Gary Vee

Gary Vee

GaryVee needs no introduction. If you don’t know who he is, just ask anyone. Or go on LinkedIn. Or Facebook, or YouTube, or your podcast player… he’s everywhere.


Guess what?


We interviewed him.


And we didn’t throw him any softball questions. (Who throws softballs to GaryVee?) We asked him what he’s going to do after he buys the jets, what he thinks about being the modern-day Robin Hood, and more.


This is the episode of the Cannonball Mindset you can’t miss.

GaryVee Is Robin Hood: He Takes Ideas From the Clouds, & Delivers Them to the Masses

I told GaryVee he’s the modern day Robin Hood. He agreed. (And then told me I was a genius. Almost.)


<“You don’t get national holidays for buying the Jets. You get national holidays for moving the culture.” — Gary Vee>


Here’s what I mean, and what he said: These collaborations, ingenious business ideas, thoughts, plans, strategies, etc., were previously only available to  a select few: the incredibly successful, the super rich, the Rockefellers. What Gary Vaynerchuk has done, is deliver those business ideas and strategies to the masses. For free.


He puts out an insane amount of free content, giving away all his best ideas. He charges his fees to Chase, Budweiser, & A-list celebrities. Huge logos invite him all over the globe for keynote speeches, which he records.


Then puts all these ideas on social for free.

GaryVee Last Great Convo Was With Travis Kalanick

I asked him about his last truly great conversation. He’d just spoken 2 days before with Travis Kalanick, former CEO of Uber. Gary loved their conversation.


I wasn’t a fly on on the wall for it, but Gary said their talk was inspiring and thoughtful. Here’s another takeaway I had from what Gary said about this conversation: GaryVee thinks past the noise.


Travis went out from Uber under a lot of fire, and perhaps some of it was well-warranted. But Gary was willing to think past the mistakes and listen to the inner genius.

Here’s What Mrs. Vaynerchuk Taught Her Son:

GaryVee talks pretty incessantly about his parents. I wanted to know more about his childhood, behind the surface-level. Here’s what he said his mom taught him, that he thinks every parent should replicate:


“Disproportionately overlove your child, in parallel, eliminate all delusion.”


<“Disproportionately overlove your child; in parallel, eliminate all delusion.” — Gary Vee>


He broke it down:


His mom loved Gary to heaven and back. You’ve probably heard him say, “When I was 9 years old and opened the door for an elderly woman at a McDonald’s, my mom reacted as if I won the Nobel Peace Prize.”


But her overlove for him never kept her from giving him a large dose of reality.


Gary has replicated these concepts in his family. He tells his kids they can do everything. He believes in them. But he also told his 6-year-old that he would never dunk. Why? DNA.


Love + Reality = GaryVee confidence-building tips for parenting.


(Gary talked more about it in this article.)

Ditch Fear & Stop Caring What Others Think

Ok, so those words aren’t what he said exactly. Gary’s words: “Try shit & don’t fear failure.”


He summed up his meaning with a follow-up question: “Do you understand what happens when you stop worrying about other people’s opinion and failure?” Everything takes off.


At the end of fear is the start of passion.

Blaming Others Gives Them Way Too Much Power

Gary blames no one. He says he believes any issues in his life are one person’s fault: his own.


Why? Because then, he owns all the power to fix the issues. When it’s “Taylor’s fault,” Taylor has the power. You have checked yourself out of control. Can anyone really imagine Gary giving anyone else the power of his own life?


Besides, when someone blames another person, it’s because of one thing, he said: hypocrisy. The blamer has some issue in their own life they are hiding. There’s something underneath, and everyone can smell it.


“Hypocrisy smells.” — GaryVee

“What Happens After You Buy the Jets?”

If you’ve been around him long, you know he’s obsessed with buying the Jets. What happens after?


He broke it down into 3 specifics:


  1. It’s not really about the Jets. It’s about the chase and the attempt to buy the Jets.
  2. Micro-moment of depression: “Wow. I actually did it. What now?” (This lasts for 0.2 seconds.)
  3. “Let’s win the SuperBowl.”

The 1 Impact Gary Cares About More Than Everything Else

Gary gets a ton of fanmail. He receives thousands of comments every day on social media. His inboxes are full of thank-yous, let’s-meet-ups, and can-I-buy-you-coffees.


But there is one thing he said he loves: “One person, telling you they were going to take their life, but my video and podcasts made then stop, is disproportionately greater than if  I bought all 32 NFL teams. And I mean that.”


Gary cares about impacting people. He cares about the emails he’s received of suicidal individuals who stopped, all because they heard him on social media.


His mission, he said, is to impact culture in a generational way. He wants to see people chase their dreams, find their passion, and drop the fear. Find their confidence. This drives him, and he gets the opportunity to hear about it frequently. He’s aware of his impact, but he takes no credit for it.


He believes he owes it to his parents who took “the clay” of his life, and formed it into who he is today. According to him, his parents and the Internet age are what really created his success.

“50 Years From Now, What Do You Want Your Legacy To Be?”

I ask this to every guest, no exceptions.


Gary’s answer was 1.2 seconds:


“He gave way more than he took.”


And that’s why he’s GaryVee.


This Cannonball Moment was based on a podcast with GaryVee. Click here for the full episode.


(If you don’t use iTunes, click here instead.)

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