Money is interesting. On one hand, it’s not one of the few things that truly matters in life. It doesn’t stand up next to family, relationships, or fulfilling work. On the other hand, it can be quite instrumental in building a foundation to sufficiently interact with those things in life that do matter most.

In 2016 I went on a cross-country RV tour. I wrote about that story on my blog a few years back. It was a passion-fueled attempt to show the world what I thought was a revolutionary discovery: that you don’t need to go to college to be successful. When I say it was passion fueled, I mean we were naively starstruck by this newfound insight and didn’t have a practical plan for how to harness it and direct it in a way that could be both helpful and sustainable.

To make a long story short, it was a massive financial failure. Fueled by credit cards and slivers of income from selling t-shirts and books, our adventure lasted about 7 months before we had to throw in the towel. Despite it being a financial failure, I look back fondly on the whole experience, knowing it was a necessary step filled with plenty of mistakes that helped me discover who I was.

At the time, those valuable lessons were hidden behind the stress of my financial instability. I was hemorrhaging cash and burying myself under a mountain of credit card debt, and I had no income and no plan for how to get out of it. Upon seeing the failure that was written on the wall, I shifted my focus from trying to take down the corrupt university system to patching up my bank account’s severed aorta.

So I did the only thing I knew how to do: start a painting business. I called it Pure Painting LLC. I printed out 1000 flyers and took to the streets in Santa Barbara, knocking on doors, dropping flyers, and doing everything I could to scrounge up some painting work. It’s actually quite funny to picture. Every day I’d park my 23-foot mobile home at the entrance of a neighborhood, hop out, flyers in hand, and start off door-to-door. After about 2 weeks of hitting the pavement hard, I found myself in the company of a husband and wife who were the first ones to take me seriously. They had a quaint little one-story house wrapped with stucco that badly needed to be repainted. They had kids of their own, about my age, and I guess they could tell I was earnest and not trying to rip anyone off. I was ready to work my ass off and earn some money to get myself back on my feet. I gave them an estimate first, and after a few days of letting them think it over I came by again and they were almost ready to go with me.

The sensible thing to do is hire a local painting company with a reputation in the area. The questionable thing to do is hire the dirtbag kid who’s living in his RV and could run away with your money at any point. I made the deal more enticing to them by offering to accept payment after the job was completed. It wasn’t the smartest thing to do as a contractor, but I was the one with zero leverage. They were taking a risk on me, so I felt it was only right to meet them halfway with a risk of my own.

Before sealing the deal, their final request was to talk with my mom on the phone. It was slightly embarrassing, and I kind of felt like I was in elementary school again. But I understood that they needed some way to vet me. After all, the whole thing was pretty unusual. They had plenty of questions when I rolled up to their house in my colorful RV for the first time. But luckily, they seemed to get along well with my mom on the phone, and soon after, we scheduled a date to get the painting done.

I spent six 10-hour days out in the sun, working my ass off like I had planned. It wasn’t fun at all, but I knew it would be worth it at the end. And on the 6th day, after walking around with the customers and doing the final touch-ups, they handed me the stack of cash you see in the picture above.

I cleaned out my equipment, and just as dusk fell on the cool California coast that evening, I pulled myself into my RV, spread the cash out on my table and snapped this picture. My paint-stained hand represents my hard work and determination. The cash on the table represents the foundation of my future that I had rightfully earned. I felt “self-made.” I felt proud. I knew there was a lot of work ahead of me, but I slept soundly that night with an aura of satisfaction floating through my RV.


I still owed about $30,000 across 6 credit cards, but this hard-earned paycheck was the beginning of my climb back into the game.

Today, I’m proud to say that I’ve paid it all down to $6,000 in under 2 years and the end is clearly in sight.

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