Uncensored: A Conversation with Gary Vaynerchuk

Disclaimer: He swears. A lot. And if you’re wondering why he has a pretty damn good reason: “I use the f-bomb to vet people. I react to the way you react. Here’s the deal: If you’re a person who gets thrown off by my use of bad language in a keynote, it becomes clear to me that you’re not looking at the big picture. At that point, you’re not judging me half as much as I’m judging you. If you’re incapable of getting over my words and seeing the bigger picture I’m trying to communicate, then you’re just not someone I want to do business with. You’re operating on a micro level, and that’s just not somewhere I want to play… so f*** you.”


Unless you’ve been living your life under a rock, you’re bound to have heard of Gary Vee. Last night, USC had the pleasure of hosting him to speak to us. Needless to say, fans were excited, with several shouting “I love you Gary!” as he sat down on stage with the host of the night, Professor David Belasco, Executive Director of the Lloyd Greif Center for Entrepreneurial Studies. Gary reciprocated the love, shouting back “I love you too!”

He explained his excitement revealing that, “I disproportionately enjoy human beings. I actually secretly dislike animals because so many people like animals more than humans.”

Throughout the night, Gary continued to foster excitement and awe as he took selfies with students that eagerly ran up to the stage, tried to extend the talk to answer more questions, and he even kissed a fan on the cheek to spread the message of positivity and love.

Who is Gary?

I’m sitting here feeling a bit stupid writing this introduction. For no one tells his story better than the man himself, whose mantra of putting family first is followed by an accomplished history of being an entrepreneur (he’s now the CEO of VaynerMedia), angel investor (with early investments in companies such as Facebook, Twitter, Uber), New York Times best-selling author, disruptor, social media phenomenon, and a man whose goal is to buy the New York Jets.

The Greatest Era of Fake Entrepreneurship

While fake news is something that people are distinctly aware of, the rise of entrepreneurship reaching “rock-star status” is hardly ever mentioned. The aftermath of this lack of awareness has caused us to be living through the greatest era of fake entrepreneurship.

He warned the audience that: “We’re living in the greatest era of financial arbitrage machines, not actual businesses.” As a result, “Everyone is about hitting metrics to get their next fundraising round. It has nothing to do with the end consumer.”

Gary also crushed the currently rosy picture of entrepreneurship with sarcasm, “That’s why everybody’s building financial arbitrage machines, starting something so they can flip. Everybody wants to be 26 and a trillionaire, and have a jet and a f***ing baby giraffe.”

Instead he urged the crowd to follow what they were passionate about, and he hoped to convey a message that could redefine the path of a successful entrepreneur, “Like if you make $130,000 a year on a business that you run and you like doing it around something you like, and you can live that lifestyle, that is a remarkable feat. But that is not the picture that we’re painting of a successful entrepreneur. We’re painting private jets, islands and all sorts of ludicrous shit. You know?”

“I’m unbelievably passionate about over-communicating the shortcomings of an environment where entrepreneurship is cool. It’s the same that being a professional athlete and rapper is cool. Very few people can actually achieve it at a high level of success,” Gary said.

He further touched on the current state of venture capital, stating that, “Raising capital is a piece of cake today at a level that we’ve never seen. It’s ludicrous.” He used that to caution the crowd about entrepreneurship, “When I see entrepreneurs failing in this environment, with how much capital and how little it costs to get in the game with the internet at full scale. Like, if you’re an entrepreneur that’s failing right now that’s a year or two in, you suck. I mean it. You suck at entrepreneurship.”

Why He Thinks Entrepreneurship Can’t Be Taught

He also spoke about his previous time speaking in USC, clarifying the statement, “I don’t think entrepreneurship can be taught.” To which Professor Belasco humorously quipped, “So that’s awkward.”

“I refine that message. I think of entrepreneurship so much like sports,” Gary said “I can be better at basketball. I could play every day. I could be substantially better in a year and half, but I will have substantially no shot at going to the League.”

He compared entrepreneurship to a “craft” and a form of innate “talent” similar to sports and art. That is why he believes that going to school to study entrepreneurship isn’t going to work out. “Its natural talent, it’s not even in it to win it. The SAT perfect kids would be in it to win it, but it’s talent. Like I’ll be in it to win it to be a f***ing pro football quarterback. I’m f***ing in it to win it. It’s not going to happen.”

The Importance of Being Self-Aware

Gary also emphasized that people should be self-aware of their strengths. “I don’t think you get the same returns by overwhelmingly working on your weaknesses as you do on tripling down on your strengths,” Gary said.

He recommended students to focus on their strengths and to hire around their weakness, rather than dwell on their weaknesses and “waste their time on something they’ll never be.”

Gary also dived deep, speaking from his heart about things that he felt still lacked conversation, “There’s a lot of things that we have not addressed. There are a lot of people right now who are all sitting around 

Instagram as entrepreneurs, who are going into deep depression and even suicide when they take a massive L (loss) on the next correction in our economy, and that’s going to be tough.”

The Right Mindset: Humble Beginnings and Hustle.

“I grew up really lucky, in the fact that I had disproportionate adversity in the first decade of my life. I was born in Belarus, came to the US when I was 3 and lived in a studio apartment with 8 family members. It was super immigrant,” Gary said, as he spoke about his early life. “I went on two family vacations in my entire life, both in Disney world in Orlando and staying at the Holiday Inn. We kept it humble. We didn’t buy dumb shit. I basically wore liquor T-shirts my whole life through High School because they were free from the liquor store.”

He gave credit to his upbringing as the catalyst for his natural ability to hustle, saying that “A lot of my ability to not worry about others was predicated on circumstance… Those lucky circumstances in my life was that I was never handed anything ever.”

“When people think that trust fund babies are lucky, I just don’t see the world that way. I actually think that they’re disproportionately unlucky,” Gary joked. Professor Belasco then pointed to Gary’s success, stating that “That’s going to be a challenge in the next part of your life, raising affluent kids.” But Gary was quick to respond, “Oh that’s a piece of cake, I’m not giving them any f***ing money.”

Success, Risk and Failure

Gary defined success as “waking up, being happy and being able to do what you want to do at all times.”

“Freedom is what everybody is chasing, but they’re confused about what it actually looks like. It’s not how much you make it’s how much you spend,” Gary asserted. “There is a lot of people who would be way more free if they didn’t over-expend themselves on what they were buying. Keeping up the Joneses – it’s the poison of our society.”

He also encouraged the audience to take more risk especially while they were still young, saying that “It is never more practical to be disproportionately risky than from 20 to 30. Yet everybody goes the other way because now they’re in the real world and it’s time to prove something, to their parents, to themselves, to everybody else, and everybody goes conservative. It’s a huge mistake. We need to flip it upside down. Everybody should go ham when they’re 20 to 30 and get in a ton of ridiculous shit before digging themselves out.”

He added, “You should go and be rouge and get to know yourself and taste shit from 20 to 30, but you have to live by the ramifications of doing that. And the cost of entry for that is living in a studio apartment with four people, eating dog shit food and not having fancy shit. When you don’t do that, and you live in a subsidized environment sponsored by your parents, then you’re living in a fake environment, and you’re super f***ed.”

Gary shared his thoughts on failure, stating how he likes “micro-failure” but not “macro-failure”, like the death of the business.

“I like failure because I think I deserve it. I hate when people don’t respect the game. When I fail, it means I f***ed up. And I like that because people get audacious,” Gary said.

Gary further clarified his view on failure, stating that entrepreneurship can occur when “you can love it (the game) so much that you were never able to do anything else and just the process of playing the game is success itself,” or “you love it so much that you actually don’t give a f*** about the trophies aka the money that comes along with it, it’s just that you really won’t know how to breathe otherwise if you weren’t in the process of entrepreneurship itself.”

Gary declared, “I will never fail because there is no failure. If I lost all my money because I did 37 ridiciously bad decisions, the ability to go back to zero, and try to buy shit at the dollar store and flip it on eBay and build the back up weirdly excites me more than where I am right now. I swear on my children’s health.”

“The thought of going to zero, having all of you judge me like, ‘See, he wasn’t as good as you thought,’ and then rising back like a phoenix and sticking it in your f***ing face. That right there is the definition of entrepreneurship: It’s when you love the game more than what the game gives you. That’s why I like losing; n the game told me I lost. Respect to the game. That’s why I like playing,” Gary elaborated. “I did this when it wasn’t cool. I’d do now while it’s cool, and I’ll do it again in 15 years when it’s not cool again because the economy will collapse and because we don’t like to be accountable, we like blaming things, so we’re going to blame entrepreneurship not the fact that you weren’t self-aware and that you weren’t a f***ing entrepreneur.”

Personal Philosophy

When asked what his personal philosophy was, Gary said that he wanted to give more than he took, “because I don’t want to owe anybody anything and I want to pay back the gifts that I was naturally given because my parents had sex at the right moment.”

“I love that everybody is so into math, big data and quant, and have not deployed the level of gratitude around the math of 400 trillion to 1 which is the odds of being a f***ing human being,” said Gary. “There’s nothing more remarkable that you can accomplish than that you have a chance to accomplish something.”

He recommended students to lean into gratitude and happiness to allow good to happen. “The internet is remarkable…if we could just tweak it around happiness instead of around success from others, it can get really, really good.”

Staying true to his word, Gary made a video filled with positivity with a fan.

When Gary Vee gives kisses you IN BOVARD

Posted by Raj Jain on Wednesday, April 17, 2019