How Would You Spend Five Minutes with Gary Vaynerchuk?

How Would You Spend Five Minutes with Gary Vaynerchuk?

Gary Vaynerchuk is the hottest person in media right now.

Since July 2015, search traffic for his name on Google has increased by over 700%. His YouTube has exploded to almost 700,000 subscribers and his reach further extends to the 1.9 million followers he has on Facebook, the 1.7 million followers he has on Instagram and the 1.5 million followers he has on Twitter. His media agency, VaynerMedia, is now bringing in nine-figures and he has just recently launched a new business, VaynerSports, as he dips his hands into athletics, assumptively, a move to support the pursuit of his ultimate goal: to buy the unfortunate mess we call the New York Jets.

The big question then is - how did I, a normal guy from San Francisco, land a five-minute sit-down with Gary?

And more importantly, what should I actually do with it?

To answer the first question, part of the success comes from Gary’s approach to thought leadership which is to care for ‘the one.’ From the earliest days of his content creation, Gary has savored the individual who watched his videos, even from the times he was literally that, just a single individual. Gary has always made an effort to engage and support his followers, even if it is just a one.

The second part of my success in landing my sit-down with Gary started in August 2016. On August 12th, Gary put out a claim on social media saying he needed Quiet Riot paraphernalia for a new conference room in the VaynerMedia HQ.

I had no freaking clue what Quiet Riot was, but I logged onto Amazon and found a listing for an old Quiet Riot record, downloaded the image and sent it to Gary.

You want this?


Email sent. Hopes were high. Also please ignore my overly eager fangirling at the end of that email.

That same day, G-man came through!


I was in. But I still needed to buy the record. So off I went to Amazon to buy the record. Below is an image of the listing I just took and, as it turns out, there are still plenty more records for sale!


As you can see, the image is still unchanged.

I didn’t really know what I was doing at the time. I had no reason to talk to Gary and I live in San Francisco but I had found him pretty inspirational over the previous year I had followed him so I figured having a conversation starter and reason to see the HQ in New York wouldn’t be a bad move.

I told my close friends this move was going to be the catalyst to my hanging out with Gary one day and, despite how the traditional story goes, they actually agreed that this was probably going to pay off.

The record came in the mail about two days later and off it went via Fedex that day.


I have no idea why I included my Snapchat name. I never got a picture of the record but that ended up working out in my favor.

So that was that. I didn’t think much about the record until I had two notable calendar overlaps with G-man. The first overlap was in Boston at a conference I was attending called Inbound, Gary was the main keynote.

I pitched hard for a sliver of time at the conference. I had lots of back and forth with his assistant, Tyler, but I couldn’t get the win. Gare man was all booked up. I did try to catch him after his keynote speech, though, by the main stage.


As you can see I did my best but no dice. Gary, you left me hanging, bro.

The second overlap is coming up this June while I attend a conference called Next Gen Summit in NYC. Gary isn’t speaking, but that’s not a problem as I will be in the VaynerMedia hometown. It wasn’t until I booked up this fateful trip to NYC that I was able to snag a big Gary’s time in a one-on-one in the HQ. It took a few emails, but I was able to get back in touch with Tyler, lock up a phone call and make my case.


Believe or not, I do not actually email like a 10-year old all of the time, but, Tyler and I have shared lots of emails at this point so we are way comfortable and definitely best buds.

And that’s the story of locking up my sit-down with Gary Vaynerchuk. It cost me about $10.00 to buy the record on Amazon and another $10 to ship the thing to NYC. A total of probably 30 emails, about 70% of which were me, but we are here.

A relatively low investment of time and money, just some forward thinking.

The big question I am left with is, what do I do with my five minutes?

Obviously, my first priority is to get the fist bump. But after that, there is a lot of uncertainty. As I have analyzed this opportunity, there are a few things I think are critical to making this the best possible experience.

  1. Doing something that shows thought for his needs: Every piece of advice you could ever need for business is covered by Gary and made completely free online. I feel very fortunate to have these as a resource. He’s already given me a mountain of value so this isn’t the kind of opportunity where I want to roll in and ask questions or pitch ideas. It’s a moment to be thankful, show thanks and come full circle by bringing support to his needs.

  2. Thanking him: Not only do I want to thank him for the motivation he has supplied to me personally but to millions. Gary keeps it raw, unfiltered and his message reaches people who traditionally do not identify with motivational business talk. Gary is driving massive behavior change into our society that is absolutely helping to improve it. And I like when our society improves, so I want to thank him for that.

  3. A reason to continue our relationship: Meeting influencers is cool but fostering real relationships is what life’s all about. I am not out here trying to become BFF’s with the guy, but conversely using this opportunity as ‘that time I got a picture with so-so celebrity’ is not appealing. The motivation is to make this interaction much more of a ‘Chapter One’ rather than a lone standing encounter.

  4. Making sure he doesn’t talk the whole time, preventing the aforementioned goals: Gary likes to talk. I’m not going to the office to be the guy talking, but I also want to make sure the first thing I say doesn’t set him off on a five-minute tangent and then there goes all of our time. So, seriously, suggestions on this?

So while this is the general approach I am taking, I actually have no idea what I am going to say. I thought this was a cool story to share and since I am kind of at a blank approach right now, I figured you creatives of the internet may have some cool ideas on what you would do.

What would you do if you had five minutes with Gary Vaynerchuk?

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