Advertise on podcast: The Burnouts with Phoebe & Sophia

Luis Von Ahn details the story behind Duolingo and its famous owl, how to do handle marketing in the TikTok era, hiring young talent, and using addictive habits for good.   Chapters  00:00:00 Intro & The Owl  00:02:35 Unhinged Marketing  00:06:09 TikTok Era  00:08:06 Owl As the Face + Approving Risky Posts  00:10:31 Hiring New Grads and “No Assholes”  00:14:29 Making Learning Feel Delightful  00:16:57 Addictive Habit Loops  00:18:38 Expanding Beyond Languages  00:19:26 Guatemala Roots + Free Education Mission  00:23:40 AI  00:31:00 Impact  00:36:58 What's Next for Duolingo?    🔗 FOLLOW US  https://www.instagram.com/phoebegates  https://www.instagram.com/sophiakianni  https://www.instagram.com/duolingo    🔥 FOLLOW THE BURNOUTS  https://www.instagram.com/theburnouts  https://www.tiktok.com/@theburnouts  https://www.linkedin.com/company/the-burnouts    📲 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 and help us grow → https://www.phia.com    About The Burnouts The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers.  Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more.  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.

Phoebe and Sophia detail the best lessons they have learned from the career playbooks of the most successful people in the world, from how to leverage relationships in your career to what makeup to wear. The Burnouts celebrate hitting 200,000 subscribers, and launching Phia, which has already reached one million users and raised a $35 million Series A. Thank you for watching, for subscribing, and for being part of this journey with us.   Chapters 00:00 - Intro  00:50 - Leveraging Relationships in Negotiating  03:12 - Screen for Niceness  05:10 - Office Culture  06:30 - What Makeup to Wear?  10:40 - Routines & Uniforms  12:06 - Future Self  12:46 - Top Goals for 2026    🔗 FOLLOW US  https://www.instagram.com/phoebegates  https://www.instagram.com/sophiakianni    🔥 FOLLOW THE BURNOUTS  https://www.instagram.com/theburnouts  https://www.tiktok.com/@theburnouts  https://www.linkedin.com/company/the-burnouts    📲 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 and help us grow → https://www.phia.com    About The Burnouts The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers. Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more. 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.

Codie Sanchez breaks down why chasing fame is a losing game—and why real wealth is often built quietly through “boring” businesses most people overlook. Drawing on her background in institutional finance and small-business acquisitions, Codie explains how she spots unfair opportunities, why she exited industries like cannabis despite strong returns, and which unsexy sectors can consistently generate cash today. The conversation dives into college versus trade school, the true value of elite networks, and how parental expectations can hold young people back from building the life they actually want. Codie shares practical advice on making more money early in your career—finding your unfair advantage, helping your boss win, stacking skills, and learning to negotiate by understanding how value is really created inside a business. They also cover sales, mentorship, investing basics, and how to start learning deals without taking reckless risks. Codie closes with a candid take on investing in your health, appearance, and resilience—arguing that winning often comes down to doing hard things early and playing the game as it actually exists, not how we wish it worked. Chapters  0:00 Rich vs Famous  3:17 Overlooked Businesses & Early Investing  9:42 Why Boring Businesses Win  17:11 College, Trade School & Social Capital  26:08 Parents, Pressure & Choosing Advice  34:19 How to Make More Money Early  42:07 Sales, Skills & Standing Out at Work  50:23 Investing Basics & Learning Deals  57:41 Health, Appearance & Playing to Win  1:03:18 Final Thoughts & Wrap-Up    🔗 FOLLOW US  https://www.instagram.com/phoebegates  https://www.instagram.com/sophiakianni  https://www.instagram.com/codiesanchez 🔥 FOLLOW THE BURNOUTS https://www.instagram.com/theburnouts  https://www.tiktok.com/@theburnouts  https://www.linkedin.com/company/the-burnouts    📲 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 and help us grow → https://www.phia.com  About The Burnouts  The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers. Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more. 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.

He started a podcast in his bedroom before most people land their first job. Now, Harry Stebbings runs one of the most influential platforms in venture capital and manages a $400M fund. In this episode of The Burnouts, Harry sits down with Phoebe Gates and Sophia Kianni to unpack what actually drives success — and why so many smart, ambitious people stay stuck. From dropping out of law school to building leverage through content, Harry shares the lessons he learned the hard way about confidence, decision-making, and playing the long game. This conversation goes far beyond startups and investing. Harry opens up about the confidence gap holding people back, why men bluff and women wait, and how likeability, storytelling, and persistence often matter more than raw intelligence. He explains how content became one of the most powerful tools in his career, why distribution now shapes opportunity, and how relationships — not resumes — drive the biggest decisions. Harry also reflects on regret, missed deals, mentorship, and the uncomfortable truth that success often comes from taking action before you feel ready. Whether you’re early in your career, thinking about building something of your own, or just feeling behind, this episode offers a rare, honest look at what actually works. Chapters 00:00 – The Reality of Entrepreneurship 00:40 – From The Social Network to Dropping Out of Law School 01:55 – Building a Fund Through Media & Network Effects 02:31 – Why Venture Capital Over Being a Founder 03:38 – Co-Founders, Breakups & Hard Personal Lessons 07:18 – What Actually Makes a Great Founder 08:55 – Gender, Confidence & Entrepreneurship 14:23 – Mentorship vs Coaching & How to Get Access 16:40 – Content as a Distribution Weapon 23:29 – Finding Your First True Fans 25:18 – Building & Managing High-Performance Teams 29:22 – Investment Mistakes & Missed Billion-Dollar Deals 31:35 – Vulnerability, Trust & People Skills 36:05 – WhatsApp, Fundraising & Relationship Scaling 37:30 – Trust, Endurance & Outworking Everyone 40:00 – Storytelling, Creativity & the Risk of AI 44:16 – Being a Great Investor When Things Go Wrong 45:02 – Final Advice: Take the First Step   🔗 FOLLOW US Phoebe Gates Sophia Kianni Harry Stebbings 20VC 🔥 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 and help us grow. About The Burnouts The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers. Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more. 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.

One day, she was racing Daytona. The next, she was shooting for Victoria’s Secret. NASCAR driver, model, and trailblazer Toni Breidinger is living two worlds, and paying the price to stay in both. In this episode of The Burnouts, Toni sits down with Phoebe Gates and Sophia Kianni to reveal the brutal, behind-the-scenes reality of motorsports. She opens up about being told she needed $1–2 million just to race, moving across the country at 18 with no funding, and surviving by doing Instacart by day and cold emails by night. Toni breaks down why talent isn’t enough in NASCAR, how social media literally saved her career, and what it’s like being the only woman racing NASCAR full-time—from unequal pay to brand sponsorship politics. She also shares how she navigates modeling in a male-dominated sport, why she turned down six-figure OnlyFans offers, and how she built a sustainable career when every race depends on sponsorship dollars. Whether you’re chasing a nontraditional career, building a personal brand, or betting on yourself when the odds feel stacked against you, this episode is packed with raw honesty, hard lessons, and real strategy. Chapters 00:00 – unequal pay & being the only woman in nascar 03:00 – starting racing at age 9 06:30 – realizing racing costs millions 09:00 – told she needed $1–2 million to compete 11:00 – moving cross-country at 18 13:00 – instacart by day, cold emails by night 16:00 – how social media saved her career 20:00 – brand deals, sponsorships & unequal pay 25:00 – modeling, victoria’s secret & sports illustrated 30:00 – turning down six-figure onlyfans offers 36:00 – funding races & surviving motorsports 48:00 – what’s next: the road to the cup series 🔗 FOLLOW US Phoebe Gates Sophia Kianni Toni Breidinger 🔥 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 and help us grow. About The Burnouts The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers. Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more. 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.

He arrived in New York with $100, slept in parks, showered at the YMCA — and went on to invent the tube top, dress Studio 54, and build a billion-dollar fashion empire. In this episode of The Burnouts, fashion icon Elie Tahari joins Phoebe Gates and Sophia Kianni alongside his son and CEO Jeremey Tahari for a rare, multi-generational conversation about survival, ambition, taste, and legacy. Elie walks through his unbelievable journey: immigrating to New York alone, working as an electrician by day and selling clothes by night, sneaking into a fashion show through a back door, and accidentally creating one of the most iconic garments of the 1970s. From disco dresses to power suits, he explains how watching women on New York streets — not runways — taught him how to anticipate what they’d want next. Jeremey opens up about growing up inside the business, stepping out of his father’s shadow, and eventually taking over as CEO — while expanding the company into real estate, licensing, and global scale. Together, they unpack what it really looks like to work with family, disagree on taste, hand over control, and build something meant to last 50+ years. This episode is about the American dream in its rawest form — luck, hustle, intuition, ego checks, and building success with heart. If you’re building from scratch, navigating family dynamics at work, or trying to define success on your own terms, this one’s required listening. Chapters 00:00 – Arriving in NYC with $100 01:00 – Sleeping in parks & finding community 03:00 – From electrician to fashion hustle 04:30 – Inventing the tube top 06:30 – Sneaking into a fashion show & landing 250K orders 08:30 – Studio 54, disco & early fashion moments 11:00 – Dressing women entering the workforce 13:00 – Building a fashion empire 15:00 – Real estate, licensing & vertical integration 17:00 – Father–son dynamics in business 19:30 – Taking over as CEO 22:00 – Disagreeing on taste & generational shifts 25:00 – Persian culture, fashion & femininity 27:30 – Leadership, hiring & humility 30:00 – Legacy, luck & advice for the burnouts 🔗 FOLLOW US Phoebe Gates Sophia Kianni Elie Tahari Jeremey Tahari Tahari Group 🔥 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. Try it now → 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 headlines to explore the real stories, breakdowns, and breakthroughs that define your 20s. Past guests include Paris Hilton, Tommy Hilfiger, Kris Jenner, Karlie Kloss, and other entrepreneurs redefining our generation. 🔔 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.

Allison Ellsworth went from oil & gas spreadsheets to building Poppi, the prebiotic soda that broke the internet, rewrote the rules on “healthy soda,” and sold to PepsiCo in a multibillion-dollar deal. In this episode of The Burnouts, Allison joins Phoebe Gates and Sophia Kianni to share how a DIY apple-cider-vinegar tonic from her Texas kitchen turned into the soda of the next generation. She walks through the whole arc: farmers’ markets, Whole Foods, Shark Tank while nine months pregnant, a risky rebrand, and the TikTok storytime that quietly did $100K on Amazon overnight. Allison also gets brutally honest about working with her husband, hiring too slowly while growth rockets, and what happens to your identity when you suddenly have both a Super Bowl ad and an exit. She shares the unglamorous side of lawsuits, burnout, mom guilt, and figuring out “what’s next” when you technically never have to work again. If you’re building a consumer brand, obsessing over content, or just trying to stay ambitious without completely frying your nervous system, this episode is a masterclass in playing the long game — and still having fun. Chapters 00:00 – From Texas kid to unexpected founder 02:00 – ACV shots, health issues & the Poppi spark 04:30 – Farmers’ market hustle → Whole Foods breakthrough 06:30 – Shark Tank at 9 months pregnant 08:30 – The risky rebrand: Mother Beverage → Poppi 11:00 – Launching Poppi during COVID 13:00 – TikTok virality & selling out overnight 16:00 – Creator-first marketing & celebrity fans 19:00 – Flavor wins, flavor fails & building a real soda 22:00 – Working with your husband (and being wrong sometimes) 24:30 – Sugar, lawsuits & building in CPG 27:00 – Inside the PepsiCo acquisition 30:00 – Life after the exit & what’s next for Allison 🔗 FOLLOW US Phoebe Gates Sophia Kianni Allison Ellsworth Poppi  🔥 FOLLOW THE BURNOUTS https://www.instagram.com/theburnouts https://www.tiktok.com/@theburnouts https://www.linkedin.com/company/the-burnouts 📲 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 now and join the community of 800,000+ smarter shoppers. 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 headlines to explore the real stories, breakdowns, and breakthroughs that define your 20s. Past guests include Paris Hilton, Tommy Hilfiger, Kris Jenner, Karlie Kloss, and other entrepreneurs redefining our generation. 🔔 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.

Founder and creative force Jasmin Larian Hekmat reveals the untold story of how she turned a scrappy side hobby into Cult Gaia, one of the most recognizable fashion brands of the last decade. Before the Ark Bag exploded across Instagram, Jasmin was wiring flower crowns at her kitchen table, hauling a flower cart to festivals, and giving away bags no one would buy. In this episode of The Burnouts, she tells Phoebe Gates and Sophia Kianni how a single product quietly snowballed into a global sensation and reshaped her entire career. Jasmin breaks down the five years before Cult Gaia “hit,” the moment the Ark Bag went from ignored to iconic, and the relentless creativity that keeps her one step ahead of imitators. She shares how she built a multimillion-dollar business without raising a cent of venture capital, how she protects the brand’s fiercely artful DNA, and why her designs are meant to stop someone in their tracks. From vase purses to playable backgammon clutches to fragrance bottles that feel like sculpture, Jasmin explains how she turns wild ideas into objects people obsess over. She also opens up about motherhood, running a 100 person team, trusting her gut when everyone says no, and staying original in an industry that copies everything. If you are building a fashion brand, dreaming up your first product, or trying to stand out in a crowded industry, this conversation will change the way you think about creativity, community, and staying power. Chapters 00:00 The Hobby That Accidentally Started Cult Gaia 02:00 The $38 Bag No One Wanted 04:00 The Viral Moment That Changed Everything 06:00 How She Built a Brand With Zero Investors 08:00 Surviving Copycats and Staying Original 10:00 Building a Team While Raising Three Kids 12:00 The Pressure Behind a “Perfect” Brand 14:00 Designing Pieces People Can’t Ignore 16:00 What Founders Get Wrong About Success 18:00 Lightning Round: Style, Risks, and Reinvention 🔗 FOLLOW US Phoebe Gates Sophia Kianni Jasmin Larian Hekmat 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe and Sophia are the founders of Phia, a new fashion-tech app helping shoppers find the best prices across retail and resale. Download now and join the community of 800,000+ happy users. About The Burnouts The Burnouts brings you raw, unfiltered conversations with top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond headlines to explore the real stories, breakdowns, and breakthroughs that define your twenties. Past guests include Paris Hilton, Kris Jenner, Karlie Kloss, and Tommy Hilfiger. Subscribe for the inside 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.

Founder and author Grace Beverley built a multimillion-dollar portfolio of brands—TALA, Shreddy, and The Productivity Method—before turning 25. In this episode of The Burnouts, Grace joins Phoebe Gates and Sophia Kianni to share how she went from posting anonymous fitness content at Oxford to leading some of the UK’s fastest-growing female-founded companies. She breaks down the pressure of being a young woman in power and the bias female founders still face. Grace opens up about juggling multiple businesses, navigating personal grief, and the hidden cost of public success. She also speaks candidly about relationships, ambition, and the standards women are expected to meet. Whether you’re building a brand, raising capital, or figuring out how to stay ambitious without burning out, this conversation offers an unfiltered look at what it really takes for young women to succeed. Chapters 00:00 – From anonymous fitness posts to Oxford 02:15 – The £1 ebooks that changed her life 05:20 – Building her first multimillion-dollar business 08:10 – Why women must stop chasing “shiny” projects 11:00 – The truth about scaling TALA & Shreddy 14:30 – Fundraising bias & the questions women still get asked 18:00 – Miscarriage, grief & running a company 21:15 – The impossible standards for female founders 24:00 – Relationships that dim ambition 27:00 – Why social media punishes successful women 30:00 – Building Retrograde & the creator economy 33:00 – How Grace makes decisions fast 36:00 – What she wishes every young woman knew about power 🔗 FOLLOW US Phoebe Gates Sophia Kianni Grace Beverley 🔥 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 and try it yourself. 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 headlines to explore the real stories, breakdowns, and breakthroughs that define your 20s. Past guests include Paris Hilton, Tommy Hilfiger, Kris Jenner, Karlie Kloss, and other entrepreneurs redefining our generation. 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.

In this episode of The Burnouts, Steve sits down with Phoebe Gates and Sophia Kianni to share the true story of how he went from a college dropout selling shoes in Queens to building one of the most influential footwear companies in the world. He talks about the early instincts that set him apart, the moment he knew he had something special, and the creative philosophy that has kept his brand relevant for more than three decades. Steve also opens up about the twists and turns of his journey — including learning hard lessons during the Wolf of Wall Street years and stepping away from the company before returning more focused and energized than ever. He reflects on the loyalty of his team, the power of staying close to the customer, and why speed, instinct, and obsession with product remain his North Star. Plus: the story behind his first viral shoe, his unfiltered take on dupe culture, the trends he loves (and hates), how Gen Z made him go viral again, and the fashion advice he wishes everyone knew earlier. Whether you’re building a brand, navigating a major life pivot, or chasing a creative vision, this conversation is a masterclass in staying true to your instincts, evolving with culture, and building something that lasts. Chapters 00:00 – Growing up in Queens and falling in love with shoes 01:45 – Dropping out of college and learning retail 03:20 – Starting Steve Madden with $1,100 06:00 – Product instinct, speed to market, and early hits 08:45 – Becoming a “pirate” in fashion 11:00 – The Wolf of Wall Street years and the IPO 14:00 – Prison, addiction, and rebuilding his life 16:30 – Reinventing the Steve Madden brand 18:00 – Dupe culture, controversy, and staying relevant 20:00 – What he hates (and loves) in fashion today 22:00 – Designing shoes women actually want 23:30 – AI, TikTok, and the future of trend cycles 26:00 – Lessons from failure and advice for young founders 🔗 FOLLOW US Phoebe Gates Sophia Kianni Steve Madden 🔥 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 Phia for free in the App Store. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Founder, author, and beauty trailblazer Alli Webb built Drybar from a simple blowout idea into a $255M beauty empire that transformed the industry. In this episode of The Burnouts, Alli sits down with Phoebe Gates and Sophia Kianni to share how she went from doing hair in her living room to leading one of the most recognizable service brands in the country. She talks about the explosive rise of Drybar, selling the company for hundreds of millions, and the personal challenges that followed at the height of her success. Alli opens up about losing her sense of identity after the sale, navigating grief and motherhood, and rebuilding her life through her new brand, Messy. She reflects on what the beauty world gets wrong, the lessons she learned as a female founder, and the real cost of fast growth. Whether you are building a brand, growing a service business, or figuring out the next chapter after burnout, this conversation is a powerful look at resilience, reinvention, and finding purpose again. Chapters 00:00 – From stay-at-home mom to mobile blowouts 02:30 – The idea that sparked Drybar 05:00 – Opening the first Brentwood studio 07:00 – When Drybar went viral overnight 10:00 – Raising capital & navigating hypergrowth 13:00 – The truth about selling a company 15:30 – Alli’s personal life falls apart 18:00 – Losing her identity after the exit 21:00 – Rebuilding from scratch & finding purpose 23:00 – Launching her new brand, Messy 26:00 – Advice for founders rebuilding their lives 29:00 – What Alli wishes every woman knew about success 🔗 FOLLOW US Phoebe Gates Sophia Kianni Alli Webb 🔥 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. Try it now for free in the App Store. 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 headlines to explore the real stories, breakdowns, and breakthroughs that define your 20s. Past guests include Paris Hilton, Tommy Hilfiger, Kris Jenner, Karlie Kloss and other entrepreneurs redefining our generation. 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.

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. Chapters 00:00 – From retail in Canada to Complex Media 02:00 – Leaving corporate life to build her own path 03:00 – The Tumblr that became Sporty & Rich 06:00 – Bootstrapping a brand: preorders, savings & hustle 07:00 – Meeting her business partner and early growth 12:00 – Going from $100K to $30M in sales 14:00 – Covid and the sweatsuit boom 15:00 – Scaling challenges and factory chaos 17:00 – Knowing your strengths & hiring smart 18:00 – Opening the first Sporty & Rich store 19:00 – Expanding into wellness with Central Sport 22:00 – Lessons from mistakes & customer mishaps 23:00 – Facing scrutiny as a female founder 27:00 – Emily’s leadership philosophy & advice for women 29:00 – Sporty & Rich today: $40M in sales, still 100% owned 🔗 FOLLOW US Phoebe Gates Sophia Kianni Emily Oberg 🔥 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 Phia for free in the App Store. 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.

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.

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.

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.