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Many investors liked the idea, but not well enough. "VCs are looking for explosive growth," says Ring. "They want something that will pay 100-to-1 in a few years. You can't put that together in a publishing deal unless you're very lucky or you lie."
Sources at Upside say that Perkins inflated circulation numbers in the pursuit of advertising, an allegation he categorically denies.
"There was a whole brat pack of rich kids from Silicon Valley who grew up to become venture capitalists," says former Managing Editor Rudder. "It was a whole lifestyle, and Tony wanted to be part of it. He liked the role. As a result, Upside suffered from a total lack of understanding about what you could and could not say to people buying ads. All the rules were being broken, and everyone thought it was fine."
Upside morale was lower than the magazine's profit margin. Perkins' life was further complicated by the death of his father and the collapse of his marriage. He acknowledges a romantic relationship with an Upside employee that resulted in a child out of wedlock. He and Karlgaard were openly feuding, and staffers feared the magazine might fold at any minute.
In mid-1990, Rudder called it quits after just nine months on the job.
"The atmosphere at Upside was unbearable," she says. "I've worked at a lot of different publications that were dysfunctional in one way or another, but none of them topped Upside. It was the only job I ever quit without having another one lined up. It was that bad."
Upside limped along, and the Karlgaard/Perkins relationship continued to decline. Karlgaard maintains his partner turned into a "total flake" -- disappearing from the office and fighting on the phone for hours with his estranged wife. "He got up every morning of his life for three years and had a giant anvil hanging over him to raise more money or miss payroll," Karlgaard says. "The pressure was certainly affecting his performance."
Karlgaard asked the Upside board of directors that Perkins be "taken out of the line of fire." A source at Upside, who asked not to be identified, says Karlgaard was much more demanding: "Karlgaard told the board, 'Either Tony goes or I go!' "
The board members, whom Perkins had recruited as investors, removed him as the publisher and CEO of Upside on May 2, 1992, eliminating him from the day-to-day operations of the company. He remained on the board until the summer of 1993, helping Upside raise one last round of financing before he left.
"The only constraints the board ever put on Tony were ethical," says Upside board member David Bunnell, who has founded several magazines of his own, including PC World and New Media. "We insisted that he represent the company in an ethical manner and tell the truth about our circulation, our business, and where we were headed."
Karlgaard left Upside less than a month later to take a job with Forbes as editor of its quarterly supplement on high tech, Forbes ASAP. The deal angered the Upside forces, because the original agreement called for Upside to produce the supplement for Forbes.
"Forbes basically stole our editor and the deal we had signed to produce Forbes ASAP," contends Bunnell. "We never pursued legal action because Forbes has such deep pockets. They would have spent us into the ground."
Karlgaard denies that his departure destroyed the Forbes ASAP deal: "They had real reservations about dealing with such a financially shaky institution. There will still be people who will say I ran away from my child, my creation. But they didn't go through what I did for three years. They didn't have a partner who began as a fundamentally good, competent person turn into a basket case because of the enormous pressure he was under."
Sitting in Buck's, a Woodside diner where VCs and entrepreneurs often come to hammer out deals, Perkins' cheery outlook evaporates as he listens to the litany of complaints leveled against him by his former Upside associates.
"I was throwing up in the shower every morning because of the pressure at Upside," Perkins says. "I'll admit that I hated going to work every morning and having to look at Rich Karlgaard's face and deal with David Bunnell. It was a bad situation."
The Silicon Valley culture that Perkins worshipped had mauled him.
"Some venture capitalists seem to forget that financial gain is really what motivates the entrepreneur," he says, his white coffee cup trembling slightly in his hands. "What really grates on you is that it's really your ideas, not the VCs', that are creating the revenues. I woke up at Upside one day and realized I had this great vision for the company, but suddenly I was only 3 percent owner of those ideas."
He pauses and gestures at the tables where groups of men in expensive suits talk intently. "A lot of venture capitalists have entrepreneur-envy. They like to come to a greasy spoon like this to feel more like men of the people or something."
Then he catches himself, a smile returns to his face, and he's back to the old Tony Perkins just like that. The tension is gone. Like a politician doing damage control, he takes the high road.