A billionaire set me free

Have you ever heard of the man who wanted everything and lost it all? He was hungry. Chasing his dreams. The more money he made, the more he needed. The more he needed, the more he risked losing it all. He was hungry. He grew up impoverished. His father a Priest, taking an oath to be a commoner. Money was tight and so was living a decent life. As a child he sat in his parent’s station-wagon, muttering to himself.

“I’ll be a millionaire, one day,” he’d tell himself. Years later he told me this story. As years turned into decades, I came to work for this man who was worth a hefty sum. I began to understand him. I saw who he was. He wasn’t hungry anymore. He wasn’t dreaming. He was chasing. Chasing a feeling. A feeling of being enough. A feeling of being secure. He craved the security he could never find as a child.

Now, wait up Josh! You’re telling me this guy had all the money in the world and still felt he wasn’t secure? Yes, I am. I’ll tell you how it cost him everything.

I witnessed this man search and hunt and chase. I was paid to help him. I watched as he would grow closer to his feeling of security. And right as he found it, something went God-awfully wrong. It happened again. And again. And again.

Back to square-one he’d go. We’d start the treacherous climb up the mountain. And as we reached the top, sure enough. Manure would end up everywhere. And the world was ending. Again.

One day, not so long ago, the world began to end for him. I thought, just another day, just another problem in his hunt to feel secure. Boy, I was wrong. As the days grew into months, he began to lose it all. It began with his marriage. Then the family breakdown. And then his multi-figure business. Within a year, he was transformed from the millionaire at the tip of the mountain to a lonely, pitiful, broken man bathing in the stream with the otters and the moose and the commoners. In between the court orders and the repossessed vehicles, I was no longer in his world. I watched from a distance.

I saw this man lose it all. I was stumped. How did a man do this to himself?

That’s when I began my own journey. And it took years for me to understand why he had lost it all.

This April held a conference in Austin. I knew the people who were attending would be worth meeting. Finding myself there, I began to mingle.

A face grew closer to me and I recognised who he was. He’s a billionaire, fairly well known in the e-commerce and marketing space. He owns some cool companies. Shaking his hand, he was everything and nothing I’d expect a billionaire to be. Nice clothes, perfectly groomed hair, a stunning smile and the charisma of a calm man. I listened to him talk to people. They all wanted answers to their questions. They were miserable — they weren’t confident–they didn’t know what to do. So they’d ask him, as if he were a God. I asked him my own question, on a completely different topic, and went about my day. It wasn’t until later did I hear something that struck me.

Someone asked him if he felt financially secure. His answer? No. Here’s a man with ten-times the money of the guy I worked for, and he still doesn’t feel secure. I listened. He explained.

He began his business to make a nice living. A nice living became an excellent one. Attracting women, cars, watches and lavish bottles of wine. And there was more of it. Yet, he confessed, the more he had, the more financially insecure he became.

He admitted that, upon giving the gift of reliving his life, he wouldn’t build his fortune by chasing the feeling of security. No, he said, he’d choose to feel secure and choose to be enough.

“Chasing something isn’t freedom. It’s a war. But if you’re just playing the game and having fun, you’re truly free.”

And in that one sentence it all made sense. It all clicked.

In one sentence, a billionaire set me free. Free of my own restraints and free from my own doubts.

It all made sense. The man I’d worked for lost it all because he was chasing something he could never have — because he never allowed himself to have it.

A billionaire showed me why the chase of money, of freedom, of sex, or love, or adventure may be fun — deep down, it’s dangerous. Because there is never enough.

“If I had to do it all over again, I’d tell myself I am enough.”