How Gary Vaynerchuk became an internet sensation: ‘I’m petrified of being wrong’

The US entrepreneur will appear at the Emirates Airline Festival of Literature in Dubai

Author Gary Vaynerchuk's new book 'Twelve and a Half' is part memoir and part business guide. Photo: Emirates Airlines Festival of Literature
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A word rarely associated with Gary Vaynerchuk is fear.

The US entrepreneur, also known as Gary Vee, turned social media star and author admits that bubbling underneath the acerbic humour and bluster is a pervading anxiety.

It’s not a crutch, he explains, but a source of motivation for extensive research before making bold and trending declarations on the next big investment opportunity.

“I am petrified of being wrong,” he tells The National. "I have a fear of tarnishing my reputation, which makes me incredibly meticulous at crossing my Ts and Is. But the second I'm done, my friend, I am very loud."

This explains his colourful and bombastic social media videos extolling the opportunities of TikTok in 2017, the trading and selling of sports cards in 2020 and the cautious optimism towards non-fungible tokens, also known as NFTs.

The digital tokens will feature during his session at the Emirates Airlines Festival of Literature on February 9, where he will discuss his career and latest book Twelve and a Half.

A frequent visitor to the UAE, Vaynerchuk is aware of the growing embrace of NFTs by businesses and organisations in the Gulf.

He stands by his assessment that while they will permanently form part of the landscape, it currently remains a high-risk proposition.

"People want to hear what they want," he says. "I have put out more content than anybody on Earth that 98 to 99 per cent of NFT projects will fail and go to zero. However, people want to hear about the money making because it's a gold rush.”

The way to avert following the herd, he says, is good old-fashioned research and common sense.

"People see others doing bad behaviour, they know it can't be right and it feels like a scam, but without deploying the hundreds of hours of homework, they can't understand what this all means. Education is important."

Swagger and humility

This is a central message of Twelve and a Half, a chatty and at times revelatory work that’s part memoir, self-help book and business guide.

Vaynerchuk delves into his own experiences, from joining the family beverage business and building a global marketing agency, based in the US, to presenting provocative hypotheticals exploring traits needed for business and personal success.

“What I am trying to get across is [that] sometimes using conviction and humility at the same time is the requirement to advance the issue or the opportunity,” he says.

Vaynerchuk acknowledges it’s a message undercutting some of the swagger making him a darling of the hip-hop world, with fans including star rappers DaBaby, ASAP Ferg and Lil Keed.

That confidence also served as a lightning rod for some members of the mainstream financial industry experts who view him as a charlatan.

The book was not written in response to the negativity, Vaynerchuk says, but to provide an insight on how he operates.

"I am not crippled by the judgement and that's not because I'm so cool but because I'm empathetic," he says. "I am empathetic to the concept that if you've only consumed four or five of my social media clips when I'm cursing with passion about something in my New Jersey-style Americana [dialect] you may not have a full read of me.”

If so, then who is the real Gary Vaynerchuk?

Is he the fun "bro" you wish to hang out with, as seen on social media, or the more taciturn yet lively presence addressing corporate events and book festivals?

"I'm the same person, but am I different in the context of the room I am in? Well, of course," he says. "I am incredibly humbled that people are allocating their time and sometimes their money to sit in a crowd to listen to me.

“So I want to deliver value, and if I have to come with a different speed and be almost like a stand-up comic then I am willing to do that.”

Telling it straight

One aspect that will never change, he says, is how his books are produced.

Twelve and a Half is Vaynerchuk’s sixth release, and all his books were orally delivered and edited by a ghost-writer.

“My publisher always says the best job is to be Gary Vee's ghost-writer because all you have to do is just turn it into grammar,” he says with a laugh.

"When I work with them, I insist that they use the exact words, even if I sometimes speak in run-on sentences.

“This is why many people come up to me when they read the books and say how wild it is because it felt like I was speaking to them. I say, 'yes, I am talking to you.'"

Gary Vaynerchuk's will be speaking at the Emirates Airline Festival of Literature on February 9. His session Crushing it with Gary Vee takes place at 8pm in the Al Joud Ballroom at Hilton, Al Habtoor City. Tickets from Dh75 from emirateslitfest.com

Updated: February 02, 2022, 8:06 AM