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Perkins went on to become student body president at Hillview Junior High, he says as he rattles off his administration's accomplishments: He successfully lobbied for a stoplight in front of the school; paid for a student patio with profits from a Popsicle sale; and left the treasury with a $2,000 surplus.
"There are two kinds of leaders in school," Perkins says. "The rah-rah, straight-A students and me, the renegade who got by more on charisma than intellect."
Perkins routinely marries braggadocio to self-deprecation, making his conceited points in such a backhanded way that it's hard not to like him. Not a bad trait for someone treading in Silicon Valley, where selling yourself and your ideas often go hand in hand.
Perkins proved that it's never too early to start networking. His closest childhood friend was Tim Draper, the grandson of Gen. William H. Draper, considered the first professional venture capitalist on the West Coast. Tim's father, Bill, founded the highly successful Sutter Hill Ventures before going on to serve as chairman of the Export-Import Bank for five years during the Reagan administration. Tim, who started a venture capital firm of his own, was Upside's first and biggest financial backer and is now a loyal Red Herring advertiser and event sponsor.
"Tony and I used to ride our Sting-Rays up at 3000 Sand Hill when it was just a big hump of dirt," Draper says. "We got into a lot of trouble together."
Perkins quarterbacked his junior high football team, but switched his focus from athletics to money when he entered Menlo-Atherton High School, getting a job at Safeway because it offered union wages. He brags that he was breaking child labor laws by working from 2:30 a.m. to 7:30 a.m. during his senior year.
"I just had an incredible will to be independent," Perkins says. "Having your own money is the best way to be independent when you're a kid."
He also adds that the best way to get girls was to ingratiate himself with their mothers while he bagged their groceries. "Why don't you date that nice Perkins boy, dear?" he says in a mocking falsetto, imitating the suburban matrons he charmed at Safeway. "It was a gold mine."
Surrounded by the sons and daughters of millionaires, Perkins made up for his middle-class roots with style. He bought a Mercury Capri with his paychecks and invested in personalized license plates reading "TPERK" -- a luxury unknown to most teen-agers in the '70s. He had more of a strut than a walk, according to his old classmates. With the help of Grant Gunderson, a friend whose father was the chief executive officer at Bay Meadows, Perkins organized trips to the racetrack where he talked adults into placing bets for him.
"If Tony wanted something, he got it," remembers Kim Young, who dated Perkins in high school and now runs an Atherton advertising agency. "When we went to the prom, he was the one who rented a hotel room and served cocktails before the dance. He had a knack for turning ordinary circumstances into an event."
Menlo-Atherton High was fraught with racial tension in the '70s, erupting in riots on more than one occasion. Poor minorities from East Palo Alto mixed uncomfortably with wealthy white kids living west of the Bayshore Freeway. Scores of whites fled to private schools, but Perkins stayed and honed his ability to get just about anyone to like him. "The black kids set the pace for cool in high school," Young says. "And Tony had some black friends who were very cool."
Perkins also stood out in the classroom, but not necessarily for his grades. "Unlike the typical 17-year-old, he was very fo-cused on economic issues," says Richard Weaver, who taught Perkins U.S. history. "He was definitely interested in saving, investing, and planning for the future. It was very unusual for a student his age."
While many of his friends headed east for Harvard or Dartmouth after graduation, Perkins enrolled at UC-Davis, and he continued to work at Safeway. During his sophomore year in 1978, he became the Democratic Party's statewide student campaign manager for California, and he keeps a photo on his desk of him with Jerry Brown at an Election Day rally in Davis. (It's a curious memento for a present-day Republican and supporter of Steve Forbes.)
The political savvy he picked up that year proved no assistance when he ran for student body president later in his sophomore year. Perkins says he thought the Safeway job would help him win as "a man of the people," but it wasn't enough. It was the first time he ever lost an election, and Perkins' can't help hinting that he would have done a better job than his victorious opponent.
"The guy who won went on to run up a big deficit," he says with a raised eyebrow. "I was disappointed. But I like to think I've continued to grow since then, while a lot of guys my age have peaked long ago."
Shortly after graduating from UC-Davis in 1981, Perkins landed a job at Silicon Valley Bank, the well-known sugar daddy for many high-tech firms. Perkins likes to brag that he made more than 200 "deals" during the five years he spent as an investment banker. These deals, however, were fairly prosaic. He established credit lines for technology companies that already had venture capital backing; he collected regular payments from the companies he handled, much like a banker in Chico or Chicago would collect from the owner of a pizza joint with a credit line. Perkins earned a good salary, but he wasn't happy.