The Who What Wear Podcast: Mary Beth Barone and Benito Skinner on Fashion in Stand-Up Comedy, the Value of Vintage, and the Designers They Ride For

Kerry O'Brien never could have anticipated that her career in public relations would lead her to become an underwear designer, but that's exactly what happened. The entrepreneur started out in corporate PR, quickly making her way up the ranks (she was a vice president at just 25 years old). However, when September 11 happened, she felt like she needed a change. She quit her job without a plan, but it wasn't long before she found her next passion: women's underwear.

17 Dec 201838min

Carla Hall was always a creative, but before competing on Top Chef, authoring cookbooks, and starring on The Chew, she was auditing at a big accounting firm and pursuing modeling in Europe. When she returned home from Europe—where she'd also taken up cooking—she stumbled into her own lunch delivery service that parlayed itself into catering, culinary school, and her rise to foodie fame. "It was really an adventure," she tells Hillary Kerr on episode 42 of Second Life.

10 Dec 201849min

Meredith Melling is proof that landing your dream job isn't the end of your career path. In fact, it might even just be the beginning. Melling always wanted to work in fashion, and with a bit of luck, good timing, and the smart decision to dress for the job she wanted, not the job she had, she landed the coveted title of a fashion assistant at Vogue early in her career. But that was only the start of her journey toward creating her own consulting business and co-founding fashion brand La Ligne.

3 Dec 201845min

Tyler Haney knows activewear. She was raised in Boulder, Colorado—a town known for its outdoor activities—and grew up running track and field. With a few courses in business and design under her belt paired with the desire to create a sporty uniform for recreational activity, Haney eventually became the CEO and founder of her own brand, Outdoor Voices. However, her journey was filled with challenges and missteps that she looks back on as lessons learned.

26 Nov 201842min

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.

19 Nov 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.

12 Nov 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.

5 Nov 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.

29 Okt 201843min