Gary Vaynerchuk and the art of the great presentation

Gary Vaynerchuk Cover Image.jpg

Chances are, at some point in your life, you’ll be called upon to get in front of a large group of people and say a few words. Maybe you’ll be tapped to give a pep talk at the monthly sales meeting. To host a breakout session at the conference in Toledo. To toast the bride on her special day. Or to be the one who delivers the eulogy.  

Regardless of the venue, no matter what the subject matter…all eyes will be on you. And how you perform in that moment matters. A lot.

Will you inspire awe? Or yawns? Will you be fast-tracked for that promotion? Or relegated to the bench? Will you create a moment you and your audience will remember forever? Or will it be a lost opportunity that you regret until your dying day?

It's not something we're born with

The ability to captivate a crowd isn’t something you’re born with. It’s a craft, cultivated and honed over time. Even the seemingly effortless, silver-tongued performances of legendary orators such as Martin Luther King Jr., President Obama, Steve Jobs and John F. Kennedy were achieved only after grueling hours of editing and rehearsal.

Over the past several years, the pantheon of the world’s most popular and influential speakers has witnessed the addition of a relatively unlikely inductee. Gary Vaynerchuk is a 37-year-old businessman, Belarusian immigrant and self-professed ‘D and F student’ who made a fortune ushering his family’s wine business into the Internet age. Today, Vaynerchuk is busy cultivating a reputation as one of the most entertaining and sought-after keynote speakers in North America.


Vaynerchuk, who is known as @garyvee to his nearly million followers on Twitter, has been a salesman since he could walk, hawking everything from flowers (sold back to the neighbours from whose yards he had just uprooted them) at the age of five, to lemonade, sports cards and eventually wine. Today, the main product he’s pitching is himself. Vaynerchuk has written two bestselling books, Crush It and The Thank You Economy. His third book, Jab Jab Jab Right Hook, is slated for release later in 2013. 

Vaynerchuk himself is quick to acknowledge that the impassioned keynote presentations he delivers at dozens of conferences each year have contributed significantly to the building of his personal brand. But public speaking was something that he got into almost by accident. “I got a random email to do an Internet conference talk and I took it,” Vaynerchuk says. “And it just kind of started from there. It went really well. And I really enjoyed myself.”

Emboldened by his success of his first major public talk, he reached out to the organizers of FOWA (Future of Web Apps), a conference he was planning to attend in Miami in 2008 and offered his services as a speaker. “That went over super well and I was like, ‘Okay, I’m onto something here.’ And then things just kind of took off and then there was the book (Crush It) and things kind of went from there.”

Having had the opportunity to watch Vaynerchuk speak at the Social Mix 2012 conference in Toronto last summer (where he dazzled a large audience that had been listening to presenters for seven straight hours) and as someone who helps executives improve their presentation skills, I was eager to learn more about Gary’s process for preparing for a high-profile keynote. I also wanted to get some insights into some of the seemingly contrarian or controversial choices he’s made along the way in the development of his personal speaking style.

On the virtues of T-shirts and hoodies

Many presenters, for example, would feel compelled to wear a suit for a major keynote. Vaynerchuk’s standard attire for one of his talks (for which he’s typically paid well into the five figures) is a pair of jeans and either a T-shirt, hoodie or collared shirt (untucked and with the sleeves unbuttoned).

“For 90% of the talks I do, I fly in the day of and fly out the same day, so it’s kind of a necessity,” Vaynerchuk says. “It’s the outfit of the sport I’m playing, which is extreme travelling and speaking. I don’t think the lighting, I don’t think the slides, I don’t think the mic, I don’t think the room, I don’t think the attire impacts. I understand and respect why someone would say all those things are really important. But for me, I like to let my words and my energy on the stage do the talking.”

 "I'm Saturday Night Live. I'm not The Academy Awards."

And in an era in which many presenters use PowerPoint like a human shield, Vaynerchuk eschews it altogether. You won’t see a single slide or bullet point in one of his talks.

“You know, listen, I’m not joking when I say I was a D and F student, right? The thing other great presenters do, like slides or something, I’m not good at it. I’m just not,” he says. “What I’m good at is building businesses and being an innovator and then moving quickly and absorbing it and going into the world and talking about it in a story-telling format. I’m improv. I’m Saturday Night Live. I’m not the Academy Awards.”

A penchant for colorful language

What Vaynerchuk does use, however, are four-letter words. And he uses them with the zeal and gusto of a sailor on weekend leave.

Whether he’s speaking to a tech crowd, a real estate crowd or pretty much any other conference that’s clamoring to add his star power to their agenda, audience members can plan on hearing at least a few dozen colorful word choices (e.g. shit, dickhead, rat's ass, douchebag and, of course, many creative variations of the f-bomb) that would get most other presenters reprimanded by their bosses or severely scolded by conference organizers.

Not only is he able to pull it off. His presentations typically end with a standing ovation.  

So where does the penchant for colorful language in his talks come from? “I was very affected by Chris Rock and Eddie Murphy and Richard Pryor,” Vaynerchuk says. “I used to listen to those peeps in my car in junior and senior year all the time. And I feel as though when I look at myself give a keynote – and I don’t really watch the videos or anything of that nature – but I can feel what I’m doing up there. I feel like I have a little bit of that comedic delivery. Pryror and Murphy and Rock…they have some pretty good mouths on them and I think that affected me."

What's the biggest mistake other presenters make?

One thing that can’t be debated is Vaynerchuk’s success as a speaker. After all, there aren’t many relative unknowns who find themselves represented by CAA, the same talent agency that handles the likes of Anderson Cooper, Cindy Crawford, Jimmy Fallon and Dr. Oz. Without any formal training, without being a great student and without years of experience on the stage, Vaynerchuk has made his mark as an exceptional storyteller, able to hold large, diverse audiences in the palm of his hand for 60 minutes.

When asked about the biggest mistake he thinks most other presenters make when preparing for or delivering a talk, he is unequivocal in his response:

“Not respecting the audience."

"I think that’s the number one thing that I feel. They don’t respect the audience. A lot of people give the same talk no matter where they go. I have a general outline but I always adjust to the context of the audience. I just think people don’t absorb the room. They don’t understand or read the room,” he says.

“One thing I’m proud of is I adjust for every talk. There have been talks where I’ve cursed a couple times and I feel like the audience isn’t enjoying it. Maybe it was in a conservative part of the US…and I’ve walked away from it…even though it’s something I do quite a bit. I think adjusting for the reality of the current state of the audience that they’re giving the talk to. Not being in the place of respecting the audience is what stands out to me.”


If Vaynerchuk had his way, he’d also spend much more time engaging with the audience in a ‘Q&A’ format. “This is something I’m obsessed with,” he says. “I feel like the reason my speaking career is going so well is that I end with Q&A, which I firmly believe is the best 20 to 30 minutes of the content. And then it’s the last thing that they remember.”

“We’re living in a different world,” Vaynerchuk says. “If we were living in the 70s or the 80s I could just give the same talk over and over forever and never hit enough audience to be stale. But now you know, especially from what I do for a living, people go online. You have to stay very fresh. Q&A is the best way to stay fresh. And more importantly, this is all predicated on bringing value to the audience. The best way to bring value to the audience is to answer their exact questions. The uniqueness of the Q&A and the fact that you can answer their questions on the spot really separates the people who know their crap from those that don’t. That’s something I really enjoy and it’s something that I can bring a lot of value to compared to the marketplace.”

His favorite talk(s) 

So…of the many of talks Vaynerchuk has given, which is his personal favorite?

“I just did one in Houston. It wasn’t recorded but it really felt great. I killed it,” he says. “I would tell you that the ‘Inc. 500’ one and the ‘Web 2.0’ where I said ‘Stop watching fucking Lost’ really put me on the map. The Inc. 500 one is the modern-day go-to for a lot of people. The other one hands down was my ‘coming out’ party, so I always have a warm feeling for that talk.”

Gary says it's his wallet, not his smartphone, in his front-right pants pocket.

Gary says it's his wallet, not his smartphone, in his front-right pants pocket.

What's in that front pocket? 

If you’ve seen Vaynerchuk speak, either online or in person, you may have noticed a bulky, rectangular object in his front-right jeans pocket. I had assumed it was his iPhone. But when he pulls out his smartphone as a prop during his talks, he pulls it out of his back pocket. So what the heck is that in his front pocket?

“It’s my wallet," he says. "I definitely have like a George Costanza wallet. Too much stuff in it.”

On the importance of public speaking to his brand

For a self-professed hustler with a lot of different businesses on the go, where does Vaynerchuk rank his public speaking in terms of the importance of building his personal brand?

“I would say that in 2008 and 2009, it might have been third or fourth on the list,” he says. “But it could be number one right now. It’s a very big part of the awareness of who I am. And it’s something I think I’m pretty good at. I would say it’s the top pillar of my career.”

And finally, for a guy who is paid to entertain audiences, who's on the list of speakers that Vaynerchuk would pay to watch?

“Boy…do I not like consuming content,” he responds. "Probably the great stand-up comics like Chris Rock, Jerry Seinfeld and Don Rickles. I would say stand up comics at the top of their game. That's where I would go.”