The Burnouts with Phoebe & Sophia

Rebecca Minkoff built a global fashion brand from a $3.25/hour internship, a scrappy “I ❤️ NY” tee after 9/11, and one breakout bag that women literally stopped her on the street to ask about. With no connections and no safety net, she moved to New York at 18, figured it out in real time, and turned hustle into a multi-million-dollar brand worn by celebrities and carried everywhere. 
In this episode, Rebecca walks through the real story behind the “Morning After” bag, what it was like losing 70% of revenue overnight during COVID, and why most founders should think twice before raising venture capital. She shares hard-earned lessons on hiring and firing, betting on yourself, building a brand in the age of social media, and navigating fame through Real Housewives. 
If you’ve ever wanted to start something from scratch, pivot when everything falls apart, or build a brand that lasts longer than trends — this episode is your blueprint. 
 
Chapters
00:00 From No Connections to Fashion Icon 
00:18 Moving to NYC With $3.25/Hour 
01:19 Intern to Founder, Starting Her Own Line 
02:00 I ❤️ NY Shirt Breakthrough 
03:17 Betting It All on Bags 
05:43 Going All In, Quitting Styling for Good 
06:11 Networking Like Cash 
09:29 Building a Brand in 2025 vs. 2005 
10:17 Hiring, Firing & Learning to Let Go 
19:52 COVID, 70% Revenue Drop & Rebuilding the Business 
31:15 Real Housewives, Brand Impact & Mental Toll 
35:04 NFL, Amazon & Building Strategic Partnerships 
36:55 What’s Next 
 
🔗 FOLLOW US 
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https://www.instagram.com/sophiakianni 
https://www.instagram.com/beckyminkoff 
https://www.instagram.com/rebeccaminkoff 
 
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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 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.

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

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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.