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By Gerald Flores

Gary Vaynerchuk knows a thing or two about the Internet. As the founder and CEO of the agency Vaynermedia, he’s one of the world’s leading experts on how to leverage social media for business. His work’s been featured in Forbes, The Wall Street Journal, and he’s even written a few books on the topic. His latest tome, #AskGaryVee, is a compilation of the most frequently asked questions he gets as an entrepreneur. One question you won’t find answered in there, however, is what he thinks about Kanye West—who just reached 20 million followers on Twitter—blowing up the Internet at 140 characters at a time. See what the expert had to say about West’s Twitter strategy.

Kendrick is a guy who’s kind of quiet on social media. Do you think there’s an appeal to not being completely radio silent as an artist?
I think there’s an appeal to authenticity. I don’t know him, but if Kendrick doesn’t want to be out there and is not that kind of guy, then he shouldn’t’ fake it on Snapchat or Instagram. But if somebody is a wild character and wants to be out and about and is very social, then they shouldn’t try to hold it back and be like, “I’m too cool.” You have to be you and I really believe in that. I think authenticity rules the day and as long as people aren’t trying to be extraverts when they’re introverts or introverts when they’re extraverts, then I think it’s cool.

Have you been keeping up with the Kanye tweets?
I think Kanye knows how to culture hack. Kanye is real smart and is really good at keeping interesting and intriguing narrative around Kanye. Kanye reminds me of Madonna.

How so?
Madonna did an extremely good job for 20-25 years keeping herself very relevant by reverse engineering American culture. I think Kanye does the same thing. I don’t know Kanye personally and I could be wrong, but I think he’s very calculated in the way he trolls.

So there’s an actual strategy behind his trolling?
He’s authentic. He’s a character, but I don’t think it’s ironic the tweets that gets people’s panties in a bunch also happen to happen around the time he has a new album out.

You’re right about that.
He’s real smart and I wouldn’t put anything past him. I also don’t think its manipulative because I think he’s just got that in him. It’s definitely not a coincidence. I don’t always think it’s calculated, though. Some of it is just what’s probably feeling.

Every time Kanye tweets, engagement on Twitter lights up. Why do you think that happens?
Because he’s willing to go to places that throw people curveballs. I was just doing Kanye word association with myself and you know one of the first words to come to mind? Vulnerable.

Yea. There’s a vulnerability in him that is very attractive to people. He puts himself out there in a interesting way and I think he’s very good at that. I think he’s equally got bravado and ego. He’s just as willing to fuck with Taylor Swift as he is to say that he’s deeply in debt. He’s a contradiction and it works for him. People are attracted to that because they can swarm to one or the other side of him. It’s like looking at a piece of art. I think he’s got both sides reality TV star and unbelievable artist. And I think that’s what everyone is drawn to.

You can get a copy of Gary Vaynerchuk’s #AskGaryVee here.