On paper the dot-com game seemed easy. But Brett Singer and Simeon Schnapper discovered it was harder than it looked.

Singer used credit cards to finance his first venture, Psychedelic Shakespeare, a multimedia company. He started creating CD covers for local bands and ended up designing graphics for large corporations like Ameritech. Yet he left the company owing more than $40,000. “At 18 percent interest,” he adds ruefully.

Next he joined forces with four other guys to come up with an exotic-travel Web site called Wanderon.com. They operated for a year out of a Wicker Park apartment, and at first some investors showed interest. Singer admits he even told his wife, “If the company is worth a billion dollars and I have 14 percent of it, I’ll be worth $140 million.”

But when the Nasdaq started to crash in the spring of last year, the money people stopped returning their calls. “It was depressing trying to get funding in a really turbulent time,” Singer recalls. “We had a sound idea but no experience and not a lot of industry expertise.”

Wanderon.com did qualify for a $300,000 matching grant under a state program meant to stimulate high-tech businesses in Illinois, but the payoff came too late. By the time the check arrived in January, the firm’s operations had been suspended for two months. Its lead investor is now trying to resuscitate the company–which had become a business-to-business site for the bicycle industry–but Singer hasn’t received a paycheck since June 2000. “I was just the creative guy,” he says. “Only the CEO and the sales guy got regularly paid.”

Schnapper had an easier time. He fell into the new economy with remarkable ease, first becoming interested in computers while majoring in theater at Columbia College.

“I got a job in the computer graphics lab and found I had a knack for reading manuals,” he says. He walked away amicably from his first company, Digital Video Artists, and his second start-up, a Web consulting firm called Digital Media Associates, is still in business. His last job–chief technology officer with an E-commerce company named Starbelly–paid off handsomely when the firm was sold to Ha-Lo Promotional Products last May.

How handsomely? Schnapper won’t say exactly. “Let’s put it this way,” he says. “I was the number one or number two employee, and I am a motherfucker when I negotiate. But I was paid in stock in Ha-Lo and how much it is worth fluctuates day to day.”

Still, Schnapper says the experience was bittersweet. Starbelly’s Internet marketing ideas were supposed to enrich the more traditional techniques of the Lincolnwood advertising and promotions agency. “There was this great promise to lead a revolution,” Schnapper says. But what had been billed as a merger began to look like a takeover, and soon Schnapper found himself a speck in a large corporation, now known as Halo Branded Solutions. “After the merger I went to two or three of the executive team meetings downtown with all the fancy conference rooms and all the VPs and regional vice presidents from Halo and the CFO. I just felt it would be more advantageous for me to look into other opportunities.”

In July Schnapper took off to do some serious soul-searching in India and Tibet. “I negotiated my severance from a mountaintop,” he says. Around this same time, Singer, fed up with his dwindling prospects, began to aggressively pitch to Schnapper the idea of doing a film. “I had been on him for over a year,” Singer recalls. “I first became interested in digital graphics, streaming and the like, because they were like little movies.”

The friends came up with the idea of exorcising their dot-com demons by making a This Is Spinal Tap-style mockumentary about the industry. They wrote a rough scenario, drawing heavily from their own experiences, and then hired a handful of actors, all of them comfortable with improvising. With a professional cameraman, they shot 47 hours of footage on digital video–most of the scenes were improvised based on the scenario–over the course of six weeks in November and December. Then they sat down with a film editor and boiled it all down to 90 minutes.

The result is Dotcom: A True Story. It follows a hapless dot-com called Zectek, run by a group of clueless, greedy twentysomethings eager to sell out and cash in but unsure of how to go about it.

Schnapper says, “We purposely never spelled out what they were trying to sell or what their business model was.”

“Or even,” Singer pipes in, “whether they had one.”

Dotcom: A True Story will be shown as part of the Chicago Improv Festival at 4 PM this Sunday, May 6, at the Vittum Theater on the third floor of the Northwestern University Settlement House, 1012 N. Noble. Admission is $5.

–Jack Helbig

Art accompanying story in printed newspaper (not available in this archive): photo/Lloyd DeGrane.