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"I was loyal to Upside and its investors to the end," he says. "I even stayed on and raised another $500,000 after I was removed as publisher. I never abandoned Upside. I feel like I made a lot of mistakes because I was new to publishing and it was a very difficult time for me. But I won't sit here and agree that I was some sort of battered lunatic. It's just not true."
Tony Perkins understands the importance of myth in Silicon Valley and the fabrications it often takes to create it. In The Red Herring Guide to the Digital Universe -- a reference book soon to be published by Warner Books -- Flipside Communications is described as "a fully-bootstrapped (i.e. no investors) Silicon Valley startup founded in early 1993 in a garage." The image of Red Herring editorial meetings taking place with editors sitting on old tires surrounded by half-empty bags of garden fertilizer artfully links the magazine with Apple and Hewlett-Packard, two Silicon Valley institutions with equally humble beginnings. But Red Herring didn't actually start in a garage. It began in a spare room above a garage. The garage just happened to be attached to a million-dollar Woodside home owned by co-founder Chris Alden's parents. In fact, the Alden family maid used to come up and tell the partners that dinner was served. Perkins explains that the room was part of the garage before being remodeled. That, apparently, is close enough for him.
Alden met Perkins in the summer of 1992. Although Perkins was still on the Upside board, he was formulating plans for a new publication of his own. The 22-year-old Alden was eager to fulfill his childhood dream of becoming an entrepreneur just like his father, Ellis, who owns a string of lucrative hotels.
"One of the things that gave me an advantage was growing up with my father, who is a very strong visionary," Alden says as he strokes his de rigueur goatee. "He took me to all his business meetings as a kid. I saw how he made decisions and stood by them. That's the key to being an entrepreneur."
Alden and his best friend, Zak Herlick, made plans to go into business together as early as seventh grade while playing bas-ketball during recess at the private Crys-tal Springs Uplands School in Hillsborough. Herlick soon left for prep school at Andover before returning to Stanford. Alden headed to Dartmouth, but the pair stayed in touch. Their senior year they started a small computer consulting business on the Peninsula that they continued after graduation. They were soon pulling in $75 an hour, but that wasn't good enough.
"Zak and I are pretty damn ambitious people," Alden says. "We had to ask ourselves how we were going to become millionaires making 75 bucks an hour. We wanted to go out there and start a company, so we began a very deliberate process of meeting anyone and everyone in Silicon Valley. We knew we had a lot to bring to a venture because we were smart, energetic, and technologically savvy."
Besides having a wealthy father with connections, Alden was an avid reader of Upside. One morning he mentioned the magazine to his father: That afternoon, Chris was having lunch with Perkins in the Palm Cafe at the Stanford Park Hotel, which is owned by Alden's dad. Herlick was introduced a short time later, and a partnership was formed. The name they picked for their company was an obvious slap at Upside, which in the post-Karlgaard/Perkins era is now profitable: Flipside Communications.
"Tony was willing to take risks," says the 25-year-old Herlick, who has since left the day-to-day workings of Red Herring to pursue a joint J.D./M.B.A. at Stanford. "He wouldn't tolerate working for someone else. That's what attracted me to him."
In the eyes of his two young sidekicks, Perkins was a Silicon Valley veteran, giving him the status of a mentor. Herlick even jokes that he calls his partner "Uncle Tony" on occasion. The youth brigade rules at the Red Herring, where the average age of the 40-some-odd staffers is around 25.
At a post-mortem of the April Herring in the Noe Valley flat of his associate editor, Perkins is the only adult supervision present as the editorial staff meets to critique the magazine over pizza and microbrews. Perkins exhorts the troops to focus on getting more new companies into the magazine. But the hottest topic of discussion isn't the coming shakeout in the bloated world of venture capital but a squabble over the relationship between headlines and the table of contents. Perkins settles the problem the best way he knows how, producing copies of the New Yorker and the Economist to see how they do it. It is all vaguely reminiscent of a journalism school seminar hosted by the professor everyone likes because he grades easy.
Perkins' initial brainstorm was a 12-page newsletter about the industry that would be so packed with vital information and ads that readers would pay $700 for a subscription. Alden shared that inspiration with an investment banker with whom he shared a chairlift at Aspen: The banker liked the concept but balked at the price. By the time of the June 1993 launch, the Red Herring was a slick monthly with a more reasonable yearly subscription price of $180 and a newsstand price of $9.50. Recently, the price dipped to $108 for a subscription and $8.95 for a single issue.