Alex Cooper breaks down the business side nobody sees: how she and her husband Matt built Unwell up from a scrappy startup, how podcasting revenue really works, and what rules she learned the hard way negotiating $60M and $125M deals.

Alex Cooper is the creator and host of Call Her Daddy and the co-founder of Unwell, a modern media company spanning podcasts, TV/film, live events, consumer products, and a fast-growing creative agency.

Chapters

00:00 - Alex on going “full circle” and revealing the CEO side

02:00 - Building Unwell from Host to Founder

02:45 - A day in the life

05:20 - How Unwell makes money

07:15 - The video ad revolution

08:10 - Live events, merch, and consumer products as revenue engines

09:05 - Launching the Unwell creative agency

10:50 - Which division is the “cash king” (and what’s catching up fast)

13:30 - Inside mega-deals: Spotify vs Amazon

16:15 - Why distribution mattered

18:30 - Agents, fees, and who should get paid first (her “wait—no” moment)

21:10 - The hard rule: keep incentives clean (and avoid cozy backchannels)

23:00 - The biggest mistakes: trust, documentation, and walking away from millions

26:20 - Hiring top operators and building a high-standard culture

31:40 - PE, acquisitions, and what it takes to go to the next level

34:25 - Incentives for execs

35:05 - How Alex and Matt split decision-making

39:25 - Handling narratives about ambition, success, and being misunderstood

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https://www.instagram.com/sophiakianni

https://www.instagram.com/alexandracooper

https://www.instagram.com/callherdaddy

https://www.instagram.com/unwell

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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.

Rachel Zoe breaks down how to build a standout career in fashion before you feel ready. You’ll also learn her practical frameworks for getting dressed with less stress and more impact...

Rachel Zoe is a celebrity stylist, fashion entrepreneur, and pop-culture icon known for shaping red-carpet style and building a major lifestyle brand. She shares the behind-the-scenes realities of creative work, ambition, and reinvention.

Chapters

00:00 Intro + the pressure of “no margin for error”

00:12 The Tommy Hilfiger break that changed everything

04:12 Huge shoots and learning on the job

05:12 The realities of styling high-profile clients

07:07 Styling for *them*, not for you

10:14 Psychology of styling

13:21 The “uniform” method

15:54 Top fashion essentials for all women

18:24 Dressing for the job you want

20:32 Photographic memory + how Rachel thinks visually

22:43 Breaking into fashion today

26:49 Relationship advice

33:57 Work-life balance

35:07 Why she joined Real Housewives

🔗 FOLLOW US

https://www.instagram.com/phoebegates

https://www.instagram.com/sophiakianni

https://www.instagram.com/rachelzoe

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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.

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

🔗 FOLLOW US

https://www.instagram.com/phoebegates

https://www.instagram.com/sophiakianni

https://www.instagram.com/sahilbloom

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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.

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

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https://www.instagram.com/duolingo

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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

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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

🔥 FOLLOW THE BURNOUTS
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.