Which is to say, this isn’t a big problem. If I hadn’t gotten into this more deeply, I wouldn’t have even pondered it at all. I’d have continued to build the business I still run now, 20 years later. Yes, I know something about starting a business, and I know this from a time before it was as cool and sexy as it is today. Then, I was just like many of the eager young people I see in Gary’s videos – looking for something – an answer, an idea, a vision, some direction that makes this stuff make sense. I was that 20-something year old too. Listless and looking for anything that takes me to the next level. Hell, if there was a Gary Vaynerchuk back then, I’d have probably watched all of his videos like my niece watches “Graveyard Girl” videos on Youtube.

All of this is to say, there’s something off about Gary Vaynerchuk and what he does. This hit home when I came across an article and it introduced me to the phrase “struggle porn”. Ah-ha! That’s what this stuff is. Now, to be fair, the article does read like a hit piece with his face covered in a red “X” and the mention of a Trump-ish patrimonial cheat when the author says he “start[ed] with a $3,000,000 wine business”. I don’t know how Gary V started, but he did reply to this with a clarification. Fair enough. Certainly, it did not seem to be the spirit of the article to disparage his early work, but let’s take Gary at face value.

This phrase “struggle porn” reveals what Gary’s all about. It’s the idea that something that is often simple, can be made sexy. Really sexy. Like his overall idea of making money by way of buying things at yard sales and selling it online for more is, on the surface, ingenious. However, once you overlay the reality of, well, reality – this thing looks much different. I don’t want to be a “downer” about the hassles of bartering, the tax implications of cash sales, the need to have transportation to cart all this stuff around and possible documentation requirements. But, what is happening here is that Gary is making the act of “working hard” and “grinding” into something like entertainment. In fact, just like entertainment. 

There is another, the deeper point about Gary’s relationship to Capitalism that could probably be made by those better than me. The essence of Gary’s covert disingenuousness relates to him coming off as a supporter of those leaving the grind of “base society”, but in the economy of attention, as it is today, the mere attention he gets for doing this raises him to the top. This lets him lord over others and dictates commands more and more (I’ve seen it in some of his videos). Maybe this is a conflict of interest, or maybe it’s just something too intertwined to be fair. But, Gary stinks of this contradiction.

Some of the best teachers in my life gave me tools. Real tools that I was then meant to either use in novel ways or not. They would nudge me in the right direction, but still forcing me to do the work of learning. That’s the essence of this, it was, I think, the idea of teaching me to learn not regaling me with the glory that I could construct something useful with C+ just because I was in front of a computer. The idea that a good teacher might say “It’s easy to build a house” and then would tell me to buy a hammer (You can do it! Stop making excuses!) seems overly simplistic, and on a larger level disrespectful to the process.

I haven’t seen all his videos, nor do I know his history intimately. I don’t need any of that to know how I feel about his work. I have been curious, yes, because Gary comes off as very genuine. Many of the core ideas that he espouses – from what I’ve seen – are things I agree with. If Mr. Vaynerchuk is as popular as I think he has become, I think he’s going to need to take responsibility for his “Entertainment First” approach to ideas. He’s going to need to share more of the actual, hard, behind the scenes process. He’s going to need to be more honest. Honesty, however, is often very unsexy. That’s what you’ve probably never heard of “Honesty Porn” (yet).