We met at a tech conference. I had designed the visual identity and was there to see the fruits of my labor. He had been invited as a panelist at one of the events. About 20 years my senior, he was still relatively young for a billionaire. He had made his fortune in tech for the hospitality industry.
At the time, I had just started working on the idea for my current startup. I thought I should get his contact info, so I asked the conference manager to introduce us.
Months later, I asked if he wanted to grab coffee with me and discuss some thoughts I had around product-market-fit. It seemed important to have a specific, genuine problem that I needed help with — something about honoring his time and acknowledging the difference in status between us.
It took some rescheduling to accommodate his busy life. But eventually, I was asked to come to his office, and we walked together to one of my favorite coffee spots.
For the moral of this story, I should first tell you some things about myself.
For most of my life, I’ve seen things a bit differently. I’ve had plenty of friends, but often had a hard time relating to them.
Instead of farting around and playing video games, I was always working on some project or busy dreaming about some grand future.
I never understood the value of the things most people spend their time on. They go to school because they are supposed to. They get a random job and devote years of their lives to it. They go get a drink to pass the time.
What’s the point of it all?
I have often felt like an alien, studying them and their interactions, like complicated ants milling around the anthill.
Frankly, I need a strong sense of purpose to find life worth living at all. When I have that, however, I get passionately ambitious.
This unusual way of seeing the world has often caused insecurities and self-doubt: Why can’t I just be normal? Why can’t I motivate myself to do normal things and enjoy them like everyone else?
The first thing I noticed as we walked together to the coffee place was how ordinary he looked. Sure, he was well dressed. Seemed like someone with a lot on his plate. And he did have that Richard Branson vibe going on, with longish hair and a rugged, unshaven face. But other than that, you could never tell he was anyone in particular.
Except, more people than me seemed to know who he was. As we entered the coffee shop, a lot of them were staring at us. Or maybe that was just in my imagination.
When we sat down together, he put his phone on the table. It was an older model iPhone with a broken screen. That said a lot about him.
We bonded immediately.
I talked about my startup and he gave lots of great advice. He told me how he never finished school because he was too busy building his first company. He told me about his cancer diagnosis 5 years prior and how that changed his whole perspective on life. How it made him a better father and husband because he finally valued his family over his work.
During our conversation, I felt a growing sensation, both liberating and reassuring. He was familiar in a way I couldn’t exactly point my finger to. He seemed so… human.
Then I understood what that sensation was:
I realized that despite our apparent differences, I have more in common with this guy than I do with any of my friends or anyone else in my life.
Now, you may be thinking, “hold on there pal, you’re not that special!”.
I know. I’m not saying I will become a billionaire anytime soon. I probably won’t. There is a lot more to being a successful entrepreneur than having a brain wired in a certain way. Besides, I don’t measure my success in billions. I’m not even sure I would enjoy having that much money. I would have to get a swimming pool to keep it all in. Seems like a lot of work.
My point is that becoming a self-made billionaire is rare. Incredibly rare, in fact. To achieve it, you have to somehow be different than almost everyone else. By definition.
Steve Jobs’s iconic voice comes to mind here:
The people who are crazy enough to think they can change the world, are the ones who do.
What changed in my brain when I had coffee with a billionaire was that I realized I am as crazy as him. And instead of letting that be a source of self-doubt, I finally decided to lean into it. Fully.
To some of you, this will be obvious. There may be nothing special to you about a billionaire. If you live in Silicon Valley or some such place, you probably know one who wears a hoodie.
But I think many entrepreneurs out there will recognize the feeling of being different in this particular way, and the self-doubt and loneliness that can come from it.
To me, meeting this man was proof that it’s okay to see things from an unusual perspective. It’s okay to dream and believe that you, of all people, have the capacity to create a radically different future from the one that would have existed if you were never here.
In fact, you have to be this way to have a shot at making it a reality.
To continue using Job’s famous words: If you are a square peg, you should not try to fit into a round hole. You should embrace the fact that you are a square peg.
So this is a reminder that it’s OK to be a square peg. In fact, we’re the lucky ones. We’re the one’s who get to change the world.
Let’s go make it happen.