The Who What Wear Podcast: BONUS: Power Stylists Wayman and Micah on Dressing Colman Domingo (and Others) for the 2025 Met Gala, Their Harlem Roots, and the Significance of Black Dandyism

Before Christina Tosi started Milk Bar—the trendy bakery known for its covetable, playful desserts—she was studying math and Italian in college with dreams of becoming a mathematician, a UN translator, or a perhaps a truck driver (yes, really). "I like to be uncomfortable," the entrepreneur tells Hillary Kerr on episode 39 of Second Life. Drawn to restaurant life with a passion for baking, Tosi moved on from her mathematical endeavors to pursue cooking at culinary school and (with a lot of hard work) went on to found her very own wildly successful bakery. Here's how she made it happen.Sign up for Christina Tosi's new Beyond Baking mailer at christinatosi.com.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

19 Marras 201851min

If you've ever visited NYC's trendy new spa-salon-café hybrid, Chillhouse, you can already appreciate the way Cyndi Ramirez-Fulton is cashing in on the wellness industry one adaptogen latte and hangover-curing massage at a time. The "destination for modern self-care," as she describes it, is stylish, relaxing, and affordable—not to mention incredibly Instagram-friendly. But Fulton wasn't always involved in the wellness world, though. In fact, she dropped out of college to work in the nightlife world promoting clubs before ever landing her first desk job.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

12 Marras 201837min

Eva Chen's résumé reads like the front row of a well-stocked magazine stand. She's held jobs at publications like Harper's Bazaar, Elle, Teen Vogue, and Lucky (where she was editor in chief, no less). Although landing a job as editor in chief of a major publication sounds like the peak of one's career, Chen was just getting started. Now, she's catapulted to director of fashion partnerships for Instagram, has written her first book (a children's story called Juno Valentine and the Magical Shoes), and is trying her hand at design with the launch of a capsule collection with Janie and Jack in conjunction with her book.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

5 Marras 201843min

Kerry Diamond has been starting businesses since she was in the third grade launching a school newspaper. "I am very fortunate in that I knew from a very early age what I wanted to do," she tells Hillary Kerr in episode 36 of Second Life. Although she started out in hard journalism, the entrepreneur pivoted to the beauty space and catapulted from beauty director at Harper's Bazaar to head of PR at Lancôme. All before striking out on her own to co-found Cherry Bombe, a biannual indie magazine that celebrates women in the food world.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

29 Loka 201843min

Busy Philipps always knew she would be an actress. In fact, she was studying theater in college when she landed her first major role as Kim Kelly on the coming-of-age hit Freaks and Geeks. While she found success early on at the age of 19, her career hasn't been without setbacks, rejection, and grit. "I never have really fit into a lot of people's molds," she tells Hillary Kerr on episode 35 of Second Life. But Philipps persevered in a male-dominated industry fraught with unrealistic expectations to come out the other side more sure of herself than ever.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

22 Loka 201847min

Interior designer Amber Lewis, the force behind Amber Interiors, is proof that you don't necessarily need a college degree or a straightforward career path to find success. With just a few semesters in an interior design program at UCLA, Lewis found work as an assistant at an interior design firm, and eventually branched out on her own. At the same time, the creative was getting married to a musician, having her first child, and taking every opportunity that came her way. "I was a perfect storm of...luck, talent, and timing," she tells Hillary Kerr on episode 34 of Second Life.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

15 Loka 201838min

Amanda Hesser is responsible for the chic e-commerce and community site Food52, which she launched with co-founder Merrill Stubbs in 2009. Before she struck out on her own, the foodie had a thriving career as an editor for The New York Times and as a cookbook author, both unexpected paths seeing as the entrepreneur studied economics and finance in college. "I had no idea really what I wanted to do, but I knew the sort of lifestyle I wanted," she tells Hillary Kerr on episode 33 of Second Life. Here's how she made the leap from cooking to writing to running her own company.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

8 Loka 201837min

If you've given or received a gift in the last six years, you've probably heard of Sugarfina, the luxury candy brand made for grown-ups. The champagne gummy bears and other adult-friendly candies wouldn't exist had it not been for Rosie O'Niell and a particularly good date she went on to see Willy Wonka and the Chocolate Factory with her now business partner and fiancé, Josh Resnick. Prior to starting her own whimsical venture, O'Niell was working in brand management at Mattel for Barbie. "When I did eventually step away and start Sugarfina, it's like I knew how to do it and I didn't even realize I knew how to do it," she tells Hillary Kerr on episode 30 of Second Life.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

1 Loka 201852min