Gary Vaynerchuk Bet Right On Facebook, Wrong on BlackJet

He helped build his father's wine company called "The Wine Library" [0]. He then went on to build Vayner media and his internet personality "Gary Vee".

[0] https://www.youtube.com/watch?v=5Vo0nykupIo

Before he became some sort of ill-defined entrepreneur/investor he used to talk knowledgeably and enthusiastically online via a podcast (or possibly several) about wine, which was his family's business - this was probably a decade or more ago. Since then I guess you could describe his career as having "sprawled".

Since I would have sympathized with this viewpoint earlier in life, I’ll give you the just-the-facts version:

He took an offline business in a regulated industry (wine) which he inherited and ~20Xed it online, got Internet famous, built one of those social media marketing companies which has fairly little lasting impact but (like Madison Avenue) has a metric truckload of money run through it, got deal flow, invested, etc.

At least one thing he's done is worth watching for many HNers: someone said "It's easy to make money when you have connections but I don't have connections so boo hoo" and he said "Watch me. Suppose for the sake of argument that I own a beer blog, instead of the blog I actually own. My new name is Steve. I Google beer accessories and see this company is advertising on AdWords, so I know they have an advertising budget. I will now cold call them live, as Steve who runs a blog no one has heard of which doesn't exist, and sell them ads on my beer blog."

He then does.

Edit: Found the video. In the intervening years I had misremembered some of the details. Very little of what I watched in 2008 I still quote in 2018; I think I will probably be able to quote this video with that level of detail in 20X8, too. https://www.youtube.com/watch?v=fG7WFxT1ySY

His primary skill is being adept at Internet marketing. His other keys to success are inheriting a successful family business and gambling on Facebook.

Some variation of this story accounts for about 95% of "personality entrepreneurs"/bullshit artists of the Tim Ferris ilk that plague us these days.

My introduction to GaryVee was through Signal vs Noise in 2006. Beyond growing his parents wine company he's in the business of producing inspiration porn, like Malcom Gladwell or the 4 hour work week, its homeopathy for entrepreneurs.

Gary V unashamedly uses hyperbole to deliver his message with simplicity and impact.

I'm sure, in his inner thoughts, he would have a more nuanced position. Is every business failure, 100% always 100% because the founder/CEO isn't good enough? I'm sure he would agree that it isn't.

But it's true enough, often enough, that it's a solid rule of thumb to use for investment decision-making.

"It is possible to commit no mistakes and still lose. That is not a weakness; that is life." - Jean-Luc Picard

Of the two I think I'd trust Picard.

Is it though? There’s a saying that goes “there are no bad teams just a bad leader”. Could you provide a common seen example where this does not hold up?

Didn't seem to work here.

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