Why Gary Vaynerchuk hits home with millennials, and why I haven’t watched his videos in months.

Theodore Richards
4 min readNov 7, 2017

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Classic Millennials Doing Millennial Things with Appropriate Credit and a Link to the License

I first encountered Gary Vee in 2014 during my gap year between high school and college. My first interaction with him was his book, Jab, Jab, Jab, Right Hook. I had found it on some website of like top ten business books for millennials or something. I loved the book and the personality behind it, but at the time, I didn’t feel as though it applied to me because I didn’t know what I was doing with myself, nevermind how to convey that to social media followers.

But about a year and a half later (early 2016 some time), I started noticing his videos popping up on my YouTube feed, (and this number only keeps increasing now). I had never seen any of his content beyond the book at this point, but I started watching because it was familiar. And the videos helped me. They gave me some perspective. They made me realize that it was ok that at twenty years old, I wasn’t a millionaire, and I didn't have a plan to blow up. It got me thinking about why I had those urges. Why do I, at now twenty-two, and a majority of my colleagues feel as though we are behind the curve and running out of time to make it? Now, I go to Parsons School of Design, so I think we are an especially impatient and determined group of people, but nonetheless.

I think it really comes down to idols, and with the rise of social media, our idols have become younger and more accessible. We see people like the Jenner sisters, Justin Bieber, Post Malone, Lil Uzi Vert, Selena Gomez, etc., etc. making millions of dollars with millions of followers, and they are our age. And not only are they our age, but we can communicate with them, see every minute of their lives, and follow their every move, so it seems like we know them. It seems like they are a distant friend who has everything you’ve ever wanted. This gets in our heads. We think we aren’t good enough. We say things like “I’m two years older than Kylie, and look where I am. Is it too late for me?”

We also grew up in the Kanye era. We saw him transition from music to fashion and on the way tell everyone that you can do anything by yourself and f — k what anyone says about you (YouTube “Kanye West Motivation” if you don’t know what I’m talking about). Almost everyone I know, myself included, watched these videos and thought, “He’s right. I don’t need a boss. I’m a god, and I can do whatever I want.” We got this feeling of entitlement almost that we don’t have to work and that if we think we are great, then we are. Now, don’t get me wrong, I love Kanye, and I don’t think I would be where I am today without those videos (truly), but I think the general message we got from his Yeezus rants and interviews was a misguided one.

Now, that is where I think Gary Vaynerchuk hits home for a lot of kids my age. He’s pretty successful and has dreams, and he, too, is accessible, but he takes the pressure off. He tells us that it’s ok to not be where we want right now, as long as we’re working toward it. It also takes a weight off of our shoulders. A lot of us really want to be successful, so that our parents can stop working and that we can provide for them and others, so there is this added pressure, which actually doesn’t help many people. This weight off allows us to actually work and stop watching what everyone else is doing, worrying that we’re falling behind.

Right now, the only social media app I have downloaded on my phone is Snapchat, which I use to talk to my sister and friends from home, because I don’t need to see every tweet, Instagram, or Facebook post of everyone I know or wish I knew, nor do I want to. I know people who are gaining traction, and that’s great for them. But I can’t spend my energy watching them. This includes Gary Vaynerchuk, himself. I watched him when I needed confirmation that I was ok. But right now I need to focus on myself so that when my time comes, I will be ready.

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Theodore Richards
Theodore Richards

Written by Theodore Richards

just trying to figure it all out.

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