(This is chapter 43 of my ongoing memoir of the Internet industry. This draft will be completed when chapter 46 is posted in three weeks.)

On one of the first warm springtime days of 2002 in New York City, I suddenly found myself accepting an unexpectedly cool and excellent new job.

The offer came from my friend Ken Jordan, who had been working the Silicon Alley arts/media hustle as long as I had. He’d worked on music sites like Sonic.Net and literary sites like Word, and now he’d hooked up with a wealthy investor and art collector named Chris Vroom to acquire a bankrupt website called ArtAndCulture.com. They planned to rebuild the site and use it as the starting point for a new art-related online venture.

Ken and Chris had great connections and were close to signing contracts with the San Francisco Museum of Modern Art and the Whitney Museum. They hired my star designer friend Leslie Harpold to be art director, rented a chic brownstone in Chelsea to serve as the office, and wanted me aboard as chief technology officer. Was I interested?

Let’s see. I was unemployed, broke and miserable. They were offering me a lot of money to build Java websites for art museums. I said yes in about two seconds.

The main thing that bugged me about this new gig was that I felt lucky to have it during such a lousy year, and I didn’t like relying on luck. Laid-off software developers were scrounging for work all over New York City, and here I’d suddenly landed in a pot of jam. I didn’t feel confident that the job could last long, because it was very difficult to build and sustain an online business in this economy. I was also concerned because Ken and Chris had very optimistic plans for ArtAndCulture.com, and were already operating at a high burn rate. I definitely admired Ken’s rainmaking skills — I didn’t know anybody else who’d managed to create an arts startup in 2002. But the way we were spending money made me wonder if Ken and Chris had seen the year 2000 happen.

This is why I balked when they asked me to begin hiring other Java developers to fill out our team. I had two good friends who wanted to join, Evan Sable and Yaniv Eyny, so I gave them my best warning and then brought them in.

During all my years in the Internet industry, I always fought against expensive “go for broke” business strategies, and usually lost the fight. This was often the source of my worst conflicts at work: I always wanted my companies to grow slowly, build firm foundations, avoid big investments in unnecessary or questionable projects. This was only partly because I hated working overtime; it was mainly because I didn’t think a company ever helped itself by taking on excess weight.

I often advised business managers to imagine themselves as travelers and the software they developed as luggage they would have to carry around. The path to success, I argued, was to travel light. Keep the costs low, the staff small, the code clean and the complexity level low.

The managers I’d been able to work best with — Charlie Thomas at Time, Dan Levy at BobDylan.com, Susan Hahn at iVillage — were the ones who were able to see the appeal of a sensible minimalist approach. I practiced what I preached on my own website, maintaining Literary Kicks with the simplest possible technology. This is why LitKicks was still around in 2002 after all the other over-produced webzines of the mid-90s were gone.

Sometimes I wondered if the urge to expand and exceed that plagued the Internet industry in its first decade wasn’t rooted in insecurity. Executives who ran good websites did not have the confidence to realize that they were producing something valuable every day, and so they would chronically over-produce to mask their shortcomings. Many dot-com executives during the gold rush years did not understand the Internet at all, and these executives were the ones most responsible for constantly raising the stakes.

My philosophy of business was similar to my philosophy of poker. In the early 2000s I became obsessed with Texas Hold ’em, mostly inspired by my older brother Gary, who’d become an expert player and won a few tournaments in Atlantic City, Foxwoods and Mohegan Sun. Gary taught me how to play a cautious and smart game, and I found that I was very good at it. I started joining him at casino outings, and found that I could usually show up at a $5/$10 table with $300 and double my money in seven or eight hours.

I always specialized in the slow play — that is, I liked to bluff weak instead of strong. Many experienced poker players would bet big with, say, trips on the flop. In this situation, I preferred to put on a worried and confused expression and limp in with the other bets, hoping to hit my full house and win big on the river. Instead of trying to overpower a table, as most players did, I specialized in making the table underestimate me — over and over again.

This seemed somehow significant to me. In business, in poker, in life, I realized, I was a slow player. For better or worse, this was the technique that worked for me. I guess it’s why the minimalist-minded Buddhist religion appealed to me so much as well.

Patience was hard even for me, though, when it came to love. In the summer of 2002, Caryn and I were finally able to begin the relationship that we’d both known was brewing. We spent our first days together in the peaceful Shenandoah Valley in Northwest Virginia, where we symbolized our new love by climbing a mountain together, finding at the peak a view more beautiful than we could have possibly expected. Birds flew underneath us as we sat there, and I think that captured how we both felt now that we were finally united.

 

 

Caryn and I had a lot in common. Like me, she lived her life with a lot of conviction and determination, and like mine her personality was an oxymoron: she was an introvert who often found interpersonal interactions frustrating, and yet she excelled in social skills and often found herself chosen for leadership positions. It was funny that we both were both considered experts in online community, because we were often surrounded by others who enjoyed online community more voraciously than we did. Maybe that’s why we were good at it.

I was very much in love with Caryn. Our situation was challenging because we lived several hours away and did not want to disrupt our kids’ lives by trying to move. We began spending a lot of time on Amtrak trains, or on the I-95 Interstate. Worth the trouble? Hell, yeah.

We were alike in some ways, mirror images in others. Caryn had grown up in a conservative household in a small Indiana town, while I was the offspring of liberal Brooklyn Jews. But this made it exciting, and we found common ground in rarer places. Two years earlier, I’d sat alone in my Times Square apartment listening to music from the ’30s and ’40s that nobody else I knew liked, never imagining that someday I wouldn’t listen to this music alone. Now I’d found someone who shared my odd musical tastes. I brought Cole Porter, Rodgers and Hart and Noel Coward to our relationship, while Caryn brought Hoagy Carmichael, Tony Bennett and the Andrews Sisters.

I had a lot of flex time with my cushy ArtAndCulture job, so I was able to visit Caryn often during our first summer. It seemed my life had taken a lot of good turns this summer, and I began to feel like a very lucky person. In this happy spirit, I began planning a second Bowery Poetry Club reading for August, this time a collaboration with a San Francisco friend named Janan Platt who ran a website called AlienFlower Poetry Workshop and suggested that every poet should carry a flower onstage with them and place it in a vase before reading.

This made sense to me, and I contributed to the reading by putting out a call for poets on Literary Kicks. Several came out of the woodwork: an irascible flute-playing character from Texas named Clay “Lightning Rod” January, a Virginia writer named Doreen Peri, the charming Bill Ectric from Florida. Jamelah Earle also flew in from Michigan, and since she and Caryn had become good friends this made it an especially joyous meeting.

We also invited some local talent: the spoken word poet John S. Hall, author of Jesus Was Way Cool and Detachable Penis, and for our big closer a reunion of the celebrated 80s retro-folk outfit the Washington Squares, backed by Billy Ficca on drums (though this was a poignant reunion as one member of the trio, Bruce Pankow, had died of AIDS).

This was also a significant evening because for the first time I’d invited my entire family to be in the audience. My oldest daughter Elizabeth was there, and my brother and sister Gary and Sharon, and all four of my parental units. Yeah, I felt lucky as I stood up there on stage, reading an excerpt from Summer of the Mets with accompaniment from flute and guitar, knowing that everyone was here just because I’d invited them, and they were all having a good time.

I was amused years later when a Bowery Poetry Club regular named Gary “Mex” Glazner wrote a book for Soft Skull called How To Make A Living As A Poet. He never mentioned it to me, but one of his comic descriptions of a typical evening at the Bowery Poetry Club was clearly a description of our event. I know this because I’m pretty sure we were the only BPC show ever with flutes, flowers, folk-rock, striped shirts and berets. I’m not sure whether or not Glazner was making fun of us, but it’s a pretty accurate description.

 

 

I get some of my life’s philosophy from poker. For instance, you may have heard the widespread myth that poker has a lot to do with luck. It really doesn’t, as becomes obvious once you consider the law of probability. During a typical poker game or tournament, a player will be dealt many, many hands. Over time, each player’s luck must eventually even out. This is a mathematical certainty.

Good luck is actually not what you need to succeed at poker. You need to be able to quickly calculate odds, and to intuitively read your opponents. But more than anything else, you need patience and self-control. Without patience and self-control, all the luck and skill in the world will not help you win.

It’s funny that people think poker involves a lot of luck, when it’s really everywhere else in life that you need a lot of luck. Example: you get a new job, and you might get a great boss or you might get a psychotic and nasty boss. Either way, it’s a sure thing that you won’t get dealt a new hand five minutes later.

Then there’s family — where you get dealt only one hand your entire life. As I stood onstage at the Bowery Poetry Club in 2002, seeing the smiling faces of half my relatives in the dark crowd, I knew I’d been lucky here.

Then there’s love. I gazed at Caryn as she read her own poem onstage that night, and wondered how I could have ever nabbed her.

I was feeling so philosophical about all of this in the late summer and early fall of 2002 that I didn’t even get upset one day in September when I walked upstairs to our Chelsea office and saw a bunch of sad faces. We’d run out of money, the second round of investors hadn’t turned up, the operation was shutting down.

Time to go home again. I still felt like a lucky guy.