- Notes To An Entrepreneur
- Posts
- The Power Move that Turned Gary Vaynerchuk into GARY VEE
The Power Move that Turned Gary Vaynerchuk into GARY VEE
Is it really that simple? Yep, maybe so!
Steve Strauss
September 17, 2025
In partnership with
Gary Vee of course is all over social media - heck, he almost invented it! But how did he do it, how did Gary Vaynerchuk become Gary Vee? It turns out to be a surprisingly simple playbook. Easy to duplicate? No, maybe not. But doable? Yes, very much so!
In the late 1990s, Gary Vaynerchuk was just another dude.
He was the son of immmigrant liquor‑store owners, helping run their “Shopper’s Discount Liquors” store in New Jersey. Gary took over the family business soon after graduating college and knew it needd something . . . but what?
A Little of This, a Dab of That
Gary first dcided to rename the business, “The Wine Library.” And he tried everything to boost sales:
Email newsletters
Pay-per-click
Local marketing
Sales
It was all, well, OK. But not great.
The business had promise, yes, but Gary was restless. He also sensed that the new battlefield wasn’t really the store, it was online, in content, in attention…
Jumping In
Vaynerchuk especially took notice of the new medium that was YouTube.
And so, even though he had no formal TV training, no studio, no slick video crew, he decided to go for it.
In 2006, he launched Wine Library TV (WLTV) on YouTube; a daily video show where he tasted wine, assessed bottles, offered opinions, joked around. The production was rough, ordinary cameras, awkward lighting, off‑the‑cuff delivery.
But it worked.
Gary made it raw, real, fun, sorta outrageous. “Authenticity beats polish, when polish costs too much” became his coda.
The Turning Point
The turning point was that Gary decided not to wait until he was ready, or the store was perfect, the video perfect, or the script rehearsed. He committed to volume + consistency.
Over time, viewership grew. And grew. And grew. And as a result, sales grew.
The Wine Library’s reputation soon surged.
What had been a modest local store transformed into a national brand: Gary grew Wine Library’s revenue from around $3 million to about $60 million/year.
The Birth of Gary Vee
And so it was that “Gary Vee” was born.
A brash, confident, fun, funny, smart talker, he was the guy on screen who was unfiltered, passionate about wine and passionate abut business.
Then he parlayed that attention into speaking, consulting, books, media, and digital agency work.
The content was the ticket.
The turning point wasn’t a lightning bolt, it was the decision to produce content before he was “ready,” and keep putting it out there.
That decision changed everything.
The Takeaway
Here’s what the Gary Vee story teaches:
Start before you’re ready. You don’t need perfect gear or a polished team. You need a willingness to be seen and the courage to get your stuff out there.
Consistency compounds. Daily content built trust and audience over time. It wasn’t flashy at first; it got better because Gary showed up.
Attention is the foundation. Once he captured attention via YouTube, everything else followed - sales, reputation, opportunity. Without content, the store might’ve stayed local. With content, he built a global platform.
How 433 Investors Unlocked 400X Return Potential
Institutional investors back startups to unlock outsized returns. Regular investors have to wait. But not anymore. Thanks to regulatory updates, some companies are doing things differently.
Take Revolut. In 2016, 433 regular people invested an average of $2,730. Today? They got a 400X buyout offer from the company, as Revolut’s valuation increased 89,900% in the same timeframe.
Founded by a former Zillow exec, Pacaso’s co-ownership tech reshapes the $1.3T vacation home market. They’ve earned $110M+ in gross profit to date, including 41% YoY growth in 2024 alone. They even reserved the Nasdaq ticker PCSO.
The same institutional investors behind Uber, Venmo, and eBay backed Pacaso. And you can join them. But not for long. Pacaso’s investment opportunity ends September 18.
Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.
Steal This Strategy!
🎥 Video / Interview – How Wine Library TV Is Catapulting Its Founder To Fame And Fortune - a video & audio interview where Gary lays out how he launched Wine Library TV and its early trajectory.
📘 Book – Crush It! by Gary Vaynerchuk. How to use passion + content + hustle to build brand and business.
💡 Article / Blog – Don’t Take Attention For Granted! — Gary’s blog post about why paying attention to how people consume content, not just reach or impressions, is critical.
🔍 Feature Article – The Guy Who Broke Wine (PUNCH) — this dives into that turning‑point moment (Episode 58) where Gary becomes himself, drops the polished persona, leans into authenticity, and starts breaking through.
About Steve
Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer (non-practicing), and an entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Need a ghostwriter or a newsletter for your business? Contact Steve!
“Be bold! For boldness has genius, magic, and power in it.”
Reply