The Mind of a Salesman Pt 2: The Dark Side

Posted by | May 05, 2014 | Uncategorized | 17 Comments

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!

  • Adrian B.

    Good post Gary. I think all of us in sales face those demons sometimes. Yesterday I was reading “Grabbing Success By The Horns” and it talked about Courage being the most important trait of successful people. It takes courage to not cross the line when commission is staring at you in the face.

  • Steve Welton

    This is awesome @garyvaynerchuk:disqus and entertaining content right there but even more because it’s always YOU man. Straight from the heart. Man how many times can you Jab in one day? Enough already! :)

  • Don Lachance

    @adrianboucek:disqus check the link in your profile, there must be something wrong with it, because it brings me to a godaddy page. Just a heads up.

  • James Schipper

    That image is the best! Glad the force is so strong with you. You’d be a monstrous dickbag if you turned evil.

  • Marquis C Jones

    My Man GaryV,,, I agree that darkside is tempting but I am so very thankful that I stayed on this side,,,,,,, there is no telling what I would be if I would not have stayed true & good,, LOL good stuff @garyvaynerchuck

  • Ryan @ RadiumCRM

    Very appropriate theme for May the 4th. I personally draw the line at am I pitching something I don’t believe in. You might not always be completely forthright on the flaws of the product but that’s ok, no product is perfect.

  • MishMash

    com’on gary why can’t I share this on LinkedIn ?

  • Liz Walz

    You’re a salesperson at your core, Gary. Boat dealers are salespeople at their core. And boating, both the industry and the small businesses that make it up, have an incredible story to tell. But we need help telling it. Come open up the Marine Dealer Conference & Expo (MDCE) in November, and I promise you it will be one of the most powerful experiences of your 2014. You can make a difference in the lives of thousands of members of the boat business — not to mention their employees and customers. We need what you have to offer. Ten years ago, I was tasked with figuring out social media for the boating trade magazine I worked for, and I picked up a book that featured you prominently. Your story made me believe in the power of social media for the boating business. Help us put it to work.

  • John T. Trigonis

    Great read, Gary. Love how you worked in the Star Wars themes so seamlessly to create quick read that packs a powerful message about the importance of staying true to your own message and trying not to cross the line. Thanks for sharing, Sir!

  • tonyubo

    Dealing with that tight rope between manipulation, hyperbole and lies is a real deal. Great article and great perspective. I haven’t seen this before but it resonates.

    Great image too.

  • jerryladera

    I’ve been selling wine for 39 years, you stole my recipe.

  • John Jollis

    There’s definitely a fine line between being a good salesman being a good bullshitter. Unfortunately, way too many people cross it.

  • Ralph Echter

    Great post and good for you Darth Vader was not strong enough to suck you into the Dark Side or better that you were strong enough to not get sucked into it.

    Can I give you, as a web designer, a small readability tip? The width of the text is too wide on bigger screens. There are too many characters on a line which makes the article difficult to read. The optimal line length is considered to be 50-60 characters per line, so either bump up the font-size for bigger screens or make the line (column) less wide.


  • Dale Weatherford

    I am 63 and started selling when I was 10..{door to door} I have seem many salesmen pick the dark side..Sometimes they become very well known but it never last..I have worked for very wealthy men who were disapointed that I would not lie..hype or super pressure customers..If you want a career selling be honest and care for your customers….Also have a sense of helps alot…

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  • Ricky Cravens, MBA

    I enjoyed this short read

  • Wanda Strickfaden

    Great content enjoyed the read. Most people seem to agree on here. Feel free to talk to me!

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