Before Christina Tosi started Milk Bar—the trendy bakery known for its covetable, playful desserts—she was studying math and Italian in college with dreams of becoming a mathematician, a UN translator, or a perhaps a truck driver (yes, really). "I like to be uncomfortable," the entrepreneur tells Hillary Kerr on this episode of Second Life. Drawn to restaurant life with a passion for baking, Tosi moved on from her mathematical endeavors to pursue cooking at culinary school and (with a lot of hard work) went on to found her very own wildly successful bakery. Here's how she made it happen.

Christina Tosi: Milk Bar Founder and CEO

Join our host, Who What Wear co-founder Hillary Kerr, as she chronicles the career changes that can come at any age in our podcast, Second Life.

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Mandy Lee, or @oldloserinbrooklyn, has made a name for herself creating thoughtful, well-researched fashion content online. Since starting her TikTok during the pandemic, Lee has amassed over half a million followers and become an authority in the world of trend forecasting. Lee started the viral #75HardStyleChallenge and hosts an annual Met Gala watch party on TikTok that is not to be missed. Last year, she predicted that Doja Cat would dress as Karl Lagerfeld’s cat, Choupette, and over 70 million of her viewers watched as her prediction came true. This week, Lee joins us to chat about the impact of her style challenge—and she’s even sharing her coveted Met Gala predictions for this year!

Who What Wear with Hillary Kerr: Trend Forecaster and Content Creator Mandy Lee @oldloserinbrooklyn on Her Viral #75HardStyleChallenge and 2024 Met Gala Predictions

In 2017, the outdoor space surrounding Allison Messner’s home in Northern California was destroyed by a devastating wildfire. In the aftermath, Allison and her husband decided to hire a landscape designer to help them rebuild their green space, but they quickly realized how difficult, long, and expensive the process was going to be. The two began developing an idea to make the process more efficient and accessible by incorporating new technology, and in 2018, they launched Yardzen, a digital landscape design and build platform. Today, the company operates in all 50 states with a network of hundreds of designers and architects. But before Allison disrupted the landscape industry, she reported as a journalist in Alaska, worked at a prestigious PR firm, was CMO of the tech company OpenDNS when it was acquired by Cisco for $635 million, and even started her own venture capital firm.

Allison Messner: Yardzen Co-Founder and CEO

Stylist Jamie Mizrahi may not look to trends for inspiration, but she's certainly been known to help set a few of them. For instance, her client Jennifer Lawrence has made fashion headlines countless times since they partnered up, and we've watched the influence of J.Law's elevated yet effortless street style ripple through the community in the recent surge of simple, polished basics. Whether she's advising Jeremy Allen White on which button to unbutton or creating a new custom black gown for Adele's Vegas residency every single weekend, Mizrahi's through line is always to give her clients a lived-in look that emphasizes their unique sense of style. This week, Mizrahi shares why she generally ignores fashion industry standards and encourages clients to rewear pieces, dig into the past seasons' archives, and dress in a way that feels authentic.

Who What Wear with Hillary Kerr: Celebrity Stylist Jamie Mizrahi on Creating Lived-In Looks for Jennifer Lawrence, Jeremy Allen White, and Adele

Shereene Idriss, MD, is on a mission to demystify the world of dermatology and skincare. Back in 2018, Idriss felt frustrated by the rise of misinformation online surrounding skincare and decided to set the record straight. With her background as a clinical dermatologist, she began posting educational Instagram Stories from her bed, and soon, a follower aptly dubbed her the PillowTalk Derm. Today, Idriss’s influence in the skincare world is threefold. Since graduating from her seven-year medical program, she’s amassed an audience of over 3 million people, opened her own dermatology practice, and created a skincare line called Dr. Idriss, which just launched at Sephora.

Shereene Idriss: Dermatologist and Founder of Dr. Idriss Skincare

In a world where shopping integrations and #sponsored posts dominate our social feeds, it can often feel like the rapid onslaught of trends and aesthetics is homogenizing personal style and killing creativity. Who What Wear assistant shopping editor Ana Escalante recently dug into the topic of style fatigue (check out the full story here!), and today, she joins Editor in Chief Kat Collings to discuss the big, bad algorithm and how it's impacting personal style. Escalante tapped a couple of fashion insiders to get their takes, so you'll also hear clips of her conversations with style curator and writer Heather Hurst (@pigmamiii) and Saks Fifth Avenue fashion coordinator and writer Jalil Johnson (@jalil_johnson_).

Christina Tosi: Milk Bar Founder and CEO

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