14 Lessons I Learned From Shadowing Gary Vaynerchuk for Two Years

An incredible friend and trainer. Thank you Mike!

So, Gary has a new book.

#askgaryvee is a compilation of his thoughts on how to win at business while living a good life (my definition).

I am nearly finished, and the book is damn good.

But I have some unique insight. You see, I train Gary under a pretty unusual arrangement.

I see the “real” Garyvee.

Vacations.. business trips.. I almost accidentally saw him naked the other day when I barged into his bedroom to announce he must finish the shrimp cocktail before leaving for the night.

So, I want to share a few lessons he’s taught me.

Some are expansive on points in the book, others aren’t in the book.

But these lessons have helped me grow my business exponentially and become a better person in the process.

14 Life Lessons Learned Shadowing Gary Vaynerchuk For Two years

1. Always Do The Right Thing

Last week, an eager fitness hustler offered to purchase 75 books if Gary would give him a five minute interview.

Here’s the thing: Gary and I had already decided that the next trainer needs to be someone we already know. The job is too personal to take a chance on a complete stranger.

Gary could have still taken the meeting.

He could have nodded along for a few minutes and waltzed one step closer to the New York Times Best Seller list.

But instead, he replied:

tell him no, would feel bad taking this.

This is a behind the scenes view of someone doing the right thing when absolutely no one is watching.

Pretty cool.

2. Be The ’98 Vikings

Do you know how many articles I posted on this blog between April 2014 and September 2014?


I’m a writer, and I wrote ONE article in 6 months.

You know why?

Because I was playing defense. I wanted everything I wrote to be better than my previous post. And I was afraid it wouldn’t be.

That pressure crippled me.

Gary taught me that putting out consistent content at 85% quality is far superior to posting “perfect” articles once in a blue moon.

You can’t win if you don’t play the game.

I guess you also can’t win if your franchise is cursed, but whatever.

Offense, baby.

3. More Important Things Than Money

I remember the first time I realized money would never be a problem in my life: I enjoy hard work and possess a skill set that people value. And I need almost nothing, so my expenses are very low.

My first thought was wow, I’ll be able to do cool things like buy my parents stuff.

I brought this excitement to GV between sets of triceps accessory work.

Man, it’s gotta feel good that Lizzie and the kids are always going to be financially secure and you provide such a nice life for them.

His nose scrunched and lips pursed, almost like he ate something too sour, which is a tell that he’s about to disagree with you.

sure, but I am wayyy way way wayyyyyyyyy more proud of the emotional support I provide

Nice things and vacations are cool, but giving your time and attention and emotional support is far more valuable.


4. You Have To Be Able To Sleep At Night

I promise my coaching clients that I will reply to email every single day.

At 11pm on March 8th, I took a deep yawn from the back of the Q&A Gary was giving. It was our first stop on his book tour, and I was beat tired after a long day of travel.

But I hadn’t been in my inbox yet.

I could feel myself rationalizing this mistake: it’s okay, people will understand if you miss one day.

And you know what, they probably would have.

But that’s bullshit.

I promise daily communication because I believe in it. And I would not have slept well without taking care of business first.

So, when the event ended, I went to my hotel room and from 2am to 5am answered emails, assessed progress, and tweaked training and nutrition programs.

It was the right decision. I was being true to my word.

And even though I didn’t sleep that night (literally, we had a 6am flight to Atlanta), I slept like a baby the following night.

4b. “How you make your money matters more than how much money you make” -G

5. Communication Solves 99% of Problems

Gary received a text late one night from an employee.

It felt a bit erratic to him; the employee was worried about some things. And given the time of day and tone of the message, Gary assumed the employee had been drinking.

Personally, an uncomfortable situation like this would have knotted my stomach to the point where I couldn’t think of anything else.

GV set it aside completely.

He later told me it didn’t impact him because he knew they would have a conversation in the morning and clear the air completely.

6. Your Employees SHOULDN’T Care As Much As You Do

I used to get pissed when walking through VaynerMedia.

People only doing three hours of real work in a day, screwing around on Facebook, taking 90 minute lunches, and going on coffee meetings just to socialize.

Yet, Gary has fun joking with employees when he walks through the office.

How are you not pissed that everyone isn’t hustling like you???

He gave me that black cherry warhead look again except with a flair of anger, like, are you an idiot Mike:

Because it’s MY company. Of course they aren’t going to care about it like I do.

Aha. Yeah. That makes sense.

7. Know Who You Are

I wanted to grow a giant business because it seemed like the cool thing to do.

I partnered with my genius friend Brett.

I failed.

Then I hired a grinder named Chris to intern for me.

I failed.

Then, after watching this video too many times, I realized something: I’m not a businessman. I enjoy coaching clients. And I enjoy creating content.

Not managing employees.

So, I have since stopped trying to grow a giant fitness business and become content doing what I do

8. Be A Practitioner

There is a reason I track my own macros every day, always have goals, train with intensity, and don’t act like I’m too cool for fitness.

It’s because you learn things by actually doing them.

Don’t be a guru sitting atop the iron throne telling everyone what to do. Get your hands dirty. You will be better for it.

9. Listening To Yourself Always Wins

10. Give 51%

Gary has been addressing this in talks lately.

But it’s a concept he instilled in me from day one, when he said:

You need to reply to every single email, Mike.

And I do.

Sometimes I get backed up a month or two, but I reply to every single email.

Most of the people I email with will never pay me a dollar. And I am 1000% okay with that. Here is why:

First, helping people is never ever a bad thing. When you look back on your life, you won’t regret lending someone a helping hand.

But second, it’s actually a good business strategy. No one expects you to help them for free because no one does it. Most are too transactional, short-sighted, and impatient.

Let me give you an example, my friend Amanda complained to me that people on Snapchat ask her questions.

What am I supposed to do? They think I’m just gonna help em for free?!

Answer then, I told her, answer every single one.

If you have time and you want to grow your business, give them massive value for free.

Many of these people will become part of your community. Some might buy from you in the future or want to work with you. Many will help you spread your message because they believe in you.

Give 51.

11. Champagne Problems

So many people are emailing me for advice.

I was being a bit whiney, in hindsight, and if there is one thing Gary hates, it’s whiney.

Oh, you mean you have TOO big an audience? You have TOO many people that care about what you say?

That’s a champagne problem, Mike.

12. Don’t Take Your Problems Home

It is completely irrational to let a problem at work impact how you treat your kids.

But most of us can’t separate work stress from our personal lives.

Gary does.

One morning during a dungeon gym workout, I asked him how he does it: gratitude.

He said he is so grateful that he gets to work as hard as he does that it would be massively unfair to Lizzie and the kids if he let work problems impact his mood and demeanor at home for even one second.

I guess he is pretty big on gratitude:

13. QBs Take The Blame

I have shared a backseat with G for a lot of internal VM calls.

And I constantly hear:

That’s my fault.

Yes, the CEO is in charge of the business therefore every issue is technically the CEO’s fault.

That’s not what I learned.

Every single one of us should be taking the heat in my life because it’s effective.

First, it saves time that might have been wasted arguing over who was actually at fault. But more importantly, it wins you respect from onlookers who know it wasn’t actually your fault.

It makes you a leader.

Plus, if you take responsibility for the losses, you get more glory during the wins.

14. We All Have 24 Hours

I hate to list this because it’s so cliche, but it is probably the single factor that grew my business the most.

The moment I got access to Gary’s calendar, I internalized this concept. Holy shit. This guy goes hard all the time.

My next thought was… this is a decision.

Any human being can choose to do this.

We all have the same amount of time.

I immediately audited myself.

30 minute walks around the block to “get in the zone” before writing. Nonsense Facebook scrolling to “refresh my brain” during the afternoon.

There isn’t anything wrong with this, except that I thought I was a hard worker.

Just remember we all have the same 24 hours. And choosing how you use it is the best way to control your results.

If you would like more lessons (340 more, to be exact) check out the #askgaryvee book.

“Crushing It” releases, January 30, 2018 ❤ If you want to submit CLICK HERE!

This publication is powered by Gary Vaynerchuk ;)

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