Reclaiming with Monica Lewinsky

Lena Waithe

Emmy-winning actor, writer, and creator Lena Waithe joins Monica on Reclaiming this week for a philosophical conversation about storytelling as a path to empathy and social change. Lena charts her journey from creating groundbreaking television like The Chi, co-writing  Netflix's award winning Master of None and more recently co-producing Cats: The Jellicle Ball on Broadway. She opens up about the profound impact of attending her first silent meditation retreat at 40 and how this daily practice has brought her life into focus. Together, Monica and Lena explore queer representation in the arts, the strange elasticity of time, and the singular magic of theater. Whatever challenges you’re facing, Grow Therapy is here to help. Visit GrowTherapy.com/RECLAIMING to get started! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Gary Vee

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Allyson Felix

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 Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

John Oliver: RERUN

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!) Get 15% off OneSkin with the code RECLAIMING at oneskin.co/RECLAIMING [http://oneskin.co/RECLAIMING] #oneskinpod #ad Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Rachel Bloom

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 [http://growtherapy.com/RECLAIMING] to get started! Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]