Casey Brown broke barriers when she became the first woman to complete a practice run at Red Bull Rampage. Having grown up out of society, she was born loving to play rough and go big when it comes to sports. Brown speaks to Ashlyn about the thrill of riding, the mental fortitude of surviving severe injuries, and the pressure that comes with being a pioneer in an event. Through Dark Horse, her insular biking event, she helps women develop careers. 

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Jameela Jamil's well known for using her voice to center important issues like period poverty, eating disorders, and discrimination against women - but she wasn't born that way. Ashlyn and Jameela discuss the power of divine femininity and how Jameela learned how to leave repression behind. Part of the secret: rush toward your crone era, destroy the patriarchy, and let spite lead the way. At almost 40, Jameela celebrates the second half of life - she knows herself better than ever, she's having better sex than ever, and she's more powerful than ever. Basically, become harder to kidnap and embrace pleasure wherever you find it.

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In this episode, Ashlyn sits down with entrepreneur, author, and motivational speaker, Gary Vaynerchuk. They dive deep into what made Gary into the man he is today. Whether it be his mother, father, or grandmother, Gary absorbs every lesson he’s taught and puts them to practice. Together they consider different approaches to parenting, observe the insecurities men and women face, and talk about how to become comfortable being uncomfortable.

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This week, Ashlyn sits down with YouTuber, actress, comedian, and author Lilly Singh. As you can tell from those titles, Lilly has accomplished a lot in her career. But this conversation reaches far beyond her accolades and gets to the heart of who she is beyond her work. Lilly talks about what she’s learned in her 15 years in the public eye, how she maintains confidence in the face of criticism, and who she looks to for inspiration these days. Plus, she tells us about the labor of love that is her new movie, Doin It, a raunchy sex-comedy that Lilly wrote, produced, and stars in. 

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This week, Ashlyn sits down with breakdancer Sunny Choi. It’s been about a year since Sunny achieved her childhood dream of competing in the Olympics, though as a kid she thought she’d do it as a gymnast. Sunny takes Ashlyn through her upbringing and the personal battles she had to overcome to make it to the largest stage of her sport. Plus, she opens up about the high of getting breakdancing into the 2024 Paris Olympics and the low of learning that it would not be included in the 2028 Los Angeles Olympics.

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Ashlyn sits down with legend and entertainer, Margaret Cho. They talk about growing up in a queer bookstore in San Francisco, why dominatrixes should be well paid, and why we laugh. Digressions include Margaret’s beloved dogs, lesbian yearning, and a laundry list of improvements to the Queer Ultimatum.

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Ashlyn sits down with model and entrepreneur Lauren Chan for a conversation about Lauren’s divorce and late-in-life coming out, becoming a queer trailblazer in the fashion world, and why leading with vulnerability can actually be a power move. Lauren also opens up about using basketball as both an outlet and an identity, the pressure girls face around body image in sports, and what it really took to pivot from corporate publishing to the runway—while shutting down online haters along the way.

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This week, Ashlyn connects with dancer, actor, and mental health practitioner Alyson Stoner. Listeners may know Alyson from their childhood roles in Cheaper By the Dozen, Camp Rock, and much more, but these days they’re exposing the “toddler to train-wreck pipeline” that child actors are up against. Alyson’s new memoir, Well Adjusted Despite Literally Everything, details their personal journey in this system and how they have begun to heal from it. Alyson and Ashlyn connect over a passion for mental health advocacy, discovering who they are beyond what they do, and protecting kids in entertainment, sports, and beyond.

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Ashlyn gets real with Marion Jones: Olympian, Tarheel, and one-time fastest woman on Earth. Marion takes Ashlyn back in time, to when she spent 49 days in solitary confinement and finally realized what she needed to tell the world. They talk through the regrets, guilt, and tears that paved the way for change– from tabloids to jail, fairweather friends to mothering when the world wants to write your story for you.

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In this episode, Ashlyn sits down with Krista Tippett — journalist, author, and host of On Being — for a thoughtful conversation about what it means to explore spirituality with openness and humility, and how meaningful conversations can help us make sense of the world. Together they unpack how hosting is an act of hospitality and dialogue is a form of adventure — a way of searching for knowledge together, one question at a time.

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