Why and How Gary Vaynerchuk is Still Killing it

Content marketing has been in the spotlight for a long time. But if you think content is king, context is god, according to entrepreneur, author, and wine aficionado Gary Vaynerchuk.

Vaynerchuk kicked off the new year by announcing he would do one interview every day of 2013.

I could not miss this chance. Despite my initial speechlessness and momentary rambling, Vaynerchuk patiently answered my question about community. Why was he so quiet in 2012? Why did he choose not to make more noise?

“I didn’t waver on my commitment to community. I just wavered a little on content,” replies Vaynerchuk coolly.


Despite not being the most verbose, Gary V still gets back to a ton of his followers. He still focuses on context: the way he is publishing, distributing, and promoting his content. I saw a photo of him with rapper Jay-Z, and tweeted him around a week after our conversation (assuming he wouldn’t remember I interviewed him and give me preferential treatment) asking him how they had met. He promptly replied with, “sxsw.” (Looks like I’ll have to make the trip this year.)

Under his suggestion, I watched his INC 500 speech. Watching that speech led me down the rabbit hole to his RE/MAX speech and his PCBC speech. I’d also previously seen him speak at Jugnoo’s Social Mix. Vaynerchuk’s speeches are repetitive, akin to a comedian’s routines. Here’s his opening:

1. He starts off with: “Who here knows who I am? Ouch, that hurts.”

2. “I started as a five year-old entrepreneur. You know Big Wheels? I used to ride that around my neighborhood collecting cash like a little Tony Soprano.”

3. Drug dealer joke. Baseball card story. Then, father pulls him out of baseball card business on the morning of his biggest take yet, in order to work at the liquor store. 13-year-old Gary Vaynerchuk cries all the way there, and composes himself before stepping into the shop. Then his dad tells him he’ll be paid $2 an hour, and that’s when he really starts crying.

4. 16 years old, comes out of basement from bagging ice at the liquor store daily and his eyes are opened to the world of wine.

Gary’s speeches are perfect examples of why content doesn’t matter as much as context. The content is effective because the majority of people at these keynotes don’t know him yet. His followers still invariably love the speeches and chuckle at his jokes. His continued relevance is a sign of how effective his context-heavy strategy is.


Every piece of content Vaynerchuk churns out sets up context. For example, Vaynerchuk once acknowledged that he couldn’t compete with Bill Gates, Mark Zuckerberg, and Warren Buffett. Vaynerchuk knows he has the potential to hit a billion (or “a billie,” as he refers to it), but not 40 billion. Despite his ambition, he remains honest. He urges his viewers to do the same.

“Being honest with yourself is very hard,” emphasizes Vaynerchuk. “If I ask them, are you good enough to be Beyonce? No, I can’t sing like that. Are you good enough to be LeBron? No, I can’t shoot like that. For some reason, in business, people lie to themselves; they don’t think of it as skillsets.”

Effort, trying, and hustling alone are not enough. You need to face the truth:  What were you good at as a child?

 “I wasn’t thinking about building the baseball card show, I wanted to be the best guy at the baseball card show. That’s what translated for me in tech: I was the best at Facebook, Twitter, or Tumblr, or I was trying to be, versus building the next Facebook, Twitter, or Tumblr, and that’s because I was honest with myself,” acknowledges Vaynerchuk. “If you were at heaven’s gate, and you were asked what you were best at, what would be your answer? Whatever that is, do more of that.”

Honesty aims you in the right direction. Vaynerchuk still recommends always punching above your weight class. Email people you don’t think you can get to. “Being realistic is important, but being ambitious with realism mixed into it: that’s a winning formula.”

Part of Vaynerchuk’s unique DNA empowers him with the intuition and courage to go all-in on new social platforms early. As he mentions in this FP Reach interview, betting early is an advantage that enables users to acquire a large number of followers relatively easily.


“The truth is, I’m not really Nostradamus. I actually am a fast follower,” Vaynerchuk admits. “When I saw something (on YouTube) with a million views in late ’05, I started Wine Library TV in February ’06, even though I first saw it in March of ‘05.”

After Vaynerchuk flirts with the platform a little bit, if it feels right to him and it can scale, he will bet big.

“I’m just so all-in that once I do it, and I do it early enough, it may feel like I’m predicting. I’m not predicting, I’m reacting,” concludes Vaynerchuk. Vaynerchuk’s all-in mentality extends to his daily interview initiative.

He contributes to this content these bloggers distribute through all their platforms, which changes up potential readers’ contexts. This is also going to highlight many areas previously unexplored by Vaynerchuk’s vlogs and speeches, such as topics ranging from lifehacking to organization health. The beauty: many of his interviews can be done while he’s in a cab, or about to board a plane. He’s betting that a young reader, or a young writer, of one of these interviews will provide him with an opportunity a decade down the line. He bets on patience.

Like everything else on his plate, Gary V doesn’t do the interviews only because he’s a good guy. He does it because it sells stuff, and it is good for business.