Someone asked this on Quora. I decided to give my sage advice on the topic.
One time I had two million dollars left. You have to be pretty damn smart to make two million dollars, I thought.
I needed to make a lot more than two million dollars. There were people running around (idiots!) with ten million, or even one hundred million dollars.
So I put the two million dollars in a single company. They made “wireless devices for deaf people.” If you ask me now what that meant I would not be able to tell you.
The company went public. For about a day, my two million dollars was worth $2,200,000. In one day I was $200,000 up! This will keep going and I’ll be RICH!
I better hold on. I need to get my $100,000 back.
I had a huge mortgage. Plus two babies. $400,000.
I put my house for sale. At three in the morning I’d sit in this big couch looking at my two story book case and thinking about how it was all over. I never slept. I sweated all the time. $300,000.
“I can’t understand,” I told him. “This house is worth more.”
Now he was cocky with me because he could be.
I said to my wife, “let’s see if we can borrow more money off of it and then we’ll jut stop paying and keep the money.” We dressed up the babies and went to the bank. They laughed at us. “We don’t do THAT kind of loan.”
So I lowered it to less than what I had paid for it. Then I had to lower it to less than what I owed the bank.
Finally we got an offer.
I went to the movies to celebrate. I forgot what I saw. But I remember going to the ATM machine to check and see how much money I had left.
I called my parents. “I need to borrow just a thousand dollars,” I said. “I’ll return it in a few days.”
They said “No” and I hung up the phone. It was the last time I ever spoke to my dad, who had a stroke a few months later that left him paralyzed and looking at the ceiling for two straight years.
I put myself in exile. We moved 80 miles north to a broken down house 1/4 the size in the middle of nowhere.
I never left the house. I gained 30 pounds. I spoke to nobody. I was trying to think of even smaller places we could live.
But then I slowly got out of depression. I started waking up early and playing basketball with myself at a court right next to the Hudson River while the sun rose over the mountains. A train would pass at 5:05 every morning and I’d see the faces blinking at me.
I lost the thirty pounds. I started to sleep better.
Then I’d take out a waiter’s pad. To remind me of humility. And because they were cheap. And because for thousands of years waiter’s pads were used to make lists.
Some ideas would bubble to the top and I’d come up with deeper ideas about those. And some ideas would disappear. Some ideas I’d try for a short time and either give or pursue further.
Some ideas I did nothing. It was all practice. It was all experiments. It was all about getting more creative so I could get myself out of the swamp of regret.
So I can really say that at first it boiled down to three things:
- Get exercise and eat well.
- Read A LOT. I’ve read 2–3 books a week for the past 15 years. I remember maybe 1–2% of what I read. And it doesn’t add up. It multiplies. Because when I learn one new thing, I connect it backwards to all the things I learned before. So every one new thing is like 1500 new things.
- Be creative every day. Because the more you know, the more ingredients you know, the more recipes you can make. Writing down ten ideas a day is like a recipe. I noticed within six months my recipes took on a different flavor. They started to have elements of good in them.
I’d surprise myself: “This is a good idea!” And I’d try it for awhile. Some I’d try for more than awhile. Some would change my life.
I was constantly connecting more and more ideas backwards and forwards to each other. Songs, books, people, companies, ideas would connect more and more like this thick matrix.
Connections and connections. It was (and is) like my brain was on fire constantly.
I just did it today. I did it yesterday. I’ll do it tomorrow. I’ll do it a year from now.
Since that time I’ve started about 20 different businesses. 17 of them have failed. That’s ok. I’ll always have new ideas.
I don’t think I’m a genius. But I know the important thing is not the destination but the direction.
I’m going in the right direction.
After my dad had his stroke I had an idea. My dad loved chess.
He was only able to lie in bed on his back and stare at the ceiling. He couldn’t talk or move. He’d stare at the ceiling for 10 hours a day and sleep for 14.
I found a fun chess position in a book. White to move and win in two moves. It involved a queen sacrifice. He once told me, “take the most powerful piece on the board and try to give it away. Do the unexpected and you’ll win.”
Then I went to his room in the medical facility and got on a chair and taped it to the ceiling right above his eyes so he could look at it.
He knew ten languages. He was a chess master. He could play every musical instrument. He had read every book. And when I was a kid he knew every answer.
Then he died.
Some day you and I will too.
I know, I know. Yet another story about LOSING money. Ok. Enough of that for now.