In 1996, at the age of 17, in a miscalculated series of indiscretions, I decided to move to Los Angeles and become an actor.
Not one of my best ideas.
It was basically over the same day it started; I worked one day for a small meaningless part on a TV show called 90210 and quit the same day.
Some of you are too young to remember that show, so consider yourselves fortunate.
On an academic scholarship (if you can believe that after this story) to Loyola Marymount University, I still needed to pay rent and support my hobby: partying.
And, this was when I first became an entrepreneur.
In Marina Del Rey, a few miles from my college, I pitched the owner of a yacht company to contract his boat-50/50 on profits, and I would cover expenses. He accepted my offer. I knew my value proposition would be profitable. I spoke with confidence, brought my numbers, and closed the deal.
You see, in international waters, the legal drinking age was 18.
While I was nowhere near celebrity status in Hollywood, one might say I was an overnight star amongst my college peers for obvious reasons.
Entrepreneurs solve problems.
And, I figured out a way to help people get hammered drunk under the age of 21, legally.
Surprisingly, The College Administration was not in full support of my entrepreneurial endeavors and brought me into “meetings” to discuss my enterprise. They could not bust me on anything since I was not technically breaking any laws or violating school policies.
At the age of 19, $2500 a night plus bartending tips was not a bad gig.
I felt untouchable, and I was having the time of my life.
I figured out a way to hack the system.
However, a big ego often comes before the fall and fall it did.
Everything changed after a trip to Mexico.
Taking a few days off from work, I visited Rosarito, Mexico. I don’t recommend this place.
While drinking outside of a bar, I was visited by a couple of officers who gave me a free night stay at their “place of business.”
12 hours in a Mexican jail was an experience that impacted me and changed my way of thinking moving forward.
I learned a few things from this experience:
1. Whether it be a college or another country, it’s important to respect the culture. Regardless of the consequences, follow the standards, policies, AND the laws.
2. Freedom is Awesome. When I came back to the U.S. after being in jail in another country for the first time, I truly appreciated what it meant to be Free and be American. There are no Miranda rights in Mexico. They could have held me there as long as they wished.
3. Entrepreneurship stuck with me, and fortunately drinking and a partying lifestyle did not. I learned my lesson. It was a slap in the face that I needed as a young punk with great ideas but no discipline or foundation of respect at the time.
I often describe my time in Los Angeles as the best time of my life, and I would never do it again.
Don’t waste your time monetizing mediocrity. At the same time, don’t beat yourself up for mistakes. They happen. It’s part of the process.
It is no coincidence that the highest home run hitters also have the most strikeouts.
Swing for the fences, but be wise to keep yourself in the game.