Lipstick on the Rim

Is good taste something you’re born with, or something you can learn? Real Housewives of New York City's Jenna Lyons is the former president and executive creative director of J.Crew. She was named one of Time’s 100 Most Influential People, and The New York Times called her “the woman who dresses America.” She says she wasn’t born with it. Not even close. She grew up surrounded by California strip malls and the Baywatch look, thinking style meant looking like everyone else. Moving to New York at 18 taught her that taste is personal. Now she’s a partner and executive creative director at Fundamentalco, helping some of the biggest companies in the world figure out who they really are.

Most companies treat brand as the wrapper: the logo, the ad campaign. Jenna puts it at the center. What’s your reason for being, and what makes you different? She explains why “you can’t tell a story that doesn’t exist” and why chasing a viral spike can leave a brand overexposed instead of built to last. The same rules apply to personal style, including the year after J.Crew when she had a closet full of beautiful clothes and couldn’t get dressed. Whether it’s a company or a closet, knowing who you are is the whole point.

Plus: what happened when a new CEO told the executive team they were all interviewing for their jobs, her honest take on CO2 lasers, Botox and facelift treatments, the comfortable heels worth hunting down and two household hacks that might change your life.

A Sony Music Entertainment production.

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We talk about our under-eyes, our necks, and our gut microbiome, so why do we almost never talk about our mouths? Integrative dentist Dr. Leedia Riman co-founded a Beverly Hills dental practice with her brother, and she believes your mouth is a window into your whole-body health. She learned it the hard way. She spent years treating patients overseas and saw some of the most worn-down mouths of her career in people who had full access to care. Then a really rough pregnancy of her own finally connected the dots between breathing, nutrition, hormones, and what shows up in our teeth.

Most people think of dentistry as cleanings and fillings. Dr. Riman practices “dentistry beyond teeth” instead, looking at body composition, saliva, stress, and hormonal history before she ever looks at a single tooth. She tells Molly and Emese why breathing is the most important thing for oral health, and how mouth breathing and snoring can leave you feeling like you’ve been hit by a truck every morning. She explains how pregnancy, perimenopause, and menopause can all show up in your gums, and why a mouth that’s aging too fast is a sign the rest of the body is too.

Plus: why she scrapes her tongue before she brushes, the two-ingredient pantry rinse she uses instead of alcohol mouthwash, why you should never let anyone file your teeth down and when veneers are worth it and when they’re not.

A Sony Music Entertainment production.

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Who are you when nobody needs you the same way anymore? After 25 years as a stay-at-home mom raising three kids, Helen Boulos faced the quiet house she'd dreaded for years and decided quiet wasn't her style. She taught herself Canva, launched an anonymous Instagram account under a made-up name, then dropped the alias to become the voice behind Out of Office, now one of the most candid, funny, and refreshingly unfiltered communities for women reinventing themselves in midlife.

Rather than overthinking the next chapter with notebooks, five-year plans, and a stack of self-help books, Helen makes the case for motion: start before you're ready, stay curious like a beginner, and stop second-guessing every decision. She opens up to Molly and Emese about the moment she decided to be okay, why the invisible load leaves so many moms convinced they "did nothing" for decades, and why she believes there's never been a better time to be a 50-something female entrepreneur.

Plus: what happened to her marriage once the kids left, surviving three teenagers during COVID, breaking a generational cycle through 18 years of sobriety, and why women in midlife should stop waiting for permission to do anything.

A Sony Music Entertainment production.

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Why can't we look away from complicated women who break the rules? May Cobb, the bestselling author and executive producer behind Netflix's The Hunting Wives, joins Molly and Emese to unpack our fascination with dark thrillers, complicated female characters, and the women we love to watch make terrible decisions.

Drawing on her upbringing in East Texas, May shares how Southern culture inspires her writing, why female friendships can feel more intense — and sometimes more treacherous — than romance, and why likability isn't necessarily the point.

Plus: her favorite thriller novels, why "bless your heart" might be the ultimate Southern threat, a tease of The Hunting Wives season two, and a round of thriller-writer hot takes, including who's the bigger red flag: the husband or the best friend.

A Sony Music Entertainment production.

Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts and follow us at @sonypodcasts

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How does a meme account turn into Not Skinny But Not Fat? Amanda Hirsch built her platform one meme at a time back in 2016, learning early on, as she puts it, that "you can get to people just by saying something about them." A Hulu hosting gig and one surprising royal pen pal later, she's back on Lipstick on the Rim to unpack the year that pushed her out of her comfort zone and into some of the biggest rooms in pop culture.

Rather than treating her "year of yes" as permission to say yes to everything, Amanda used it to figure out exactly what's worth her time — landing on a lesson Molly sums up perfectly: the power of saying no is your biggest yes. She opens up about staying fair with her opinions on an increasingly divisive, algorithm-driven internet, and about the two interviews that left the biggest mark on her.

Plus: the story behind Amanda's one-way pen pal relationship with Meghan Markle, her take on the internet's escalating influencer-culture debates, her dream of hosting a late-night talk show, and an honest conversation about having kids in your 40s.

A Sony Music Entertainment production.

Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts and follow us at @sonypodcasts

To bring your brand to life in this podcast, email podcastadsales@sonymusic.com

Mentioned in the Episode: https://shopmy.us/shop/collections/7959350

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