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

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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.

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

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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 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.

Model, creator, comedian, and Forbes Top Creator—Haley Kalil has lived a thousand lives (from science labs to Sports Illustrated covers to viral comedy).

In this episode of The Burnouts, Haley Kalil sits down with Phoebe Gates and Sophia Kianni to share her rollercoaster journey: trading biomedical science for beauty pageants, paying her way through college, breaking into modeling without an agent, and then going viral overnight to build a multi-million-dollar creator career.

She opens up about navigating divorce, escaping an abusive relationship, reinventing herself through comedy, and betting everything on content creation. Plus: how she made her first $50k/month off YouTube shorts, why brand deals aren’t always the answer, and the financial realities (and taxes) of being a top digital creator.

Haley also gets real about the stigma of divorce, the pressure successful women face while dating, her viral “Billionaire Boyfriend” series, and what it really takes to stay authentic while scaling a $6M+ creator business.

Whether you’re dreaming of a career in content, modeling, or building your own creator-led brand, this conversation is packed with lessons, raw honesty, and plenty of laughs.

Chapters
00:00 – From biomedical science to beauty pageants
04:30 – Winning Miss Minnesota & paying for college with scholarships
06:00 – Sports Illustrated open casting call via Instagram
10:00 – Early modeling days & mental resilience
12:00 – Viral apartment tour → pivot to content creation
15:00 – Betting everything on YouTube & posting 5x a day
19:00 – Hitting $50k/month in ad revenue
22:00 – The viral “Billionaire Boyfriend” series
24:00 – Divorce stigma, healing, and rebuilding
29:00 – Going from red carpets to Oscars & Met Gala
33:00 – Social media backlash & accountability
37:00 – Advice for creators on finding your voice
41:00 – Monetization: ad revenue vs. brand deals
46:00 – Staying authentic in partnerships
48:00 – The true costs of creator life (taxes, management fees)
50:00 – What’s next for Haley

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Haley Kalil

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📲 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 reveal the real blueprint for building power in your 20s.

Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more visionaries redefining the brands—and the blueprints—of our time.

Subscribe now for the insider playbook to build your dream career.

From Disney Channel star to outspoken mental health advocate, Alyson Stoner has lived a life in the spotlight—and paid the price.

In this episode of The Burnouts, Alyson joins Phoebe Gates and Sophia Kianni to open up about the truth behind child stardom, the eating disorder that forced them to step away from Hollywood, and the box of documents that changed everything they thought they knew about their childhood.

They share what it was really like growing up famous, the toxic systems that exploit young talent, and the powerful tools they use today to protect their mental health. Plus: how they’re redefining success, finding purpose beyond fame, and why they named their memoir Semi Well-Adjusted.

📖 Alyson’s memoir Semi Well-Adjusted Despite Literally Everything is out now.

CHAPTERS

00:00 – Growing up on Disney Channel & Missy Elliott
02:15 – The moment Alyson stepped away from Hollywood
05:00 – The “toddler to train wreck” pipeline of child performers
06:45 – Losing childhood in the age of social media
08:00 – Playing firsts on camera without living them in real life
09:20 – How toxic Hollywood work environments really are
10:45 – Why “exposure” doesn’t pay the bills
12:00 – The hidden costs of going viral
13:40 – Tools Alyson uses to shake off stress
16:00 – Mind-body practices for anxiety & burnout
18:30 – Why different states of mind need different mindfulness tools
20:00 – Stillness vs. somatic tools for busy minds
22:00 – Reading their Camp Rock diary years later
24:00 – Why now was the time to write Semi Well-Adjusted
25:10 – The box of documents that changed their life story
27:00 – What “Semi Well-Adjusted” really means
28:15 – Choosing causes and building advocacy work
30:00 – Purpose as a constellation, not a North Star
32:00 – Advice for navigating anxiety and depression
34:45 – How to process rejection without losing yourself
37:00 – Focusing on what you can control

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Alyson Stoner

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💙 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 

❤️‍🔥 Get a Free 90 Day Trial of Movement Genius:

1. Go to Movement Genius

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Beauty founder, podcast queen, brand builder—Lauryn Bosstick turned a $50 blog into The Skinny Confidential empire.

In this episode of The Burnouts, Lauryn joins Phoebe and Sophia in Austin, TX to talk about building a cult brand from scratch. From sleeping in her car during sorority rush to creating one of the world’s most downloaded podcasts, Lauryn shares how she built her brand brick by brick—with no investors, no shortcuts, and no selling out.

She gets real about early burnout, building slowly with intention, and why executing (not overthinking) is the secret to everything. Plus: what makes someone a great podcast guest, how she evaluates brand deals, and the hilarious parenting trick she swears by (cookie water, anyone?)

Also: foot spas, Think Week, and how not having an iPhone gave Phoebe character.

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CHAPTERS
00:00 – From sorority dropout to brand founder
02:30 – Why she launched The Skinny Confidential
05:00 – Blogging 7 days a week for 3 years (with $0)
10:10 – Turning down money (and why she’s proud of it)
12:30 – Lauryn’s funnel: how she vets guests + brand deals
16:10 – The advice she gives every 20-something brand builder
17:00 – The one hire every founder should make first
20:45 – Think Week, foot spas, and strategic solitude
27:00 – How she uses branding tricks to parent toddlers
30:00 – Personal vs public: what Lauryn won’t post online
35:00 – Resourcefulness over resumes in the age of AI
38:00 – The biggest mistake most creatives make

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He’s redefined how millions think about money. But what Morgan Housel says about paychecks, wealth, and regret will completely flip your idea of what it means to be “rich.”

In part 2 of The Burnouts interview, Morgan Housel joins Sophia Kianni and Phoebe Gates for a conversation that unpacks the biggest money myths we’ve been sold—from why chasing a high salary will never make you wealthy to how the American Dream became a lie our generation can’t afford.

They go deep on:

The psychology of feeling broke even when you’re not

Why wealth is built with ownership, not income

What 90-year-olds wish they did differently with money

How gender impacts the way we’re taught to think about risk, equity, and ambition

And the real reason no amount of money ever feels like enough

Also: MrBeast vs. the media industry, what kids actually learn about money, and why comparing yourself to others is the fastest path to lifelong financial anxiety.

This is the part they don’t teach in school—and the stuff most financial “experts” get wrong.

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CHAPTERS

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Morgan Housel

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He didn’t go to high school. He valeted Ferraris he couldn’t afford. Now he’s one of the most trusted money minds in the world.

In this episode of The Burnouts, bestselling author and VC partner Morgan Housel joins Phoebe Gates and Sophia Kianni for a conversation that will completely rewire how you think about wealth, ambition, and what “enough” actually means.

He shares how fear—not ambition—drove him to work two full-time jobs at 19, save every dollar like the apocalypse was coming, and obsess over flashy cars as a way to feel worthy. They unpack why most people are playing the wrong financial game, why trying to “beat the market” backfires, and why some of the richest people you know still feel broke inside.

Also: dating while broke, how having a kid ended his materialism overnight, and the one expensive gift he regrets buying to impress his now-wife.

This is the money education you should’ve gotten—but probably didn’t. It’s about psychology, not spreadsheets. Scarcity, not flexing. And no, you’re not the only one faking it.

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Chapters

02:45 - Why everyone’s playing a different money game

05:20 - Dropping out + the fear that made him save

08:30 - What the guy with the yellow Ferrari taught him

12:55 - How becoming a dad changed his financial goals

15:00 - The most common investing mistake

20:10 - The dumbest flex gift he ever bought

23:40 - Talking money while dating in your 20s

29:00 - His current investing strategy (it’s very boring)

34:30 - How to stop chasing status and start building wealth

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Morgan Housel

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📲 Download the Phia app to start saving money: www.phia.com

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

Legend. Disruptor. Tech’s sharpest critic. Kara Swisher doesn’t just cover Silicon Valley—she holds it accountable.

On this episode of The Burnouts, Kara sits down with Phoebe and Sophia for an unfiltered conversation about building a career on her own terms (and never waiting her turn). From calling out mistakes at The Washington Post as a college student to becoming the most feared interviewer in tech, Kara shares the bold decisions, brutal lessons, and behind-the-scenes power moves that shaped her journey.

She gets real about the early days of tech reporting, navigating anti-gay and anti-women environments, the importance of always asking for more (and walking away if you don’t get it), and what it really takes to own your IP in a world built by and for powerful men.

Plus: Why women need to ask for more (and not wait their “fucking turn”)

Come for the stories about Steve Jobs, Elon, and Succession-style media drama—stay for Kara’s hard-won wisdom on surviving, thriving, and never selling yourself short.

Also: why “fuck you money” only matters if you’re willing to use it.

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Chapters
00:00 — Who is Kara Swisher?
02:30 – Getting hired by criticizing The Washington Post
06:00 – Losing her dad young & finding independence
09:15 – Money mistakes and financial advice for women
12:30 – Learning to negotiate, ask for more, and own her IP
18:00 – Walking away from Dow Jones and the New York Times
21:30 – Why power makes tech moguls weird
27:00 – The shrinking world of billionaires and “cashmere prisons”
29:00 – On grilling Zuckerberg, interviewing Jobs, and the point of journalism
32:00 – Advice for building a career in media today
35:00 – Kara’s blueprint: Be useful, be entertaining, be unique

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Kara Swisher

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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

Model, investor, activist, founder—Karlie Kloss has worn a lot of hats (and a lot of couture).

In this episode of The Burnouts, Karlie sits down with Phoebe and Sophia to talk about what happens when your “dream job” turns into something more. From getting scouted at 13 and walking Dior at 15, to launching Kode With Klossy and acquiring i-D magazine, Karlie shares the real story behind the headlines—and how she’s used her platform to build power on her own terms.

She opens up about early burnout, learning to trust her instincts, and the pressure of growing up in public. Plus: how she used brand deals to fund a coding nonprofit, why she angel invested in tampons, and what she’s learned about failure, focus, and building a career that actually lasts.

Also: how she made $10k flying economy???

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CHAPTERS
00:00 — Who is Karlie Kloss?
02:15 – Getting scouted at 13
04:10 – Saving every dollar (even mid-Fashion Week)
06:30 – Modeling as a means, not the end
09:20 – Using social media as a business tool
11:00 – Starting Kode With Klossy
15:10 – Investing in women-led companies
18:45 – Mistakes, pivots, and building something real
24:00 – Why she uses her dinner parties to fund reproductive rights
29:20 – Reimagining i-D for the next generation
33:00 – Advice for young women entering fashion
35:00 – Letting go of the pressure to have it all figured out

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📲 Download the Phia app: www.phia.com

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

From teen drama star to angel investor, Sophia Bush joins Phoebe Gates and Sophia Kianni for an unfiltered conversation about building wealth, walking away from toxic systems, and making purpose profitable.

In this episode of The Burnouts, Sophia reveals how a surprise $10,000 angel check into Uber kickstarted her investment journey—and how that single move led to millions. She opens up about the real economics of being a young actress, fighting for equal pay on One Tree Hill, and the dark side of working in Hollywood. Sophia also shares what it means to build power as a woman in business: launching inclusive salons, shaping the future of femtech, and helping fund America's first women-founded bank.

She breaks down the difference between angel investing and venture, gives practical advice for women who want to build wealth without gatekeeping, and explains why doing good and doing well should never be mutually exclusive.

Also: The best financial advice she’s ever received.

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CHAPTERS

0:00 - Intro

1:20 - From aspiring heart surgeon to unexpected actress

6:45 - The economics of young Hollywood

13:00 - Building an inclusive salon in Detroit

17:20 - Investing in Uber with $10K

20:45 - The power of sweat equity

25:30 - Femtech, abortion access & why periods matter

30:15 - Talking money without shame

34:00 - The group chat every woman needs

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Sophia Bush

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📲 Download the Phia app to start saving money.

Subscribe to The Burnouts for bold, raw interviews with the thinkers, athletes, and founders redefining ambition. Hosted by Phoebe Gates and Sophia Kianni—former Stanford roommates turned startup co-founders—each episode dives into the unpolished truths of building a life and career that matters. This isn’t another founder podcast. It’s what building something in your 20s actually sounds like—unfiltered, in-progress, and a little bit chaotic.