Gary Vaynerchuk - #AskGaryVee: One Entrepreneurs Take on Leadership, Social Media, and Self-Awareness

TO THE VAYNIACS AND THE VAYNER NATION, AND ALL THE PEOPLE WHO HAVE WATCHED EVEN ONE VIDEO OVER THE LAST TEN YEARS. YOUR ATTENTION IS MY OXYGEN.

Nothing I do is possible without the support of my family. My heart belongs to my wife, Lizzie, and my kids, Misha and Xander. As always, tremendous thanks also goes to the rest of my family: my parents, Tamara and Sasha; my sister, Liz, and her wonderful husband, Justin, and their kids, Hannah and Max; my brother, AJ, and his wife, Ali; my grandma Esther, my fantastic brother-in-law, Alex, and his wife, Sandy, and their kids, Zach and Dylan; and my mother-and father-in-law, Anne and Peter Klein.

A huge thank-you to my team, aka the Dope Den: Steve Unwin, Zak Moy, David Rock, India Kieser, Alex De Simone, Andy Krainak, Andrew Greif, Staphon Lawrence, Brittany Hoffman, Siddarth Astir, and Rebecca Wright.

My gratitude also goes out to the whole team at HarperBusiness. And especially to Hollis Heimbouch, who says this is the best book Ive written. Thank you for your consistent support and allowing me to roll the way I need to.

Finally, thanks again to my writer, Stephanie Land, who beside my brother and dad has been my closest partner in business. I cant believe this is book number four!

On February 21, 2006, on a YouTube channel with zero followers, the worlds first wine video blog launched. Without fanfare, it opened on a guy in a blue sweatermaybe it was black, the bad lighting made it hard to tellseated in front of a blank beige wall. On the table in front of him rested three wine bottles and a small, dark bucket that looked like it might have once held a potted plant. His skin was sallow in the sickly fluorescent light that barely illuminated his face, but he had a wide, optimistic smile. Looking straight into the Flip cam, he announced himself to his nonexistent audience in a subdued, serious, but friendly voice: Hello, everybody, and welcome to the very first episode of Wine Library TV. Im Gary Vaynerchuk. The echo was so intense he might have been filming inside a cave.

Over time the show got more dynamic and exciting. The host started to let his huge personality shine. He wore Jets shirts. He paired wines with Lucky Charms and described flavor profiles in colorful, colloquial language, like grape-flavored Nerd candy and dead deer mixed with cherries.

He filmed another 999 episodes before announcing on March 14, 2011, that the show was over.

Well, not quite over. On that same day he launched Daily Grape, a kind of Wine Library TV 2.0 for the mobile era. That lasted eighty-nine episodes. And then he realized he really was done. He loved wine but he was an entrepreneur first, and there were just too many other things to do.

That character was me, of course. At the time I really did think I was done with daily video blogging forever. I could imagine the occasional interview or one-off video (have you ever seen my Monday Morning Motivational spot?), but a full show was too much. There was only one thing I didnt count on: you, Vayner Nation. I missed you! I missed talking to you every day. I mean, sure I could talk to you anytime I wanted to on Twitter, Instagram, or Facebook, but video elicits a different energy and encourages a spontaneity and vibrancy that cant be replicated on any other platform. I should have known that something was missing in my world when I realized that during every forty-five-minute speaking engagement the part I most looked forward to was the last fifteen minutes of Q&A. In fact, at one point I seriously considered making my whole presentation nothing but Q&A forever.

Meanwhile, the emails kept pouring in. Despite access to three books and hundreds of videos, people still had questions about how to successfully use social mediathe new platforms and the old standbysto build their brands, or how to market with native content, or even just how I do what I do. There was so much content I wanted to put out to help them, but with all my other obligations at VaynerMedia and elsewhere I just couldnt get to it.

Then DRock emailed me. DRock is David Rock, and he wanted to make a short film about me. The story of what he did to convince me to agree shows up somewhere later in this book, and its a good onea classic example of how to get yourself to the next professional level. He followed me around for a day and produced a gorgeous short film that perfectly encapsulates my entire philosophy about business and entrepreneurship. Its called Clouds and Dirt. I enjoyed working with DRock so much I hired him to create videos for me full-time.

Then I looked around and saw that by bringing him on board I had accidentally formed the perfect content creation teamDavid for video, Steve Unwin for copy (a job eventually shared with India Kieser), and Zak Moy for design. On a whim, I pulled them aside and announced that I wanted to film a video, and they were going to help me.

And thats how on July 31, 2014, on a YouTube channel with 30,000 subscribers, one of the worlds first business Q&A video blogs was launched. It opened on a guy in a blue-striped golf shirt smiling into the camera: Hello, everyone, and welcome to the first #AskGaryVee. Though the first episode started off almost as low-key as its wine-themed predecessors, by the second, the light and sound quality were professional grade and the host was bringing hard energy and straight thunder. He started posing weird random objects, Jets paraphernalia, and eighties collectible toys on the sleek blond wood table in front of him as he answered his viewers questions about social media, marketing, branding, and more. Subscriptions to the channel and eventually to the accompanying podcast ballooned as viewers kept asking questions, and he kept answering them.

At first I thought the show might be an every-now-and-then thing, but it was like riding a bikeas soon as I filmed the first episode, I wanted to do more. And so we did (DRock, Steve, and Zak didnt know what hit them). Its a challenge, of course. The world is much more mobile and much smarter than it was in 2006, when I started WLTV, and there is a lot more competition for eyeballs even than in 2011, when we finished Daily Grape. Which means I have to be even better. And I think I am, because Im speaking from five more years of experience. Thats five more years of watching new technologies rise and fall, experimenting with platforms, advising clients, and talking to people about their dreams and goals.

Thats one of the things I love best about The #AskGaryVee Show. Its not a platform from which I talk about things that are important to me; its a place where I talk about things that are important to you. You, the viewers, entrepreneurs, executives, and dreamers are the inspiration for the show just as the wines were the inspiration for WLTV and Daily Grape. And just as I could never run out of new wines to taste, there will never be a day when theres nothing new to say about the state of business. Its a constantly evolving and growing topic.

The other thing I love about this show is that in the end, I really did figure out a way to extend my favorite part of my keynote speeches. If youve never seen me onstage, I model my performance after the comedians I idolized in my youth, like Eddie Murphy, Chris Rock, and Richard Pryor. My presentations are salty and brash, but even as they shock they tend to make people laugh. Hopefully, they also make people think. I like the Q&A part best because thats the moment when people realize that Im not a clever speaker with a few good ideas, but a devout practitioner with endless ideas. I can literally see the skeptics expressions switch from cynicism to admiration and respect as they realize that they can ask me anythinganything!and I wont dodge and I wont rehash and I will do my absolute best to give them detailed, tactical answers they can start using right away.