Finding Wealth in Humility: Lessons from My Money Mess

Thu, Mar 28, 2024

I started my first real business at 20, making way more money than I deserved.

Naturally, I got myself the house on the hill, the luxury car, the designer watch, and God only knows how much I spent on other frivolous garbage.

It was all gone in under 3 years.

The 2008 recession taught me an invaluable lesson: None of those things were mine.

This surprised me at the time, but the bank was very quick to remind me how little I owed just as soon as I stopped paying them their money. It was all vapor.

At 23, my house had been foreclosed on, my car had been repossessed, I was six figures in debt, and I had already been evicted from one apartment (while diligently working on my second one). I had no real business to speak of and was supremely unemployable.

It felt hopeless.

On weekends, my expired Costco card would get me in, where I would make as many trips to the free-sample stations as I could before starting to get suspicious looks. On really good days, I’d have the $1.50 it took to buy that shockingly inflation-proof hotdog. Not my shining moment.

This was the most stressful, most difficult time in my adult life. I felt like I was in a hole 50 feet deep with no way out and no one coming to save me. Ironically, it ended up being the best thing that ever happened to me and the perfect way to start my entrepreneurial career.

First, it taught me what money is.

Like most born on the lower rung of the socioeconomic ladder, I thought money was the goal. The result. The reward. And once you have it, you spend it. Then they give you credit! You could spend that 10X faster. Gee golly, what a deal.

Money is fuel. It’s what makes things (life, business, opportunities) go. Without money, you’re a car without gas. Get good at pushin’. With money, you can go fast. When I spend, I do so with that in mind. I’m spending fuel.

Would I rather have [whatever], or would I rather keep the fuel?

Second, it taught me humility.

There was stuff I thought I was above. Work I thought was beneath me. I was wrong. I’ve always been good at the hustle.

Before the collapse, I was hustling big deals. Afterward, I was hustling for grunt work and was truly grateful when I got it.

Finally, it taught me how much I’m capable of if I’m just willing to put my head down and work.

I paid off all of my debt and slowly built back from less than zero. I made it all the stupid way: $1 at a time. But I learned to rely on myself. I learned I could rely on myself.

I remember I could finally scrape together enough money to buy myself an old Mitsubishi Eclipse for $4K cash. That little car meant so much more than the luxury car I drove but never really owned.

It was mine. I earned it. No one could take it away from me.

What’s the hardest thing you’ve gone through in your business life? What did you learn from it?