StartUp

Aline Brosh McKenna got her big break as the screenwriter of The Devil Wears Prada. But even after successful box office hits and many years in Hollywood, she found herself having to compromise her vision over and over again. So she took matters into her own hands.

Janice Bryant Howroyd’s company started in the front of a rug shop with just a phone, a fax machine, and a lot of hustle. 40 years later, that company is a huge multinational serving some of the biggest Fortune 500 companies in the world. It earns over a billion dollars in revenue, making Janice the first African-American woman to start and run a billion dollar business. But her journey to CEO wasn’t an easy one. Janice talks with Alex about the people who encouraged her down that path, and her realization that being brilliant and owning your brilliance are two different things.

Comedian Nick Kroll became a star by playing a cast of over-the-top characters like Bobby Bottleservice and Gil Faizon. But for years he was careful to keep his own story out of his comedy. Now, with his hit show Big Mouth, Nick is taking on his most challenging material yet: his adolescence. 

This week, we’re sharing the first episode of Esther Perel’s new show How’s Work? In it, the couples therapist behind the beloved show Where Should We Begin? sits down with coworkers, cofounders and colleagues, and brings her inimitable perspective to workplace relationships and conflicts.

In November 1995, Ira Glass quietly launched the first episode of This American Life. The rest, as they say, is history. Today his show is a colossal success and Ira Glass is a household name. But in the intervening two decades, Ira has left an indelible mark on the industry by helping to shape hundreds of podcasts as well as hundreds of podcasters — including Alex. On this episode, Alex sits down with his mentor and former boss to talk about the early days at This American Life, what Ira taught Alex, and how being a good boss means learning to set people free.