I basically have 20 more friends now than I had in 2009 when I started Wine Library TV. At the same time, I have maybe 17,000 more acquaintances. That is really fascinating to me (and probably the foundation of a more in-depth blog post to come), but let me get back to the original question.

Gary is an outlier.

17,000 acquaintances sounds overwhelming.

And 20 friends is more than most people have.

I agree that Gary is an outlier, but I think the idea of having thousands of 'fans' certainly isn't crazy for many people. I like how Gary distinguishes between true friends and acquaintances.

Oh, I see. Gary's acquaintances are actually his followers / fans.

I still think having 20 true friends -- and actually he says he has 20 MORE friends than in 2009 so the implication that he has more than 20 true friends -- is unusual.

Gary V's definition of friendship:

The way I choose my friends is completely predicated on one thing: Life is hard enough, and there are a lot of people in your life that you can’t pick (although I’ve been pretty fortunate in that regard), so when I have the luxury of picking, the number one thing I’m looking for is ease.

Of course I want someone who brings me happiness, and shares my interests, but most of all, I want someone who makes it easy. I want a friendship I don’t have to work for, a relationship that comes naturally. You don’t expect anything, and I don’t expect anything, other than the friendship. That, to me, is gold.

So... his definition of friendship is not having to work at the relationship. Huh.

His definition sounds like hiring waiters for a restaurant...

Only hire the ones you don't have to train?

Ideal waitperson:  "...someone who brings me happiness, and shares my interests, but most of all, I want someone who makes it easy..."

I interpreted 'ease' as a relationship coming naturally vs. being logistically easy.

That's right, just like a good waiter...