It's 2017. I'm in San Francisco.
I have a meeting with a well-known billionaire because I'm looking for money to keep growing my startup.
With a single yes, this billionaire could change the course of my life.
I walk into the room. I shake his hand, and his assistant gets ready to take notes.
He's wearing a slim blue suit and a crisp white shirt and does a double take as he sees the scuffs on my sneakers.
We start talking, but I'm nervous. I hear my voice cracking.
I feel like if I get something wrong, he'll incinerate my pitch deck. I can picture his assistant sweeping up the ashes of my dreams.
But over that next half hour, this billionaire asked me questions that showed me how he thinks. Because the truth is, getting rich enough to buy sports teams or help millions of people through charity means you need to think differently.
Billionaire thinking isn't about productivity hacks, morning routines, or overpriced green smoothies. It's about a perspective that anyone can apply to their life.
So, in this article, I'm going to share lessons I've learned about the billionaire mindset. And at the end, I'll share the email the billionaire sent me after we met that's helped make my own wealth journey more fun and rewarding.
The first lesson is the most foundational one: without it, we've got no chance of making serious money or having a big impact on the world.
Lesson #1. Give yourself a chance
I've got a confession to make…
I spent too much time early in my career doing side hustles that were never going to go anywhere. Importing junk from China, getting shirts tailored, or small-scale consulting.
It breaks my heart to see lots of super smart people making the same mistake I did.
No one has made real dough by doing this stuff.
Now don't get me wrong, there's nothing bad about these things. You can learn a tonne, and it can be a fun hobby in itself.
But if the goal is to think like a billionaire and create massive wealth, there are only a handful of things that can have that sort of potential.
And this is where we need to focus.
You may know the story of Steve Schwarzman, the guy who co-founded Blackstone, one of the world's biggest investment firms.
In his book What It Takes, something he highlights over and over again is:
"It's just as hard to run a small business as it is a big one. You'll suffer the same emotional and psychological heartache.
So if you're going to dedicate your life to a business (and that's the only way it will work), you should choose the one with the biggest potential."
An analogy I find helpful for remembering effort versus reward is the lion and the antelope.
Lions need to eat and have choices on where to invest their time and energy. They can spend the day chasing lots of field mice, or they can hunt one big antelope.
Billionaires chase antelope because they recognise it's the bigger reward.
But thinking alone won't get you there, which is why you need to keep the second billionaire lesson in mind.
Lesson #2. You must be different
When I outlined my business and the vision to the billionaire, one of his first questions was: "Why now?"
It's a super common question that experienced investors know to ask. Because when most people look at an investment, they often think about a business in isolation.
But that's not the case…
For a business to really succeed, it needs to take advantage of changes in the market.
When markets change, it creates opportunity but also huge amounts of risk. Because of that, companies don't always make it.
And that's okay for the venture investors.
Because with this portfolio approach of lots of bets, 1 or 2 of them will have extreme outcomes and make it all worth it.
If you look at the list of self-made billionaires and how they did it, though, you'll find something common in most of their stories. They identified and rode a wave of change. Something happened in the market or an industry, and they found a way to ride that wave to make billions.
So when a billionaire asks "Why now?", they're searching for something happening more broadly in big industries that represents an opportunity for an extreme outcome.
Now that may sound like guesswork… but here's a secret.
There are really only three ways this type of massive change occurs, so you can focus on these three things to find great opportunities.
Regulatory change
In the 1970s, investors in the US were turning away from the stock market.
There was a lack of information about stock prices and trades, and different exchanges were doing their own thing.
This would have been like shopping for a used car in a city with multiple car dealerships, but each dealership has its own set of rules, and there's no central database showing all available cars, their conditions, and prices.
Because of this, people didn't trust the system and were reluctant to make decisions, leading to a lack of confidence in the foundation of capitalism.
So the government stepped in to bring more transparency to financial markets. They changed the rules of the game, and that change created an opportunity.
Michael Bloomberg launched a terminal focused on real-time financial data. Over the next 40 years, he built a massive company and a fortune worth over $100 billion, and he has given billions to charity.
Now the second type is actually where most fortunes have been built.
Technology change
There's no better example of this than one of the greatest business builders this world will ever see. And he's done it repeatedly by either starting or helping scale companies in space, electric vehicles, and solar power.
I'm talking about Elon Musk.
He's one of the richest men in the world and the perfect example of thinking like a billionaire by identifying technology change and then riding that wave with innovation.
So we've now covered two: being alert to big changes in regulation and technology. Let's talk about the third one, the most disruptive one and my favourite.
Business model change
Do you remember the early 2000s? If you didn't have a car and needed to get somewhere fast, you had to go out on the street and try to hail a taxi before someone else got it?
Then, when you got wherever you were going, you were shocked by how much the ride cost. Yeah, that sucked.
But things were changing. Soon everyone had a computer in their hand with the iPhone… but it wasn't just the iPhone.
Uber introduced a business model to connect drivers directly with passengers.
Over the next decade, this transformed urban mobility, and Travis Kalanick became a billionaire along the way.
The key takeaway: as with regulatory and technology change, when business models change, there's scope for billion-dollar ideas.
But did you know that Uber wasn't the first ride-sharing app?
Another company called Zimride offered long-distance ride-sharing between college campuses before Uber, and even Zimride got the idea from Zimbabwe, where locals were using crowdsourced carpools to get around.
This leads to the third big lesson I learned from that billionaire.
Lesson #3. Good artists copy, great artists steal
If you haven't heard that quote before, it's usually attributed to one of the world's greatest painters, Pablo Picasso.
It may sound strange hearing that from someone held in such high esteem in the world of art. But it's true. Time and time again, billionaires talk about shamelessly copying stuff that works.
The billionaire that I was pitching started asking about competition and reminded me that…
"You don't need to reinvent the wheel. There are plenty of wheels already out there. You just need to make them bigger, spin faster, or in new directions."
What he was saying is to focus on innovation, not invention.
However, he also told me that copying alone won't get you there. You need two other ingredients to get an edge, which I'll tell you about in a second.
But he was right about the power of iteration. That's how a small discount store in the 1960s became the world's biggest retailer.
Walmart is a beast, and it's probably going to be the first company to crack a trillion dollars of revenue in the next decade.
The founder, Sam Walton, passed away with $10 billion to his name. But what makes Sam's story so unique is that he didn't invent anything.
All the pieces of the business he put together already existed. Sam just copied other people's stuff and scaled it.
This matters in thinking like a billionaire because you don't want to spend all of your time in the game of creating ideas. Like the story about the lion and the antelope, it's about the trade-off of effort and reward. You want to spend your time on the game of making money.
And when you see another game being played where the outcomes can be even bigger, you shouldn't be afraid of changing the game you're playing.
When you look at the histories of some of the wealthiest people, they weren't afraid of change. They embraced it, modified the wheel, and got going.
Ray Kroc was selling milkshake machines to McDonald's, then figured out that their business was better than his and took it over.
Zuckerberg looked at platforms like Friendster and MySpace, then took the idea and launched "Thefacebook" into colleges.
We could go on and on, but the lesson here is this:
It doesn't need to be an original idea to make huge amounts of money.
Remember how the billionaire told me that copying can help, but you need two other things?
The first one is capital. You've got to invest money to make money.
But everyone knows that, and that won't help you think like a billionaire. The other thing you need is people.
Lesson #4. You can't do it yourself
After learning about our business, the billionaire then started asking about our founding team, key people and advisors. He wanted to make sure it wasn't just me.
I know why. It's teams that build the biggest companies, and there are no billionaires who did it themselves.
Not one.
That may seem like a simple insight, but it tells you something.
If you want to think like a billionaire, you need to be thinking about how to motivate other people to work on your vision.
This is something I struggled with in my early career. I thought I could do everything myself.
But over and over again, I was reminded...
If you want to go fast, go alone. If you want to go far, go together.
You can see this trade-off everywhere, from startups all the way to the bigger end of town, where leaders of massive global companies spend all their time recruiting.
Steve Schwarzman has an awesome way of thinking like this that stuck with me for years. He would describe people as 8s, 9s or 10s.
8s will do what you tell them.
9s execute well and can develop strategies.
But 10s… 10s are where it's at.
They sense problems and design solutions. They raise the bar for everyone around them.
Thinking like a billionaire is about assembling and empowering the right team. One that can take your vision and turn it into a reality. But even with a great team, things will go wrong.
And many billionaire stories are littered with decades of betrayal, disasters, and heartbreak.
This is why, to think like a billionaire, you need to…
Lesson #5. Develop a thick skin
In the mid-1980s, Apple was struggling, and Steve Jobs got booted from the company he co-founded.
Instead of being crippled by the defeat, he went off to start another company, NeXT, whose operating system later became the foundation of Apple's.
Then a decade later, when Apple was knocking on the door of bankruptcy, they brought Jobs back.
A year later he was the CEO, and from there, he led one of the sharpest turns in corporate history, launching many of the products we're addicted to today.
Why is this important?
Well, there's a saying: you know you're out in front when you have arrows in your back.
To think like a billionaire, you need a thick skin for all the problems and setbacks that will come your way. That sounds tiring.
You might think the logical thing to do once you have a billion is to hire someone else and go relax somewhere.
But guess what? Almost none of them slow down.
That's because they almost always seem to have this final trait in common, and it's the most important one.
A few days after I met the billionaire, I got an email from him. It was a buzz just seeing his name in my inbox.
Then I opened the message…
He passed. This billionaire wasn't ready to invest in us. That hurt.
But, as much as I wanted that funding, I eventually saw that the billionaire gave me something more valuable than his money.
He taught me that the most important trait of successful people is to:
Enjoy the chase
Most successful people never seem to stop.
Because they love the game, the money doesn't matter. That's just a way to keep score.
As Jim Rohn teaches us:
"You've got to be happy with what you've got while you chase what you want."
And if you walk away from this article with one thing, I hope it's this:
The billionaire mindset isn't about the money. It's about the joy and thrill of the ride.
As Naval says, if you can't be happy with a coffee, you won't be happy with a yacht.
It's the experience and the journey that matter.
So if you're chasing more wealth and impact, enjoy the ride, because it's going to take time and some luck… and there are proven ways to channel more luck into your life.
I read the top 4 books on it so you don't have to. You can check them out here.