4 Lessons for Life and Business from GaryVee

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I grew up near a fancy liquor store in New Jersey called Wine Library.

Whenever we drove by, my parents would mention that the guy who runs it is a big deal in the business world.

Still too young to worry about wine, I couldn’t have cared less.

A few years later, I came across a video by some guy named GaryVee. He was talking about spending his twenties scaling up his father’s liquor store before focusing on his own projects in his thirties.

Nothing clicked.

In my mind, a “liquor store” was a dingy place that sells beer to “23-year-old” high schoolers, not an upscale building with a vast selection of premium wines.

When he finally named Wine Library, I was shocked. This ultra famous guy built up the liquor store I drove past on my way to school every day?


Already bought into his story because of this connection, I started watching more of his videos. It was some of the first business and self-development material I got into.

At first, I just sat there listening to him talk about producing content and working hard, but I wasn’t doing anything. I’ve now realized I was using his videos to procrastinate, so I’m not watching much GaryVee these days.

With that said, his videos were instrumental in my decision to start writing online.

There was no singular business advice or tactic of his that changed my life. Instead, he just showed me how he lives his life and inspired me in the process of doing so.

Don’t Accept False Binaries

Almost everything GaryVee does makes little sense from an outsider’s perspective.

  • He makes his money through successful business ventures, but he first comes across as another guru who only makes his money by telling other people how to make money
  • He’s a millionaire, but he spends his Saturdays going to garage sales to maybe make a few thousand dollars
  • He angel invests in ascendent Silicon Valley start-ups, but he hangs out with rappers like Gunna and Lil Keed before most rap fans even know who they are
  • He documents most of his life, but he’s managed to keep his family out of the public eye
  • He’s one of the most successful people out there, but he got terrible grades in school and jokes he “majored in Madden” at Mount Ida College, which no longer exists
  • He speaks at prestigious conferences, but shows up in a t-shirt and curses up a storm

See what I mean? He’s a walking contradiction. Everything in society tells us our lives consist of a series of binary choices where the question is or, not and.

  • You can be analytical or creative
  • You can be athletic or intelligent
  • You can be a coder or a writer
  • You can be a doer or a thinker

Gary is one of the best examples of and that I’ve come across.

Macro Patience, Micro Speed

One of Gary’s key wisdoms is another rejection of false binaries. A lot of people preach intensity, and a lot of people preach patience. GaryVee preaches both.

The idea of macro patience, micro speed is simple. Work as hard as possible on a daily basis, but understand it takes years for a lofty vision to come to fruition.

Gary’s life is a testament to this ideal.

Based on traditional societal metrics, it probably looked like Gary was going nowhere for most of his life. With grades like this and little college pedigree, things didn’t look great.

Image from https://www.garyvaynerchuk.com/my-2017-manifesto/
Image from https://www.garyvaynerchuk.com/my-2017-manifesto/

Some entrepreneurial spirit was there from the start, but this was before entrepreneurship was the cool thing to do.

Things didn’t change immediately after college.

While some of his peers went to fancy schools, got cushy jobs, and seemed to have “made it,” Gary went to work at his dad’s liquor store.

“They would pull up at my dad’s liquor store in their expensive cars, order a case of expensive wine (and I would be ringing up their order). Then they’d wait while I carried it, walked outside, and loaded it into their trunk for them.”

They probably thought he was a loser, but it didn’t matter to him. He knew the path he was on and he was willing to pay the price to walk it.

I can’t imagine the amount of patience that takes. Everyone knows they’re supposed to think long-term, but few can execute on that advice to the extent Gary has.

In terms of developing patience, one exercise has always stuck out to me. In this interview, Gary gives a caller a new perspective on age. He tells an 18-year-old that when he lives his entire life again, he’ll still only be 36. The idea is that most people can double their age and still be fairly young. Those who can’t can probably still live half of another life. Talk about macro patience.

Give and You Shall Receive

Considering his reach, it’s almost shocking that Gary doesn’t sell any online courses.

In fact, he does the opposite.

I haven’t seen him sell anything. Sure he sells his books, but even then it’s a simple ask without an invasive marketing campaign.

Instead, Gary gives out his advice for free.

While others convince their audience that “anyone” can achieve their success with some “secret hacks,” Gary has a more honest approach.

He admits some people are better off as the seventh employee at a company than trying to start the next unicorn. He makes it clear that not everyone should be an entrepreneur, and not everyone needs to dedicate their lives to making millions of dollars.

All of these tactics, or lack thereof, seem like a missed opportunity. Gary could easily sell a thousand dollar mastermind to thousands of his fans, but he’s very clear about why he doesn’t:

“I don’t want your money, I want your admiration.”

Notice the date

Ultimately, this thinking is why I’m writing about Gary over other people I’ve actually bought something from.

You Can’t Think Push-Ups

At a core level, all of Gary’s teachings praise taking action.

As he says, you can’t read about doing push-ups.

After months of thinking about writing, this mantra recently popped into my head and told me it’s time to start.

Best of all, he lives his own advice.

Here’s Gary’s first YouTube video. It’s pretty much a vlog about wine, but from 2006. I wasn’t old enough to know what was going on back then, but I have to imagine it seemed like an absurd idea at the time. Look where we are now.

Gary doesn’t read about push-ups, he just goes out and executes.

He knows what his strengths and weaknesses are, and he’s doubled down on his strengths instead of spending his life trying to cover his weaknesses.

Take Your Flowers

This is the first Flower Friday I’ve written about a living person.

GaryVee wants everyone to show up to his funeral, but I’m thankful to have the chance to thank him before then. Whether he reads this or not, I’ll know I’ve celebrated someone who’s helped me start doing something I’ve wanted to do for a long time.

Who’s your GaryVee? Have you given them their flowers?

If not, today’s a great day to do so.

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