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I think as humans we all have a preoccupation with looking dumb.
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We are social creatures, hierarchical creatures and we don't want to shame ourselves, humiliate
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ourselves.
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But recognizing that by zigging when everyone else is zagging with that particular context
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you can actually develop a super power.
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And that is asking dumb questions.
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And this came up repeatedly when I was interviewing incredible performers, world class of performers,
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meaning investors, entrepreneurs, writers, you name it for Tools of Titans the new book.
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And asking dumb questions can take many forms.
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I'll give you a few examples.
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Malcolm Gladwell is very good at asking so called dumb questions.
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And he learned that from his father who was a mathematician had no intellectual insecurities
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whatsoever, just did not care about looking stupid.
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And he would constantly ask or he would first say I don't understand.
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Please explain that.
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I don't understand.
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Can you explain that?
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I don't understand.
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Can you explain that?
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And he literally might ask that ten times in a row and Malcolm mentioned that he imagined
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sometimes what the conversation would it look like between his dad and Bernie Madoff because
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his dad never would have invested, he just would've said I don't understand that at all.
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Explain that to me over and over again until Madoff left or his dad got so frustrated he
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had to leave.
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But if we look at another sphere, say investing, Chris Sacca, a close friend of mine, billionaire,
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incredible tech investor, just immaculate track record, is very good at asking dumb
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questions.
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And this applies to in the very early days where he did something very clever, which
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was at Google when he was just an entry level guy really compared certainly to say the Wonder
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Twins, the founders and others, he would go to as many high level meetings as possible,
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most of which he was not invited to.
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And so he would show up at a meeting with say Surgie or whatever and he would walk in
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and he'd sit down and they'd kind of look at each other and ask him what he was doing
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there and he go, "Oh I'll just take notes."
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And they're like oh okay.
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So he got to sit in on all these high level meetings.
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And eventually at some point let's say he got through five or ten of those and people
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started to just expect him to be around, he would then ask these dumb questions.
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Sort of the pink elephant in the room why is no one asking this what seems like a very
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obvious question?
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And he's created some incredible breakthroughs in investing as a result of that.
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The asking of dumb questions can certainly apply to exploring any topic or interviewing.
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So Alex Blumberg, who's cofounder of Gimlet Media which has a slew of gigantic podcast
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hits, just a factory for podcast blockbusters, he was the co-creator of Planet Money, which
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is a very successful radio and podcast show.
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For instance, during the subprime economic crisis he asked the question that no one else
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seemed to be asking but it was just sitting right in front of millions of people who couldn't
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quite figure out what the hell happened.
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And it was why would banks lend money to people who stand next to no chance of paying it back?
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And so very often the dumb question that is sitting right there that no one seems to be
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asking is the smartest question you could ask.
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Not only is it the smartest most incisive, but if you want to ask it and you're reasonably
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smart, I guarantee you there are other people who want to ask they're just embarrassed to
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do so.
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And in this case if you can override that embarrassment and be the one who asks dumb
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questions you can end up having best-selling books, you could end up having a huge blockbuster
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of a podcast or many, you could end up picking the next Uber.
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It is a super power in a world that is governed by shame and perhaps political correctness
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more and more so people are not saying what's on their mind, they're not asking what's on
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their mind and the questions here are the most powerful.