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I Wasn’t Prepared for Gary Vee to Cry in Front of Millions of People

by | Feb 6, 2023 | Entrepreneurs

Gary Vee is radically misunderstood.

It pains me. His face is everywhere and I feel like so many people don’t know the truth about him.

It’s time we get to the bottom of it.

The one person who got to Gary Vee

Gary has pretty thick skin.

You probably wouldn’t want to get into an argument with him. He unashamedly admits he has the gift of the gab.

On a recent podcast with Steven Bartlett another side of Gary emerged. As someone who is a fan of Gary, even I learned a lot I didn’t know.

Get ready to be surprised.

So Gary admits that in 2018 an article on this platform titled “No More “Struggle Porn” got to him (now deleted). The story’s author is someone I look up to but this was my least favorite article of his.

What got to Gary is this writer said he inherited his dad’s wine business. He wasn’t an entrepreneur. He was a glorified trust fund baby living in denial.

If you look back at Gary’s life you’ll see why this comment is one of the few times he’s lost his mind.


Gary was born in the Soviet Union. His family escaped (barely) thanks to some rare political circumstances at the time that allowed a few people to leave and migrate to the US.

His family was poor and had to work their butts off to survive. Entrepreneurship for Gary was a means of survival. He didn’t have all the perks other kids had.

Between the ages of 20–30 Gary gave his life to his dad’s liquor store because he loved his parents and appreciated their huge sacrifice so much.

“I built my dad’s liquor store for him, I didn’t inherit it.”

Gary says he never made more than $120k a year working at his dad’s store, and started his media company at 34 with $0. He was broke as a joke.

When someone said he had a silver spoon in his mouth and blew up online because of it, the pain cut deep.

The supposed king of hustle p*rn

A few critics think Gary is a bad man.

They say he promotes hustle p*rn and struggle p*rn. They believe he’s responsible for the burnout epidemic.

But after listening to many of Gary’s recent interviews, I think people have misunderstood his message. It’s easy for randoms on the internet to jump to conclusions. They do it to me all the time as a writer.

I talk about money and then they twist my message to be some white boy privilege that suggests everyone should work a job and start a side hustle and never see their family.

The fact my message is the opposite makes me laugh. I’m trying to help people see money buys time and luxury existences enslave people.

But people will believe what they want to believe, as Gary learned.

What’s bizarre is Gary says he spends way more time with his children than people think.

If you dig below the surface of his loud and proud New York personality you’ll see a softer side. In recent interviews, it’s clear the importance of family is perhaps his most important message.

The moment that made Gary cry in front of millions of people

I consider myself a big Gary fan.

I was lucky to meet him in Australia a few years ago. I’ve consumed a lot of his content. So I was surprised when I recently found out in a Steven Bartlett interview that he cried in front of a large audience at his live event.

When Steven brings it up Gary’s whole demeanor changes. He goes from the confident yankee to an inwardly shy person. His voice softens. His fast-moving lips slow down to a snail’s pace.

Steven passes a photo of Gary and his mother in Russia across the desk.

Tears start to fill his eyes.

The tough guy turns to jelly. What makes Gary so emotional is the thought of his mother. She didn’t have a mother. So she did the best she could to make Gary insanely happy.

Now, oddly, Gary says he wants to scale the happiness he has experienced.

People may have thought it was money, fame, or entrepreneurship that Gary represented. But more and more I realize that’s not the case at all. He’s a deeply complex human (as we all are).

What you see him do online is done for attention. Once you get passed the messages that draw you in, you get served up ideas and wisdom you didn’t expect or ask for.

Gary is a misdirection.

His whole online brand is like a magician that shows you a trick while another simultaneous trick happens in the background. He doesn’t do it for evil. It’s done for good. I just wish people could see it.

Gary’s dark secret he hasn’t revealed

Over the last few years, podcaster Tim Ferriss shared his secret of being r*ped as a child. It changed who he was forever.

More importantly, it helped millions of people feel seen.

To my surprise I learned in this interview that Gary has a similar dark secret, although he won’t say what. There’s a part of me that secretly wants him to reveal it so he can be more understood. And so people can see the humanity he represents.

When you’re the tough guy on social media it’s hard to reveal a trauma that risks making you look weak. It’s a challenge I’ve faced.

What I’ve learned is that vulnerability is perhaps the greatest superpower that exists. It’s not about the individual. It’s about the collective.

Let’s wait and see if another side of Gary comes to the light. And if you’ve ever been skeptical of Gary, perhaps it’s time to watch this emotional interview and be bold enough to change your mind.

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