Reclaiming with Monica Lewinsky

Serial entrepreneur and digital marketing icon, Gary Vee joins Monica on Reclaiming this week for a candid conversation that pulls back the curtain on his early investments in some of the biggest digital platforms of our time — including Facebook, Twitter, Venmo, and Resy, the wildly popular restaurant reservation app he co-founded. Though often seen as the patron saint of “hustle culture,” Gary reveals the counterintuitive philosophies that actually drive him: kindness as a competitive advantage, patience as the true engine of success, and radical accountability as the antidote to victimhood. Expect a raw, provocative, and surprisingly vulnerable conversation that goes far beyond marketing tactics — offering a masterclass in building a life, not just a business.
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The most decorated American track & field athlete in history, Allyson Felix joins Monica this week on Reclaiming for a conversation about what it takes to turn a moment of rejection into a movement. Allyson retraces her path from a shy, 'head-down' competitor focused solely on winning medals to the powerful advocate who risked everything to challenge a corporate sponsor system that penalized women for becoming mothers. She opens up about the isolating experience of hiding her pregnancy from Nike, negotiating her job security when her pregnancy became public, and the terrifying condition that threatened both her life and her daughter's. Allyson reveals how that confluence of personal crisis and professional injustice ignited her voice, leading her to walk away from a sponsorship, publish her groundbreaking New York Times op-ed, and ultimately build her own footwear company, Saysh, from the ground up. Expect a conversation filled with quiet determination and hard-won wisdom. * Since we taped this episode, Allyson made the exciting announcement that she’ll come out of retirement to compete in the 2028 Olympics is Los Angeles
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This week on Reclaiming, we’re playing one of our all time interviews with comedian, writer, and host John Oliver— a candid and thoughtful conversation about comedy, shame, and the power of laughter. John and Monica first connected in 2019 when she was interviewed for Last Week Tonight and she shares how that moment ultimately became part of her reclaiming journey. They explore the ethical tightrope of making jokes in a world full of gray areas and how humor can be both a coping tool and a way to call power to account.John shares what really surprised him about interviewing the Dalai Lama and the unexpected way His Holiness threw him off balance. With wit and depth, he and Monica dig into the weight of public shame, the risk of accountability, and why, for John, getting into trouble might just be the point. (And they use the C Word quite a bit!)

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Emmy-winning creator and star of the TV series Crazy Ex-Girlfriend, Rachel Bloom joins Monica this week on Reclaiming for a revealing conversation about turning your personal trauma into creative expression. Rachel retraces her path from childhood OCD and early career love triangles, to creating Crazy Ex-Girlfriend—a show that brilliantly dismantled romantic-comedy tropes and reclaimed the "crazy" label with a raw, honest portrayal of mental illness. Expect a conversation brimming with intellectual curiosity, radical candor, and a masterclass in how to find the perfect punchline for your deepest pain...plus Rachel dishes on her latest role in The Devil Wears Prada 2.

Thanks to Grow Therapy for sponsoring the show!

Whatever challenges you’re facing, Grow Therapy is here to help. 

Visit GrowTherapy.com/RECLAIMING to get started!
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Actress, entrepreneur, and 90s icon Jennie Garth joins Monica this week on Reclaiming for a conversation about surviving global fame, reclaiming your purpose, and the profound power of choosing yourself. Jennie retraces her path from a quiet horse ranch in Illinois to the center of a cultural phenomenon as Kelly Taylor on Beverly Hills, 90210. She opens up about the personal cost of that fame—developing crippling anxiety and agoraphobia at the height of her success—and how she has since reclaimed the toxic “rivalry” narrative with and her 90210 female co-stars Jennie reveals how a single line from a 90210 script became the mantra for her second act, and how a pivot at 50 offered a different kind of healing than her acting career ever could. Expect a conversation brimming with surprising vulnerability, hard-won wisdom, and a roadmap for how to reclaim your own story, no matter how the world has tried to write it for you.
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