Who What Wear with Hillary Kerr: Supermodel Ashley Graham on Becoming an Entrepreneur, Putting Her Money Where Her Mouth Is, and Mentoring Female Founders on Her New Show, Side Hustlers
Second Life20 Maalis 2024

Who What Wear with Hillary Kerr: Supermodel Ashley Graham on Becoming an Entrepreneur, Putting Her Money Where Her Mouth Is, and Mentoring Female Founders on Her New Show, Side Hustlers

After making history as the first size-14 model featured on the cover of Sports Illustrated Swimsuit in 2016, supermodel and entrepreneur Ashley Graham has used her star power to repeatedly confront and redefine the fashion industry’s archaic beauty standards. Graham has actively pushed brands to take a chance on her—learning the business of fashion, developing her own lines, and becoming an investor along the way. Today, Ashley’s sharing how her own entrepreneurial journey led her to her latest role as co-host and executive producer of Roku’s Side Hustlers, where she and Good American Founder Emma Grede mentor and invest in female entrepreneurs looking to turn their side hustles into full-time gigs. You can watch the full first season of Side Hustlers for free at roku.com! This episode was brought to you by eBay.

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Lauren Conrad: Entrepreneur and The Little Market Co-Founder

Lauren Conrad: Entrepreneur and The Little Market Co-Founder

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.  Originally broadcast on June 25, 2018.

26 Elo 201938min

Emma Grede: Good American Co-Founder + CEO

Emma Grede: Good American Co-Founder + CEO

Emma Grede is the CEO and co-founder of Good American, the hugely successful, size-inclusive fashion brand that she started with none other than Khloé Kardashian. But starting this business wasn't the first time Grede struck out on her own. She'd long been making a name for herself in the fashion and entertainment industries on the business side of things and had already checked starting a company off her list. "I am a person who can sell anything, and I think I just had that naturally," she tells Hillary Kerr on today's episode of Second Life.  Originally broadcast on September 24, 2018.

19 Elo 201951min

Ellen Bennett: Hedley & Bennett Founder and CEO

Ellen Bennett: Hedley & Bennett Founder and CEO

If anyone has mastered the art of the hustle, it's Ellen Bennett. The entrepreneurial powerhouse behind Hedley & Bennett, a Los Angeles–based chef wear and handcrafted apron company, started her own business at age 24 while working as a line cook at not one but two prestigious restaurants in L.A. "I was permanently running on adrenaline, and I loved it," she tells Hillary Kerr. Now, she's outfitting top chefs around the world, including the likes of Martha Stewart, Jamie Oliver, Jon Shook, and Vinny Dotolo. Originally broadcast on September 10, 2018.

12 Elo 201956min

Aurora James: Brother Vellies Founder and Creative Director

Aurora James: Brother Vellies Founder and Creative Director

There was a time when Aurora James never thought she'd have a seat at the proverbial table. Now, after dipping her toes in multiple industries, she's at the helm of the sustainable fashion company Brother Vellies and is proof that if you have a goal, you can make it happen, even if that means finding a new way of getting there. "I always knew that I wanted to work in fashion. I just knew that fashion wasn't working for me in a way that I needed it to," she tells us.  Originally broadcast on August 8, 2018.

5 Elo 201947min

Jen Atkin: "The World's Most Influential Hairstylist"

Jen Atkin: "The World's Most Influential Hairstylist"

In an updated and extended interview from our very first episode, Hillary sits down with Jen Atkin, celebrity stylist and founder of cult haircare line Ouai. Dubbed the "most influential hairstylist in the world" by The New York Times, Atkin counts Bella Hadid, Chrissy Teigen, and Kendall Jenner as clients. Here, she gets candid about the power of social media, reflects on her journey from salon apprentice to CEO of a thriving business, and explains why mental toughness is the most underrated quality. This extended episode has an additional 20 minutes of previously unreleased audio from when it first aired on February 19, 2018.

29 Heinä 201946min

Anine Bing: Founder & Chief Creative Officer of Anine Bing

Anine Bing: Founder & Chief Creative Officer of Anine Bing

Anine Bing launched her successful clothing and accessories line in 2012, but her days once revolved around modeling, music, and blogging. Listen to the story of her career pivots on this week's episode.

22 Heinä 201947min

Jennifer Meyer: Jewelry Designer and Founder of Jennifer Meyer Jewelry

Jennifer Meyer: Jewelry Designer and Founder of Jennifer Meyer Jewelry

Jennifer Meyer’s career has taken a non-linear path that went from psychology to fashion editorial to PR before she founded her now wildly popular jewelry brand. Listen to her story on Second Life.

15 Heinä 201954min

Lauren Kleban: Celebrity Trainer and Founder of LEKFit

Lauren Kleban: Celebrity Trainer and Founder of LEKFit

Lauren Kleban started out as a professional dancer and now runs L.A.’s popular LEKFit workout studio. Hear about her career journey and what’s next for her company on Second Life.

8 Heinä 201947min

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