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How Gary Vaynerchuk is CRUSHING IT

An Evio Exclusive by Lori Harito

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Figuratively and literally. In a new partnership with sneaker brand K-Swiss, Gary launched an entrepreneurial sneaker aptly named “Crushing It.” During his Canadian exclusive launch, we had the opportunity to speak with him one-on-one.

You may know Gary Vee from his brash, no-nonsense advice about life, goals, entrepreneurship and social media. He’s the type of guy that demands you stop making excuses and adjust your attitude and behaviour. People flock to his YouTube videos, podcast and live performances simply to hear his inspiring soundbites.

Sometimes all he has to say is “Fuck Mondays,” and he has a generation of people on their feet ready to Fuck Monday and Crush Their Goals. So, 42-year-old Gary Vee definitely impresses.

Gary is the CEO and co-founder of VaynerMedia, a full-service digital agency serving Fortune 500 clients. His brand is so popular that it’s taken a life of its own expanding to VaynerNation, a TeamGaryVee Instagram account, four New York Times bestselling books, and the Gary Vee Experience podcast. But more than that, he’s a sought-after public speaker, and an early investor in Twitter, Tumblr, Uber and Venmo.

His latest venture with K-Swiss is in tandem with the release of his new book also named, Crushing It.  Consumers have an infatuation with business and entrepreneurs. K-Swiss identified that, along with Gary’s massive popularity, and jumped on the opportunity.

Gary saw the collaboration as a win-win for him. If the sneaker bombed, he could laugh about being naive enough to think he could do a shoe. If it was a success, (spoiler alert: It was), it would be his moment to remember as his first real entrepreneur/sneaker collaboration and leave it as part of his legacy.



He’s rooted in the idea of ‘crushing it.’ And not just personally. His purpose is to arm a group of really motivated millennials and self-starters to crush it for themselves.

It feels like Gary has hacked social media and lifestyle culture. You’ll see him peppering you with advice on Instagram in a quick 60-second video clip, generating quote-worthy memes and releasing snippets of radio interviews on Twitter. It’s how he keeps you interested, and hanging on to his every word. It’s why he has 3 million Instagram followers and a cushy 1.3 million on Twitter.

According to Gary, entrepreneurship is in its rock star moment. In fact, he claims - and this is a big one - now is the BEST time to be alive. The possibilities really are endless. You can do what you like, and fill a need that’s missing. Think of an idea, come up with a concept, and you have all the tools to make it happen. We’re living through an interesting time of entrepreneurship because the internet is making everything possible. But it comes with a caution.

“I’m okay when it’s over, and it will be over,” says Gary. “Because everything that goes up, goes down. I love the game of entrepreneurship till the end. And I’ll talk about this era when I’m 84 sitting on a stage remembering the era of entrepreneurship." Entrepreneurship is not sexy. It’s far from sexy says Gary.  “There are no private jets, cash and models in my Instagram feed, and I’m proud of that.”

“What most people don’t touch on about being an entrepreneur is that it’s awfully lonely,” says Gary. “You have to be unbelievably strong to talk about loneliness.”

He wants to make the loneliness topic a bigger part of the conversation. “Everybody’s watching and judging. And that’s lonely. The world is watching,” says Gary. “You have to be very grounded and you have to know why you’re doing what you’re doing. If your ROI is private jets, dating and exotic spas...if that’s your KPI and you lose money when you’re struggling and you can’t have those things, then you’re in trouble.”

For Gary, the journey is the trophy. “There are a lot of people out there that are really good number twos, number fours, number sevens that should attach themselves to the Number Ones. Because a lot of the time, Number Ones can’t get from one to 100 without the number twos and threes.”

And that’s the part of the missing puzzle that Gary is trying to piece together. To help Number Ones understand that they need the space for other people. And to help the rest understand that there’s no sugar coating business. The reality is that 95% of entrepreneurs don’t succeed.

That’s why Gary is a big advocate for you. According to him, the biggest reason people are unhappy is that they value someone else’s opinion more than they value their own. When you are unfazed by someone else’s opinion, that’s what Gary calls “emotional structure.” It’s what allows you to climb the mountain to success and leave the rest behind.



“Sustaining a lifestyle that makes you happy based on the thing that you enjoy doing. Waking up every day, seven days a week, and actually being happy because you are allocating more than half your time to work is important to me.”

It’s not about having the most money. It’s not about having the most followers. It’s about being genuinely happy with what you do. 


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