Gary Vaynerchuk – serial entrepreneur, co-founder and CEO of VaynerMedia, best-selling author (most recently of Jab, Jab, Jab Right Hook), angel investor (in companies that include Uber, Birchbox and Grand St.) and professional speaker – often advises audiences that if they aren’t 100 percent in love with what they’re doing, they should walk away.

Of course, it’s “always more complicated than that,” he admits. But he repeats the sentiment it anyway, condensing a complex issue into a simple, actionable mantra. “Ninety-nine percent of people in that audience aren’t going to do anything about it anyway, so if I can somehow help one person triple-check their happiness, than I’m doing my job in that moment.”

He finds that while he can be very persuasive onstage, the vast majority of the people he speaks to ignore his advice.

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While he doesn’t come out and say it, that’s probably a good thing. He may advise thousands of people he speaks to each year to walk away from a job they’re only, say, 80 percent in love with, but for most of them that would spell absolute disaster.

Vaynerchuk admits he’s full of contradictions; while in many of his speeches, he offers himself up as an example of the benefits that come from refusing to succumb to complacency, he also firmly believes that most people don’t have the skill set to do what he does.

“Entrepreneurship, because of the way the American dream has been built over the last 200 years, is grossly underestimated as a skill,” he says. “There’s a level of belief that anyone can be one, and I do not see that at all.”

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He compares it to rap. You can want to be a rapper, but in order to be successful, you need a certain skill set, most of which derives from raw talent. “I think we’re living through the greatest period of fake entrepreneurship that we’ve ever seen because it’s very trendy right now,” he says, fully aware that he’s helped popularize the lifestyle.

So what is the skill set? What, in his opinion, sets apart the successful serial entrepreneurs from everyone else?

  • Ambition. Through savvy marketing that showcased his charisma, Vaynerchuk was able to grow his father’s wine business from $4 million to $60 million in five years. But when he hit 30, he had an epiphany: “I said, you’re bullsh*tting yourself if you think this is how you’re going to buy those [New York] Jets. It’s great everyone around you thinks you’ve made it but you know you haven’t made it. I had a very self-aware moment where it became obvious that my intuition for where the market was going had a bigger upside than just within my business.”
  • Love of the journey. The Jets thing – and I talk about it a lot – is a big deal for me. I do want it, but I’m more interested in the climb than I am in the actual result. I’m pretty adamant that the day I buy the Jets won’t be as happy a day for me as one would think. I love the climb. I love the chase. I love the game. And so I don’t think buying the Jets is important as the thought of working towards an obnoxious billion-dollar goal that will take an enormous number of victories.”
  • Tolerance for risk. “I find a lot of Type A organized types crumble under the notion of entrepreneurism. The reality is being an entrepreneur is being able to adjust in real time, always. I have tons of people who run my businesses who could never be the actual driver of any of them because a train going off track is paralyzing to them.”
  • Passion. “It’s impossible to work and pour the energy that I pour into things without it being my life, my dream, my everything. It’s like love, right? Love is hard. Being that happy and that sad, the thought of losing a loved one, is borderline crippling to me… That’s how I feel, not only for my businesses, but also for the people who help me run my businesses. And in a weird twisted way, for my competitors. I love my competitors because they drive me, the trolls and the haters and the enthusiasts and the maniacs.”
  • Sacrifice. “There’s a big difference between Kobe Bryant, Magic Johnson and Lebron James and an all star at the NBA level, and then there’s a difference between that all star and an [average] NBA player. How do you become that one percent in your trade? I think that takes a darkness. A competitive, workaholic darkness. For me, there’s no other way. Very honestly, I think about it daily. I didn’t get to walk my daughter to school today; she’s only going to be five for so long. I have to be a hundred percent all in, because it’s so hard. I do think other people can do it at 75 percent, 80 percent and still be successful and have better work life balance, but I don’t think history books will be written about them.”
  • Strategy. “Would I like more credit for my own strategic thinking? Of course. I’ve done so many things right that get thrown to the wayside; everyone thinks it was just my charisma or self-promotion. I take a lot of pride in my ability to be strategic; I just happen to be a personality. My personality has brought me a lot of opportunities and my personality has made me underestimated in the marketplace at times, which in some weird way may be an advantage as well. People who dig a little bit deeper realize that it’s not just luck.”

At the end of the day, Vaynerchuk says, he wants to preach self-awareness. Not everyone is cut from his hyper-energetic, entrepreneurial cloth, but if happiness is your ultimate goal, that’s fine; he says he’s seen people achieve that on $24,000 a year.

While in his speeches he uses hyperbole to incite action, meaningful change can come from measures far less drastic than walking away from your career for good. Vaynerchuk may be a walking contradiction – inflating the trendiness of entrepreneurship while acknowledging most people simply aren’t wired for it– but he is a permanent advocate of taking your own temperature. “My advice to people is, set up goals and gut-check yourself everyday.”

Correction: An earlier version of this article misstated Vaynerchuk's comments about the Jets.

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