The Burnouts with Phoebe & Sophia

• Meet The Psychology Major Who Became The Highest Paid Female On YouTube (Lilly Singh)

  Comedian, creator, actress, author, and activist Lilly Singh has built a career on breaking barriers and rewriting the rules.In this episode of The Burnouts, Lilly Singh sits down with Phoebe Gates and Sophia Kianni to share her journey: from growing up as the “disappointing” second daughter in an immigrant household, to becoming YouTube’s breakout superstar with 15M+ subscribers, to launching a late-night show and producing her own films.She opens up about the chip on her shoulder that fueled her rise, how gender equity shapes everything she does, and why she believes storytelling—not just politics or protests—is the most powerful tool for change. Plus: her new raunchy sex comedy Doing It (why Hollywood called it “too niche”), what she learned about money, gratitude, and negotiating as a woman, and how she built Hyphenate to support South Asian creators.Lilly also gets real about therapy, unlearning likability, the pressure of “relevancy” on the internet, and why connection—not algorithms—is the only metric that really matters.Whether you’re dreaming of becoming a creator, breaking into Hollywood, or building a career that actually aligns with your values, this conversation is packed with lessons, raw honesty, and plenty of laughs.Chapters00:00 – Growing up in Toronto & immigrant expectations02:00 – The chip on her shoulder: proving girls can do anything04:00 – Why storytelling is activism05:00 – Doing It: sex comedy as cultural intervention08:00 – Lessons from early YouTube days & feeding the algorithm10:00 – Losing (and regaining) authenticity & connection12:00 – Hollywood, “noise,” and drawing boundaries14:00 – Building her first team & hiring smarter people18:00 – Hyphenate: supporting South Asian creators20:00 – Diversifying income & passive revenue23:00 – Passion projects vs. profit projects28:00 – Negotiating money & the weaponization of gratitude31:00 – Unlearning likability & embracing being “unpopular”34:00 – Hollywood vs. YouTube: who really knows the audience36:00 – Defining success when relevancy is weaponized38:00 – Boundaries, therapy, and not being “what you do”42:00 – Why being a lifelong student is the smartest move43:00 – Tattoos, spirituality & protection🔗 FOLLOW USPhoebe GatesSophia KianniLilly Singh🔥 FOLLOW THE BURNOUTSInstagramTikTokLinkedIn📲 Support What We’re BuildingPhoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a fashion-tech app helping shoppers find the best prices across retail and resale. Download the app, try it out, and help us grow this communityAbout The BurnoutsThe Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to share the real stories, lessons, and mindsets that define your 20s.Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and Tommy Hilfiger.🛎️ Subscribe for the insider playbook to build your dream career. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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• Rainn Wilson Reveals Why Playing Dwight on The Office Didn’t Make Him Happy

  Rainn Wilson is best known as Dwight Schrute from The Office, one of the most iconic characters in TV history. But behind the legendary role, he faced burnout, fame overload, and the realization that success alone would never make him happy.On The Burnouts Podcast, Rainn Wilson joins Phoebe Gates and Sophia Kianni for an unfiltered interview about life after The Office. He opens up about chasing bigger movies, more money, and more fame in Hollywood, why it left him unfulfilled, and how he reinvented himself through spirituality, mental health practices, and his bestselling book Soul Boom.This Rainn Wilson interview is filled with behind-the-scenes stories from The Office, hilarious unscripted Dwight Schrute moments, the lessons he learned from sudden wealth and celebrity, and why finding purpose matters more than success.Whether you are a longtime fan of The Office, curious about Rainn Wilson’s career beyond Dwight Schrute, or searching for meaning in a burnout culture, this conversation is raw, funny, and packed with insights you will not forget. Chapters00:00 – Dwight Schrute & the paradox of fame04:00 – Why The Office didn’t make Rainn Wilson happy09:00 – Burnout, ego, and chasing “more” in Hollywood12:00 – Reinventing life through spirituality18:00 – From SoulPancake to Soul Boom24:00 – The mental health crisis & phones30:00 – Behind the scenes of The Office (Dwight improv moments)37:00 – Money, fame, and family lessons44:00 – Advice Rainn Wilson wishes he knew in his 20s50:00 – The future of storytelling and purposeFOLLOW USPhoebe GatesSophia KianniRainn WilsonFOLLOW THE BURNOUTSInstagramTikTokLinkedInSupport What We’re BuildingPhoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a VC-backed fashion-tech app helping shoppers find the best prices across retail and resale. Download the app, try it out, and leave us your feedback.About The BurnoutsThe Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to share the real stories, lessons, and mindsets that define your 20s.Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and other icons redefining culture today.Subscribe for more interviews with leaders, creators, and entrepreneurs shaping our generation. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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• How Bobbi Brown Went From Vogue Makeup Artist to Building a $160M Brand at 63

  Makeup artist, mogul, author, hotelier—Bobbi Brown has built more than one empire (and reinvented herself along the way).In this episode of The Burnouts, Bobbi sits down with Phoebe Gates and Sophia Kianni to talk about what it really takes to build an iconic brand, sell it for millions, and then start all over again. From mixing her first lipstick with a chemist and cold-calling agencies out of the Yellow Pages, to selling Bobbi Brown Cosmetics to Estée Lauder and later launching Jones Road Beauty, Bobbi shares the unfiltered version of how she built—and rebuilt—her career on her own terms.She opens up about confidence, burnout, and building businesses with her husband and family. Plus: the 25-year non-compete that changed everything, why “retirement” is not in her vocabulary, how she clapped back at viral TikTok criticism (and won), and the simple beauty rules she swears by for every generation.Also: how she accidentally went from makeup artist to hotel owner, why she still cold-DMs influencers, and her #1 piece of advice for young women chasing their dream career.🔍 CHAPTERS00:00 – Starting Bobbi Brown Cosmetics06:30 – Reinventing beauty around natural looks09:20 – Vogue covers, Naomi Campbell, and early breaks12:00 – Building a billion-dollar brand with Estée Lauder20:00 – Family, partnership, and working with her husband27:20 – Selling for $74M and the 25-year non-compete30:00 – Going viral with Jones Road Beauty on TikTok34:30 – Personal brand, social media, and DMs that changed everything40:00 – Jones Road’s growth and what’s next46:00 – Advice for entrepreneurs (luck vs. hard work)51:00 – Hiring, culture, and leading a scrappy team57:00 – Self-care, health, and why she’ll never retire🔗 FOLLOW USPhoebe GatesSophia KianniBobbi Brown🔥 FOLLOW THE BURNOUTSInstagramTikTokLinkedIn📲 Download the Phia app.Subscribe to The Burnouts for exclusive conversations with today’s top founders and culture-shaping entrepreneurs. Hosted by former Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, this isn’t just another founder podcast—it’s untold conversations and the unfiltered reality of what it takes to build your dream career in your 20s. Guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more visionaries defining the brands—and blueprints—of our time. Whether you’re dreaming big or building now, these are the conversations that will show you how it’s done (and what no one else tells you).🔔 Subscribe now to get the blueprint for building your dream career Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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• How Tommy Hilfiger Manifested a $9 Billion Fashion Empire After Going Bankrupt!

  Fashion legend, entrepreneur, and cultural icon—Tommy Hilfiger has spent over four decades shaping global style, from bell-bottom jeans in upstate New York to a fashion empire sold in more than 100 countries.In this episode of The Burnouts, Tommy Hilfiger sits down with Phoebe Gates and Sophia Kianni to share his incredible journey: growing up with undiagnosed dyslexia, opening his first jean shop at 18, going bankrupt in his twenties, and betting everything on a disruptive billboard campaign that put his name alongside Ralph Lauren and Calvin Klein.He opens up about the viral Snoop Dogg SNL moment that made Hilfiger logos a worldwide phenomenon, reinventing his brand when it began to plateau, and building one of America’s most successful lifestyle companies through bold collaborations with Beyoncé, Aaliyah, Gigi Hadid, Zendaya, and Lewis Hamilton. Plus: the challenges of balancing creativity with business, why manifestation has guided him from the start, and how AI is set to transform the future of fashion.Tommy also gets real about resilience, reinvention, and family—sharing the lessons he learned from bankruptcy, the importance of finding smart business partners, and his journey raising children with autism while scaling a global brand.Whether you’re dreaming of launching a fashion label, building a lifestyle brand, or simply learning from one of the most iconic designers of our time, this conversation is packed with lessons, raw honesty, and timeless inspiration.Chapters00:00 – From dyslexia to dreaming big02:00 – Opening People’s Place at 1804:00 – The “4 Great Designers” billboard controversy06:00 – Bloomingdale’s rejection & Snoop Dogg’s viral rugby shirt08:00 – Bankruptcy, resilience, and rebuilding in NYC10:00 – Reinventing the brand with European influence12:00 – Why young creatives need business partners16:00 – Fragrance licensing and going public19:00 – Global expansion & international success21:00 – Dressing musicians, Beyoncé, Aaliyah & early influencer marketing24:00 – Collaborations with Gigi Hadid, Zendaya & Lewis Hamilton28:00 – Fashion + AI and the future of creativity30:00 – Manifestation, resilience & creative process34:00 – Family, autism advocacy, and staying grounded🔗 FOLLOW USPhoebe GatesSophia KianniTommy Hilfiger🔥 FOLLOW THE BURNOUTSInstagramTikTokLinkedIn📲 Support What We’re BuildingPhoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a new fashion-tech app helping shoppers find the best prices across retail and resale. Download the app, try it out, and help us grow this community from the ground up.About The BurnoutsThe Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to share the real stories, lessons, and mindsets that define your 20s.Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and other visionaries redefining the brands—and the blueprints—of our time.Subscribe now for the insider playbook to build your dream career. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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• How a Teen Model Left Sweden & Built a $100M Fashion Empire From Her Garage (ft. Anine Bing)

  Danish-born model, blogger, and entrepreneur Anine Bing went from selling her secondhand clothes online to building one of the fastest-growing contemporary fashion houses in the world. With 40+ retail stores, a global online presence, and a signature rock-and-roll yet timeless aesthetic, Anine has redefined what it means to be a creative founder in fashion.In this episode of The Burnouts, Anine Bing sits down with Phoebe Gates and Sophia Kianni for an intimate, unfiltered conversation about her entrepreneurial rise — from moving to Milan at 14 to model, blogging before Instagram was a thing, and launching her brand out of a Los Angeles garage while raising two kids.She opens up about the early hustle of packing orders by hand, finding confidence amid constant naysayers, and building a brand that puts authenticity and creativity above quick money. Anine shares stories of her viral fashion moments (like Kendall Jenner’s Coachella bralette), bringing Kate Moss into her campaigns, navigating burnout, and raising venture capital while staying true to her vision.Plus: how she blends fashion with music (including her upcoming album Chapter Two), her creative process behind collections, the power of founder-led marketing, and why her ultimate mission is to empower women through timeless design and self-belief.Whether you’re a fashion lover, aspiring founder, or just seeking the motivation to follow your gut and block out the noise, this episode is packed with lessons on resilience, creativity, and building a brand that lasts.👜 SHOP ANINE BING'S FALL COLLECTIONChapters00:00 – Anine Bing joins The Burnouts01:00 – Leaving Sweden at 14 to model in Milan03:00 – From blogging to selling her secondhand clothes online07:00 – Starting a fashion brand out of a garage while raising kids09:00 – “Fuck the rest”: dealing with naysayers and self-doubt11:00 – The creative process: mood boards, playlists, and designing the Anine Bing woman13:00 – Why retail presence still matters in the digital age15:00 – Raising kids while building a global brand18:00 – Burnout, balance, and finding self-care as a founder22:00 – From Rosie Huntington-Whiteley to Kendall Jenner: viral celebrity fashion moments24:00 – Founder-led marketing vs. personal branding26:00 – Music as therapy and the making of Chapter Two29:00 – Taking VC funding and scaling globally32:00 – Iconic pieces: denim, blazers, boots, and beyond35:00 – Mistakes, resilience, and why you can’t give up🔥 FOLLOW THE BURNOUTSInstagramTikTokLinkedIn📲 Support What We’re BuildingPhoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a fashion-tech app helping you find the best prices across retail and resale. Download the app.About The BurnoutsThe Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to share the real stories, lessons, and mindsets that define your 20s.Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and other visionaries redefining the brands—and the blueprints—of our time.Subscribe now for the insider playbook to build your dream career. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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