welcome to big think on the go

today’s topic is become the smartest

person in the room

develop superpowers by investigating

what others won’t

presented by tim ferriss

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


world-class performers meaning investors


writers you name it and asking dumb


can take many forms i’ll give you a few

examples malcolm gladwell

is very good at asking so-called dumb


you 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 would literally he might ask that

ten 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

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 to leave

but uh if we look at another sphere say


chris sacca a close friend of mine


incredible tech investor just immaculate

track record is very good at asking dumb


and this applies to in the very early

days where he did something

very clever which was at google when he


just entry level guy really compared

certainly to say

the 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 sergey or whatever

and he’d walk in and

sit down and they’d kind of look at each

other and ask him what he was doing

there you go oh

i’ll just take notes and they’re like


and so he gets 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 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 uh bloomberg who’s co-founder of

gimlet media which has a slew of

gigantic podcast hits

just a a factory for podcasts


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


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


who stand next to no chance of paying it


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


if you look across all of the icons

titans world-class performers that i’ve

interviewed in the

say wealthy section right if we’re

dividing them into healthy wealthy and

wise we look at the

the business side of things one of the


common patterns that you spot is absurd


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


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 x prize

he might ask the founders of companies


looking at as potential investments if

you had to 10x the economics of your


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 your head

how would you attempt to do that these

type of absurd questions

don’t allow you to use your default


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


are valuable if you ponder them for 10

seconds and go hmm

yeah maybe i would do this and then move

on with your day i think that

journaling as an adjunct to asking these

questions is

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


interesting ideas uh and there might be


garbage but if you have 10 percent that

leads you in an interesting direction

that could completely revolutionize your


or your life if you take that seed and

do something with it and that’s been the


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


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 when i still

have my feet you can’t see but they’re


and at the same time though one of them

was take a complete break from startup


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


to summarize ask dumb questions

as social creatures we worry about

looking stupid in front of other people

the possibility of embarrassment keeps

us from asking about things we don’t


try letting go of your intellectual


if you don’t understand something speak

up say

i don’t understand can you please

explain that

persist until you grasp the answer

when possible surround yourself with

people who are more experienced or

knowledgeable than you are

don’t be afraid to ask obvious questions

you might help uncover a potential


oftentimes the dumb question is actually

the smartest question you can ask

if you want to ask it others probably

want to ask it too

in a world governed by shame asking

what’s on your mind

can lead to success


ask absurd questions try asking yourself

questions that seem crazy

why can’t i accomplish my 10 year plan

in the next six months

if i had to 10x the growth of my company

in the next three months

how would i do it it can’t be done

is not an acceptable answer

absurd questions can provide positive


they keep you from falling back on your

default frameworks for solving problems

the idea is to set aside your current

assumptions and force yourself out of

your comfort zone

don’t treat absurd questions as a

fleeting thought exercise

take them seriously try journaling to

flesh out your answers

asking absurd questions can

revolutionize your business or your life

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