Kissing Cowgirls founder Emma DeMarco joins Bailey Taylor to talk about building her fashion brand, finding her creative identity, and learning the realities of entrepreneurship along the way. Emma opens up about the expensive side of manufacturing, why she finally learned to hire people who know more than she does, and the surreal moment she discovered Brandy Melville was selling clothing using her brand’s name and imagery. She also shares how community, pop-ups, and social media have helped shape Kissing Cowgirls and where she hopes to take the brand next.

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In this solo episode, Bailey Taylor gets candid about body image, self-esteem, and the pressure to keep up in a world shaped by social media, fashion trends, and Ozempic culture. She opens up about her own weight loss journey, falling out of routines, and what it feels like to start over when your confidence is low. Bailey also shares her honest take on the return of ultra-skinny beauty standards, why she believes health and strength should be the goal, and how comparison online can distort your sense of reality. From small daily rituals to movement, skincare, mindset shifts, and learning to slow down, this episode is a raw conversation about taking your power back and building confidence in a healthier, more lasting way.

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Mia Calabrese joins Bailey for a candid conversation about the realities of dating in New York City, why situationships have become so normalized and what she’s learned about dating more intentionally. They get into whether success makes dating harder for women, men who resent ambitious partners, splitting the bill and why you should never have to question whether someone actually likes you. Mia also shares one unforgettable Hinge date, helps Bailey officially block and delete an ex, and gives her take on everything from red flags to the classic “if he wanted to, he would.” Plus, she opens up about what she’s looking for in a partner now, her career goals and why her mom will always be her ultimate It Girl.

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Claudia Li Johnson and Gabby Kono-Abdi, co-founders of Vin, join Bailey to talk about turning their shared love of vintage and statement accessories into a fast-growing fashion brand. They share how their iconic Fishy bag came to life, why launching before everything was perfect worked in their favor, and how intentional gifting helped get Vin into the right hands.

They also get into running a business with your best friend, learning when to compromise, protecting the brand as it grows, and why good taste is about so much more than following trends. Plus, Claudia and Gabby talk personal style, finding inspiration around the world, what they’ve learned as first-time founders, and what they’re manifesting next.

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Dieux Skin founder Charlotte Palermino joins Bailey Taylor to talk about building one of the most trusted skincare brands by leading with science, evidence, and transparency. She opens up about leaving the corporate world, why she wanted Dieux to be more than another trendy beauty brand, and how distrust in healthcare and “clean beauty” culture can radicalize women online. Charlotte also gets into what it really takes to make a product, the expensive realities of clinical testing, why restraint matters in business, and her mission to create a legacy brand that lasts far beyond her own face.

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Artist and NYC cool girl Taylor Quitara joins Bailey to talk about building a creative life, developing your personal style and learning to embrace the things that make you different. Taylor shares how she turned painting into a career, used social media to get her work discovered and learned to tune out other people’s opinions. They also get into vintage shopping, developing your taste, escaping the pressure to constantly be productive, finding creativity outside of your phone and why being a little weird might just be your superpower.

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Levi Sebree is back for a candid catch-up filled with dating confessions, friendship advice and the reality of building a career in fashion. She and Bailey compare New York and Los Angeles dating, debate underrated green flags and explain why the usual relationship rules rarely work. Levi also shares how she went from cold-emailing hundreds of fashion companies to working with major brands, proving that confidence, persistence and genuine connections can completely change your career. Plus, they open up about the trust behind their friendship, refusing to compete with each other and always reminding one another that they are that girl.

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In this solo episode, Bailey answers listener questions about building confidence, recognizing your worth and becoming the version of yourself you want to be. She shares practical advice for moving past self-doubt, rebuilding your self-esteem and refusing to let insecurity keep you from opportunities, relationships or new experiences. Bailey also explains why confidence starts with your mindset, how small investments in yourself can change the way you feel, and why a little “delusional confidence” might be exactly what you need to stop overthinking and start going after the life you want.

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