversations with extraordinary and influential figures. They join Jessi in the studio to talk about what changes when two people interview one guest, what they’ve learned from their collaboration and their advice for others pursuing improbable careers.

In this episode, Jessi, Malcolm and Kenya discuss:

• How Kenya introduced himself to Malcolm at a restaurant, and why he hasn’t let him go

• Why Malcolm challenges the idea of an “unlikely pairing,” and what his parents’ marriage taught him about what people have in common

• Kenya’s orchestra metaphor: why a hundred musicians playing slightly off is what makes the music beautiful

• What changes when two people interview one guest, from an Amy Sherald conversation neither could have had alone to the Dr. Dre moment where Kenya and Dre traded LA bus routes

• What every guest has in common: someone who set out to do something hard and did it well

• Why Malcolm was drawn to Ursula Burns, and the self-possessed women he grew up around

• Why interviewing powerful people is more fun than meeting them, from Adam Silver to Sue Bird

• Where the fun comes from, and why two people with careers moving fast in other directions made a second season

• “Hamlet was wrong”: why Malcolm thinks uncertainty is what frees you

• Malcolm’s filter for saying yes or no: is it fun?

• Kenya’s advice for anyone chasing an improbable career: dream about it, then put in the time alone doing the work

Follow Malcolm Gladwell (linkedin.com/in/malcolm-gladwell-42747687) and Jessi Hempel (linkedin.com/in/jessihempel) on LinkedIn

Join us for Office Hours (lnkd.in/p/ex3Mpxc4) this Wednesday at 3pm EST, live from Jessi Hempel’s LinkedIn page