I was trying to remember the exact day when I met Gary Vaynerchuk. It might have been at a private dinner hosted by the organizers of one of the most progressive social media events at that time, the BlogWorld Conference in 2008. I was sitting at the table with a small group of very smart people, including an obnoxious East Coast guy throwing down F-bombs, spouting off about the wine business as he sniffed open bottles at the table. His head was shaved, and he was wearing a green and white raglan baseball shirt and matching green sweatbands on his wrists, carrying on about his new book, Crush it. I thought to myself, "Who is this guy?? I've never met someone as outspoken about the idea of cashing in on [my own] passion. I need to become friends with Gary Vee."

I remember feeling a little out of my league at that table but desperate to make things happen in my startup, a new kind of brand strategy agency and video production company hybrid focused on storytelling and great content. A few months prior to BlogWorld, I cut the cord at a very comfortable and lucrative corporate job in Hollywood. I worked for several years on the team at Universal Pictures, home entertainment division. I had a $40 million P&L, walked the red carpet with movie stars, and was on the brand team in charge of the studio's biggest films at the time. 

2008 was also the beginning of the end for a lot of people; the Great Recession was just ramping up and I had no idea what was happening to the economy under my nose. I did have a sense that something big was happening in digital and social, and that's why I showed up to BlogWorld without a plan or agenda.

I graduated from Pepperdine University in 1999 with a degree in business. I was watching and studying the market closely when digital was really getting traction. I dabbled in tech and taught myself HTML to code my first personal website. Looking back, MySpace seems like a blip on my radar. So does Facebook and the moment Google acquired YouTube in 2006. Social media was hot new territory and there was a land grab, similar to what's happening on TikTok now, to stake your claim on emerging platforms. I joined Twitter in 2008 and created my first YouTube channel in 2009. 

Around this same time, and inspired by Seth Godin's book Tribes, I started hosting private events of my own in Los Angeles built around my new video series, Behind the Brand. These were fireside chats with me interviewing great minds on stage. In fact, one of my first events was with Godin, and there were about 900 people in attendance who each paid me between $50 to $100 per ticket to see Godin in person. 

I was stunned that so many people showed up. From that moment on, I understood the power of attention and how content is the new currency. I had unknowingly built a tribe of loyal, connected people in my community and it was suddenly worth a lot. I recognized that there was a short supply and high demand for inspiration, education, and access to innovative speakers at the time. No Simon Sinek or Mel Robbins in my purview yet. For comparison: travel, hotel, and event pass to Austin for SXSW or a conference like CES and BlogWorld in Las Vegas was expensive during the recession years when money was scarce.  

Having an actively engaged tribe wasn't unique. But I doubled down on the strategy and it earned me some unexpected attention in 2010, when Julien Smith wrote about me in his best-selling book, Trust Agents. I used my (limited) growing influence from the book and recent track record with Godin to invite Vaynerchuk out from New York to LA for a keynote about his new book, The Thank You Economy

I knew Vaynerchuk cared about getting the book into as many hands as possible. Not because of any optics or to boost his ego, but to make an impact. Expectations (or not having them) is a major theme for Vaynerchuk. For this reason, I didn't want to expect that he would offer, as a friend, to come out and speak for free. Instead, I asked what kind of book threshold he needed me to commit to in order for him to come out. His answer was 1,500 books--a cost of more than $30,000. Keep in mind we were still in the recession. $30,000 to me as an independent operator in SoCal felt like $30 million at the time. But I learned from the event with Godin that my tribe could do big things if we all pulled together. I guess I kind of discovered crowdfunding before it was popular. Within a few hours of announcing that I was planning something with Vaynerchuk, my tribe spoke and we easily raised the funds to buy the books. The rest is history.

Since then, Vaynerchuk's audience has grown 100-fold with loyal fans. But there are some who misunderstand the real Vaynerchuk (my wife was one of them). At first glance, he may seem like a foul-mouth narcissist who can't shut up about the Jets, giving business advice to entrepreneurs, how his hustle is different than your hustle, tireless predictions and pontifications, and slinging of admonitions for more of things like: self-awareness. Patience. Kindness. 

Vaynerchuk is obsessed about telling his story and has put his entire business life on camera since 2006. He preaches documenting versus producing, and not getting romantic about the quality of the video, as much as the quality of the content. "Value is the deliverable" he says. "It's the chopping [I love], not the tree coming down," he told me in a 2011 interview. If nothing else, Vayernchuk is about leaving a legacy. The lens through which he sees the world is based on how many people will show up at his funeral. This isn't a joke. Vaynerchuk has been a mentor to me but also a great friend. 

Vaynerchuk might tell you he got his start early selling lemonade or trading baseball cards with arbitrage in elementary school. He talks with a tremendous amount of respect and admiration for his parents, especially mother, whom he credits with teaching him unrivaled self-awareness and confidence. Vaynerchuk's family immigrated from communist Belarus in the 1980s to give Vaynerchuk and his family a better life in the United States. His dad opened a small local liquor store in the suburbs of New Jersey and with pure grit and determination started making a good living. 

Vaynerchuk was a terrible student in school and was near the bottom of his graduating class. Perhaps it was his active spirit or inability to sit still and focus on something he deemed boring, like social studies. Whatever the case, his teachers verbally abused and bullied him. They called him "a loser" and said he wouldn't amount to anything. 

Forgive the pop psychology here. But to me, the childhood trauma of moving to a new country, being raised by hard working immigrant parents who escaped a Communist regime and took nothing for granted, not knowing English well in the suburbs of New Jersey, and being bullied for not conforming to how academia thinks people should perform at school paints a clear picture of why Vaynerchuk is the way he is. 

Somehow he's able to use the hurt and abject cruelty of the past as fuel. Even more mind-blowing is that he goes out of his way to be generous and kind to those who may have wronged him. This is his essence. No vendettas, just a personal path to redemption and proving to kids (and adults) who may be getting bullied that they don't need to play by the rules of the establishment. Vaynerchuk wants to crush it. But he also wants you to find what makes you happy. "Everyone can do it ... there are so many ways to win," he says.

After graduating from Mount Ida College in Massachusetts, Vaynerchuk returned home to help with the family business. Vaynerchuk expected zero equity in the business and collected a modest $27,000 per year salary. While his friends were partying at Staten Island, Vaynerchuk toiled away seven days a week at the shop. No vacations. No holidays or time off in his 20s. If you can believe it, Vaynerchuk remained silent without a soapbox to speak, or anything to say, for nearly the first three decades of his life. Why? Because he was head down, busy working on and in the business.

Two classic Gary Vee quotes come to mind here: "You can't fake being good at push-ups.You have to just do the work." And, "you can't be half-pregnant [about your idea]. Go all-in." Vaynerchuk walks the talk. He went all-in on his family business and within a short time, when almost no one was selling wine online direct-to-consumer, Vaynerchuk grew the company from $3 million to over $60 million in revenue. He was also one of the early pioneers in content as a strategy, and Vaynerchuk launched a daily YouTube show called "Wine Library TV" to showcase his chops. His talent and charisma caught the attention of journalist Joel Stein, who wrote an article about the show. The attention catapulted Vaynerchuk to a new level of fame, including appearances on TV with Conan O'Brien.

When he eventually left the family business, he left without ownership stake or a cash payout. In fact, he left with nothing and reset his life, focused on executing his new plans to launch a media empire. "I didn't really have any experience [yet] so I needed the dirt under my fingernails," he explained. Vaynerchuk got to work building VaynerMedia with his brother AJ and other key hires. They blew it up, proving Madison Avenue ad industry naysayers wrong.

Vaynerchuk has been one of those people who has been predicting the future, and taking action on it since I've known him. His name should appear next to the word, "entrepreneur" in the dictionary. Vaynerchuk's a media company CEO, author, speaker, online personality, and more. He runs Vayner X with offices worldwide and has his hands in many verticals, including pro sports, tech, and food and wine, to name a few. He's an avid investor but also transparent about the opportunities he's missed, like passing early on Uber (twice).

Vaynerchuk told me, "Being an entrepreneur is like being a UFC fighter ... You're going to get punched in the face." He followed that by saying, "You also have to learn to love losing," as if to say that the market will reward winners and punish the losers. His advice to me on a regular basis is to not worry what other people think, or to dwell in the past. "It's bad for your neck to keep looking back like that," he says. Vaynerchuk is now investing heavily on what might be called Web 3.0 and the world of NFTs.

He tells me that he seems to know what people want or will want. He accurately predicted the popularity of online dating, the rise of social media and how attention is the asset, the sale of Instagram to Facebook, the rise in the value of trading sports cards, even flipping toys at garage sales. Over the last decade, he's become fascinated with crypto-currency and now NFTs (non-fungible tokens). 

Recently, he's launched VeeFriends--a website that he hopes will become a marketplace and social media platform of sorts for people who are creators, collectors, or curators. In addition to that, he's very passionate about helping to usher in Web 3, which people in the crypto world are hoping will become the future of the internet. It's a potential new iteration of the internet that would run on public blockchains rather than by major tech corporations.

Vaynerchuk has been in the crypto game for a long time, but the beginning of this year was when he says he really had an aha! moment about the future of NFT's and Web 3.

"I am an entrepreneur through and through and through and through," he says. "This whole Web 3 thing ... When I really had my epiphany moment in January around NFTs and Web 3, literally out loud--not like I normally do to myself--but out loud I said, thank you, God!" 

He says it wasn't until late December of 2020 that he really had a chance to study the future of crypto and the internet's potential third iteration. It became a bit of an obsession.  

"I had bought Ethereum many, many years ago, and I understood the concept of building on top of Ethereum ... I'd bought Bitcoin before Ethereum and loved both, and they were the only two crypto currencies I'd ever owned from 2015 to 2020. I was getting really re-kindled the last two years into sports cards. I had started looking at video games and comic books as alternative investments." 

Vaynerchuk's curiosity about the future of currency grew. After a friend introduced him to CryptoPunks, he went down a 50-hour rabbit hole learning about it. This was the moment where he decided that Web 3 was coming, and he'd better jump onboard to usher it in. He tells me that he feels that intellectual property, collectability, supply and demand, storytelling, community building, trading on popular culture, and collateralizing are all things he expects will move towards blockchain in the future. 

"Now I'm 45 and this is the third time I've [had] these spider senses. This was the exact same feeling--which is, I can't do anything else except spend every minute on this 'cause this is gonna be big. I didn't own a computer when I had an epiphany moment in a dorm room in 1995 that I was going to put my dad's liquor store on the internet. I don't know what to tell you. I did not own a computer, I thought computers were for nerds. In 2005 when I had the epiphany that social media and content was going to change the world, it had never even crossed my mind to be a known personality or do a TV show, radio show, local show, speak, nothing! I immediately sent somebody else to get a camera, sat down, tasted three bottles of wine, and started on February 20, 2006, Wine Library TV. And a couple of months later, I joined Twitter to promote it. And then everything that I'm pretty much known for started. Literally the moment before that, I was running a retail wine store and was a retailer, a businessman. And that's what I was going to do. So I know what my body does when my spider senses tell me the world's about to change. I believe that NFT infrastructure is going to change the entire society and I've gone head-first [into it]."

Vaynerchuk's new book is called, Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success. Here are a few top line lessons from my time with Vaynerchuk.

Everything Is Your "Fault"

It's really easy to be cynical and negative, and to sit in the place of being a victim of circumstance in life. But when you can take a step back and look at the role that you play in your own life, it changes the experience from you being a victim to you being in charge. 

 "When you believe things are your fault, you feel like you're in control and you have the ability to fix it," he says. "I feel like when you point fingers, it's an incredibly sad place to be. Because you feel helpless, which leads to a lot of levels of anxiety, depression, and unhappiness."

If you're not happy in your work, you can look at the people you work with, or the circumstances you're working in, and feel anger or frustration. Or you can look at the part you're playing and how you can adjust. I like to think about what I can control. Am I frustrated because I'm not getting enough sleep or eating well? Do I need to make more time for exercise? Do I need to stretch more? Am I not communicating my needs, or communicating my boundaries effectively? What can I adjust to be happier in the situation I'm in? And if I'm in a leadership position and something isn't going the way I'd like it to, then it's on me to figure out a way to right the ship.

"I'm aware that not everything is my fault. But I can tell you at VaynerX [with] 1,500 people globally, I do believe everything is my fault because my brain goes to this place ... I don't believe that I'm in charge of how everybody acts in every situation. But there is this beautiful symphony in my head of, 'This is my song. I am driving this car.'"

This leads us to Gary Vee's great love of accountability, and how it's empowering and shouldn't be a way we drag ourselves down. 

Accountability Doesn't Mean You're Getting Down on Yourself

"When people hear accountability, an enormous amount of people convert it into beating themselves up," he says. "Accountability is a beautiful thing. Deciding that you're a loser and beating yourself up ... judgement on oneself is a bad thing. There's such a fine nuance there. But this is something I'm trying to spend more time on and call out, which is why I'm doing it right now. Being accountable doesn't mean boo-ing yourself."

Vaynerchuk tells me that he believes aiming negativity towards ourselves is a product of our environment. There may be people in our pasts--be it friends, family, teachers, role models, etc.--who might have given us reason to doubt or look negatively at ourselves. I have my own theories on this: To me, it seems that being negative and criticizing ourselves is easier than sticking with something, and putting ourselves out there, time and time again, risking falling on our faces. 

Use Happiness Over Fear and Negativity

"The easiest thing in the world is to be cynical, pessimistic, and negative," he says. "It's why everyone is doing it on social [media]. The hard thing is to be optimistic and kind, and be the bigger person. It is dramatically harder and even worse, most people that have it don't have time for everybody else that's negative and just live their merry way. And I'm trying to get other happy, abundant, kind people to take on the responsibility of taking the misunderstanding and judgement from the masses--to deploy more, to bring more happiness. We live in a world where many people use fear and negativity as an offensive weapon, as an agenda. And very few that use optimism and kindness as a weapon to counter it."

Gary Vee says that he believes that the people in the world who feel fed and whole emotionally have a responsibility to use kindness and optimism to raise the collective consciousness. He says he's willing to combat a lot of negativity and misunderstanding about himself, because he feels it's more valuable for him to add to the world in a positive way. 

Nice Guys Finishing Last Isn't True

Vaynerchuk is a clear proponent of being kind and nice, and putting positivity out into the world. He doesn't believe that it has affected his ability to be successful and have a place in the world where he feels powerful and succeeds. I ask what he would say to people who'd say that kind people get walked all over. And to that, he tells me he's not buying it.

"I actually think a lot of people use the narrative of being nice as a manipulation tool to try and get somebody to do something they want. Most people who cry about getting taken advantage of actually had an agenda. And they weren't being kind, they were trying to manipulate a situation. Being kind is predicated on what the other person wants, not what you want to give. So when people say, 'Well, I'm a nice guy [and so I get walked all over]' ... It's just not true ... Maybe it's not your kindness, it's your inability to have conflict. It's your inability to be candid that leads to you getting walked all over. But I believe the walked-all-over crew was trying to manipulate an outcome by giving something that they wanted to give, not what the person that they were trying to get something from wanted."

More of my catch up with Gary Vaynerchuk here: