Chris Sacca is very good at asking dumb questions, says Tim Ferriss – and Ferriss means it as a compliment. Years ago, Sacca got an entry-level job at Google and invited himself along to executive meetings where, once people got used to his strange presence, he started asking dumb questions, chiming in with the obvious things that no one was bringing up. “He’s created some incredible breakthroughs in investing as a result of that,” says Ferriss. In a world where everyone is afraid of looking stupid, a lot of basic improvements and ideas get missed for fear of embarrassment. Through several anecdotes amassed during the writing of his new book Tools of Titans, Ferriss makes a case for being more intellectually secure in yourself so that you can raise your hand without fear, ask a dumb question, and actually become smarter. And in Sacca’s case, wealthier. Tim Ferriss is the author of Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers.

Tim Ferriss’ most recent book is Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers.

Tim Ferriss:  I think as humans we all have a preoccupation with looking dumb. We are social creatures, hierarchical creatures and we don't want to shame ourselves, humiliate ourselves. But recognizing that by zigging when everyone else is zagging with that particular context you can actually develop a super power. And that is asking dumb questions. And this came up repeatedly when I was interviewing incredible performers, world class of performers, meaning investors, entrepreneurs, writers, you name it for Tools of Titans the new book. And asking dumb questions can take many forms. I'll give you a few examples.

Malcolm Gladwell is very good at asking so called dumb questions. And he learned that from his father who was a mathematician had no intellectual insecurities whatsoever, just did not care about looking stupid. And he would constantly ask or he would first say I don't understand. Please explain that. I don't understand. Can you explain that? I don't understand. Can you explain that? And he literally might ask that ten times in a row and Malcolm mentioned that he imagined sometimes what the conversation would it look like between his dad and Bernie Madoff because his dad never would have invested, he just would've said I don't understand that at all. Explain that to me over and over again until Madoff left or his dad got so frustrated he had to leave. But if we look at another sphere, say investing, Chris Sacca, a close friend of mine, billionaire, incredible tech investor, just immaculate track record, is very good at asking dumb questions. And this applies to in the very early days where he did something very clever, which was at Google when he was just an entry level guy really compared certainly to say the Wonder Twins, the founders and others, he would go to as many high level meetings as possible, most of which he was not invited to. And so he would show up at a meeting with say Surgie [ph] or whatever and he would walk in and he'd sit down and they'd kind of look at each other and ask him what he was doing there and he go, "Oh I'll just take notes." And they're like oh okay. So he got to sit in on all these high level meetings.

And eventually at some point let's say he got through five or ten of those and people started to just expect him to be around, he would then ask these dumb questions. Sort of the pink elephant in the room why is no one asking this what seems like a very obvious question? And he's created some incredible breakthroughs in investing as a result of that. The asking of dumb questions can certainly apply to exploring any topic or interviewing. So Alex Blumberg, who's cofounder of Gimlet Media which has a slew of gigantic podcast hits, just a factory for podcast blockbusters, he was the co-creator of Planet Money, which is a very successful radio and podcast show. For instance, during the subprime economic crisis he asked the question that no one else seemed to be asking but it was just sitting right in front of millions of people who couldn't quite figure out what the hell happened. And it was why would banks lend money to people who stand next to no chance of paying it back?

And so very often the dumb question that is sitting right there that no one seems to be asking is the smartest question you could ask. Not only is it the smartest most incisive, but if you want to ask it and you're reasonably smart, I guarantee you there are other people who want to ask they're just embarrassed to do so. And in this case if you can override that embarrassment and be the one who asks dumb questions you can end up having best-selling books, you could end up having a huge blockbuster of a podcast or many, you could end up picking the next Uber. It is a super power in a world that is governed by shame and perhaps political correctness more and more so people are not saying what's on their mind, they're not asking what's on their mind and the questions here are the most powerful.