The Burnouts with Phoebe & Sophia

Alli Webb, founder of Drybar and creator of Messy, transformed a mobile blowout idea into a $255 million beauty empire. She discusses the explosive rise of Drybar and the challenges she faced post-sale, including identity loss and personal struggles. Alli shares valuable lessons on navigating entrepreneurship and the pitfalls of rapid growth. She also reflects on her new venture, Messy, which champions natural hair, highlighting the importance of embracing imperfections and the emotional connection with her brand.

Founder, creative director, and cultural icon Emily Oberg has built one of the most recognizable lifestyle brands of our generation: Sporty & Rich.In this episode of The Burnouts, Emily Oberg sits down with Phoebe Gates and Sophia Kianni to unpack her journey from Complex producer to fashion entrepreneur, building a multimillion-dollar business rooted in wellness, design, and timeless style, without ever taking a dollar of outside funding.Emily opens up about turning a Tumblr moodboard into a global brand, growing from $5K in savings to $40M in annual revenue, and the realities of running a company after a public breakup with her business partner. She shares what it’s really like to scale quickly, navigate burnout, and stay creatively fulfilled while leading a 40-person team.Plus: how she built Sporty & Rich without investors, why preorders fueled her early success, what she’s learned about leadership (and ego), and the importance of building a world. (not just a brand).Whether you’re dreaming of launching your own label, staying independent as a founder, or defining success on your own terms, this conversation is a masterclass in creative control, discipline, and staying true to your vision.Chapters00:00 – From retail in Canada to Complex Media02:00 – Leaving corporate life to build her own path03:00 – The Tumblr that became Sporty & Rich06:00 – Bootstrapping a brand: preorders, savings & hustle07:00 – Meeting her business partner and early growth12:00 – Going from $100K to $30M in sales14:00 – Covid and the sweatsuit boom15:00 – Scaling challenges and factory chaos17:00 – Knowing your strengths & hiring smart18:00 – Opening the first Sporty & Rich store19:00 – Expanding into wellness with Central Sport22:00 – Lessons from mistakes & customer mishaps23:00 – Facing scrutiny as a female founder27:00 – Emily’s leadership philosophy & advice for women29:00 – Sporty & Rich today: $40M in sales, still 100% owned🔗 FOLLOW USPhoebe GatesSophia KianniEmily Oberg🔥 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 Phia for free in the App Store.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.

In a captivating discussion with Phoebe Gates and Sophia Kianni, Simon Squibb, a multi-millionaire entrepreneur and founder of the Give Without Take movement, shares his incredible journey from homelessness to success. He reveals how losing his father at 15 reshaped his perspective on life and success. Simon emphasizes the importance of sales skills, authentic relationships, and turning adversity into motivation. He also discusses the real value of mentorship and urges aspiring entrepreneurs to pursue their passions and start now.

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.Timestamps00:00 Can we be the first generation that doesn’t die?04:12 Selling Braintree Venmo + redefining success08:05 Spending $2M/year on health10:52 The #1 fix for burnout (it’s free)14:30 Bryan’s exact food + supplement routine17:15 Should founders ever sacrifice sleep?22:00 The science behind alcohol, caffeine, and your trash sleep26:40 Sleeping alone, no phones, and other hot takes30:45 Sunlight, seed oils & the truth about sugar face34:20 How to stay healthy without becoming obsessive🔗 FOLLOW USPhoebe GatesSophia KianniBryan Johnson🔥 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 → https://www.phia.comAbout 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.

Sophia Amoruso, founder of Nasty Gal and author of Girlboss, shares her incredible journey from thrift store seller to CEO. She candidly discusses the meteoric rise and fall of her brand, detailing lessons learned through bankruptcy and recovery. Sophia emphasizes the importance of empathy in leadership and how failure can be a powerful teacher. Now, as an investor with Trust Fund, she redefines success and champions the entrepreneurial spirit, offering invaluable insights on resilience, risk, and making meaningful connections.

Lilly Singh, a comedian, creator, and author, transitioned from an immigrant upbringing to becoming a YouTube sensation. She shares how storytelling serves as a tool for gender equity and the inspiration behind her raunchy sex comedy, Doing It, aimed at normalizing female sexuality. Lilly discusses the challenges of authenticity in the age of algorithms, the importance of connection with her audience, and her commitment to supporting South Asian creators through her initiative, Hyphenate. She emphasizes the value of therapy, negotiating pay, and unlearning the need for likability.

Rainn Wilson, best known as Dwight Schrute from The Office, shares his journey from fame to fulfillment. He reveals how the success of the show didn’t bring him happiness and discusses his battles with burnout. Rainn dives into his transformation through spirituality and mental health practices, highlighting daily routines that ground him. He shares hilarious behind-the-scenes stories from The Office and emphasizes the importance of finding purpose over chasing external milestones. This candid conversation is filled with insights on success, self-acceptance, and meaningful work.

Bobbi Brown, renowned makeup artist and entrepreneur, shares her inspiring journey from a Vogue makeup artist to building a $160M beauty empire. She reveals the secrets behind launching Bobbi Brown Cosmetics, her emotional connection to makeup, and how she successfully navigated a lengthy non-compete. Bobbi candidly discusses her viral TikTok moment, the importance of a supportive partnership with her husband, and her passion for mentoring young women. Plus, her refreshing take on beauty rules that resonate through generations!

Tommy Hilfiger, a fashion designer and entrepreneur, shares his inspiring journey from a young dreamer to building a $9 billion global brand. He opens up about overcoming dyslexia, surviving bankruptcy, and his transformative billboard campaign that catapulted his brand to fame. Hilfiger discusses key collaborations with stars like Beyoncé and Zendaya, the impact of manifestation on his success, and how he views AI shaping fashion's future. He combines raw honesty with invaluable lessons on resilience, family, and creativity.

Anine Bing, a Danish-born model and entrepreneur, transformed her life from selling secondhand clothes to launching a $100M fashion empire from her garage. She shares her early hustle, balancing motherhood while packing orders and navigating naysayers. Anine discusses her viral moments, including collaborations with Kate Moss and the influence of music on her brand. Her mission? To empower women through timeless designs and self-belief. Join her unfiltered journey from Milan to global fashion icon, filled with inspiring lessons on resilience and authenticity.