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Meeting Gary Vee

Meeting Gary Vee


Usually the answer has to do with the main topic of discussion during the conversation. What I've found is that the lesson that takes us the longest to learn, once learned, sets us free. It's usually that thing that keeps us from taking the next step, or becoming the best versions of ourselves. It's almost always engulfed in fear, which begs an interesting question: why would we be fearful of something that potentially reaps grand rewards?

Today I'm asking myself this very question. I have a story I want to tell and I want to be totally transparent - which is uncomfortable for me - but it's important that I tell it in this way.


You may know him as Gary Vee. He's that wine guy who turned into a self-made businessman and brand, turned into the guy who constantly pops up on any of your social media feeds because of the insane amount of content that he puts out into the world. He's the very same guy who is the CEO of VaynerMedia and can now be seen on Apple's new show 'Planet of the Apps'. He's also the guy who's been on every single podcast that exists. He's been interview by Tim Ferriss, Chase Jarvis, Larry King, Joe Rogan, and has given talks on pretty much any platform that you can think of. He is a self-proclaimed hustler. So believe me when I tell you that he's everywhere.

At this point, you should be asking, why? Well, in my opinion, it's because what he's saying is the most honest, cutthroat, no bullshit, straight to the point, advice that one can give another. He's not "nice" by societal standards. Meaning, he's not the guy to feel sorry for you if you bring up excuses for why you're not jumping straight into the fire. Let me just add, a fire that makes sense to jump into. He's not the type to preach jumping just for the sake of jumping. You have to know what you want, do the many hours of work, and really believe in it before you jump. But you know, most people don't want to hear that. They want success, yesterday. Which is the other reason why I like Gary and why I'm writing about him today.


At the time, I was moving to New York City to further pursue my career in hosting. One of my first gigs was an event at the NHL store in Midtown Manhattan. I was told that my guests would be Chicago Blackhawks Jon Toews and Patrick Kane, and that I would be co-hosting the event with Greg Wyshynksi (Puck Daddy) and a dude named Gary Vaynerchuk. Please keep in mind that this is the same Gary Vaynerchuk whose net worth currently stands at $160 million. Yes. Technically, he had a smaller position than me in this particular gig. Keep reading.

(Gary's the one holding the 9 card below if you scroll.)

Now, I don't remember exactly how this exchange occurred but if memory serves me right, Gary had reached out to me either via twitter or email, to say hello before the event. He also mentioned that he grew up in New Jersey, and that when my Dad played for the New Jersey Devils, my dad would come into his family's wine shop. So, long story short, his dad, knew my dad. And now, here we were, the kids of our Fathers, working on a thing together.

Here's what you need to know. At the time I didn't know who he was. We had a pleasant conversation and then he mentioned that he worked at a wine shop and did some kind of YouTube show and said that it would be great to have my dad on as a guest. I politely said yes, but inside I thought 'cool, you're just like everyone else. trying to play nice to me to get to my dad' and 'if you're so important why is your show on YouTube and why are you working on the same thing as me, someone, who's just starting out in the business'. (i cringe as I write this)

So, when our event wrapped and he said let's connect, I said sure but I walked away rolling my eyes. 

I didn't look him up until some time later - maybe months - when I found myself back in Michigan, telling my Dad about this dude I met called Gary Vaynerchuk. I told him that he's an immigrant like me, and that he worked at a wine shop that his dad owns in New Jersey. My dad said, 'oh yeah, i remember his dad'. I told him that I looked at Gary's Wine Show online and that maybe he could go on as a guest. I even told him that Wayne Gretzky had done the show. My dad kind of scoffed at the idea.

Side note: My dad isn't one to do promotional things. In fact, he's so humble that he's humble to a fault. I always wonder, what's the point in achieving such amazing heights in one's career if you're just going to hide behind it. But that's a different story, the point is, he didn't scoff at my bringing it up, nor at Gary's proposal. He just doesn't do media, really. But I took it to heart. 

I felt like a jerk for bringing up the wine show idea. This is a recurring theme in my life. I'm always looking for approval from my dad and I HATE asking him to do things on behalf of someone else, especially when it is done in the hopes of it somehow helping me in my career. (This was common in the industry. People would ask to be connected to my Father and then say they'd help me in return. IT MOSTLY ALWAYS WAS A BIG LIE.)

I thought Gary was doing the same. So, I built up a bit of a resentment towards him for not only throwing me out on the line like that - to suggest something that my Dad wouldn't even want to consider, but for using me to get to my dad.

Pause Right Here. This is obviously not what happened (unless I'm still naive and it was. Maybe Gary can set the record straight.) He wasn't using me. And he certainly wasn't trying to make me look less than in front of my dad. These are my own personal issues of self-esteem when it comes to my relationship with my father. So, Gary is not to blame here. But I internalized this anyway.

But because of this, I started to look at Gary in a slightly different way. I no longer looked at him as the dude who worked in the wine business with his father. I looked at Gary as the dude who was USING wine to get to a bigger platform, which to me meant that he wasn't authentic and wasn't to be trusted. I felt like he was exploiting his dad's business for his own benefit. Of course, NOW, I look at this differently. The thing about Gary is that he always had bigger plans for himself and knew what he wanted. And that was my big mistake. I didn't realize until much later that you have to know what you want and there's absolutely NOTHING WRONG WITH USING WHAT YOU HAVE TO GET TO WHERE YOU WANT TO GO. After all, YOU'VE GOT TO START SOMEWHERE.


I was reminded of him again when I learned that he was hired to help the Nets re-brand as they transitioned out of New Jersey into Brooklyn.

At the time he was the social media guru that major brands would hire to take them to the next level. I was a year-in hosting at Barclays Center and the Brooklyn Nets, and I wasn't sure how much longer I wanted to stay in the position. So, this time, I reached out to him first and asked if we could get together for a coffee. Of course he said yes. He's Gary Vee. And he's all about taking meetings and giving out advice. 

I expected for him to reach out casually when he had time. To shoot me a text to say, 'hey yeah i'm available such and such days. just let me know.' But this wasn't the case. This time he connected me with an assistant and they slotted me in for a half hour meeting with him. I knew he was busy, but I didn't assume that he was so busy that all I deserved was a lousy thirty minutes.

(Side note: this is a glass half-empty way of looking at things, which is the wrong way of looking at things. it's also semi-entitled. which is another topic i have many thoughts on and will write about at a later time. the point is: time is money. he was doing me a favor and I should have seen it as such. Also, I cringe when writing this, too. But hey, I said I'd be transparent.)

Here's what happened. I arrived on time to our meeting. He was running a bit behind. He was on location but he was finishing up another meeting. When I sat down, he said he had another meeting after me. Again, here's my self-entitlement. I thought 'okay, kinda rude of you to just slot me in, but fine'. (It's not.)

Once I sat down, his entire focus was on me. Unlike most of the conversations I have with people, he didn't really give me the opportunity to ask about him. (Which in hindsight, is kind of incredible, especially if you follow him now, because it would be easy to assume that he ONLY talks about himself. This couldn't be further from the truth.) Gary asked me everything about what I had been doing since the last time we met, what I was doing now, what made me happy, what made me restless. He asked me about my interests, my likes and my dislikes. He asked about my strengths and my weaknesses. He asked about my skills.

And then he said, 'alyonka, WHAT do you want to DO. WHO do you want to BE." I gave him my standard answer which I'd given to countless others while in pursuit for other opportunities. "You know. I feel like I could be a conduit of sorts. Use my interviewing skills to ask experts questions and get those answers to the masses. I feel that we're missing this generation's Oprah. I, as a woman, have no one to look up to. I feel like I could host a magazine-like show. Start conversations. Introduce ideas. Include women. Talk about my experiences. Reconnect with my Russian background. Educate people on topics that aren't talk about, etc.


I was floored. Disgusted, actually. What do you mean, do it?! What kind of answer is that? How can I do something that I can't do on my own. How does this help me? I came here for this? Where was my guidance? A to-do list? Anything! Just not that.

He continued. "Why don't you start a YouTube channel, or start blogging, or start writing, or reaching out to all the people that you know. Use your connections. Start asking questions and getting answers, and giving that back to the people. Create the content you want and gain the audience you want. Just do it."

I, looked at Gary, and in the same way my Dad scoffed at me, I internally scoffed at him. I thought, YouTube? What? Be like all those people who sit in their room and create videos which no one will see? And if they are seen, then they're not taken seriously once they apply for "real" jobs with "real" networks and "real" tv shows? I might have even said something along these lines to him. "Wouldn't my credibility be shot? Isn't it worthwhile to build out your portfolio with established networks? I feel like YouTube is so lowbrow." 

(Note: please keep in mind that this is the guy who started on YouTube before anyone was on YouTube.)

To which Gary answered a similar answer that you can now see in MOST of his YouTube and social media clips, "dude, I want to buy the New York Jets. I hustle. I work hard. I'll do whatever it takes because I want it that bad. And I'm not afraid to take on any work that will get me there. How bad do you want it?"

I said, "bad". He said, "okay, so do the work." But here's the thing: it didn't register. It's not that I didn't want to do the work. I'm a workaholic, remember? It's just that I didn't want to do THAT kind of work. That kind of work felt like it was below me. I felt I had already paid my dues. So why would I go back to zero? 


During my time of starting tUFp, I did a lot of research on the entrepreneurs who had it figured out. No matter where I looked, Gary was everywhere. I think my Dad might have even mentioned him randomly. So I thought 'okay! fine! fuck. if this isn't a sign, then i don't know what it is.' I subscribed to his medium letters.

And then on June 9, 2017, this popped into my inbox. Here's the first paragraph:

"It baffles me how many people think that they are bigger than they actually are. I hear people say, “Well, how do I get in the New York Times?” or “How do I get that meeting with that CEO?” and often times, I just say, “One is better than zero.” Now this might catch you off guard, but let me explain. The concept around one is better than zero is simply a call to action to do. It’s understanding that one view is better than zero and that humility and patience is the foundation for success."

If this were a newspaper, it would have dropped to the floor. But because it was my iPhone, I was a bit more careful. But you get my drift:

ALMOST SEVEN YEARS TO THE DAY I MET GARY, HE WAS TALKING ABOUT ME. I was that person who scoffed at his wine YouTube show, when instead, I should have asked him to mentor me and to teach me in the world that would prove to be, not only lucrative, but a world where I could be in control of my image, my voice, and my content. I was that personwho sat with him when he gave me SOLID advice to "Do it. Create your content" aka "one is better than zero". Instead I was that person who walked out of that meeting, shunning the idea of starting what I had been crafting in the privacy of my home since 2008 - the very idea I pitched him. I was that person who felt bigger than I actually was, and so I continued on a mediocre path, continuously ignoring what had been calling my name all along.

Now. Let me say this. I will go ahead and tell you that I am NOT a cocky person - hello self-esteem issues. I am NOT a lazy person. I AM humble. Almost too humble, like my Dad. I follow rules because I feel that cheating or taking a short-cut is unacceptable- and not fair. I AM a workaholic. I practice patience to a fault. I am all the things that would be beneficial in creating the life and business that I have dreamed of creating for a long time. BUT HERE'S MY TRUTH. I am consumed with fear that I will not be good enough. I am consumed with fear that I will not attain my standards of perfection. And MOST importantly - which is why I didn't follow up with Gary when we first met - I am consumed with fear that I will let my father down. 

So, when I found myself jobless and in the state of mind that I wrote about in The Email, it would have been easy for me to sit in my disappointment, regretting that I wasted a decade of my life trying to hit my standards of good enough, perfection and pleasing my father. I could have applied to other production gigs and continued on the path that I had been on for almost a decade. I could have continued avoiding my fears. That would have been easy.

What I chose to do instead, was hard. I started over. I started back at one. I FACED MY FEARS. I started DOING. I started doing what I had been putting off for far too long. Of course, there are moments where I'll sit and wonder 'what if i started this back in 2010' and 'what if i listened to Gary back then'. The point is that I didn't. And I can't change the past.

However, what I can do, is change the present for a better future. I can face my fears and move past them. I can start creating. I can start even though things aren't to the level I've grown accustomed to having them. Because, here's the thing: the alternative SUCKS. The alternative is playing it safe. The alternative is never taking a risk to follow your dreams FULLY. The alternative is NOT believing in yourself. 

So I finally started the project I began dreaming up almost ten years ago. It's this one and it's called The Untitled Female Project.  It's a work in progress, as is my Podcast - which I'm launching in July. I even created these low grade YouTube videos to explain who I am and what this platform is all about. EVEN THOUGH THEY'RE NOT UP TO STANDARD.


What I know is that as much as this is scary it feels REALLY GOOD.  I can't get back the last ten years and that's not why I'm writing this. I'm writing this so that whatever it is you're putting off right now, you can start TODAY. That goes for anything. Do it. Not tomorrow. Not when you have time. Not the next time. Not when you muster up the courage or when you get over your fear of feeling small, embarrassed, ashamed, vulnerable. Do it, today.

If not for you, then for me. And if not for me, then for Gary Vee.