Gary Vee Changed my Perspective of Happiness, Hustle, and Honesty

Martijn Keesmaat
6 min readAug 27, 2019

Gary Vee is a great motivator. Immediately when I first heard him speak I got motivated to do something positive. He changed my perspective on hard work. Hustle is the word that often comes up.

99.9% of you are not hustling.

This is what Gary said on a Christmas night.

He, on the other hand, had still 3 meetings planned and was creating content for Youtube.

Gary often talks about how you should grind and grind and then some. Don’t watch tv-shows, don’t take days off, don’t follow celebrities, etc.

His mindset is extreme in the current culture of comfort and usability.

You would imagine that a person with this lifestyle wouldn’t be happy.

Yet, I saw a man that was truly happy.

Why?

Perspective

Gary was born in Belarus in the former Soviet Union. He witnessed his older relatives being imprisoned and ostracized for being Jewish. In hopes of a better life, Gary and his family immigrated to the United States.

They all lived together in a tiny apartment in Queens, and as the foreign kid, he got often bullied.

Gary experienced difficulty adapting to the American culture and was notorious for being a terrible student.

His father was very extreme about hard work.

With very little money, Gary’s dad made ends meet by working as a stock boy in a liquor store. He set the example for Gary by working 14 hour days 7 days a week.

Gary was fired by his father once. Gary was fired because he asked to leave at 5 pm on a Saturday night to go to prom instead of 7 pm.

You are not committed to this business, his father said as he fired him.

They have grown a strong relationship through adversity. In this video, his father talks about how hard he worked but is still amazed by how hard Gary works. The video shows the rare emotional side of Gary.

To me, this puts things into perspective.

Gary is an incredibly hard worker that deserves all the credits he receives.

His childhood was tough, really tough.

Yet he was tougher.

Gary dares people to give him reasons to be sad. When you find out where he came from and the culture he grew up in, you realize how he can say that.

Self-awareness over Hustle

You’re an outspoken advocate for both hustle and self-awareness. But if you had to put them in order, even if it’s…

Self-awareness said Gary immediately.

Self-awareness and it’s not even close.

It would be cooler for like the people listening for me to say hustle ’cause it’s cooler. Self-awareness is the game.

But when you know yourself, you win.

In business, the reason I’ve been so successful is I know what I’m good at and I know what I’m not good at.

Gary loves winning, which is why I find it so interesting he expresses his flaws.

How do you teach it

Asked Larry King when talking about self-awareness.

I don’t know.

But I know it’s damn important.

And so, I know where I start and where I stop, Larry.

And I wish, honestly, I’m curious to see over the next 40, 50 years of my career, if I figure it out.

You would assume that this super competitive guy — this guy that even want to beat his kids from 6 and 8 years old in a basketball game — would not admit things like this.

Having your life figured out

If you’re twenty-two, eighteen, twenty-five, thirty and you think you should have your whole life figured out?

That’s ludicrous.

I think self-awareness if you are capable of accepting yourself for who you are, is actually the brightest light of it all.

I love being self aware. I suck at a lot of things. I just don’t think about them.

Like, I can’t read for s***.

I interrupt people when I interview them 24/7 everybody’s super pissed on the internet about that, not good.

There’s plenty of things that I’m not good at.

I love self-awareness, it’s kept me so happy. You know, I’m not upset at myself that I’m selfish in certain areas.

That’s human.

Clouds and Dirt

This is the theme of the K-Swiss shoes Gary helped design.

It means to be ambitious and work hard but stay grounded and be patient.

The macro and micro is the motto he often talks about.

Work hard every day, morning till evening, and don’t expect something for the next 6 years.

This is such a freeing concept to me. To not have any expectations. Just reading this excites me. Don’t expect anything and work hard. If something happens great. Otherwise, you can still feel happy because you know you pushed yourself and won't feel regret. That is a guarantee.

Play yourself, not the market

“Any artist that blames the audience, already lost.”

Every second you spend thinking about what someone else has, it is taking away from time that you can create something for yourself. Spend that energy on your visions and execute. Speaking the hard truth

I leave you with this my friends. How you make your money is more important than how much you make

The fear of being lucky

Do you know that I do not play the lottery?

Because I’m scared to win?

You’re scared to win?

I do not play the lottery because I’m scared to win. Then everybody will say that it was the lottery ticket that enabled me to do the things I plan on doing in the next 50 years.

Easy money scares you, then.

100%

I think that’s the first time I’ve heard you say that. It’s the first time I’ve said it out loud.

The biggest goal of Gary is to one day own the Jets. It is not the idea of owning the Jets that it is about the journey. Which sounds like a cliché. With Gary, this feels like a divine truth.

Speaking the hard truth

One thing I will try to never lie about again is myself.

You know why?

Because I did for most of my life.

The secrets and insecurities I didn’t tell people about made me feel trapped.

It became a barrier between who I was and who I wanted to be.

Everybody’s biggest, fearful secret right this second is the jail of their happiness.

This advice really struck me. I am normally a very reserved person and don’t share much about my life. Especially not my insecurities. My mentality was to not embrace my insecurities so it would seem like I didn’t have any.

The thing I realized with insecurities is that you are the only person that suffers from them.

Love your work

I fucking hate Friday.

I'm blown away by people celebrating the end of the week.

Like the weekend is your escape from your reality like at its basic form.

If you genuinely celebrate Friday you need to rethink your entire fucking game.

See the full video

In short

  • Hustle, because it is the one thing you have control over.
  • Gary dares people to give him reasons to be sad. When you find out where he came from and the culture he grew up in, you realize how he can say that.
  • Fully understand where you start and where you stop. If you are woken up in the middle of the night, you should answer this without hesitation.
  • Work hard every day, morning till evening, and don’t expect something for the next 6 years.
  • Be afraid to win the lottery
  • Everybody’s biggest, fearful secret right this second is the jail of their happiness.
  • If you genuinely celebrate Friday you need to rethink your entire fucking game.

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Martijn Keesmaat

Developing my world view every day. It is about finding your morals and philosophy as an individual. Everybody has their perspective. Here is mine.