Develop Superpowers by Investigating What Others Won’t

Become the Smartest Person in the Room: Develop Superpowers by Investigating What Others Won’t, with Tim Ferriss, Investor and Author, Tools of Titans and The 4-Hour Workweek

Ask dumb questions

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 superpower. And that is asking dumb questions. And this came up repeatedly when I was interviewing incredible performers, world class performers, meaning investors, entrepreneurs, writers, you name it. 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 and 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 would literally– he might ask that 10 times in a row. Malcolm mentioned that he imagined sometimes what the conversation would look like between his dad and Bernie Madoff because his dad never would have invested.

He just would have 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 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.

So he would show up at a meeting with Sergey or whatever, and he’d walk in and he’d sit down and they’d look at each other and ask him what he was doing there and he’d go, “Oh, I’ll just take notes.” And they’re like, “OK.” So he gets to sit in on all these high-level meetings and eventually he would then ask these dumb questions. So the pink elephant in the room, why is no one asking 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 co-founder 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. And 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 can 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 can end up having a huge blockbuster of a podcast or many. You could end up picking the next Uber. It is a superpower 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.

Ask absurd questions

If you look across all of the icons, titans, world class performers that I’ve interviewed in the, say, wealthy section– if we’re dividing them into healthy, wealthy and wise– if look at the business side of things one of the most common patterns that you spot is absurd questions. And the power of the absurd question is really something that I’ve paid a lot of attention to in the last few years. Whether that’s, say, Peter Thiel– so, serial billionaire. Certainly an incredible entrepreneur but also an incredible investor, good at betting on presidents turns out as well. And he would ask questions such as, “Why can’t you accomplish your 10-year plan in the next six months?”

And if you talk to, say, Peter Diamandis, Chairman of the XPRIZE, he might ask the founders of companies he’s looking at as potential investments, “If you had to 10x the economics of your startup in the next six months, three months, how would you do it?” And if they say it can’t be done, it’s impossible, his response is, “I don’t accept that answer. Try again.” Those types of questions, I think, are– whether it’s 10x thinking, 100x, however you frame that– it could also be a constraint. For instance, if you had to accomplish all of your work or grow your company 2x while working two hours a week, if you had a gun against her head, how would you attempt to do that?

These type of absurd questions don’t allow you to use your default frameworks for solutions. They don’t allow you to use your base of current assumptions to come up with answers. It forces you to think laterally. It forces you to break some of the boundaries on the sphere of comfort that you’ve created for yourself. And that is what makes them, I think, in a way, so powerful. And these are not questions, by the way, I think are valuable if you ponder them for 10 seconds and go, hmm, yeah, maybe I do this and then move on with your day. I think that journaling as an adjunct to asking these questions is very, very important.

So I will sit down very often in the morning, one of my rituals– also borrowed from a lot of these people– is morning journaling of some type. And I tend to use either Morning Pages, Five Minute Journal, or just a separate type of freehand, sort of goal dissection. And this would be a case where I would ask one of those questions and I would write freehand for, say, three pages, three to five pages, and drink some tea as I’m doing it. And that is when you will not only come up with interesting ideas– and there might be 90% garbage– but if you have 10% that leads you in an interesting direction that could completely revolutionize your business or your life, if you take that seed and do something with it.

And that’s been the case for me for a very long time. I actually created a list at one point after observing this pattern among these people I was interviewing. And I just made a list of what are the most absurd things I could do right now related to my life and business. I created this long list and some of them were terrible. I mean, literally I was at a conference, I was bored, and that’s why I was doing this. And some of them were very specific, business-related. One of them was cut off my own feet? I mean like, what the hell?

And so I disregarded that one. I still have my feet. You can’t see, but they’re intact. And at the same time, though, one of them was take a complete break from startup investing. So retire from startup investing because that had become a source of stress due to the inbound, the deal flow. And that was a real game changer for me, taking my indefinite startup vacation about two years ago, which has led to incredible growth in other areas including in my own businesses. So there you have it. The power of absurd questions.