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Dumb Questions and Weaknesses

It’s better to be ignorant of the rules so that you don’t have to play by them.

Some food for thought the next time someone asks in an interview “What is your greatest strength and weakness?”

A lot of my business success is rooted in naivete and asking “dumb questions”. When you don’t know the rules of the road in a particular industry or business you can use it to your advantage. My weakness of not being well read has actually been extremely advantageous for my entrepreneurial career.

“Where does good music come from?

It comes from people who grew up being influenced by things, but it’s naivete. The same thing is what happened here at Vaynermedia. I came in to the marketing agency world not knowing anything and now we are becoming one of the fastest growing agencies, because I’m asking “dumb questions”.

Those dumb questions are grounded in business. When you know what the rules are you play within them, this has been long figured out, there is a science and psychology that goes into them. I’m not well read and there is a lot that I don’t know and that is my advantage.

I say things that people think are brilliant and those are statements that have already been said before, but they have been said in a different way. If I knew how they were properly said then I would use that quote, but I don’t. It’s a funny thing to think that I get a lot of credit for a lot of things that are actually grounded in my weaknesses, not my strengths.

See the rest of this interview here:

Gary Vaynerchuk is a New York Times and Wall Street Journal Best-Selling author, self-taught wine expert, and innovative entrepreneur. Find more at

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