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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The Who What Wear Podcast: Is Your Closet Making You Cancel Plans? Overcoming Fashion Frustration With Evereve Co-Founder Megan Tamte

The Who What Wear Podcast: Is Your Closet Making You Cancel Plans? Overcoming Fashion Frustration With Evereve Co-Founder Megan Tamte

This week, Hillary Kerr hosts Evereve co-founder Megan Tamte and Who What Wear's Executive Editorial and Style Director Lauren Eggertsen to delve into the results of Evereve’s national fashion survey....

25 Maalis 42min

Monica Dinsmore: Head of Esports at EA

Monica Dinsmore: Head of Esports at EA

Monica Dinsmore is the head of esports at EA, or Electronic Arts. Before working in gaming, Dinsmore worked in the tech industry during the dot-com boom of the late 1990s and then transitioned into fi...

23 Maalis 54min

The Who What Wear Podcast: 2026 Red Carpet Recap With Zanna Roberts Rassi: The Best Dressed, Behind-the-Scenes Details, and Standout Beauty Moments

The Who What Wear Podcast: 2026 Red Carpet Recap With Zanna Roberts Rassi: The Best Dressed, Behind-the-Scenes Details, and Standout Beauty Moments

In this episode, Who What Wear cofounder ⁠Hillary Kerr⁠⁠ sits down with style correspondent and red carpet expert Zanna Roberts Rassi to talk all things 2026 award season. Rassi discusses the buzzy st...

18 Maalis 41min

Cofounder and Chief Creative Officer of Loeffler Randall

Cofounder and Chief Creative Officer of Loeffler Randall

Jessie Randall is the cofounder and chief creative officer of the global lifestyle brand Loeffler Randall. Before she started her company, Randall began her career in advertising but, after a few year...

16 Maalis 51min

The Who What Wear Podcast: Spring 2026 Shopping Guide: Glamorous Dressing, Advanced Layering, and Oversized Sunglasses

The Who What Wear Podcast: Spring 2026 Shopping Guide: Glamorous Dressing, Advanced Layering, and Oversized Sunglasses

This week, Who What Wear Shopping Director Bobby Schuessler is joined by Associate Shopping Editor Audry Hiaoui and stylist Brie Welch to give you the ultimate spring shopping guide. They break down t...

16 Maalis 22min

Kahlana Barfield Brown: Founder of KBB by KAHLANA

Kahlana Barfield Brown: Founder of KBB by KAHLANA

Kahlana Barfield Brown is the founder of her namesake clothing brand, KBB by Kahlana. Before she became a designer, she was an icon in the editorial world. Her career started at InStyle, where she wor...

9 Maalis 52min

The Who What Wear Podcast: Celebrity Stylist Petra Flannery on Emma Stone’s '90s-Inspired Press and Award Show Looks for Bugonia

The Who What Wear Podcast: Celebrity Stylist Petra Flannery on Emma Stone’s '90s-Inspired Press and Award Show Looks for Bugonia

In this episode, Who What Wear co-founder Hillary Kerr sits down with celebrity stylist Petra Flannery. She's best known for her long-term partnerships with Oscar-winning clients like Emma Stone, who’...

4 Maalis 39min

Jenn Lueke: Culinary Creator and Cookbook Author

Jenn Lueke: Culinary Creator and Cookbook Author

Jenn Lueke, aka Jenn Eats Good, is a culinary creator, recipe developer, and newly anointed cookbook author. She started her now-famous Instagram account while she was in college studying business, fi...

2 Maalis 53min

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