Your Cheatin’ Dotcom

A Spy in the House of Work

It’s just an excuse, and I know it now. But at the time, I was only feeling one thing: tired. Tired of being an entrepreneur. Tired of shilling one idea after another. Tired of dealing with the steady drumroll of dotcom deaths. Tired of being on the receiving end of unanswerable questions such as, “Can we count on your being profitable by Groundhog Day?”


For once, I wanted to be the one asking for additional information. I wanted to have the joy of knowing that some of the finest young business minds in the world were wasting their time — er, burning the midnight oil — trying to fashion a pitch that would respond to my love for wind-up robots, muscatel, and Quake.

I don’t blame Aunt Irene for leaving me that tidy little nest egg, her earnings from purchasing AT&T for a penny a share shortly after the invention of the wheel. Still, if it weren’t for her, this never would have happened. I’m not really that kind of guy. I just wanted to try something … different.

The Great American Venture Capitalist Conference was taking place in another state. My partners and fellow entrepreneurs at, Spud and Darth, were off at a startup conference for entrepreneurs in another city. I begged off, explaining that I was getting a growth removed. That one always works.

I bought a Rolex and a slate-gray Armani suit. I registered under the name Ronald Gold. My pulse raced as I took my hotel key: For once, I wasn’t going to be the sweating doofus with the pathetic PowerPoint presentation.

I ate the free pâté and swilled the free muscatel. And I watched while all those guys who are just like me — all ideas and no capital — looked me in the eye and opened their arms wide on cue, group-hug-like, just as they had learned to do in their how-to-land-a-big-fish training seminars.

And then it happened. I fell for this sleek, sexy little startup. I won’t tell you its name — even after everything that took place, I am still an investor. But here are three words that tell you everything you need to know about this hot little dotcom honey: Wireless. Fantasy. Baseball.


At first it was such a rush. I’d never felt so young, so alive! For once, I wasn’t begging for money. And then, late one night, after too many glasses of wine and too many slides — I wrote the check.

Edwin was the CEO of my new play. Chita was the CFO. They were 22. Or maybe that was their combined age. “Can you help us with the offices?” asked Edwin, the day after my check cleared.

My first thought was, “How cute! They need me.” I returned the call from the corner phone booth. Space is a little tight at, and I was worried that Spud might overhear me.

“You want me to go look at some spaces with you?” I asked Chita. “Don’t you have a building for us?” she shot back. “What about the rest of your portfolio?”

I couldn’t very well tell them that I had a startup too, that world headquarters was Darth’s mom’s garage. I went back to Darth’s mom’s garage. I had a brilliant plan: Disconnect my cell-phone. They’d never find me.

A week later, Chita called me at the office. On the land line. She and Edwin had been given offices by another VC, one who could provide “resources.”


“How did you get this number?” I whispered. “Never call me here again.” It ended the way these things always do. Spud found a receipt. “Ronald Gold bought six-dozen personalized tote bags?” he asked, holding the receipt away from him as if he had a dead rat by the tail.

Chita had insisted upon them to boost morale. I confessed to all of it. My boredom, my frustration, my desire for novelty. I really did love I couldn’t imagine my life without it. I would never consider leaving. That other startup had been just a fling. But now Spud says that he has trust issues. And I feel so cheap and tawdry. Plus, I have to wrap this up and run over and install Quake on Edwin’s computer.