Most Things Don't Work Out

When I was in college I started a business called College Card. It was 1987. Hedge fund manager (then Morgan Stanley chief strategist) Barton Biggs invested $30,000. It was combined with a delivery business. I delivered everything from pizza to gyros. College Card was a debit card that offered discounts to every store that accepted our card. The movie theater in town used to be a beautiful opera house. They offered a 75% discount to anyone using a college card. They made most of their money on the popcorn. College Card lasted for a semester. It didn’t work out.

My first girlfriend, Tracey, once took my popcorn from me and threw it all over that same opera house theater in anger at me right before the beginning of the movie. Everyone looked at us. She said, “I HATE your popcorn and I HATE you!” I walked out and told the woman at the concession stand I dropped my popcorn. She gave me another one. A large. I then sat on the opposite side of theater from Tracey. That relationship didn’t work out. But not for another two years.

I went to graduate school in computer science. While there, when I was supposed to be in classes, I played the game Go for 10 hours a day. Other times, I wrote novels for ten hours a day. I got thrown out of grad school. They told me I could come back when I had “maturity”. Every few months they still ask me if I’m mature enough. It didn’t work out.

I wanted to be a digital artist. I worked in the art department at the same school that threw me out. I wanted to merge art with computers. It didn’t work out.

I was employee #10 at Fore Systems. I wrote their manuals. I made the game, missile command, using their chips. I hitchhiked every morning back and forth from work which resulted in a date or two. They IPO-ed a few years after I left there. I hated everyone there. Hate’s a very strong word. Maybe I shouldn’t use it. But I hated them. I would’ve made millions at a very young age. Maybe 25. It didn’t work out.

I went out with, Sue. My dad asked me, “are you going to marry her?” On our second year anniversary of dating, Peter helped me go shopping for a wedding ring for Sue. We went downtown to a department store.  We watched tihe office workers in their tight skirts. All the salesgirls showed heavy cleavage. I was 23 years old. I found a ring with an emerald. But my body started to shake. “Can I think about it?” I asked permission from the salesperson. Think about what? I knew it wasn’t going to work out. So I didn’t buy the ring. Sue left for Sardinia. Bad things happened.

I started work at HBO. There were eight levels of hierarchy between me and the CEO of Time Warner. I thought maybe I had a chance to become CEO if I worked hard every day. I was confident. I worked in the IT department in a division of the largest media company in the world. Eventually I had too many conflicts of interest. Everything became a ripped spider web of conflicts. I had to leave. It didn’t work out.

I wanted to do a TV show for HBO. “III:am”. I did it as a website for three years. It didn’t work out. Sheila Nevins said to me, “for HBO, you either have to show me someone killing his mother while naked or you need to show me your neighbors fucking at three in the morning.” She’s now the head of HBO Family Productions, the shows for kids. It didn’t work out.

(part of my III:am website)

I pitched another TV show, “Blind Date”. It was about me spying on people while they were on a date and videotaping the whole thing. One guy said afterwards, when he found out that we were spying on him for the purposes of making a TV show, “life is to be lived, not televised!” He was crying on the message he left for me. Dave Bartis at HBO loved it. Sheila Nevins thought it was “too mean”. Then they stopped returning calls. There was a political battle and I had lost. It didn’t work out.

I helped someone write a spec script for MTV. It didn’t work out.

I wrote a comic book script for DC Comics. There’s a character called “Dream” that’s very popular in the Sandman comics. I had an idea for a spinoff comic based on his sister “Delirium”. I knew one of the editors, Lou Stathis. He died of a cerebral aneurism at a young age while sitting in his apartment watching TV, shortly after I showed him my script. I never followed up with whoever replaced him. It didn’t work out.

(Delirum from the “Sandman” series)

I got married. 13 years later I was divorced. It didn’t work out.

I started a company, Reset. We sold to a company, Xceed. I stayed at Xceed a year. At the end I disappointed everyone when I quit to start a new company. Two years after that Xceed was bankrupt. The guy who brokered the deal to sell my company went to jail. Nothing in that whole chapter worked out.

I bought a 5000 square foot penthouse loft in Tribeca. Hugh Jackman  lived across the porch next door. He would jump over and play peek a boo with my little kid. Eventually I couldn’t afford the $40k a month in mortgage and maintenance and was forced to sell right before I hit $0. It took 18 months to sell and we switched real estate brokers three times.I had no job or money during this period. It didn’t work out..

(Hugh Jackman as Wolverine)

I started trading for various hedge funds. One year I was up 100%. I thought I would be able to raise a huge amount of money based on that. Some people said because I was up so much I was too volatile so they couldn’t put money with me. “There’s zero chance I’m going to put money in someone up 100% in a year. You can be down 100 % in a year also!” Many of those same people (including that guy) put money with Bernie Madoff instead. He was consistent. I was too erratic. I was reality. It didn’t work out. One of my old investors still wants to put money with me. He doesn’t know I stopped a long time ago. It just didn’t work out.

I started some friendships. We played Scrabble every morning at six am. I played until about 8:30am when I knew my kids were done with their morning ritual and off to school. Then I went home to work when it was empty and my mind could just be quiet. All of those friendships are spread out now and gone. I haven’t played Scrabble in years. Nothing worked out.

I traded for a hedge fund manager for a few years. One time at a dinner with his mistress and daughter I asked the daughter what she thought of the mistress. The daughter has produced some excellent movies. She turned to the mistress and said, “I think she’s a money hungry slut” and walked out of the restaurant (the Four Seasons in NYC). The mistress started to cry. I was no longer trading for that manager a month later despite being up over 100% for him. It didn’t work out.

I started a fund of hedge funds. My main investor threw a chair at me even though we were up 10% for him in the first three months. The chair missed. He had a disability and couldn’t throw very well. He had an uncontrollable tick and he was overweight. He needed his money back because he was running what I now suspect was a Ponzi scheme. On the last day of each month someone told me he’d buy way out of the money long-dated currency options that were illiquid so he could mark them way up and show fake returns to his investors. His CFO called me crying because he was afraid of the FBI. Nothing worked out for any of us. My lawyer, Jay, said sometimes you just have to give up. I yelled at him: I don’t give up! Eventually that fund of funds didn’t work out.

I started a company, Stockpickr, and sold it to We had a million users a month. We were very profitable. One person told me to block his account because he was addicted to Stockpickr and needed to get off his addiction. basically got rid of me after two years. Stockpickr now languishes on their site with no real care and love behind it. It didn’t really work out. I had written for for seven years. I had done 100s of videos for them. I really loved them. I told them I would write for free. It didn’t work out.

I wrote for the Financial Times every Tuesday without missing a deadline for five years. The editor in chief at a party once told me, “we’re going to make you a star”. Some gut reflex in me blurted out, “I don’t want to be a star” and later that night I regretted it because I was afraid I insulted him. In March, 2009, at the bottom of the financial crisis when I was most bullish, they got rid of me. I told them I would write for free. It didn’t work out.

At that time I used to live at the corner of Wall Street and Broad Street. The same building JP Morgan worked in 90 years earlier, across from the New York Stock Exchange. I would wake up in the morning, go outside , and hand out chocolate to the people going into the New York Stock Exchange. I wanted them to cheer up before they began trading. This was on March 9, 2009. I single-handedly stopped the bear market with chocolate. I don’t even like chocolate. I get a gag reflex when I taste it.

(the first terrorist/bomb attack on US soil occurred at my future home on Sept 16, 1920 – 36 people died)

I wanted to be a world-class chessplayer, go player, poker player, scrabble player, novel writer. None of those things worked out.  I daydreamed about traveling the “Europe Circuit” just playing games. I liked all the game players I knew. They lived alternative lives. Always scratching the surface of the fake snow globe where everyone else lived. They couldn’t get in even if they tried. The people in the snow globe can’t get out. Its nice and pretty and snowing and everyone is pretty. Why would they want to leave?

I’ve written five books published by major publishers. Other than one fateful coincidence, most of them have not worked out.

I started a few more companies. One was JungleSmash which I wrote about here. None of them worked out. For no particular reason.  Sometimes I would just lose interest.  I’ve made 12 investments since then. We’ll see.

Its 7pm and I have an article I need to write for Marketwatch. My daughters were here for the weekend and now they are gone so I miss them. I hear some band playing music in the background, probably near the gazebo at the river.   What else can I even say about today? I hear birds. Cars go by about one every minute. I have this painting staring right at me. I have a talk I have to prepare to give in Chicago next week  to an audience of about 600. I’m a little nervous for that one since I’m going to try a few new tricks.

Tomorrow, like I always do, I’ll do my Daily Practice. I’ll try and imagine all the things I’m grateful for. All the people I forgive, all the ideas I can come up with, all the people I love to be around. All of the people I want to be around. All of the things I want to do and all the things I want to keep doing.

Most of those things won’t work out…I don’t know.  But I like to keep trying.


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