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.
And then I had an idea. Or rather, an opportunity presented itself.
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.
I was smarter than them!
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.
The next day it was at $1,800,000. Then it kept sinking. My two million was worth $1,000,000. Then $800,000.
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.
The real estate agent begged me to lower the price of the apartment. I did. Then he begged again. I did. Then he didn’t have to beg anymore. I kept lowering the price of the apartment. Nobody was buying.
“I can’t understand,” I told him. “This house is worth more.”
Now he was cocky with me because he could be.
He said, “This house is only worth what someone is going to pay for it, and it’s a lot lower than what you have it at now.”
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.
I couldn’t afford the mortgage anymore so I stopped paying it. I ignored all the calls from the bank. I ignored all the calls about the housing taxes. The true owners. I’d pay these people after I sold the house.
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.
“He has no brain left,” the doctors all said but I think he was just locked in there.
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.
Nobody returned any calls at all. Everyone wants to be your friend when you have money. “I always knew about that guy,” they all would say later.
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 read for two hours. I read every day from one fiction book, one non-fiction book, one self-help book, and one book about games. I love games.
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.
And I’d make my own list. The list might be “10 businesses I can start.” Or…”10 books I can write.” Or…”10 ways XYZ company could be better.” Or…”10 articles I could write.” And on and on.
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.
I did pray to God a lot. But mostly because I wanted the stock market to go up. I’d go to the church across the street and pray to Jesus. But I was Jewish and I don’t think he listened to me.
So I can really say that at first it boiled down to three things:
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.
And every six months, the ideas would get better and better. It was like I was graduating through classes and grades and schools and getting the graduate degrees I had never gotten.
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.
This was the secret for me. I don’t know if it would work for anyone else. Every day I have to do this or I think I’m going to die.
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’ve written 18 books. Some of them were horrible. Maybe most of them. That’s ok. I’ll write more.
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.”
So I took that position and I went to the local printer and printed it up three feet by three feet.
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.
He would stare at the position. I could see his lips trying to move. I knew he knew the answer but the doctors would shake their heads and walk away.
Then he died.
Some day you and I will too.
Ok, Josie my daughter, get a good night’s sleep.
I know, I know. Yet another story about LOSING money. Ok. Enough of that for now.
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