How to Think Like Andrew Wilkinson

I just finished reading Never Enough - the behind-the-scenes story of how Andrew went from a barista to a billionaire.

It's a 4.5 hour read that shows you how he thinks about business, life, and having that much wealth to your name.

Here's how you can think like Andrew:

Think of Life as a Poker Game

Annie Duke explains this well in her book Thinking in Bets.

Life is much more like a game of poker than chess.

Andrew applies this thought process from Charlie Munger:

How to Think About Starting a Business

"Anyone with a little sweat and hustle, a sprinkle of bullshit on top, and a heaping of luck could start a company."

How to Think About Growing a Business

• Create demand

• Build systems and processes

• Hire other people to do the work

• Charge enough for whatever is is that you're selling turns into profit

"It's a machine that converts raw materials (client leads, opportunities, and introductions) into a fully formed product (an app, website, logo, whatever clients wanted)."

How to Think About Creating Your Dream Lifestyle

You have a list of all the goals you want to achieve.

But it's more powerful to make a list of things you want to avoid.

These are your Anti-Goals:

Andrew has a great Medium article explaining this concept.

Just Google "Andrew Wilkinson Antigoals" and it'll come up.

How to Think About Throwing Hail Marys

Andrew ran a tech blog with a few friends when he was a teenager.

He threw a Hail Mary asking to interview Steve Jobs at the Macworld conference.

His lesson:

"Shoot for the moon and ask for something that's hard to give. The compromise you get will be better than you could have hoped for."

This reminds me of how Tim Ferriss talks about becoming an asking machine and flexing your "asking muscle" as much as possible.

How to Reflect on Yourself

You can understand yourself by understanding the story of your parents.

"You can always understand the son by the story of his father."

Some questions to help you reflect on this:

• What perspectives that my parents have drive me the most crazy (ex. money is hard to acquire)?

• How am I accidentally applying those lessons in my life?

• How would someone that believed the opposite think and act?

How often do you think about how you're thinking?

Every week I send a weekly reflection that turns AI into your thinking partner.

Take a quiet moment to cut out the noise and refocus with psychology principles, mental models, and questions from your favorite entrepreneurs.

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