Second Life

All of our guests have changed careers at some point, but Susan Tynan's path took several different turns on her way to raising $67 million in venture financing for Framebridge, a quick and affordable custom framing site. The founder and CEO, a Harvard Business School graduate, shares advice on how to accept "no" in your career, how to run a business ethically, and how to lift women up.

It started with a crush. Renowned chef, restaurant owner, and author Nancy Silverton first developed an interest in the food industry because she had a crush on a student cook at the dining hall of her college dorm and convinced him to hire her in the kitchen. Learn how she went from being a pastry chef to running her own empire and winning the food industry's highest honor.

L.A.-based retailer Revolve paved the way for influencer trips that now take over your Instagram feed, and Raissa Gerona is the brains behind the site's innovative strategy. Early in her career, she dealt with her parents' disapproval of her career path and a business failure, but you can bet she learned a thing or two on her way to becoming Revolve's chief brand officer.

Erin and Sara Foster are nothing if not honest. In the newest episode of Second Life, the sisters get real about feeling in over their heads, pursuing careers that paid the bills but weren't fulfilling, and regretting not going to college. Whether you know the Fosters from their parody-reality show on VH1, Barely Famous, or from their current positions as the heads of creative at Bumble, you'll learn a whole new side to the sisters.

Shiona Turini has the résumé that anyone with a dream of working in fashion envies. In episode 50 of Second Life, she shares what she learned cutting her teeth at the industry's major print magazines before fearlessly moving into freelance styling and finally transitioning into costume design for HBO's acclaimed tv series Insecure.

Everyone has interests outside of work, but not everyone knows how to turn their side hustle into a successful business. But it's safe to say that Sierra Tishgart, co-founder of cookware brand Great Jones, knows a thing or two about the transition. In the newest episode of Second Life, Tishgart tells Hillary Kerr how she went from being a Teen Vogue intern to becoming an entrepreneur in home cookware.

How do you go from being a hat maker to running a billion-dollar jewelry brand? In episode 48 of Second Life, Kendra Scott tells Hillary Kerr about the embarrassment of dropping out of college, learning retail "the hardest way possible," and how she transitioned from running a hat store to creating one of the most successful jewelry brands on the market.

Like many of us, Hannah Bronfman's most valuable college experience came from outside the classroom. Bronfman successfully pivoted from being a sculpture major to becoming fashion's favorite DJ and wellness master. In episode 47 of Second Life, Bronfman tells Hillary Kerr how she's learned to cope with the failure of a business venture, understand her worth, and inspire fans to lead a healthier, happier life.

Aimee Song's rise to fashion blogger stardom is a lesson in what you can accomplish by following your passions. The fashion guru behind Song of Style got her start working as a receptionist at a construction company right out of high school while saving up money to pay her own college tuition. It was there that she got her first taste for architecture and design and decided to go to school at the Academy of Art in San Francisco. However, one job interview changed everything. "I got the job because of my outfit," she tells Hillary Kerr on episode 46 of Second Life.

Jamie Kantrowitz co-founded Countertop with Nicole Rice based on the goal of helping people focus on wellness through simple and delicious home cooking. Today, the duo sells a variety of products from seasonings to honey, all meant to enhance both the flavor and nutritiousness of your food. But before all this, Kantrowitz was following a very different career path. She spent her twenties working in politics and digital media at companies like Rock the Vote and Myspace. "Even though I've jumped industries, there are common threads that go through it," the entrepreneur tells Hillary Kerr on episode 45 of Second Life.

Everybody knows that before Jennifer Lopez was the multihyphenate superstar she is today, she was Jenny from the block. But most people don’t know how she made the leap from a dancer to an actor to a singer to an icon. “I always knew from a very young age that I loved performing,” Lopez tells Hillary Kerr on episode 44 of Second Life. With the help of Elaine Goldsmith-Thomas (then her agent, now a producer), who’s had a few career swaps of her own, J.Lo catapulted herself to international success. Lopez’s philosophy for mastering the pivot? “If you feel like you need to move, move.” Find out how both women paved their own paths.

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.

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. 

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.

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.

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.

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.

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.

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.

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.