Gary Vee on the Biggest Bets of His Career — And How You Can Make Yours

“Ten, Eighty, Ten.”

That’s how Gary Vaynerchuk scales billion-dollar ambitions.

In his words, “I open and close. The middle is the problem.” It’s one of many frameworks he’s developed over a lifetime of building — from a basement wine store in New Jersey to VaynerX, a 350+ million dollar-a-year holding company, and beyond.

But Gary’s journey wasn’t fueled by corporate polish or 10-year business plans. It was built on intuition, patience, and betting big when it mattered most.

In his recent interview on The Big Deal Podcast with Cody Sanchez, he shares how he made his biggest bets — and how wantrepreneurs and early-stage founders can learn to make their own.

1. The First Big Bet: Betting on People, Not Just Ideas

Before Gary was a “multiple 9-figure entrepreneur,” he was just a guy with a gut feeling — and a knack for spotting human potential.

“Facebook, Twitter, and Tumblr were my first investments. I judged what I smelled. Pure intuition about the human and the thesis.”

But Gary admits he briefly lost that instinct when he started chasing ideas over founders.

He invested in a startup called Yobongo — a social mobile app — that flopped. Two years later, Tinder launched with a similar concept and exploded.

The difference?

“The kid [behind Yobongo] didn’t have the stomach or merit,” Gary says. “I didn’t spend enough time analyzing him. I got seduced by the idea.”

Lesson: Founders who win bet on jockeys, not just horses. If you’re building, make sure you are the jockey investors want to ride with. If you’re investing, trust your pattern recognition — and your intuition.

2. From the Register to the UX: How Gary Learned to Think Like a Consumer

Gary’s second big bet wasn’t financial — it was behavioral. As a teenager bagging wine bottles behind the counter, he became obsessed with one thing: Why people grab what they grab.

“I would watch every customer. They’d walk in — what do they grab first? Where do they look? That’s why I was great at UI and UX later. I thought like a retailer.”

He applied this mindset to e-commerce early, inventing one of the first “abandoned cart” email systems for Wine Library in the early 2000s.

Lesson: Learn your customer better than anyone else. Watch how they behave. Ask why they click — or why they don’t. The edge is in the nuance.

3. Scale the Unscalable

If there’s one Gary Vee mantra every founder should write on their whiteboard, it’s this:

“Scale the unscalable.”

Gary personally replied to every tweet from 2007–2011. He DMs. He texts. He shows up.

“The best studio in the world is the world,” he says. “Your laundromat is the set. Just show people how you live.”

That mindset of high-touch, low-ego interaction built his audience — and his empire.

Lesson: Community management is your moat. Especially if you're under 10K followers. Respond. Care. Repeat.

4. The Philosophy Behind It All: Confidence Over Insecurity

Most founders are driven by insecurity. Gary’s not — and he thinks that’s why he’s built so much with such joy.

“I continue to believe that most people get successful because of insecurity. But there’s a rare breed that gets there through confidence. I’m in that group. But that’s my parents — not me.”

Gary’s immigrant upbringing, brutal honesty from teachers (“You’ll be a loser”), and early entrepreneurship (baseball cards, anyone?) shaped his internal game.

Today, he knows founders who fake it with big talk and bravado — and it never lasts.

Lesson: Self-awareness trumps hype. Humility beats hustle porn.

5. Where the Underpriced Attention Is Today

Gary has always made his biggest bets where others aren't looking.

“If you sell anything physical, TikTok Shop and Whatnot are massively underpriced. Live social shopping is the new QVC. China's already at 30% of e-commerce there.”

He coined it “commerce-tainment.” Think: TikTok lives where someone’s cutting hair while selling shampoo — and making bank.

Lesson: Attention is currency. Get there before the crowd.

The Real Takeaway: You Can Do This Without a Studio, Funding, or Flash

Gary’s loud, sure. But he’s also radically practical.

“Everyone who says they can’t afford content? You’ve got an iPhone. That’s it. Nothing else.”

You don’t need an agency. You need conviction. Your “studio” is the laundromat, the back office, the shop floor.

Want to make a million? Good — just know it’s insanely hard. Most people won’t. But if you have the stomach for it — if you can live in the dirt and the clouds — you just might.

Gary Vee’s 5 Power Lessons for Founders:

• Invest in people, not just ideas.
• Obsess over customer behavior.
• Scale the unscalable.
• Operate from confidence, not insecurity.
• Go where attention is underpriced.