From Folly to Fortune: The Art of Asking ‘Stupid’ Questions

The surprising path to financial prosperity

Sebastian Zoellner
Read or Die!
2 min readApr 2, 2024

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Rich people must be smart. But smart people aren´t always rich.

Being overly analytic and bright can stand between you and a possible life-changing idea.

Because stupidity rules, in some way.

I´ll show you:

➡How it can lead to wealth.

➡Who has done it?

➡How you can do it, too.

First of all, I know asking stupid questions may seem:

  • silly,
  • a waste of time,
  • embarrassing,
  • and annoying to others

BUT, they are a tool to uncover the essence of what you’re looking at.

They’re not meant to make you look smart, but to help you understand a subject.

Once you deeply understand a game, you can rewrite the rules.

This process works in this way:

Condense information >grasp first principles > rearrange components

You’ll get rich if you create something more efficient in an already existing demand or by birthing a new craving.

Both ways need a portion of courageous dumb questioning.

If you don’t want to trust me — okay, but this guy has done it — many times.

Elon Musk.

He is good at asking stupid questions.

By stomping Tesla into life he was led by certain questions:

1️⃣ Why can’t we create a sustainable transportation future?

  • Stupid questions to ask in 2004.

2️⃣ Why can’t we make more efficient and longer-lasting batteries?

  • Stupid question for the car industry, because there was oil.

3️⃣ Why can’t electric cars be as aesthetically pleasing and powerful as conventional cars?

  • Stupid question to ask, because no one wants them anyway.

The result: 744.821 billion market cap

Tony Robbins famously said:

“The quality of your questions determines the quality of your life.”

He is right.

Questions shape the world we perceive.

When we change it, our perspective changes.

That is why the path of our solution is going to change if we change the starting point — the question.

Here is how you can start asking dumb questions:

Challenge the most obvious concepts with a why.

Why can´t I rent out spare space? → AirBnB

Why can´t I take all my favorite books along ?-> Ebooks

Why can´t I take all my musica along on my vacation? → Ipod

Imagination is a big pond of possibilities and a question is the rod to fish them.

Most of all, have fun.

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