Time For Amateur Hour
The worst mistake I made in my first business is that we were profitable.
Unprofitable internet companies were valued on the dream. Profitable companies were valued by profits.
Another mistake I made was I never returned calls. And another mistake was not firing clients fast enough.
This is what is known as “amateur hour”.
In 2010, the Wall St. Journal hated me so I stopped writing for them. In 2009, the Financial Times hated me. In 2008 thestreet.com hated me.
So I decided to write for just me.
I didn’t know what to write. So I started writing incredibly embarrassing things about myself and what I learned from them.
Many people in the financial biz are afraid to admit they make mistakes. So I decided to share all of mine.
At the time everyone thought I went completely mentally ill. Even some relatives stopped talking to me.
One person said, “this is like watching a train wreck in slow motion”. Another well-known writer called me a criminal because of something I did when I was 16.
Another person, a CEO of a company I once worked for, thought I had a nervous breakdown.
But I was just an amateur, trying to figure my way around. And I still am.
I’ve been podcasting for a few months. Sometimes I hit home runs and sometimes I strike out.
In the podcast posted this past Friday I struck out so bad we had to do a podcast OVER the interview so I could point out all the ways I could’ve done better.
I feel sorry for my guest, the rapper Biz Markie. He even hung up on me (as you can hear at the end).
I went into that podcast with the wrong approach. I sort of wanted to be best friends with Biz Markie after that podcast. Like we’d hang out on Sundays and throw a football back and forth and he’d teach me how to rap.
And we’d laugh about how hard it was for me but he would say, “don’t worry, it took me at least a week also.”
We’d be “just a friend” to each other.
But it didn’t work out that way. Aaron Brabham and I rewound the interview and did the blow by blow (over the interview with Biz) of where I went wrong so the podcast became like a “meta-podcast”.
A friend of mine once worked for what seemed like a great hedge fund. But he wanted to advance in his career so he asked for my advice.
Since I considered myself a genius, I freely gave my advice: why don’t you set up a separate fund and raise money for it and put that money into the hedge fund you work for since it’s normally closed to outsiders. This is called a “feeder fund”.
He didn’t really like my idea. He wanted to trade instead so he quit his job, moved to a different country, and started trading. Which is just as well because my advice was to have him set up a feeder fund for Bernie Madoff’s hedge fund.
I love being an amateur. Sometimes I make mistakes but that’s ok. Within the next 1000 or so years I’ll be dead anyway I hope.
Every day I figure out what I’m an amateur at and I focus on it. Every single day (today was “Cubism”).
Why?
- Amateurs get to play. Because we have no clue what we are doing we get to try everything. Even really stupid things. Playing releases oxytocin. Reduces stress.
- Amateurs have a steep learning curve in front of them. I love that learning curve. Its like there’s a forest fire in my brain.
- When I’m in amateur mode I feel like I’m an outsider. Being on the perimeter of a group, in evolutionary terms, is dangerous. It means the predators eat you first.
So I try to read and learn and study and do everything I can to avoid being on the perimeter. I love reading and learning and studying and doing. Rather than just protecting.
- If I’m an amateur at one thing and an amateur at a completely different thing, sometimes I’m the only person in the world who is in the intersection.
The ONLY way I’ve ever made money in my life is inside the intersections.
- Amateurs meet a lot of new people. In fact, they have to meet everyone in their new field.
I find that every area I’ve ever been interested in has had people who love helping amateurs. I’m really grateful for that and have learned a lot just by listening.
- Expectations are very low for amateurs. The body triggers dopamine, a neurochemical that makes you feel happiness, when you exceed expectations. Often, when I’m an amateur, I exceed expectations.
- There’s nothing wrong with being a professional. But even professionals should find ways to be amateurs in their fields.
Trust me there’s always a way to be an amateur. I spend an hour every day finding a new way to be an amateur. It’s pretty easy to set your mind to figuring out what you can screw up today.
People sometimes are upset and say, “I have to find my purpose in life. I KNOW it’s out there”.
This seems very difficult. If I have a new interest, I go for it. I learn everything I can about it. If a month later I have a new interest, then great, I’ll go for that also. I’m an amateur starting from scratch again.
Then people say, “but don’t you have to settle down sometime?”
I’m not sure. I’ve had severe ups and downs. But the most severe downs happened when I thought I was a professional at something.
I’m 46 years old. I’m still so new at being human. At being a husband. At being a father / friend / writer / podcaster / entrepreneur / etc.
Maybe one of these days I’ll learn and I’ll be smart.
But for now and maybe forever I’m going to stay being a professional amateur. 
