Second Life

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Rating
4.8
from
2840 reviews
This podcast has
683 episodes
Language
Publisher
Explicit
No
Date created
2018/02/11
Latest episode
2026/04/22
Average duration
46 min.
Release period
4 days

Description

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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Podcast episodes

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The Who What Wear Podcast: Behind the Fashion of The Devil Wears Prada 2 With Costume Designer Molly Rogers
2026/04/22
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!
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Courtney Smith: Enneagram Coach and Author
2026/04/20
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.
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The Who What Wear Podcast: Fashion Analyst Mandy Lee, aka @oldloserinbrooklyn, Talks Met Gala Predictions, 2026 Trend Forecasts, and AI in the Fashion Industry
2026/04/15
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!
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Renee Montgomery: Vice President and Part Owner of the Atlanta Dream
2026/04/13
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.
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The Who What Wear Podcast: Lauren Conrad on the Laguna Beach Reunion, Millennial Nostalgia, and Her Favorite 2000s Fashion Trends
2026/04/08
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!
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Jenna Goldring: Founder and CEO of The High Confectionary
2026/04/06
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.
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The Who What Wear Podcast: Makeup Artist Pati Dubroff on Blush Placement, Gray Mascara, and Making Press-Tour Magic With Margot Robbie
2026/04/01
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!
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Priscilla Tsai: CEO and Founder of Cocokind
2026/03/30
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.
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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
2026/03/25
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!
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Monica Dinsmore: Head of Esports at EA
2026/03/23
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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The Who What Wear Podcast: 2026 Red Carpet Recap With Zanna Roberts Rassi: The Best Dressed, Behind-the-Scenes Details, and Standout Beauty Moments
2026/03/18
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 stylists of the season, dissects fashion Easter eggs you may have missed, and brings us behind the scenes of what it’s really like to be in person on the red carpet.  Watch this episode ⁠⁠here on our new YouTube channel⁠⁠, and be sure to subscribe!
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Cofounder and Chief Creative Officer of Loeffler Randall
2026/03/16
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 years, made the leap into the fashion industry. Starting from scratch as an intern at Katayone Adeli, while also taking fashion classes, she then transitioned to Banana Republic, working as a junior designer. However, in 2005, alongside her husband, she decided to start her own footwear company, which quickly garnered recognition and expanded beyond shoes into the global success it is today. In 2007, she was awarded the CFDA Swarovski Award for Accessory Design, and in 2022, British Vogue dubbed the brand's Camellia heel “one of the best-selling bridal shoes in the world.” Currently, Loeffler Randall products are sold worldwide across retailers such as Nordstrom and Bergdorf Goodman as well as in its own digital and physical retail stores.
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The Who What Wear Podcast: Spring 2026 Shopping Guide: Glamorous Dressing, Advanced Layering, and Oversized Sunglasses
2026/03/16
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 the biggest trends they saw on the S/S 26 runways and give their styling recommendations for seasonal staples like trench coats, sunglasses, and low-profile sneakers. Plus, they discuss their favorite spring outfit formulas, including a controversial capri pant pairing. Watch this episode here on our new YouTube channel, and make sure to subscribe!
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Kahlana Barfield Brown: Founder of KBB by KAHLANA
2026/03/09
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 worked her way up from intern to the publication’s first-ever beauty and fashion editor at large. Her work steering the outlet’s coverage earned her widespread recognition, including the title of Editor of the Year from Harlem’s Fashion Row. She led the outlet for a decade before leaving in 2018 to build her personal brand online in the fashion space. Brown made the leap from reporter to designer in 2022, when Target tapped her to be the first designer for the Future Collective—the company’s first-ever creator-led fashion line. After her first collection sold out quickly, Brown decided to partner with the company again to launch her own brand, KBB, exclusively with the chain. Her designs continue to be wildly successful, as Target plans to expand her collection to over 500 locations nationwide this year. 
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The Who What Wear Podcast: Celebrity Stylist Petra Flannery on Emma Stone’s '90s-Inspired Press and Award Show Looks for Bugonia
2026/03/04
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’s currently up for another Oscar, and Zoe Saldaña, who just wrapped up a global press tour for Avatar: Fire and Ash. Tune in to hear Flannery share her approach to color, her biggest styling disaster, and how a haircut can impact an entire press run. To see all of the looks discussed, watch this episode ⁠⁠here on our new YouTube channel⁠⁠, and make sure to subscribe! Listen to Petra’s episode from 2024 here!
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Podcast reviews

Read Second Life podcast reviews


4.8 out of 5
2840 reviews
morris123456798 2026/01/25
Loved!
Your interview with Jamie Haller was so interesting. It’s great to know the backstory of her line.
Briaunarose13 2025/05/25
Inspiring!
Thank you for sharing so many inspiring stories! It’s expanded my perception of what could be and how even the most successful women have felt imposte...
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Masha R. 2025/12/12
Pls stop with Kat
I love the podcast but Kat has the most unpleasant voice it’s hard to listen to
xuey555 2025/11/05
Kat Colling’s voice…NO
I actually think this is a wonderful podcast overall but every time they let Kat Collings speak, it’s time to switch off. This woman sounds like she h...
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helpmeunderstandthis 2025/04/27
Generally solid but sometime misses
These guests are such gets and even if we know a brand or a product, I still want to know the backstory. Like how did Pistola get its name? May seem ...
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ShanieceNY2LA 2025/03/12
Jeni’s Ice Cream
I have been a long time listener of the show but never wrote a review. This last episode with Jeni of Jeni’s ice cream was hands down my favorite! In ...
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Eva Jannotta 2024/10/21
Love the focus
How often do I look at someone and think, “how the heck did she get there?” This podcast answers my question! I love the focus on the nonlinear career...
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oliviaschne 2023/07/18
So inspiring!
As someone who just took the leap and decided to trust myself and go all in on building my dream business, this podcast is a huge source of inspiratio...
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kaytwall 2024/07/18
Love Second Life…WWW Pod, not so much
I’m not a fan of when hit podcasts try to piggyback their success with another show. Love love Second Life and have listened to literally every episod...
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HYOSTIGGP 2024/03/17
Credibility matters
I seemed to vaguely know about you and this show before being sent the episode where you interview my CEO. But nothing prepared me for self-aggrandizi...
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