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    Business

    Second Life

    Hosted by Who What Wear co-founder Hillary Kerr, Second Life spotlights successful women who have made major career changes. Guests share lessons they’ve learned through fearlessly daring to pivot, and how they’ve used skills from their “first lives” to navigate their winding career journeys.

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    Latest Episodes:
    The Who What Wear Podcast: Behind the Fashion of The Devil Wears Prada 2 With Costume Designer Molly Rogers Apr 22, 2026
    Show notes

    This week, Who What Wear senior fashion and social editor Tara Gonzalez sits down with costume designer Molly Rogers to discuss the upcoming film The Devil Wears Prada 2. Rogers’s résumé includes work on Sex and the City, And Just Like That…, Ugly Betty, and the original The Devil Wears Prada. So, of course, they chat about nostalgic looks from the first film (such as the Chanel boots and cerulean sweater) and how Miranda, Andy, Emily, and Nigel have evolved style-wise over the past 20 years. Plus, she shares behind-the-scenes stories about what are sure to be the most talked-about looks from the sequel.

    Watch this episode ⁠⁠here on our new YouTube channel⁠⁠, and be sure to subscribe!


    Courtney Smith: Enneagram Coach and Author Apr 20, 2026
    Show notes

    Courtney Smith is an enneagram coach, author, and consultant who works with individuals as well as Fortune 500 companies. After receiving a degree in mathematical economics, she graduated from Yale Law School with her JD and intended to start her career in law. She then decided to change course to consulting, where she worked at McKinsey & Company before transitioning to Condé Nast, briefly working for a real estate start-up, and even considering a career as a doctor. She soon joined the board of Planned Parenthood and received her masters in public health, but was forced to pivot due to the start of the pandemic. After this career shift, Smith, who had used the Enneagram personality system herself, began using the tool to help others. This led to where she is today: coaching and consulting high-profile clients such as Brené Brown and co-authoring the book Choosing Wholeness Over Goodness: A Process for Reclaiming Your Full Self.


    The Who What Wear Podcast: Fashion Analyst Mandy Lee, aka @oldloserinbrooklyn, Talks Met Gala Predictions, 2026 Trend Forecasts, and AI in the Fashion Industry Apr 15, 2026
    Show notes

    This week, Who What Wear Senior Fashion and Social Editor Tara Gonzalez sits down with fashion analyst Mandy Lee (aka @oldloserinbrooklyn) to discuss everything from Met Gala fashion forecasting to 2026 trend predictions. Lee also shares her thoughts on AI’s place in the industry (hint: nowhere) and the rise of utilitarianism. Plus, she shares which emerging brand she thinks we’ll all be buying by the end of the year.


    Watch this episode ⁠⁠here on our new YouTube channel⁠⁠, and be sure to subscribe!


    Renee Montgomery: Vice President and Part Owner of the Atlanta Dream Apr 13, 2026
    Show notes

    Renee Montgomery is the vice president and part owner of the WNBA team the Atlanta Dream. Before owning the team, Montgomery was a WNBA player on teams including the Atlanta Dream, the Minnesota Lynx, and the Connecticut Sun. Before that, she played division one college basketball at the University of Connecticut. After 11 years as a professional WNBA player, Montgomery opted out of the 2020 season to focus on social justice and activism before retiring from the WNBA in 2021. Shortly after retiring, Montgomery became the first former WNBA player to be an owner and vice president of a team. Today, Montgomery continues to serve as part owner and vice president of the Atlanta Dream and runs her own clothing brand, C Suite 21, and the media production company Think Tank Productions.



    The Who What Wear Podcast: Lauren Conrad on the Laguna Beach Reunion, Millennial Nostalgia, and Her Favorite 2000s Fashion Trends Apr 08, 2026
    Show notes

    In this episode, Who What Wear Editorial Director Lauren Eggertsen sits down with Laguna Beach star Lauren Conrad to talk all about the show’s 20-year reunion and her enduring influence on fashion. Conrad discusses her early fashion staples—from Rocket Dogs to C&C tank tops—and a fashion moment she still regrets from the show. Plus, she reveals an early 2000s trend she wears today.

    The Reunion: Laguna Beach Streams on Roku on April 10.

    Watch this episode ⁠⁠here on our new YouTube channel⁠⁠, and be sure to subscribe!


    Jenna Goldring: Founder and CEO of The High Confectionary Apr 06, 2026
    Show notes

    Jenna Goldring is the founder and CEO of the low-dose edible brand The High Confectionary. Before she launched her brand, Goldring spent the beginning of her career in ad sales. As she worked her way up to the VP level, she learned about the advertising nuances for highly regulated brands, such as those in the cannabis category. Goldring realized the cannabis industry was excluding consumers like herself: busy women who enjoyed taking edibles to wind down but didn’t want to feel out of control. After learning there was a need for low-dose edibles in the cannabis market, she launched The High Confectionary in 2021. Under Goldring’s leadership, The High Confectionery continues to grow its reach and has recently partnered with Broma Bakery’s Sarah Fennel to expand the product line into low-dose chocolates.


    The Who What Wear Podcast: Makeup Artist Pati Dubroff on Blush Placement, Gray Mascara, and Making Press-Tour Magic With Margot Robbie Apr 01, 2026
    Show notes

    Pati Dubroff is one of the most coveted makeup artists in the business with a portfolio full of iconic imagery—from Britney Spears's Circus album cover in 2008 to Mary-Kate and Ashley Olsen's Got Milk? ad from 2004. More recently, we've been closely following her work with Margot Robbie on the Barbie and Wuthering Heights press tours. Today, Dubroff joins Hillary Kerr to share the products and techniques she used to achieve our favorite looks.

    Listen to Dubroff's 2021 episode here!

    Watch this episode ⁠⁠here on our new YouTube channel⁠⁠, and be sure to subscribe!


    Priscilla Tsai: CEO and Founder of Cocokind Mar 30, 2026
    Show notes

    Priscilla Tsai is the CEO and founder of the skincare brand Cocokind. Before she started her company, Tsai worked on Wall Street as an equity research analyst. She had always wanted to be an entrepreneur, and after years of feeling isolated by the beauty industry due to her acne and sensitive skin, she decided to start her own skincare brand. In 2014, Tsai left her finance career to start Cocokind with the goal of developing simple products that felt like a prestige experience at an accessible price point. The brand quickly gained traction on social media and developed a loyal customer base. Then, in 2019, Target began stocking Cocokind products. A few years later, in 2022, Cocokind launched in Ulta Beauty as well. Today, Cocokind’s products are available at every Target and Ulta in the United States, as well as having a huge retail presence at Whole Foods.


    The Who What Wear Podcast: Is Your Closet Making You Cancel Plans? Overcoming Fashion Frustration With Evereve Co-Founder Megan Tamte Mar 25, 2026
    Show notes

    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. Evereve, a fast-growing womenswear retailer based in Minnesota, offers its own collection alongside 150+ brands across more than 100 stores nationwide and online. Tamte and the Evereve team conducted a survey to understand the real problems women face when shopping and getting dressed, and she’s sharing the results with us today. In a roundtable discussion, the trio addresses the responsibilities that fashion companies have to truly listen to their customers, shares which brands are getting it right, and offers practical advice for overcoming fashion confusion.

    Watch this episode here on our new YouTube channel, and make sure to subscribe!


    Monica Dinsmore: Head of Esports at EA Mar 23, 2026
    Show notes

    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 finance for nearly 15 years. She then pivoted to the gaming industry with a move to Riot Games, working on League of Legends and eventually working her way up to head of publishing for esports Europe. After realizing her passion for the esports world, she got an opportunity to move to EA, known for its real-life sports titles like Madden NFL, and ultimately became the head of esports. Since Dinsmore arrived at EA, the company has broken engagement records for its esports brands. Today, she’s been in the esports world for over a decade and continues to find innovative ways to expand the industry and reach new audiences.


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