Sahil Bloom had everything society tells you to want: Stanford degree, private equity job, money, status — but he was miserable. Drinking seven nights a week. 40 pounds overweight. Seeing his parents once a year.

In this episode, Sahil breaks down the moment that changed everything: a friend calculating he’d only see his parents 15 more times before they died. Within 45 days, he quit his high-paying job, sold his house, and moved across the country to redesign his life around what actually mattered.

Now the New York Times bestselling author of The 5 Types of Wealth, Sahil shares why money only buys happiness up to a point, how to build real wealth beyond just finances, and why “nobody is thinking about you” might be the most freeing advice for your 20s. We talk about quitting safely, replacing your salary with side hustles, AI as the biggest mispriced opportunity right now, finding a mentor (yes, including Tim Cook), building leverage through content, and how to design a life you won’t regret.

If you’ve ever felt successful on paper but empty in real life, this episode is for you.

Chapters

00:00 The Life That Looked Perfect (But Wasn’t)

02:40 Private Equity, Status & Silent Burnout

05:55 The “15 Times Left” Wake-Up Call

09:30 Quitting a High-Paying Job in 45 Days

13:15 Redefining Wealth Beyond Money

17:05 The 5 Types of Wealth Explained

21:20 Measuring Yourself on the Wrong Scoreboard

25:10 Does Money Actually Buy Happiness?

29:00 Replacing Your Salary Before You Quit

33:10 AI as the Biggest Mispriced Opportunity

37:00 How to Find (and Earn) a Great Mentor

41:10 “Nobody Is Thinking About You” & Designing Your Life

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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.

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

🔥 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.

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.