Second Life

When Linda Wells landed her first job as an editorial assistant in the beauty department of Vogue, she didn't have so much as a five-year-plan. She admits she could never have planned how her professional life—beauty editor turned editor in chief of a new magazine (a little publication called Allure) turned chief creative officer of Revlon and creator of the cosmetics line Flesh—would have turned out. On episode 24 of Second Life, Wells dishes about how she leaned into challenges and major changes to build the impressive career she has today.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Former broadcast journalist Whitney Casey and model-turned-actress Brooklyn Decker know something you don't. You spend years of your life—10 to be exact—picking out clothes to wear and to pack for all of life's many occasions. After identifying a massive white space in clothing and tech space, Casey and Decker figured out a way to give that precious time back to people with a seriously smart app called Finery. On episode 23 of Second Life, the two share how they turned one brilliant idea into a thriving company (without any formal business school or training).See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

People with curly and straight hair alike know the power of a good blowout. It was this simple idea that catapulted Alli Webb from former hairstylist and stay-at-home mom to the haircare maven behind Drybar, the blow-dry bar that specializes in blowouts. Before discovering this untapped market in L.A., Webb honed her craft at beauty school on the East Coast, pivoted to a career in PR, and eventually found her way back to hair, where it all began. "It was just a whim and a hunch," Webb tells Hillary Kerr on episode 22 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.

Andrea Lieberman knew that she was meant to work in fashion ever since she moved to Manhattan at age 13. "I realized at a very early age that I just found what I was meant to do," she tells Hillary Kerr in episode 21 of Second Life. Lieberman parlayed her passion for the fashion industry, an education from Parson's School of Design, and over 10 years experience as a celebrity stylist to eventually launch her own line A.L.C. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Not everyone is lucky enough to stumble upon a career they're passionate about early in life. For April Gargiulo, the founder of skincare company Vinter's Daughter, it took three college degrees, stints in the design world, and time spent working for the family wine business for her to truly find her calling, and she's just getting started. Despite her untraditional path, she tells Hillary Kerr on episode 20 of Second Life, "There's nothing I would have done differently."See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Lauren Conrad ended up on one of the world's first major reality TV shows at the tender age of 17. Since then, she's grown into the cunning, experienced entrepreneur you know today. According to her, she wouldn't be where she is now—a New York Times best-selling author eight times over, designer of her own fashion line LC Lauren Conrad for Kohl's, and philanthropist behind the non-profit The Little Market—without the mistakes she made along the way. “I believe in mistakes," she tells Hillary Kerr on episode 19 of Second Life. "I think that everything I know is because of a mistake I made.”See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

When you grow up in Ohio with dreams of moving to Los Angeles, becoming a TV host, and owning a Range Rover, people don't always take you seriously, according to Marianna Hewitt. However, with a bit of luck, perseverance, and the skills to turn her dreams into reality, Hewitt moved to L.A. and not only became a TV host but parlayed her experience into a career as a YouTube star, blogger, influencer, and now skincare brand co-founder. "My mentality is someone out there is doing the thing you want to do. Why can't it be you?" she tells Hillary Kerr on episode 18 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.

If you asked Jen Gotch in her 20s what her career might be like today, she'd have had absolutely no idea. "I'm a late bloomer," she tells Hillary Kerr on episode 17 of Second Life. The businesswoman and founder of the stylish gifts and accessories brand Ban.do spent college studying literature and philosophy with the goal of becoming a lawyer, only to realize that wasn't the path for her. Little did she know it would be a career in food styling that would ignite her creativity and lead to the beginning of her own brand then, later, a podcast about mental health.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

From an early age, Cassandra Grey understood that you have to work for the things you need in life. It's part of what motivated her to not only work at a children's store in high school but eventually go on to manage said store and become a buyer. It's also part of what drove her to create her own, nontraditional PR business in both San Francisco and New York City and what, ultimately, led her to draft the business plan for what's now a multiplatform beauty empire by the name of Violet Grey. "I'm still on the day-to-day hustle," Grey tells Hillary Kerr in Episode 16 of Second Life, where she explains how her entrepreneurial spirit and passion for people guided her through multiple career paths.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The fast-paced world of advertising couldn't seem more opposite to vintage furniture shopping. However, after pressing pause on a career in marketing to raise her quickly growing family, Anna Brockway found herself using her advertising know-how to start her own website for selling vintage furniture. Brockway explains how she turned a little website called Chairish into the curated online marketplace for vintage home goods that it is today on episode 15 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.