I MADE $15B WITH CHAT GPT

Would you bet EVERYTHING on one idea?

Michael Saylor did.

Michael is a technology entrepreneur and the founder of the company now called Strategy. Long before Bitcoin, he built businesses in business intelligence, speech recognition and smart-home technology. Today, he is probably best known for turning his company into the world’s largest corporate holder of Bitcoin.

In 2020, his company was worth around $600 million when he made what I described to him as an “early, very contrarian bet on Bitcoin”. At its peak, the company reached roughly $125 billion.

I wanted to understand what Michael saw that almost everyone else didn’t, where that level of conviction comes from, and why his thinking goes far beyond Bitcoin.

We discussed things like:

- How he says AI helped him create $15 billion last year.

- Why he believes buying a house might not be the best way to build wealth.

- What he would study if he was 18 today.

- Which careers AI could completely transform.

- What is happening to the value of the money sitting in your bank.

- Why he still has such enormous conviction in Bitcoin.

Michael’s whole point is that technology, money and careers are not separate conversations.

He sees them as connected parts of where the world is heading, and believes the decisions we make now could matter far more than most people realise.

Even if you see the world differently to Michael, there is a lot to take from the way he thinks. His experience building technology companies, making enormous financial bets and thinking deeply about AI gives him a perspective on money, work and the future that is worth listening to.