The Memoir

(This is chapter 26 of my ongoing memoir of the Internet industry.)

The day I began working at iVillage was the first day I ever found myself truly excited to meet the president of a company I worked for. But there has never been, and probably never will be again, a CEO like Candice Carpenter.

This wiry and fierce woman was one of the most controversial figures in the Internet industry in the early months of 1999. Her company's IPO was widely expected to succeed, despite the fact that many industry commentators considered her a bewitching fake. It was true that she could thrill a crowd (I had become inspired to join iVillage myself after hearing her speak), and she was obviously thrilling Wall Street as well, even though iVillage was the epitome of a money-losing, big-spending dot-com, with a highly uncertain financial future.

To those who wanted more substance in their dot-coms -- more e-commerce revenue, more advertising dollars, fewer press releases, fewer TV commercials -- iVillage represented the worst of hype-crazed Silicon Alley. I guess that's why I thought Candice Carpenter was so cool.

She would take the criticism and spit it back in their faces. On talk shows and newspaper or magazine interviews, Candice Carpenter would insist that iVillage had a great business model and true staying power (despite the current lack of revenue), and I never heard her back down or hedge this bet. She always spoke with style and verve, often while wearing skin-tight leather dresses, pink jungle-print mini-skirts or other truly strange outfits, and was known to say outrageously philosophical things about the true meaning of work, about why people are afraid to compete, about the business world as a character-building exercise. Most of the things she said made sense to me.

(This is chapter 24 of my ongoing memoir of the Internet industry.)

"I'm making short-term goals ..."
-- Jay-Z, "Can't Knock the Hustle"

I had vague dreams of getting rich in early 1999 when I left Time Warner to join iVillage.com, a high-flying start-up about to go public on the NASDAQ stock exchange. It's a fact, though, that I had no desire for wealth or luxury. I was pursuing money, but material things and lush comforts meant nothing to me. I was pursuing money because I was trying to buy my freedom back.

Nine years of "exciting work" as a software developer in New York City's financial and media sectors had convinced me that I was going insane. Truly -- but gradually, slowly, artistically -- I really was. By early 1999 I was spending my waking days as a nervous wreck in a Manhattan skyscraper -- paranoid, over-caffeinated, angry. I was not enjoying myself. I felt deeply alienated from the "Silicon Alley" lifestyle that swirled around me, I did not feel I fit in, did not think I could keep "playing the game". But I was stuck in this lifestyle because, despite my decent salary, Meg and I had no money in the bank, no cushion to fall back on, big bills and a mortgage to pay.

Like many who work in the media industry, I had become hopelessly cynical about my work. I spent more time every day competing with my co-workers than competing with my company's competitors. I bitterly remembered every insult I'd received, every promotion I hadn't gotten, all the good work I'd done that nobody understood or appreciated. My work on Literary Kicks offered little satisfaction; I had lost track of why I was running this site again, and wasn't doing any original writing at all. I was grumpy and tired all the time. I ate too much junk food and was out of shape.

I needed a break, to save my blistered soul. I needed to cleanse Manhattan from my system for a few months. I felt battered, wasted, exhausted with no chance to rest.

(This is chapter 23 of my ongoing memoir of the Internet industry.)

In July 1998 a three-year-old Internet streaming audio startup called Broadcast.com began selling shares on the NASDAQ stock exchange. The shares opened at $18 and shot up to $74 on the first day -- a stunning success, and one of the biggest first-day stock jumps in modern financial history.

Internet stocks had been exciting high-risk buys on Wall Street since Netscape's historic initial public offering in August 1995, but it was still a shock to see a small, little-known company like Broadcast blow the ceiling open. I had visited their site once or twice, but they didn't have much music and were mainly known for college basketball webcasts. Yet somehow Wall Street's many-to-many mind chose Broadcast.com as a super-winner must buy, and shot it to the sky on its first day.

Future anthropologists studying the strange event known as the dot-com bubble of the late 1990s must understand that there were two separate phenomena operating at once: there was a dot-com craze, and there was an IPO craze. The dot-com craze happened when it became the fashion for investors to take unusual risks on futuristic Internet companies with very hazy business models. More and more professional and amateur investors began playing the dot-coms, even as traditional and conservative investors naturally scoffed at the airy stocks. My savvy stepfather Gene had always enjoyed playing the stock market, and had made out very well over the years with blue chips like IBM and General Electric. He advised me to go ahead and work for a dot-com -- Pathfinder was a dead end, he said -- but said I should never, ever put my own money into one.

(This is chapter 21 of my ongoing memoir of the Internet industry.)

And then, every once in a while ... you try something different and it works out just fine.

When I started my "Notes From Underground" movie project I had no idea what I was going to do with it. I was just working something out for myself, getting a few things out of my system. By staging the movements of Fyodor Dostoevsky's sad-sack aging hipster through the worst night of his life in intricate detail, and reliving these scenes over and over and over and over and over and over and over again as I edited the thing to the last microframe of its life, I was doing something I needed to do, and that was the only reason I was doing it.

But when it was done, almost miraculously, I had made a good movie. I knew it was good because I saw it in people's faces when they watched it. I could tell that they related to the story, and to the main character, as much as I did.

So this is the wonderful lesson I learned: sometimes it's only by creating something truly private and personal that you can be understood by others.