Gary Vee: Businesses Nobody Knows About That Can Make You RICH (Without a 9-to-5!)

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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📲 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.