What @GaryVee Is Really Doing With the #AskGaryVee Show

Kyle Reed
7 min readFeb 4, 2015

Gary Vee knows a thing or two about building things. Whether it’s wine, books, or shows, he is a master craftsman who is several notches above everyone else. And his latest project, the #AskGaryVee show is another masterpiece in the making.

After watching Episode 63 of the #askgaryvee show something hit me, “Gary Vee is a genius.” Now to be honest, I have said this many many times, much to my wife’s amusement. But this time it was different. All the pieces fell together in front of me and all the years of following Gary all made sense. Let me take you down this journey…

Back in 2006 Gary created a show called Wine Library TV aka the Thunder Show. Like most, I tuned in every day to see what Gary was going to do next. It wasn’t about the wine for me, but more about his personality. I was fresh out of high school at the time and never even thought about drinking a glass of wine. But it didn’t matter for me, this guy was so entertaining he could have been selling pencils and I would have watched. He was changing the game one sip at a time. And in the midst of this, was selling a lot of wine. This led to the start of @GaryVee as we know him today…entrepenuer and marketer all in one.

Fast-forward a couple or more like 6 years to Gary and his keynotes.
We have all watched them on youtube (I’ve seen almost every one, so I consider myself an expert in this matter). His talk almost never changes: He ask how many in the audience know who he is, tells his story, and then moves to a point he wants to nail home (often about hustling to get stuff done…stop playing madden or watching lost, marketing in the time we live in or the power of caring). But, in every keynote he always tries to do one thing, Q&A. This might be something you skip over, but I never do. I love his Q&A time. This time seems to be most important to Gary as well. I think he gets energy as he hears from others and helps. In fact, that seems to be all he ever wants to do when he does keynotes. He often remarks about only doing Q&A sessions for his keynotes.

Gary loves to answer questions. Email him and he will respond. Send an @ reply and he will answer. Gary has the answers, he just needs to find the questions. Which leads us to the #AskGaryVee show. After the release of his book Jab Jab Jab Right Hook, Gary moved to focusing on content creation. What better way to do this then take questions from his Million plus twitter followers. And after watching Episode 1, I was hooked and so was Gary.

But episode 1 did a lot more than just give him an outlet to do Q&A. For I believe his desire to answer our questions was his way to create an unstoppable media company. And this is where his genius becomes evident.

Let’s dive deeper

With the first episode of the #AskGaryVee we get exactly what we love about Gary, personality, honesty, and passion. I remember when my question was answer in episode 9. I felt like we were friends and I had made it. I even had people tweeting me congratulations on making it on the show. And for the first 20 or 30 shows it appeared that Gary was having fun answering questions and giving back to his community…he was jabbing.
But really, he was building something. He was setting us up for the longest right hook in the history of the game.

Gary loves to help people. The why of the show is to help people. But what you really have to do is dig deeper to see the underlining why. For I believe Gary has about 4 or 5 other reasons for the #askgaryveeshow.

  1. Content
    This show is a content machine. It centers around gathering questions, but alternatively is used to create content for all the channels Gary uses to spread his brand. What channels? Twitter, Facebook, Medium, Instagram. GV.com, Linkedin, Snapchat, YouTube, SlideShare, Email…and I’m sure I missed a couple, but you get the idea. The most important thing here for Gary is gathering tons of micro-content he can use for the rest of the week. He even said it himself, he is playing the long game.
    This show produces so much micro content he had to hire staff to keep up.
  2. Staff
    You don’t have to watch the show long to know the people behind the camera. First we have my man, @DRock. @DRock has his own interesting story: Offering his services to create a day in the life video featuring Gary (Between the Clouds and the Dirt). @DRock hustled his way to impress Gary, and Gary saw the opportunity/need for more video content, so he hired him. But @DRock’s not the only one, there are 4–5 more staff members that work on the show.
    There is @TheRealDeis who is a content creator, capturer, and a key figure for the show.
    There is @Stunwin who is editor-in-chief for Gary Vee and helps write content with Gary and manage his brand.
    There @zakmoy who designs shirts, posters, and memes from the show and other content Gary produces. Like these.
    There is India aka @heartbread who is another key content creator and helps gather questions submitted for the show.
    These are just the people we see. There’s Staphon who had to count the almonds, and there’s Matt DeMayo who is Gary’s assistant (seen here). I’ll stop there, but as you can see, the staff is robust and great. And Gary uses each of them to create each show and gather micro-content. This point alone should show you his brilliance, but let’s keep going.
  3. Crowd Sourcing
    The show centers around the crowd that gathers. Without the crowd there would be no questions. Gary created a place of gathering, sharing, and learning. This is the ultimate form of crowdsourcing. Using your audience to create content, and most importantly, listening to your crowd. But this type of Crowd Sourcing goes even deeper. Because we don’t see all the questions asked. We see about 3–5 per show. In fact, Gary could be taking every question and organizing them by category, subject, and demo for future content and products (which he might be doing). And if this sounds crazy, refer to point 2, he has a staff to do this. What better way to see which way to take products, books, ideas, and content then to hear from those that follow you all while giving away your time and energy. We are now 66 shows in (as of 2/3/15) and you better believe the equity in the jabbing bank account has been filled by Gary. His withdrawal, when taken, wont even feel like an ask, but more like something we get to do.

“I attract a crowd, not because I’m an extrovert or I’m over the top or I’m oozing with charisma. It’s because I care.”
Gary Vaynerchuk

4. Distribution
If Gary is all in on Instagram for 2015, then YouTube is his lover on the side. With each video he post, subscribers and view counts grow. Whether you were there for the first episode or discovered half way through, the show allows the binge watching opportunity that YouTube is known for. YouTube is the warehouse where the content gathers and then is distributed to every social network you can find Gary on. He is even creating micro-content of himself in the show for fans of the show (that was as confusing to type as it was to read). The key in distribution for Gary is time. He takes the time to answer the questions and knows he will get a huge return on his time to distribute more content later. What better way for a very busy person to use 15–20 minutes of his day to soak up as much as he can. He even said it in Episode 64, how do you find extra time? You work smarter with the time you have. If Amazon is the distributor of the internet, then Gary is distributor of content creation.

Ultimately, Gary has been focused from day one. Going the opposite direction of marketers. Finding places people are not and beating them to the spaces we all want to be.
In a recent episode he said something I loved: “If you want to be an anomaly, you have to act like one.”

The geniusness of Gary Vaynerchuk is seen often, but this specific example started long before episode 1. This content plan was well crafted, thought out, and perfectly executed. And just when you think Gary is slowing down or others are catching up to him, we all realize we are several steps behind him. Much like the beautiful science of boxing, he has been setting us up all along for the right hook.

This is the way you become a media company.

Cheers to you Gary and thank you for all you have done.

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Kyle Reed

Digital Media Company owner. Enneagram 2. Things I love: STL sports, @cremacrema, @garyvee, green peppermints.