The World According To Gary Vaynerchuk Enter the mind of Gary Vaynerchuk and discover his love of failure, entrepreneurship and the 1980s.

By Julie Lokun, JD

Opinions expressed by Entrepreneur contributors are their own.

Gary Vaynerchuk

Garry Vaynerchuck is the real deal.

Gary Vaynerchuck breaks tradition from the typical thought leader, who is overmanaged and under-inspired. Gary Vee slides into a room, winking at his fans and pulls them into his magnetic energy. He draws people close into his ecosystem while he dispenses advice, quips and stories that leave onlookers hungry for more. Everyone is important to Gary Vee and he makes sure that you know this. He delivers a universal message that becomes a signature stamp that makes him unforgettable.


This is Gary Vaynerchuck — the man, the myth, and the legend

Surrounding himself with the likes of Arianna Huffington, Drew Barrymore, Deepak Chopra, Eric Thomas, and Jessica Alba definitely lends support to his iconic pedigree. Yet, while hob-knobbing with these A-Listers, he remains connected to his origin story. His humble beginnings began in Russia, and his clear dedication to his parents and siblings is striking.

His devotion to his daddy and brother, AJ (who were on stage for his kick-off speech), gave me an intimate glimpse into the man who has built an entrepreneurial empire. He knows what is important. He understands the anchors that keep him grounded and focused.

Everything he learned was directly attributed to his father's mission as an immigrant to improve his family's life. Vaynerchuk's childhood became the incubator for curiosity and an unparalleled drive. It began at age 5, curating a neighborhood lemonade stand and then morphed into a viable baseball card collector business. He learned the power of sweat equity as an indispensable employee at his dad's liquor store. His DNA was programmed from day one to be an entrepreneur.

And this was just the beginning.

He takes entrepreneurship to the next level and then triples it.

I had the opportunity to spend a weekend with Gary at his iconic conference, aptly named VeeCon. VeeCon is a business conference infused with pop culture, which pulsates in every nook and cranny of this prolific event. This event offers a rainbow-colored slide for guests to jettison from the top of the stadium to the convention floor.

Related: The Headline That Made Gary Vaynerchuk's Head Explode

Loveable mascots roam the halls greeting guests, a.k.a. VeeFriends, and the stadium is aglow with neon lights smattered throughout the venue. It was clear from the moment I walked into this conference that his event was for the fans, not for him. He understands his audience, is keenly aware of their needs, and does everything in his capacity to facilitate their dreams.

Gary gives off a contagious energy

The opportunity to sit nose-to-nose with Gary Vee gave me a perspective unlike any other. For years I have lapped up this garage-sale-guru turned marketing legend's every word. His ability to allocate focus, predict trends and manifest a dream proves entrancing.

The meat and potatoes of his message are simple. Do what you love and do it well.

VeeCon 2023 drew in over 10 thousand loyal followers who wanted to experience a piece of his influential magic. The kick-off was snuggled in the heartland of the United States, Indianapolis, Indiana. Exiting your plane at the Indianapolis airport, you immediately recognize that you are somewhere important, as VeeCon signage adorned the floors, the walls, and every marketable space of the airport.

Sitting down with Gary was not only a privilege, it was electrifying. The backdrop to our conversation was the main stage, clad in bright pink and blue lights, while the famed Jessie Itzler's speech drew raucous applause. With all the commotion and distractions of his event, and 20 cameras focused on our conversation-he was deeply connected to our talk. His gaze was intense, compassionate and alert.

As a trained journalist, I poked and prodded into areas I hoped would elicit a fresh response. Who is Gary Vee? What makes him tick? How has he done things differently than anyone else? What was his biggest mistake?

Related: Gary Vaynerchuk's 3 Keys to Increasing Your Winning Percentage

His answers were raw, directed and insightful

His commitment to connecting with people extends into his conference. He made it very clear that he had no expectations regarding the event's outcome but only focused on the execution of the experience. As our conversations deepened, he extolled the humanity of building this experience for his fans and the missteps of his planning.

As we were knee-deep in the topic of failure, he quickly pointed out the stage's placement and the chairs' misplacement. As his critic, he constantly strives for a better value — and learns from his dance with "failure."

As I walked away from his event, internally praising his vision, I believe he is re-calibrating future events to offer an even better conference next year.

What is Gary Obsessed with?

The 1980s.

Vaynerchuk grew up in the '80s and loved the decade that produced brightly-hued cultural phenomena. This nod to an outlandish decade is evident in the touch and feel of VeeCon. The '80s seeped into his DNA and, ultimately, his branding. Everything he touches spoke to the happy-go-lucky '80s when Saturday morning cartoons reigned and Wonder Bread and Happy Days governed our days. The brilliance behind Vaynerchuk's brand is that he extracts an iconic cultural ideology and modernizes it.

There is no such thing as an original idea. Every idea or experience has the potential to be elevated in a modern way to reach a new audience. Vaynerchuk clearly understands the concept of rebranding magnificence.

Has Gary made a mistake?

Yes. Yes and Yes.

He laughed at this question. He made four mistakes that morning. And he has regrets. He struggled with candor. Or, more specifically, keeping his cool when releasing someone from his life. He states with bold indignation that he still struggles with candor and facilitates sloppy personal and professional exits. His vulnerability is clear as he emphasizes how he fumbled relationships in his youth. Gary Vee is a work in progress and knows the power of learning from mistakes.

Mistakes are what make Vaynerchuk better than anyone else. Gary was adamant about his distaste for the trophy culture — the vanity culture where everyone is awarded a trophy or an A +.

As Vaynerchuk sees it, the crux of the problem is that failure is the biggest predictor of success. When we fail, we learn and re-asses. Failure gives us the template for becoming better.

Image Credit: Julie Lokun

When is enough, enough for Gary Vaynerchuk?

Gary leans over and instantly answers the question. He taps my shoulder and says, "Enough was enough on day one."

He has amassed a fortune by doing things bigger and better than his predecessors. Vaynerchuck is touching more industries in business than anyone else I know. His office is notably decorated in memorabilia, yet he made it clear that he understands the power of doing what you love, which is enough.

He is adamant that collecting accolades and wealth is a by-product of his passion to play. This took me a minute to think about. Vaynerchuk executes his passion for entrepreneurship with such veracity that it is impossible to ignore. He loves what he does, and this is all that matters. Vaynerchuk remains present, grateful and humble.

If you find him at a neighborhood yard sale or on stage speaking with notable thought leaders, know that Gary Vaynerchuk is driven by a deep-seated passion and doing it with excellence.

You can watch my full interview with Gary Vaynerchuk here.

Julie Lokun, JD

Entrepreneur Leadership Network® Contributor

Founder Of The Mediacasters

Julie Lokun, JD, is the founder of The Mediacasters, a mission-based company that elevates the visibility of entrepreneurs and creatives through podcasting, publishing, and public speaking. Julie is the author of 4 best-selling entrepreneurial books and hosts three podcasts.

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