Cloudrovia WS
Thursday November 4, 2021 By Cloudrovia
Break the Matrix with Curiosity, Empathy & Serenity

You get up, you brush your teeth, you eat cereal. You go to school. Do as you’re told, sit up straight, show up on time. Don’t talk back. Be a good person. Fit in. Don’t make waves. Stay in your lane.

The nail that sticks out is hammered down. But isn’t that the problem?

A whole system, a whole society, a whole civilisation dedicated to telling you how to live and what to do and how to think. But there is a way to break out and it’s a way that repeats over and over again.

And the founders that I’ve worked with who have gone on to create massive businesses.

What do you need to break out of it? Let’s get started.

What do you need to break out of it?

You need First Principles thinking.

Can you start from what you are absolutely sure is true? Can you have direct experience with a thing or get more experienced such that you can make a more well-informed decision or guess as to how something works or the state of a particular thing?

Remember where we started, the classroom, the workplace.

These places where we sometimes spend years and years of our lives are designed to teach you to stay in the box that you live in. You learn the history. You learn how it’s been done and then you were programmed to believe that that is how they will be for forever.

And this is where first principles thinking can help you.

Because in contrast, you will end up challenging the preconceived notions and the thinking by analogy that the rest of the world has imposed on us. Outside the box.

There are ways you can make something new and different and it starts with three things I think you need.

Number one is CURIOSITY. Number two is EMPATHY. And three strangely is actually SERENITY.

Those are the three key things that will allow you to start on your path towards first principles thinking.

Here’s a little video of the richest man on earth explaining first principles.

First comes curiosity

Asking questions and digging further to understand how those systems work. One of the key ways to do this is actually the five whys analysis.

It’s something that the Toyota production system came up with years ago in Japan.

Toyota Factory developed the ‘5 whys analysis’

Here’s one of my favourite examples:

So imagine your website’s down. First why, why was the website down?

Well the CPU utilisation on our front end servers went to a hundred percent.

Second why, why did the CPU usage spike? Well, some code contained an infinite loop.

Third why, well, why did that code get written? A programmer made a mistake.

Why did that mistake get checked in? He didn’t write a unit test for the feature.

Well, why didn’t he write a unit test? He’s a new employee and he wasn’t properly trained to do test-driven development.

So if you ask why it will allow you to fully explore why something happened.

They say because the most common problems keep recurring, your prevention efforts are automatically focused on the 20% of your product that needs the most help. That’s also the same 20% that causes you to waste the most time.

So five whys actually pays for itself awfully fast and it makes life noticeably better almost right away.

The five whys is why the Toyota production system made Toyota so successful.

Today we think Japanese cars are incredibly reliable but they had to come up with a process to get there.

And curiosity is a key part of understanding why things are and then how to fix it.

Then comes Empathy

Second is empathy, getting an intuitive sense for the lived experience and feelings of other people particularly customers.

Listening to users and getting their direct experience is something that a lot of people know how to do.

When you do it well sometimes it can help you create a billion dollar startup.

Airbnb had a unique connection to their early users

Airbnb just had an incredible IPO, but when it first came out, a lot of people said, Airbnb, wasn’t going to work.

It was literally just air beds and breakfast. Brian and Joe at Airbnb worked on something that was kind of a fringe idea. They needed money for rent and a design conference was in town. They thought they could make rent by making a website and letting people crash on the floor of their San Francisco Soma loft on Roush street. This is what Brian said when describing what it was like to host people for the first time:

“We ended up hosting three people from around the world. A 35 year old women from Boston, a 45 year old father of five from Utah and a  30 year old from India. And now I got to tell you, the reason we started doing this is ’cause we thought it was funny, cool and we make money. ‘Cause we had to make rent. There’s something that happens though when somebody lives with you, it’s kind of like the arc of a friendship gets contracted from a year or to a day. In other words, if you were to meet somebody maybe here at Stanford or in the real world, and you get to know them how much time does it take to like invite them over your house and have dinner with them? It might take like months, even a year. Like you don’t just get to know people. And indeed we realise is it contracted this year-long friendship into a couple of days. And so these people came as strangers. They literally left us friends. We ended up keeping in touch with them. In fact, one of the guests ended up inviting me to his wedding. The other guests, this woman moves from Boston to San Francisco. And I think we’re realising there’s a bigger idea here”.

This is a really interesting experience in empathy because it was so direct. You can’t get closer to someone than literally sleeping under the same roof with your users. And what they heard in that first experience was what they use to pursue that idea.

They had direct experience which gave them direct belief and conviction that this was something that was going to work.

Airbnb is now worth more than a hundred billion dollars and counting on the public markets.

Third and most counterintuitively, comes serenity.

The ability to accept things that you cannot change. This of course is from the serenity prayer by theologian Reinhold Niebuhr.

God, grant me the serenity to accept the things I cannot change, courage to change the things I can and the wisdom to know the difference.

One of the best recent examples is actually DoorDash.

Dooordash avoided early battles with giants

They reached 50% market share in the United States through a brilliant mix of strategy but also extreme customer focus.

Now picture this, you’re DoorDash, your competitors like Uber have incredible access to capital and they’re fighting it out in the cities in a pitched battle for market share.

Early DoorDash employee Michael Block, recounted this in a recent tweet storm:

“Seamless had a 17 year headstart. Uber had x50, their marketing budget. They retreated, they retrenched to Long Island, New Jersey, Westchester and Connecticut. They found product market fit there and were profitable in a matter of months.”

Door Dash had the serenity to accept things they could not change.

They went to the suburbs where their competitors were not. And here’s the key thing.

They took the profits in the suburbs and won the cities and a capital war.

There are two ways to win. One is just to raise more money but what can you do if you can’t raise more money?

You’ve got to do what DoorDash did- be more profitable, outflank and outsmart.

Don’t fight a losing battle.

Fight the battle you can win.

DoorDash is now worth over $55 billion on the public market.

If you have first principles thinking, you’ll have the curiosity, the empathy and the serenity to find a better path.

You’ll break out of the standard script. You’ll go direct. You’ll learn more about the customer and you’re going to fight the right battles. You can win this.

Thanks for reading & as always, good luck.

If you want to reach out, my email is

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If you’re unfamiliar with our blog, try starting with these:

1. Blog to Business in 6 Steps

2. How to win business in your city.

3. How to build a website that makes money

4. Build your eShop for income in 6 steps

5. You’ve been promoting your business wrong

6. Get started on social media

7. How to Content Market with No Budget

8. Social Media Toolkit

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