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.

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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

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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
Phoebe Gates

Sophia Kianni

Rainn Wilson

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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 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.