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Episode 260: Set a Flag on YOUR Thing

Is Gary Vaynerchuk a lunatic?

This is what I ask myself every time I sit down to interview him.

He’s everywhere. He’s constantly spreading a message I strongly believe in: if you don’t choose yourself, someone else will and the results won’t be good.

For Gary, “choosing himself” has been about entrepreneurship. First, “Wine Library”, then VaynerMedia. Then investing (we have been co-investors together on several deals). And…

He wants to buy the New York Jets. That’s lunacy.

But I am not one to judge.

I have my own dreams that are lunacy. The important thing is this: make the process of achieving that dream…a work of art.

Maybe he will own the Jets and maybe he won’t. But watching his process every day is watching a painter splash across the canvas. We’re watching art happen.

For some reason, when I talk to Gary, I start off with concern.

Is his ambition going to sink the rest of his life? Is he going to die of a heart attack?

Gar! (I feel comfortable without the “y”). “Gar!” Are you taking care of yourself?

I don’t know why I get concerned for him in this way. More than I do with all of my other podcast guests. it’s like i want to make sure he’s ok.

Will he get the Jets? Will he inspire a billion millennials along the way? I have no idea.

Maybe. Probably. I don’t know. I don’t care.

But I learn from him. Every time we talk, I learn.




Gary set up this example: Pokemon. Imagine this is your passion. You set up a blog. Then it becomes a video blog and then a podcast. “You become the foremost Pokemon gal, Sally the Pokemon Gal.”

It’s your passion. You love it. But what will happen next? Here’s the thing: something ALWAYS happens next.

You’re owning it. You go to Comic-Con, you get random sponsorships on your blog. You’re getting by.

And then, Pokemon Go comes out!

You’re now on CNN and FOX. You’re getting paid five grand to give a talk. The world has just walked in to you. Everybody who’s listening right now is looking for trends.

“They’re trying to walk to where the world is NOW and by the time they get there, the world moved on.

“If you go to your thing and set a f*cking flag on your thing, THE WORLD COMES TO YOU!”

I look at every interest that created success for me.

It only created success because I fell in love and I CREATED before anyone else knew there was something to create.

Don’t worry about the outcome. Immerse yourself in the process. TODAY.


“Instead of trying to make Three’s Company or MASH, try to make the Kardashian’s,” Gary says.

Why would he say that? That almost seems like make “garbage” instead of “make art”.

He’s talking about documenting instead of creating. Process is art. Gary documents every moment of his every day.

We no longer want to see just the final outcome. We want to see how the movie is made, the art is created, the business started. We want the origin story. We want the arc of the hero as he or she creates a business. We want to know how, what, where, why.

Process is Art.

This is the mantra of all success right now. Don’t just write an article of how to do something. Tell the story of why this is important to you.

Why you need to do this. How you are doing it. What will you do next. What tools you used. How you failed. What tools you are learning. Let us peek inside your heart.

Process is Art.


“Nobody has ever built anything meaningful that hasn’t taken an obnoxious amount of time,” Gary said.

He’s planning on buying the Jets. This is his lifelong dream. And everyone knows it. But he’s not buying them in the next year. Not even in the next ten. “You have to be macro-patient,” Gary tells me.

I’ve done hundreds of interviews with the best in the world:

Tony Hawk (skateboarding), Garry Kasparov (chess), Sara Blakely (business), Ken Follett and Judy Blume (writers who sold 100s of millions of copies), and on and on and on.

Everybody took shortcuts. That’s how you succeed. You find the fast ways to learn. I love learning how to find those shortcuts.

BUT THEN, time + persistence + love + creativity = success.

What is success? It’s always finding new ways to explore what you love. Every day.

Does this mean you won’t have success until 20 years pass?

No! Of course not. Celebrate the small successes along the way because they will be there. Gary, for instance, had Wine Library, then his first books, then his first clients in VaynerMedia.

And maybe much later..the Jets.

Celebrate small successes. Be patient.

Process is Art.


In Gary’s words, he “eats shit for a living”. This is his profession. He’s an entrepreneur. And Vayner Media is an enormous success.

But being an entrepreneur is stressful. I can say: it is pure pain.

Everything is your fault. You have to like losing. And you lose everyday.

A true entrepreneur fails almost every day. And it’s what they do with that failure that determines success.

Stephen Colbert was recently talking about being on stage. When you are bombing, he said (and I am paraphrasing), learn to enjoy it RIGHT THEN.

That’s how you succeed.


“You wanna hear something weird,” Gary says. “I don’t celebrate shit,” he said.

I didn’t understand. I like celebrating everything. All the little things. He told me this: “I hate that people think that I’m built around buying the Jets. They don’t understand, it’s the pursuit.”

I still don’t believe him. He celebrates the pursuit. I celebrate getting to write this article. And later today, interviewing on stage one of my good friends about the topic of creativity.

I celebrate how every day I try to do a little bit more of what I love than the day before.

Loving the pursuit allows you to be creative about the process. Celebrate every day.


Gary is making Vayner Media the “Death Star” of marketing.

It’s a machine. And one day he’s going to buy Puma, Hershey’s, Keds, all the classic, nostalgic brands he loved as a kid. This is how he’s going to buy the Jets. By linking his life today to his life as a kid. And carrying that into the future.

“There’s a real correlation around doing things you love,” Gary said. “It makes it easier when things are bad. If you do not do what you love, that’s on you.”

EXERCISE: list the things you loved from ages 6-14. Figure out what you can do around those interests right now.

This is a good way to kick-start building your idea muscle.

Come up with 10 ideas a day for next week around creating content or business around the things you loved as a kid.

Come up with ideas for those companies if they are around now.

Just like you shouldn’t ignore the people you love, to please the people you dislike – don’t ignore the things you’ve always loved to do in order to “pay the bills”.

The person who is doing what they love, will always out-compete, out-succeed, the person who is just doing it to pay the bills.


“If you don’t know who you are it’s over,” Gary said.

What does that mean?

Exercise: Write down the ten things you value most in the world.

Do you really value them? Dig deep. Write them down again.

Dig deeper. What are you doing about them today?


Gary doubled down on documenting because he realized he has the responsibility to help young people who might get sucked into the wrong message.

“I cut through the bullshit,” he says.

For me, this is why I STOPPED writing about finance.

I find most finance writing to be boring and BS. But I did double-down on my own stories of failure and how I came through the other side.

And then I double-downed again and again.

For me. telling stories honestly was a way of doubling down and has opened so many opportunities for me.


“There’s never been a day since I was 22 that haven’t been operating a business,” Gary said. “Gary V is my side hustle. I don’t spend 100% of my time building a brand.”

He operates and runs businesses because he knows he couldn’t “talk” if he didn’t.

Too many people lecture or write about entrepreneurship or art without actually DOING it a single day in their lives.

Everyone is a critic. Only a few people DO.

“Personal Branding” is a way of lying.

Don’t change yourself into a brand.

Personal branding will kill you. Personal DOING will save everyone around you.


Years ago, no one believed you could choose yourself. You needed gatekeepers. You NEEDED someone who was not qualified to say, “I like you”.

Now we have YouTube, Instagram, self-publishing, easy tools for entrepreneurship, and many platforms to choose yourself.

“Now it’s the standard,” Gary said. If you cut out all the reason why you can’t do something, then you cut out all the infrastructural and financial problems stopping you.

“The only thing left is your f-cking head.”

So is Gary a lunatic?

Of course he is.