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
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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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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
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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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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
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Sophia Kianni

Rainn Wilson

FOLLOW THE BURNOUTS
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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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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
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Sophia Kianni
Bobbi Brown

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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

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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
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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.

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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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.

He got booed for saying “f*** Steve Jobs.” He built a media empire out of his dad’s liquor store. And now, Gary Vaynerchuk—better known as Gary Vee—is the brutally honest voice redefining what success really means.

In this episode of The Burnouts, entrepreneur and bestselling author Gary Vee joins hosts Phoebe Gates and Sophia Kianni for a raw, unfiltered conversation about money, ambition, and why patience—not hustle—is the ultimate flex.

Gary opens up about how growing up as an immigrant kid shaped his obsession with work, why he thinks making $100K can be “making it,” and why kindness beats IQ when it comes to leadership. Together, they unpack why Silicon Valley glorifies the wrong heroes, why social media isn’t dying anytime soon, and why most young founders are chasing clout instead of building real businesses.

He also shares the hidden strength behind VaynerMedia—the Chief Heart Officer who keeps the company together—the “convenience always wins” rule shaping the future of AI and shopping, and the exact moment he realized millions wouldn’t make him happier.

This isn’t motivational fluff—it’s a masterclass in long-term thinking from someone who’s seen it all. If you’ve ever wondered whether you’re on the right path, Gary Vee will change the way you measure success.

Chapters
00:00 – Who is Gary Vee?
06:10 – Why most influencers will fail (and the rise of live shopping)
08:10 – The key to a successful business: eliminating friction
10:05 – Why Gary Vee said “F*** Steve Jobs”: EQ over IQ in leadership
14:44 – The best marketing strategy for the AI consumer era
21:38 – Why chasing clout isn’t worth it
24:10 – The simple ask that drives real business growth
30:44 – Gary’s advice for building your dream career

🔗 FOLLOW GARY VEE
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🔥 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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Global pop icon Ava Max went from a first-generation immigrant household to topping charts in over 20 countries with hits like “Sweet but Psycho,” “Kings & Queens,” and “Maybe You’re the Problem.” With over 70 billion streams and a signature fearless style, Ava is rewriting what it means to own your power in the music industry.

In this episode of The Burnouts, Ava Max joins Phoebe Gates and Sophia Kianni for a raw, unfiltered conversation about her rise to stardom — from moving to LA at 14, surviving predatory industry environments, and nearly quitting music, to finding her voice, building her sound, and creating a global pop phenomenon.

She opens up about the grind behind her success, the trauma and resilience that shaped her, and the inspiration behind her new album, “Don’t Click Play." Ava shares stories of losing her voice at the peak of her breakout hit, navigating fame while staying grounded, and why protecting her energy has become her top priority. Plus: what it really takes to build a lasting career in pop, the pressures of being “always on,” and her vision for a future stadium tour.

Whether you’re an aspiring artist, a longtime fan, or just looking for motivation to keep going when life knocks you down, this episode is filled with lessons on persistence, self-belief, and embracing your unique voice.

🎶 STREAM AVA'S ALBUM "DON'T CLICK PLAY"

Chapters
00:00 – The moment Ava Max walked into our studio…
01:00 – From Virginia to LA: the bold move that changed everything
04:00 – The brutal reality of chasing a dream at 14
07:00 – Five years of rejection… and the one “yes” that changed her life
09:00 – “My vocal cords exploded” — what really happened at the height of her first hit
11:00 – The night the Max Cut was born (and why it changed her career)
13:00 – Finding her sound: the secret to songs that empower millions
16:00 – What going viral really feels like (and why it’s not always what you think)
19:00 – Behind the curtain: the exhausting truth about touring
22:00 – The business of pop: labels, teams, and staying in control
24:00 – Why she disappeared from social media (and how she’s coming back stronger)
26:00 – Stadium tour dreams and a secret creative project you haven’t heard about
28:00 – How Ava Max turns doubt into fuel
30:00 – “Don’t Click Play”: the album that almost never happened

🔗 FOLLOW AVA MAX
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TikTok
Website

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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.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.