How Picking A Fight With Gary Vaynerchuk Made My Career

When I was a teenager, I spent most of my time making zines, playing guitar, and scribbling stories. I assumed that when I grew up, I’d play in a band that changed the course of rock ‘n’ roll. If that didn’t work out, I’d settle for writing novels. The one thing I knew I would never ever do was go into business.  

Fast forward a decade. I had kicked around in downtown New York for a few years after college trying to make it in a rock group. The group had broken up, my confidence was low, and I was tired of grownups asking me when I was going to get serious. So I broke down. I got a corporate job.

I figured I’d only be there for a little while, but time has a way of slipping by when you have a comfortable paycheck. Before I knew it I was eight years in, reporting directly to the Chief Marketing Officer, and had the title of “Vice President of Solution Development.”

On the day my boss told me I was getting a VP in front of my name, she also let me know I was getting a raise and a bonus. I told my wife about it, and she was thrilled for me, especially because we had a baby on the way. I was less so. Achieving something I had never really wanted symbolized to me how far I had drifted from anything I had ever dreamed of doing with my life. I imagined myself in ten years, twenty years, thirty years and did not like what I saw.

So I quit. I decided I was going to become a freelance copywriter. I did the math and figured out that if I completed a project a week, I could replace my salary. Easy, right?

The Power of Benevolent Mischief

As soon as I decided to make my move, my work ethic kicked into high gear. I made cold calls all day. I went to networking events every evening. I wrote copy late into the night with my newborn perched on my chest. But the handful of clients I convinced to work with me still didn’t pay enough for my family to live on. It was bad. I didn’t know what to do. Then, during one sleepless night, I had an idea that would change the course of the rest of my life.

Ever since I can remember, I have been interested in benevolent mischief makers— the pranksters, tricksters, svengalis, and weirdos who stand out by playing with people’s assumptions. Since the standard marketing books I was pouring over weren’t doing me any good, it occurred to me to shift my focus and figure out how these more unconventional operators got the results they did.

I started with the legendary rock promoters who came on the scene before the genre got respectable. A standout was Andrew Loog Oldham, the teenage promotional wizard who transformed a group of well-behaved, middle class blues players in London into the scourge of polite society with slogans like, “Would you let your daughter marry a Rolling Stone?” From there, I moved on to studying notorious propaganda artists to learn how to mold perceptions. I dug into the biographies of founders of new religions to reverse engineer how to generate charisma. I studied political agitators to learn how to attract attention on the cheap.

Then, to find out if I could make these tactics work for me, I conducted an experiment.

Taking Down A Guru

One of the strategies I saw these hype artists using time and again was what I now call “picking fights and making enemies.” In short, they identify a person or a status quo idea and position themselves and their ideas in opposition to it. I had become convinced the tactic was effective. What I now needed to figure out was who my target was going to be.

For those of you who aren’t familiar with Gary Vaynerchuk, he’s an Internet marketer who made his name by preaching the gospel of hustle. In his books, videos, and talks, he constantly tells aspiring entrepreneurs that the only way to succeed is to spend the majority of every day promoting yourself. For example, he talks about his habit of prepping his tweets from the toilet as a healthy lifestyle choice.

His point of view had struck me as misguided for a long time. Now I finally screwed up the courage to say something about it. In an article I wrote on the subject, I publicly wondered why the only person who really seemed to be getting rich from the Vaynerchuk approach was Vaynerchuk himself. I posed the possibility that his advice was best suited for bolstering his own career rather than helping his followers bolster theirs. I presented the idea that a better strategy would be to stop paying attention to what he says to do and start modeling the mass psychology tactics he actually uses to turn young people into slavish acolytes.

My finger hovered over the mouse for a full thirty seconds before I clicked “Publish.” Within an hour of posting the article, Gary Vaynerchuk himself recorded a video chewing me out by name. Vaynerchuk’s horde of worshipful fans immediately began to berate me, calling me lazy, stupid, and jealous.

Here’s what also happened: I gained fifty new Twitter followers in twenty minutes. I received messages from readers who thanked me because they had always felt the same way. Within a week of publishing that article, I got my biggest client to date.

Today I own a marketing agency, and I’m proud to say we’re doing quite well. I work with an awesome team. People even look up to me as an advice-giver in my own right. And I can track every one of these accomplishments to when I published that contrarian article about the dominant Internet marketing guru of our time.

Since articles like this one are supposed to have a moral, let’s think about what you can learn from my story. One, if everyone is getting their ideas about how to attract attention, gain followers, and get new customers from the same information sources, it’s almost certainly too late for the advice provided in those sources to be effective. Instead, look to unconventional sources for your ideas. Two, don’t be afraid to take on the masters of the universe in your industry. There are probably a lot of people who feel the same way, and they’re the ones who will probably form the core of your own die hard following.

Finally, be courageous. Have guts, take chances, and make mischief. Your bank account and your mental health will thank you for it.

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