Challenge Accepted, Gary Vaynerchuk Alpha Doodle

By bobby.t

February 24, 2022


This was such an amazing interesting story and for those who rather watch than read please check out this video here.

Who is Gary Vaynerchuk aka GaryVee?

Gary Vaynerchuk is the chairman of VaynerX, a modern-day media holding company, and the active CEO of VaynerMedia, a full-service advertising agency servicing Fortune 100 clients across the company’s five locations and I got a chance not just to meet him but also found his one of one doodle. 

Interviewing GaryVee

So, Gary Vaynerchuk came down to Edmonton, Alberta, for his first keynote in 2021. Luckily before his talk, I was fortunate enough to have a 10 minutes interview with him for my podcast.

My interview was only 10 minutes, but it felt like 10 seconds with Gary because he was so insightful. 

My questions were more about my community, and I asked for advice for Black Canadians and reference to what traits from his new book would be valuable for Black entrepreneurs and creators.

What are Alpha Doodles?

It all goes back to September of 2021 when Gary Vaynerchuk had a series of doodles that went to auction at Christie's Auction House. He managed to sell five digital doodles for a total of $1.4 million; yup, you read it right, it was for $1.4 million. 

This artwork sale destroyed many acclaimed and famous artists, as he is a new and emerging artist in the space of NFTs'and now original artwork. 

You may have gotten the idea by now why I wanted the doodle.

GaryVee challenge in Edmonton

Fast forwarding to October 21 that month, while in the city of Edmonton, Gary at the Fairmont Hotel MacDonald, left a gift where he put out a challenge on Twitter for someone to “figure it out.” 

The Mo’ You Know

Now I had no clue this alpha doodle was in Edmonton, and to be honest, I had no motivation to find that doodle, thinking it was likely already gone, but I had a friend who kept pushing me to check it out.

After the keynote, I debriefed my friend Moh, who discussed his day and the Twitter post Gary shared before the keynote.  

“It's at Fairmount” 

I was curious at first, but I did not want to go because I was super tired. It was a long day, and on top of that, I thought the doodle was gone.  More importantly, l didn't want to look like a crazy man coming to this prestigious hotel requesting if they could find a doodle from an artist. 

Nonetheless, my dear friend Moh convinced me to see if I could grab it.

Reaching the Fairmount Hotel Macdonald Front Desk 

You know that awkward walk that makes you feel like everybody is watching, judging, and wondering what you're doing? 

That's what it felt like to be walking into this hotel in the middle of the night. As I walked up to the hotel, I was met with anxiety because I immediately thought about what I would say to the front desk team. 

 As I walked through the doors, I was greeted by a friendly bellhop who asked about my day and greeted me. As I got into the main lobby, I took a right and was immediately greeted by two young ladies working the desk and instantaneously, I felt the pressure about what I was about to do or say; I did not want to sound stupid. As I looked at them, I made eye contact with both individuals, and then the lady asked, how can I help you?

So I cleared my throat through my mask and said,

“Hello, my name is Bobby, and there is an individual named Gary Vaynerchuk and D roc,  who recently were staying here and left a doodle. And both of them said that I could claim it, which they left for me in their hotel room.”

And then I just smiled through my mask. Once I uttered those words, I thought to myself I had already messed up; I used the nickname name of D-Rock, and I  should have chosen better words.

What was their Room Number? 

“Do you have a room number?”

Instantaneously, I drew blank, and I was like, holy cow. 

I don't even have the essential information to get this doodle. Luckily I remembered I got D-Rock's phone number and sent him a text message. 

Here's our room number, and I had an instant sense of relief. As I shared the room number, the staff at the hotel were able to pull up their accounts. 

 I couldn't believe the following words out of their mouths.

“Sir, I cannot let you in the room because they are still checked in”

So Close yet So Far 

To make them understand better, I showed them the picture of the doodle on my phone. The lady looked at me a little bit more puzzled, a little bit more intrigued. 

She then spoke to a colleague who then informed me that they could not let me into the room unless they had a direct conversation with the occupants that were staying there. 

Again, instant grief and sadness went over my body. I had to ask these fantastic and super busy individuals, who are actually at the airport, to take the time and speak to these front desk clerks.

I D-Rock yet again another text requesting if he could talk to these ladies. 

“cool, we’ll give him a call, Bobby, just give us five minutes.”

Almost Gave Up 

As I sat down, my mind flooded with thoughts like, is this doodle still here?

Did someone already claim it?

Am I wasting my time, these people's time and, even worse, both D Rock and Gary Vee's time trying to pursue this particular doodle?

As I sat and pondered all this information, I was texting my Moh micro-updates, but I didn't want to disappoint him; however, I didn't want to give them false hope that I was about to get this doodle.

What felt like five hours later, D-Rock called and gave these two ladies the green light,

“we're setting someone up to check the room to grab the doodle.”

Upon hearing those words, I got so pumped! One of the ladies behind the desk went upstairs to grab the doodle. Overhearing the ladies talk through walkie talkie’s

“Hey, I've checked the desk. I've checked the counter. This doodle is not here.

Do you know where they left it? “

With a big deep sigh and disappointment, I have no clue where they left it. Here is the picture again of the doodle.

The Gold Desk 

Just like in a movie, when that tiny detail, a small moment changes everything, happened. The lady downstairs asked the other lady in the room.
Did you check the gold desk?

I'll check the gold desk.

My mind was racing at this point; there's another place? What the hell was the gold desk??

30 seconds later, I heard,

“I have it on the radio. I'm coming back downstairs.”

I can't believe this is happening.

A Piece of Stationary, A Piece of Gold!

As I was handed the doodle, I gave her the biggest smile I could (through my mask), Thanked everyone, and I walked out the door excited for what was next.

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