“Dan, you owe $250,000 to the IRS back taxes.”
This was the moment that defined me as an entrepreneur, but let’s back up…
My entrepreneurial journey started in my early 20s. I was a young musician that spent most of my time playing guitar and working as a pizza boy.
I spent seven years with the same daily schedule. Get up, research how to be a successful entrepreneur. Go to work and deliver pizza. Come home, wash the grease smell off, play music. Repeat.
Seven years. Seven years of hoping to get a five dollar tip at my next delivery so I could pay my rent…
Until the day I finally cracked.
It was -16°. With windchill factored in, it was -51° in the Chicago suburbs. I drove to the outer limits of our delivery zone. I spent 15 minutes alone scraping the windshield just to get out of the parking lot.
I walked up six flights of stairs because the building had no elevator. I delivered pizza to a man named Gupta. I was sure I would get an amazing tip for basically risking my life to travel through a frozen tundra to get him his medium pizza.
Not only did he stiff me, but he complained the pizza wasn’t hot enough. My manager made me take the entire trip all over again. Yes, even the second time out, I didn’t receive a single penny.
A week later I quit and decided to start my own business.
The next several years were rough. I did everything. I started an Italian ice cart and traveled with a carnival. I then expanded to cotton candy and even airbrush tattoos at birthday parties.
Later on, I started a blog and an SEO agency, and probably several businesses I don’t even remember…
I started to become somewhat successful and even bought my first nightclub.
I thought things were going extremely well. I developed several skills as an entrepreneur, learned how to market online, acquired some sales skills, and things were generally looking up.
I sold my night club for a pretty big profit, and instead of being smart, I did what any young person with new money would do.
I lost it all.
I made a bad investment, went all in on one thing, and lost everything.
Things got so bad at one point that the electricity kept getting shut off. I took my last few dollars and instead of buying food, I bought water bottles and tried to sell them on the side of the road to get the lights back on.