Gary Vaynerchuk wears many hats: serial entrepreneur, investor, and CEO.

While juggling all those roles, he’s also a social media wizzard regularly speaking in videos on Instagram and YouTube, encouraging people to start a side hustle, build their business and grow their social media presence.

The co-founder and CEO of VaynerMedia often speaks directly to his audience on online platforms, and I was curious to see what it’s like to be “Gary Vee” as he’s known — and find out if he’s as energetic as he appears to be online.

I had the opportunity to shadow him and his team at National Achievers Congress, an event teaching people how to maximize their personal and professional life. The event, held in Dubai, was put on by Success Resources in which Gary spoke onstage to teach and inspire entrepreneurs.

Here are seven things I learned from my afternoon with him:

1. Gary doesn’t get jetlag, but he needs adequate sleep

Gary flew in from London on the day he arrived in Dubai to speak. The 6.5-hour flight was too short for him to get enough sleep. He said that he never typically suffers from jetlag, but that he does need an adequate amount of sleep.

Even though, he is often advocating people hustle hard and work late nights, he also advises people get between six to eight hours of sleep.

During a sit-down interview he had with Channel4 Dubai, he joked, “You want the cameras and the lights, you got to pay the price.”

2. Self-critique, but don’t judge yourself

Gary doesn’t necessarily subscribe to the famous quote from America’s founding father Benjamin Franklin: “By failing to prepare, you are preparing to fail.” Before speaking on stage, Gary said he didn’t know what he was going to talk about.

That’s probably fair considering he’s done more speaking engagements than he can count, and is regularly giving entrepreneurial advice in meetings and podcasts.

As he came off stage after about an hour of speaking, I asked him what goes through his mind once he gets off.

“I usually critique. Some days are sharper than others,” he said. “I try to think about what really just hit, I put it in my head one more time. I felt it up there, but I think one more time.”

And even though he critiques himself, he says he doesn’t judge himself. While answering a question from the audience about whether he ever felt stuck, he responded: “Nope. Because I don’t judge myself.”

3. Ask questions before giving answers

While many celebrities are adorned with praise by fans, Gary is often asked questions by his.

In most of his interactions, rather than immediately responding to a question, he asks them a question instead. That way, it not only ensures that he understood what they were asking, but also conveys that he was truly listening. He even often responds with a question to some reporters’ questions.

4. Remember the ‘four-second interaction’

Gary Vaynerchuk meets with media backstage at National Achievers Congress tour in Dubai

Uptin Saiidi | CNBC

He owes this rule to his own humble beginnings of remembering what it was like to meet an idol.

“I’m so grateful and so in tune at the ‘four-second interaction’ I had with a Jets football player or at a baseball card show,” he said. “The fact, that I’m on the other side now — it’s intense.”

5. Be concise in your words

Gary is very deliberate in his choice of words and as a result, he often conveys what’s on his mind through an example or visual image. Here are some examples from him:

  1. The best thing you can do is listen. Communicate your truth and let whatever happens happen.
  2. You take compliments too high and pushback too deep. People who are winning don’t take either that seriously. He said that when people tell him, “You suck,” or “You are a god,” he doesn’t care much about either.
  3. Too many people put money on a pedestal. Do you know how many millionaires who are miserable?
  4. Success is the ability to do what he wants, when he wants.

6. Truly present in every interaction

7. See change as a constant

Despite being the expert in the room, Gary is quick to admit how much of his advice changes.

For example, in his book, “Crushing It,” published two years ago, he didn’t mention the importance of China’s popular video sharing app TikTok and professional networking site LinkedIn.

Now, however, he finds them imperative and even highlights the fact that his advice changes as it’s important to remain fluid.



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