“Bet the Farm”: Gary Vee’s Bold Prediction for Social Media, Entrepreneurship, and What Most Founders Get Wrong

"I'm Telling You Right Now..." — Gary Vee on the Next Big Shift

In a recent episode of The GaryVee Audio Experience, Gary Vaynerchuk sat down with Bear Handlon, founder of Born Primitive, for a conversation that cut through the fluff and exposed the real, raw truths behind modern entrepreneurship.

At the top of Gary’s mind? Live social shopping.

“Bet the farm on it,” he said, pointing to TikTok Shop and Whatnot as the next frontier for entrepreneurial opportunity. “Social shopping has already happened in China. It's happening in real time here.”

Gary doesn’t make predictions lightly — and historically, he’s rarely wrong. He was early to TikTok (and even earlier to Musical.ly), long before it became a pandemic phenomenon. This time, his bet is just as clear: Live social commerce will dominate “For You” feeds within the next year or two.

Practitioner First, Visionary Always

What separates Gary Vee from every other business guru shouting on Instagram?

He’s in the trenches.

Not just as the face of a brand — but as the founder of VaynerMedia, a 2,500-person marketing agency executing billions in media spend and hundreds of millions in creative output globally. He’s running the plays he preaches.

“I’m a coach-player. This morning at 8:47, I was writing the copy for my Instagram post. Not reviewing. Writing.”

This practitioner mindset is what allows Gary to spot trends before they become obvious. He listens — for 15 hours a day — before he talks.

The Quiet Pain of Entrepreneurship

Bear’s journey with Born Primitive echoes a sobering truth Gary brings up often: entrepreneurship is brutally hard — and rarely glamorous.

“Seven years — didn’t make a penny,” Bear says of his early journey. “You have to put everything back in.”

Gary doesn’t sugarcoat it either:

“99.9999% of people have to eat sh*t, face judgment, deal with self-doubt, and live in the foxhole — every day, every hour. No wonder most people don’t do it.”

It's not about the viral headline wins. It’s about long-haul survival, pivots after failure, and micro losses stacked until a macro win shows up.

Entrepreneurship = Baseball + UFC

In Gary’s words, entrepreneurship is like a hybrid of two sports:

• Baseball: If you bat .300 — fail 7 out of 10 times — you go to the Hall of Fame.
• UFC: Even the best get knocked out sometimes. One punch changes everything.

This mindset shift reframes what "success" looks like. Losing is built in. What's rare is the willingness to get hit again — and keep stepping into the arena.

Story > Product: The Born Primitive Playbook

Handlon, a former special operations veteran, shared the evolution of Born Primitive from a garage-based hustle to a multi-category apparel brand. His realization?

“Good product is table stakes. Story is the differentiator.”

In June, Bear launched a limited edition D-Day commemorative shoe, including:

• Sand from Omaha Beach (with permission from the French government)
• A hand-built crate crafted by transitioning veterans
• A donation of $50,000 to fund a reunion for WWII vets

Every detail told a story. And it wasn't marketing fluff — it was legacy, rooted in the values of his team and customers.

Gary’s response?

“That’s the shit. That’s the secret sauce. The art always beats the math.”

Why Gary Vee Yells While Others Whisper

Many founders play their insights close to the chest. Not Gary.

“A lot of my sophisticated friends get quiet when they see a trend. I get loud.”

Why?

Because impact matters more than exclusivity. “Do you know what it feels like when someone DMs you saying, ‘I was a miserable lawyer, saw your TikTok advice, and now I’m making $3.3 million selling t-shirts?’ That’s why I do this.”

Final Takeaways for Founders

• Be early, be loud: Don’t wait for trends to be obvious. Build brand equity while the cost is low.
• Fall in love with the work: Not the outcomes. Entrepreneurship is micro losing with the occasional macro win.
• Story over math: Good product is required. Great story builds tribes.
• Stay humble. Stay hungry: Whether you're a startup founder or a $100M brand, the work doesn’t stop. And neither does the learning.