Gary Vee’s Philosophee (With Poetree!)

Kirk j Barbera
6 min readOct 23, 2017

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Gary Vaynerchuk often claims that he loves to fail. He lies. He does not love to lose. He loves the game.

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You can’t love boxing if you are not in love with punching. If you are in love with punching you must at least appreciate being punched. Afterall, how fun would the sport be if only one boxer is allowed to punch?

“I’m romantic about the journey and the process,” Gary once said to a 22 year old caller into his show #askgaryvee. “[That] is why I’ll pull it off.” He goes on to explain that people are always asking him if he’ll buy The Jets football team in 2 years. And he says no. It’s going to take at least 20 years, or it may not ever happen. And he doesn’t mind, because he loves the climb, the hustle, the work.

For Gary, The Joy of Life, is not buying The Jets or bragging about his dream to buy The Jets; it’s not marrying the girl or buying a yacht or traveling the world; it’s not even the failures or punches or late nights or the loneliness. For Gary, The Joy of Life is THE GAME.

In the early 1900s there was a poet, Berton Braley, dubbed “The Minstrel of Business.” He wrote poems about the romance of business. Here is one of his poems, which was once syndicated across the United States, It’s called, aptly, “The Joy of Life.”

1) I’d rather risk gamely

And lose for my trying

Than grind around tamely

— A cog in the mill.

I’d rather fail greatly

With courage undying

Than plod on sedately

With never a thrill!

2) The game’s in the playing

And, losing or winning,

The fun’s in the essaying

Your bravest and best,

In taking your chances

While fate’s wheel is spinning

And backing your fancies

With nerve and with zest!

3) Let stodgy folk censure

and timid folk quaver,

But life sans adventure

Is weary to bear,

The dangers we’re sharing

Give living its savour

I’d rather die daring

Than never to dare!

Now, I’d bet that not every line made perfect sense to you, but I also bet some part of it did ring true. That’s good poetry. This minstrel of business was a predecessor to Gary Vee. Gary echoes the sentiments that were once common in America. The romanticization of the hustle.

Here’s a breakdown of the poem. It opens with a challenge to you the reader. Would you rather live a sedate, humdrum life or a risky one chock full o’ failure? Or would you rather be a cog living without a thrill, without the enjoyment of adventure? As to the poet, he’d rather fail greatly. As Gary puts it 100 years later, “Life shrinks and expands on the proportion of your willingness to take risks and try new things.” The more adventure, the more hustle, the grander will be your life.

In the second stanza we get a perfect emotional encapsulation of the Gary Vee philosophee, which can be summed up: “For Love of the Game.”

The fun of playing the game is “essaying” — the effort, the hustle, the grind± — your bravest and best. “I loved the game,” Gary once said to an audience, “waking up at 5am, going to the flea market, buying stuff for 4 bucks and selling it for $11 bucks. I wasn’t going to buy mansions with my $7 profit, but it was the action.”

And how does The Business Minstrel tell us all to act in the game? You had better “back your fancies with nerve and with zest.” In Gary’s words, “Map your ambitions to your actions.” For those ambitious individuals who want to own a private island, you’d better act accordingly. You’ve entered a big game, so you have to play the big game. For those who want to make $100,000 doing something they love and spending all the time they can with their family, great, you’re playing a different game. Go play that game. Whatever the size or scope of the game you play, play that game.

And finally, loving to fail sounds like a cool thing to say, but most of us can’t grasp the total life philosophy it represents. “I love losing: it’s a motivator to me,” says Gary. In fact, he hammers that point home constantly. Love to lose. Losing is part of the game. Take 10,000 punches to the mouth and keep going. Adjust. Lose again. This is a constant theme of Gary vee’s philosophee.

The last stanza sounds good. We don’t want to live life sans (without) adventure. And adventure necessitates the possibility of failure.

This is the hardest to grasp component to Gary’s philosophee. It can best be understood by the idea that there are no conflicts of interests among rational men and women. Though we often believe there is a conflict.

Imagine sitting for a job interview in a large NYC office building, and beside you is a row of other applicants. There’s only one job opening. Doesn’t this put you in conflict with all the other applicants?

Or, imagine, going to the gym every day. Isn’t it frustrating to go to a piece of equipment only to find there is someone already using it? Wouldn’t life be better — go smoother — if there were less people who went to your gym?

This scenario happened to me recently. I went to my local Gold’s Gym and in the weight room there were exactly zero people. It was paradise, since I deal with amateurs and goons hogging the equipment on a daily basis.

Then it struck me. If the gym was dead like this every day, then there would be no gym. The very people who I complain about are the people who make it possible for there to be a gym so close to where I live.

This is true of the interview, too. If there were no other applicants for the job, there could be no job. After All, the business is operating in an environment where they must hire in order to grow and survive. Thus, if there are not operating in a flourishing environment — with many customers and many applicants — then they would not have the means to hire.

Failure works the same. By failure, we of course mean civilized failure, not jungle failure. To fail in the jungle is to die. If I fail to escape this lion, I’m… Well you get it. In civilized failure we mean in sports, romance, schooling, business, fundraising. In other words, someone fails when multiple parties are vying for the same good.

Gary Vaynerchuk has a high likelihood of failing to ever buy the NY Jets. There can only be one owner. There are other people who may want to buy the Jets. If there were no other people wanting to own the jets, then the Jets could not exist. Put different, we live in a society that enables there to be a Jets team. Without the society there would be no Jets to desire.

You can apply this logic to anything in life where so-called competing interests exist.

Many men want to win the heart of a young lady. If we lived in an environment where there was no competition, say for instance, a deserted island, then there would also be no woman to desire.

The fact of competition creates the reality of any specific desire.

The next time you fail, understand that it is merely part of the game. We watch the superbowl because it is inherently dramatic. One team has to lose. If one team could not lose, then we wouldn’t watch, and then there would be no teams to compete.

Take this not as pessimism but optimism. There are things we all want. They exist, because we want them. This merely means that failure is no more a negative of playing the game as Night is a negative to the day. It merely is part of living in civilization.

Once you fully accept that Truth, you will be more likely to take failure, or loss, or too many people at your gym as a positive. These “in the way people,” are in fact the “making it possible people.”

Gary Vee’s Philosophee is actually quite simple. The poem helps to encapsulate his view. Fortunately, his view is an oldie but a goodie.

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