Who What Wear's Hilary Kerr mixes career-pivot interviews with fashion trend and red carpet talk.
Second Life is an interview series about women whose careers did not move in a straight line. Conversations follow the pressure points behind pivots, from sports and finance to skincare, cannabis, gaming, fashion, and media.
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Second Life airs under two closely linked formats within one feed: the show's namesake segments profile women who left one career for another, including a former ad-tech and out-of-home advertising marketer who launched a 1mg THC gummy brand, and a ten-year WNBA veteran who moved into team ownership and executive leadership at the Atlanta Dream. The remainder of the feed runs as The Who What Wear Podcast, a fashion-industry interview and panel show covering trend forecasting, jewelry and accessories founders, seasonal shopping guides, and awards-season red carpet recaps. Hilary Kerr, co-founder of Who What Wear, hosts most episodes and conducts one-on-one interviews with designers, brand founders, and entertainment-adjacent guests. Other Who What Wear staff, including shopping director Bobby Schoessler, join for shopping-guide and trend-focused episodes that sometimes run as multi-host panels rather than single-guest interviews. Guests are typically founders of direct-to-consumer beauty, jewelry, or fashion brands, along with fashion commentators, stylists, and occasional entertainment or sports figures discussing a career pivot. Episodes mix personal origin-story narratives about how a product or brand started with tactical discussion of current trends, bestsellers, and styling advice. Red carpet and award-season episodes bring in style correspondents to break down specific celebrity looks and designer collections. Running times vary from about 22 minutes for quick trend or shopping segments to nearly an hour for in-depth founder profiles. Listeners interested in fashion industry mechanics, brand-building stories, or women's career-change narratives make up the core audience. Production is conversational and closely tied to Who What Wear's own editorial content, with episodes frequently referencing the outlet's articles, shopping guides, and staff by name.
Made for: Fashion-industry followers alongside listeners interested in women's entrepreneurship and career-reinvention stories.
What sets it apart: It runs a career-pivot interview format and a separate fashion-trend, shopping-guide podcast in one shared feed rather than a single format.
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.
Based on 6 episodes we listened to · September 2026
Second Life makes career reinvention concrete by tracing how prior experience becomes operating judgment, leadership and a viable new venture.
Second Life follows the moment a career change becomes a working business, with Hilary Kerr asking women to explain both the decision and the execution. The conversations stay close to transferable skills, early constraints and the practical work of starting again.
Career reinvention gets delightfully literal before you can romanticize the leap: day jobs, investor decks, stainless-steel pots.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A fashion conversation that links Met Gala forecasting and AI to Mandy Lee's years inside the industry.
Mandy Lee, also known as Old Loser in Brooklyn, sits down with Tara Gonzalez for a conversation that moves from Met Gala forecasting to AI's role in fashion.
A leadership story shaped by setbacks, not slogans.
Renee Montgomery comes through as a leader shaped by hard seasons, not polished talking points. Benchings, trades, a serious illness, and the grind of building back toward a Minnesota title give the story its weight.
A tidy nostalgia trip with just enough fashion detail to land.
Lauren Conrad's visit to Who, What, Where feels like a quick, easy return to Laguna Beach and the early 2000s look it helped lock in. The hosts keep things moving, and the best parts come when the conversation stays on what teenagers were actually wearing on camera and how…
A founder story about turning a personal gap into a low-dose edibles brand with a clear point of view.
Jenna Goldring's story lands as a clean example of a brand starting from a specific missing piece. The profile follows how low-dose, hemp-derived edibles that felt more approachable became The High Confectionary, after work at Hulu, Vistar, and in ad sales for highly regulated…
A product-heavy makeup conversation about gray mascara, blush placement, and press-tour polish.
Hilary Kerr hosts a close, detail-heavy beauty conversation with the makeup artist, moving from the Barbie press tour to the Wuthering Heights press tour, then the 2004 Got Milk ad with Mary-Kate and Ashley Olsen, and on to bridal makeup for a wedding.
A scrappy founder story that turns a skin problem into real retail traction.
Priscilla Tsai's path is built around a problem plenty of listeners know too well: hormonal acne, and the decision to turn that frustration into something useful.
A practical reset for anyone whose closet has started to feel like work.
Fashion frustration is the real subject here: what happens when life gets busier, habits change, and style starts to feel a step behind. Megan Tamte and Lauren Egerton keep the talk rooted in how real women dress, which makes the focus feel useful instead of abstract.
A polished award-season fashion chat that makes the red carpet feel easy to read.
This episode treats award-season fashion as a working system, not just a parade of expensive clothes. Zanna Roberts-Rossi walks through how dress codes, themes, and brand involvement shape what lands on the red carpet, and the conversation is strongest when it gets specific,…
Stephen Dubner tests bourbon economics, Alzheimer's research, and money advice against hard data.
Daily business news with Kai Ryssdal, tracking Fed policy, oil shocks, and private credit.
Galloway rotates Office Hours Q&A, Raging Moderates politics, and China Decode geopolitics weekly.
Joel and Matt answer listener money questions weekly in the show's Ask HTM segments.
Brené Brown's long-form conversations linking grief, caregiving, politics, and nonviolence to her vulnerability research.
Mandy Lee is back on the pod.
The guest had to start over.
Lauren Conrad looks back.
Jenna Goldring saw the gap clearly.
Gray mascara gets the gasp.
Priscilla Tsai started with her own skin.
Closet frustration gets practical here.
This episode features an interview with Monica Dinsmore, EA's head of esports, discussing her career journey from tech and finance to pioneering leadership in the male-dominated gaming industry.
Awards-season fashion has become its own main event.
Hillary Kerr interviews fashion entrepreneur Jessie Randall about her career pivot from advertising to founding the successful brand Leffler Randall.
Shopping feels fun again.
Hillary Kerr interviews fashion designer Kalana Barfield-Brown about her career pivot from fashion editor to entrepreneur and designer.
Host Hillary Kerr interviews celebrity stylist Petra Flannery about award season fashion, the complexity of simple dresses, and her favorite custom looks.
Hillary Kerr interviews Jen Mookie, a former finance professional who became a full-time culinary content creator and published a bestselling cookbook.
Makeup artist and groomer Tasha Reiko Brown discusses her work with celebrities like Michael B.
Hillary Kerr interviews cookbook author Alison Roman about her career evolutions, including launching a brand and opening a grocery store.
Hillary Kerr introduces a special episode where fashion editors recap New York Fashion Week fall-winter 2026 collections.
Hillary Kerr interviews fashion influencer Carla Rockmore about her career pivot from retail and design to social media stardom and launching her own fashion line.
This episode features an interview with celebrity stylist Karla Welch, discussing her career, the power of styling, and her work with clients like Tessa Thompson and Renate Reinsve during award season.
Hillary Kerr interviews Priyanka Ganju, founder of Kolfi Beauty, about her career pivot from business consulting to beauty entrepreneurship.
Jennifer Fisher tells Bobby Schussler how a Shane dog tag made after chemotherapy became a direct-to-consumer jewelry brand, with early wearers including Uma Thurman and Ashley Simpson.
Hillary Kerr interviews children's book author Andrea Beatty about her career transition from tech support to writing bestsellers like Ada Twist Scientist.
Denim expert Jane Herman discusses the five essential jean styles for year-round wardrobes and shares predictions for future trends in this fashion-focused interview.
This episode features an interview with Leslie Tessler, founder and CEO of Hanni, discussing her journey from fashion and beauty marketing to creating an innovative body care brand after a transformative decade in Argentina.
Hillary Kerr interviews celebrity aesthetic provider Vanessa Lee about her career pivot from art to founding a beauty concept bar, sharing insights on effective skincare treatments and business lessons.
Hillary Kerr interviews fitness entrepreneur Senada Greca about her career pivot from financial analyst to personal trainer and supplement company co-founder.
Fashion Director Joseph Tang discusses 2025 shopping trends and Spring-Summer 2026 runway predictions.
Hillary Kerr interviews Rachel Mansfield about her career pivot from PR to food blogging and founding a kid snack brand.
Fine jewelry designer Jean Doucet discusses starting his own brand, using lab-grown diamonds, and engagement ring trends.
Costume designer Paul Taswell discusses his work on Wicked for Good, explaining how he transformed the witches' wardrobes to reflect their character arcs.
The Who What Wear team discusses holiday gift recommendations for fashion enthusiasts and swaps gifts in studio.
Hillary Kerr interviews Jennifer Anderson, founder of Kids Eat in Color, about her career pivot from nonprofit work to nutrition and building a social media business.
Hillary Kerr interviews Sarah O'Leary, CEO of Willow Innovations, about her career pivot from consulting to leading a femtech startup.
Hillary Kerr interviews Sarah Harrelson about her career pivot from politics to founding Cultured Magazine.
A fashion podcast episode discussing fall-winter runway trends and providing a shopping guide for fall outerwear, accessories, and styling tips.