The Burnouts with Phoebe & Sophia

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

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Alli Webb

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📲 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.

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

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Emily Oberg

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📲 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.

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

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Sophia Kianni
Simon Squibb

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📲 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.

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

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Bryan Johnson

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📲 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.

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

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Sophia Amoruso

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📲 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.

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

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Sophia Kianni
Lilly Singh

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📲 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.

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

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Rainn Wilson

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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.

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

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📲 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

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
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Sophia Kianni

Tommy Hilfiger

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📲 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.

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
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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.