For all of the talk I do about social, marketing, and legacy, what gets passed over is the fact that I’m a salesman at heart. Before WLTV, before VaynerMedia

, before VaynerRSE, I developed my chops and my fortune by selling stuff.

With that in mind, I’m putting out a series of pieces about sales. From my personal experiences, to “what it means to be a salesperson.” It’s something that’s really important to me, and I want to speak more about it.

Read more here:

Pt1: How a 15-year-old sold a ton of wine

Pt3: Disrespect for Customers


I could have become a Sith Lord of wine sales... Let me explain.

As you may know, yesterday was May 4, otherwise known as Star Wars Day for the popular quote: “May the fourth be with you.” That got me thinking about the Dark Side. In Star Wars, the dark side tempted Jedis into becoming evil, but in the world of sales, there is a dark side, too. It’s the temptation to do whatever it takes to make the sale even though it might not be good for the customer. It’s the side that doesn’t care about repeat sales, and only goes for short-term conversion. It’s temping, it’s scary, and I know first-hand how easy it would be for a good salesperson to get sucked in.

I honestly believe that a great salesperson is the pinnacle of human behavior. In fact, it blows me away to think that the idea of the “salesman” has a negative connotation. It’s fascinating that the purest 3% of salespeople are among the best people I know, and the other 97% are close to the worst. It’s a truly interesting game.

To be a great salesperson, there is an element of manipulation. When you have that ability, you have the choice: Do I do something great with it, or do I do something evil? Some of the most evil men and women across history were only inches away from being some of the greatest. They had the power, they just didn’t do the right thing with it.

I am extremely aware of how close I am to the dark side. I’m so thankful that whatever moral compass I was born with (and was subsequently shaped by my parents) prevented me from going fully sleazy. I mean shoot, I was close. I was so close. I was Luke Skywalker, man. He could taste it, and so could I. I crossed the line in my youth in the form of bullshitting and exaggerating to a much higher degree than I would deem acceptable today. There is embellishing and hyperbole, and then there is straight-up lying. It took me a little while to get those handlebars straightened out. In my late teens, I was still finding my way.

What saved me was being so public. I’m scared of being called out and so I stay in my zone. Sure the hyperbole still happens. That’s half the fun. But I’m never ever ever selling anything that I don’t think is going to be the best thing for you (or for me).


Thanks for reading! When I add a new piece to the series, I’ll add links to this one. If you got any value out of this, I’d really appreciate it if you shared it out on Facebook!