The Burnouts with Phoebe & Sophia

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As former Stanford roommates and now business partners, Phoebe Gates and Sophia Kianni share their experience as startup founders and the complexities of being young professionals—from financial literacy, social impact, and navigating networking (ever been hit on through LinkedIn?). With exclusive access to top experts, they offer an inside look at their chaotic lives alongside career insights from their network of thought leaders. Watch The Burnouts pursue their dreams while trying to keep their lives from going up in flames. Will they burn out? We’ll find out.

  1. 2 DAYS AGO

    From Homeless Teen To Millionaire Founder: Simon Squibb Reveals How To Change Your Life Fast

    From homeless teen to multi-millionaire entrepreneur, investor, and mentor to millions, Simon Squibb has lived one of the most extraordinary entrepreneurial journeys of our time. In this episode of The Burnouts, Simon Squibb sits down with Phoebe Gates and Sophia Kianni to unpack how losing his father at 15 and spending weeks homeless reshaped his view on success, purpose, and money. He opens up about sleeping on the streets, starting his first business out of survival, and building a creative empire that led to financial freedom, and a mission to help 10 million people start businesses through his “Give Without Take” movement. Simon reveals the mindset shifts that turned trauma into drive, why he believes happiness is a trap, and the three sales principles that made him a millionaire. He also shares what most entrepreneurs get wrong about mentorship, why purpose matters more than profit, and how “bad luck” can be your greatest advantage. Whether you’re just starting out, stuck in a 9-to-5, or dreaming of building something that actually matters, this conversation is packed with raw honesty, purpose-driven wisdom, and actionable lessons from one of the internet’s most followed business voices. Chapters 00:00 – From homeless teen to entrepreneur 03:00 – Losing his father at 15 and becoming homeless 06:00 – The first business that changed everything 10:00 – Learning to sell (and why school failed him) 15:00 – The truth about happiness and purpose 19:00 – How Hong Kong taught him work-life integration 25:00 – Building and losing companies (and learning from failure) 30:00 – Mentorship myths & why advisors matter more 35:00 – The 3 sales principles that made him a millionaire 40:00 – Why purpose > happiness 44:00 – The one question everyone in their 20s should ask 🔗 FOLLOW US Phoebe Gates Sophia Kianni Simon Squibb 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe 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 About the Burnouts The 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 Kris Jenner, Paris Hilton, Chelsea Handler, Karlie Kloss, and other visionaries redefining what success looks like. 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.

    37 min

  2. 23 OCT

    Bryan Johnson: “The Biggest Lie In Hustle Culture” - How Phones Are Quietly Aging You!

    Welcome to the episode that might change your life (or at least your bedtime routine). Bryan Johnson made bank building Braintree Venmo. Then he walked away from it all to spend $2M a year turning his body into a science experiment. Now? He says he’s the healthiest human alive, and he’s got the organ scans to prove it. Hosts Phoebe Gates and Sophia Kianni get deep with Bryan about biohacking, founder burnout, the dirty truth about our food system, and why optimizing your sleep might be the most rebellious thing you can do as an entrepreneur. This convo gets real: blood transfusions, lonely sleep routines, and "sugar face" real. Timestamps 00:00 Can we be the first generation that doesn’t die? 04:12 Selling Braintree Venmo + redefining success 08:05 Spending $2M/year on health 10:52 The #1 fix for burnout (it’s free) 14:30 Bryan’s exact food + supplement routine 17:15 Should founders ever sacrifice sleep? 22:00 The science behind alcohol, caffeine, and your trash sleep 26:40 Sleeping alone, no phones, and other hot takes 30:45 Sunlight, seed oils & the truth about sugar face 34:20 How to stay healthy without becoming obsessive 🔗 FOLLOW US Phoebe Gates Sophia Kianni Bryan Johnson 🔥 FOLLOW THE BURNOUTS Instagram TikTok Linkedin 📲 Support What We’re Building Phoebe 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 → https://www.phia.com About The Burnouts The 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.

    37 min

  3. 16 OCT

    How Sophia Amoruso Turned a Side Hustle Into a $350M Brand (Nasty Gal)

    Sophia Amoruso built a $350M fashion empire from her bedroom—and lost it all before rebuilding her life from the ground up. In this episode of The Burnouts, the original “Girlboss” and founder of Nasty Gal joins Phoebe Gates and Sophia Kianni for her most unfiltered conversation yet. From selling thrifted clothes on eBay to becoming a CEO on magazine covers, Sophia reveals how she built a cult brand that defined a generation—and what really happened when everything came crashing down. She opens up about walking away from a company she founded, navigating bankruptcy, and learning to lead with empathy instead of ego. Sophia also shares the untold lessons behind Girlboss, why she believes failure is her greatest teacher, and how she’s redefining success through her new venture fund, Trust Fund. Whether you’re building your first business, chasing creative independence, or trying to rebuild after a setback, this conversation is a raw, honest masterclass in resilience, reinvention, and freedom. Chapters 00:00 – From eBay seller to $100M brand 05:00 – Building Nasty Gal and first hires 10:00 – Leaving eBay and going solo 13:00 – Going viral before social media 18:00 – Raising venture capital too soon 24:00 – The downfall and lessons learned 30:00 – How Girlboss was born 35:00 – Starting over with Trust Fund 40:00 – Life in London & redefining success 46:00 – The truth about ambition and burnout 🔗 FOLLOW US Phoebe Gates Sophia Kianni Sophia Amoruso 🔥 FOLLOW THE BURNOUTS Instagram TikTok Linkedin 📲 Support What We’re Building Phoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a fashion-tech app that helps shoppers find the best prices across retail and resale. Try it out and join the movement. About The Burnouts The Burnouts brings you raw, unfiltered conversations with today’s most iconic founders, creators, and entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond headlines to share the real stories, lessons, and mindset shifts that define your 20s. Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and Tommy Hilfiger. 🛎️ Subscribe for more unfiltered stories on success, failure, and everything in between. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    52 min

  4. 9 OCT

    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. Chapters 00:00 – Growing up in Toronto & immigrant expectations 02:00 – The chip on her shoulder: proving girls can do anything 04:00 – Why storytelling is activism 05:00 – Doing It: sex comedy as cultural intervention 08:00 – Lessons from early YouTube days & feeding the algorithm 10:00 – Losing (and regaining) authenticity & connection 12:00 – Hollywood, “noise,” and drawing boundaries 14:00 – Building her first team & hiring smarter people 18:00 – Hyphenate: supporting South Asian creators 20:00 – Diversifying income & passive revenue 23:00 – Passion projects vs. profit projects 28:00 – Negotiating money & the weaponization of gratitude 31:00 – Unlearning likability & embracing being “unpopular” 34:00 – Hollywood vs. YouTube: who really knows the audience 36:00 – Defining success when relevancy is weaponized 38:00 – Boundaries, therapy, and not being “what you do” 42:00 – Why being a lifelong student is the smartest move 43:00 – Tattoos, spirituality & protection 🔗 FOLLOW US Phoebe Gates Sophia Kianni Lilly Singh 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe 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 community About The Burnouts The 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.

    44 min

  5. 2 OCT

    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.  Chapters 00:00 – Dwight Schrute & the paradox of fame 04:00 – Why The Office didn’t make Rainn Wilson happy 09:00 – Burnout, ego, and chasing “more” in Hollywood 12:00 – Reinventing life through spirituality 18:00 – From SoulPancake to Soul Boom 24:00 – The mental health crisis & phones 30:00 – Behind the scenes of The Office (Dwight improv moments) 37:00 – Money, fame, and family lessons 44:00 – Advice Rainn Wilson wishes he knew in his 20s 50:00 – The future of storytelling and purpose FOLLOW US Phoebe Gates Sophia Kianni Rainn Wilson FOLLOW THE BURNOUTS Instagram TikTok LinkedIn Support What We’re Building Phoebe 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 Burnouts The 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.

    59 min

  6. 25 SEPT

    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. 🔍 CHAPTERS 00:00 – Starting Bobbi Brown Cosmetics 06:30 – Reinventing beauty around natural looks 09:20 – Vogue covers, Naomi Campbell, and early breaks 12:00 – Building a billion-dollar brand with Estée Lauder 20:00 – Family, partnership, and working with her husband 27:20 – Selling for $74M and the 25-year non-compete 30:00 – Going viral with Jones Road Beauty on TikTok 34:30 – Personal brand, social media, and DMs that changed everything 40:00 – Jones Road’s growth and what’s next 46:00 – Advice for entrepreneurs (luck vs. hard work) 51:00 – Hiring, culture, and leading a scrappy team 57:00 – Self-care, health, and why she’ll never retire 🔗 FOLLOW US Phoebe Gates Sophia Kianni Bobbi Brown 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 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.

    1h 1m

  7. 18 SEPT

    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. Chapters 00:00 – From dyslexia to dreaming big 02:00 – Opening People’s Place at 18 04:00 – The “4 Great Designers” billboard controversy 06:00 – Bloomingdale’s rejection & Snoop Dogg’s viral rugby shirt 08:00 – Bankruptcy, resilience, and rebuilding in NYC 10:00 – Reinventing the brand with European influence 12:00 – Why young creatives need business partners 16:00 – Fragrance licensing and going public 19:00 – Global expansion & international success 21:00 – Dressing musicians, Beyoncé, Aaliyah & early influencer marketing 24:00 – Collaborations with Gigi Hadid, Zendaya & Lewis Hamilton 28:00 – Fashion + AI and the future of creativity 30:00 – Manifestation, resilience & creative process 34:00 – Family, autism advocacy, and staying grounded 🔗 FOLLOW US Phoebe Gates Sophia Kianni Tommy Hilfiger 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe 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 Burnouts The 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.

    35 min

  8. 11 SEPT

    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 COLLECTION Chapters 00:00 – Anine Bing joins The Burnouts 01:00 – Leaving Sweden at 14 to model in Milan 03:00 – From blogging to selling her secondhand clothes online 07:00 – Starting a fashion brand out of a garage while raising kids 09:00 – “Fuck the rest”: dealing with naysayers and self-doubt 11:00 – The creative process: mood boards, playlists, and designing the Anine Bing woman 13:00 – Why retail presence still matters in the digital age 15:00 – Raising kids while building a global brand 18:00 – Burnout, balance, and finding self-care as a founder 22:00 – From Rosie Huntington-Whiteley to Kendall Jenner: viral celebrity fashion moments 24:00 – Founder-led marketing vs. personal branding 26:00 – Music as therapy and the making of Chapter Two 29:00 – Taking VC funding and scaling globally 32:00 – Iconic pieces: denim, blazers, boots, and beyond 35:00 – Mistakes, resilience, and why you can’t give up 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe 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 Burnouts The 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.

    36 min
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As former Stanford roommates and now business partners, Phoebe Gates and Sophia Kianni share their experience as startup founders and the complexities of being young professionals—from financial literacy, social impact, and navigating networking (ever been hit on through LinkedIn?). With exclusive access to top experts, they offer an inside look at their chaotic lives alongside career insights from their network of thought leaders. Watch The Burnouts pursue their dreams while trying to keep their lives from going up in flames. Will they burn out? We’ll find out.

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