Gary Vaynerchuk and assistant Matt DeMayo in Downtown Manhattan

How I Knew it was Time to Get an Assistant

My first assistant was Matt Sitomer. Originally an employee at Wine Library, he was actually the only WL employee who ended up coming over to VaynerMedia with me (which makes it even more fun that he’s currently battling Brandon, who runs Wine Library, for this year’s fantasy baseball title).

A recent question on my show got me thinking about how I even ended up with an assistant in the first place, and the answer was one that even surprised me: It came when I realized I was disrespecting people.

For me the big thing was that I began to go places where I didn’t hold all the leverage. When I ran Wine Library, and was in the store for 12 hours a day every day, I didn’t schedule a lot of things. If I did end up scheduling something, I would just go off of memory instead of having any kind of real organizational system. This was never a problem, though, because if I screwed up and made an appointment wait, it didn’t particularly matter. Yes, I’d disrespected their time, but at the end of the day, I was their biggest wine buyer, and they were there to sell me. That was just the way things worked. I had the leverage.

Fast forward a few years, and now I’m having to show up to conferences, and interviews. I no longer had disproportionate leverage. If I made someone wait, it was actually a real problem.

Now this is all predicated on the fact that I am a totally disorganized person. I’m not into the details, and I recognize that. So when it got to the point where I needed to travel, and be on TV shows, I turned to Matt and I said “I need to stop being disrespectful of other people’s time, and figure this out.”

I felt that I couldn’t follow a schedule. That I was just totally un-schedulable in the same way that I just thought I would never be able to work out. And I’ll tell you that now being able to follow a schedule (with the help of an assistant), and being able to work out (with the help of Mike) are two of the biggest confidence builders in me. To know that I’m capable of changing 35 years of just going with whatever came easy to me is a huge accomplishment for me. It actually makes me believe that maybe I could have been an A-student. Who knows? What I do know is that now I’m confident that I can spend the next 40 years of my career growing and molding by using someone else’s strengths within my own ecosystem, even while I continue to bet heavily on my strengths.

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