Former Amazon star exec killed in bike accident by Patricia Sellers @FortuneMagazine September 19, 2013, 4:37 PM EST E-mail Tweet Facebook Google Plus Linkedin Share icons FORTUNE — Joy Covey, who was Amazon.com’s CFO in its startup days and guided the company through its IPO, died Wednesday in a bicycle accident in California. Covey, 50, was reportedly struck while cycling on Skyline Boulevard in the mountains of San Mateo County. She leaves an eight-year-old son, Tyler. One of the breakout women in tech during the first Internet boom, Covey ranked No. 28 on Fortune’s Most Powerful Women in Business list in 1999. I interviewed her, as well as her boss, Jeff Bezos, at Amazon headquarters in Seattle, and captured her extraordinary life in that year’s MPW cover story: Among the newcomers, Joy Covey has led the most unfettered life. Actually, her life has been a lot like her company, Amazon.com: unconventional, expansive, high risk, with a pitch that goes something like this: “It may not seem logical, but trust me. I know where I’m going. And it’s far.” Covey is the younger of two daughters of a Northern California doctor and nurse. They were frugal, self-reliant parents. “They had a complete and utter disregard for social expectations,” says Covey, 36. She did too. Bored with school during her freshman year at San Mateo High, she dropped out. Did her parents come down hard on her? “No,” says Covey. “They knew it wouldn’t do any good. I thought, They won’t beat me or throw me out. If I don’t obey, what can they do? I decided, there’s no more following the rules.” Actually, she did follow some rules: She returned to school for one more year. Then she used her 173 IQ to pass California’s high school-equivalency exam. At 19, she graduated from California State University at Fresno and took the CPA exam (scoring second best in the country that year). After working at the accounting firm Arthur Young for a while, she headed to Harvard to collect an MBA and a law degree. Three years ago, following an interlude in Silicon Valley, Covey arrived in Seattle, pumped at the prospect of being a pioneer. Amazon.com was then an unproven e-commerce curiosity. “I thought, Wouldn’t it be great to build one of those new business models like Microsoft or Intel or Dell?” She helped break retailing out of its box and did the same with her job as CFO. Covey has been an unusually influential finance chief, working with Amazon founder and CEO Jeff Bezos to recruit senior management and steer the company into businesses far beyond books. Says Bezos: “I can budget only four days a year to talk to investors, so Joy has been Amazon.com’s primary contact with Wall Street. In the Internet space, that’s really unusual. She’s doing what a CEO would normally do.” Covey is a sports fanatic who goes rock-climbing and wakeboarding (for the uninitiated, that’s snow-boarding behind a boat). But even at work, she is altogether unbound. During a dinner last year at a Seattle restaurant to celebrate Amazon’s big junk-bond offering (the first by an Internet company), she joined her boss on the floor for a round of leg wrestling. “She won,” Bezos says. Recently, when Covey said she wanted a new position as chief strategist, Bezos says the decision was easy. “Joy is really good at figuring out what’s going to be important six months from now, which, in Internet companies, is very hard to do.” I also featured Covey in a 1999 story about Fortune MPW and their mothers–and this, about Joy’s mom, gives you a sense of where Joy got her remarkable will: During World War II, Joan Covey, who is Dutch by heritage, lived in Indonesia (then the Dutch East Indies). When the Japanese invaded, she was sent to a prison camp for two years. She watched her own mother starve to death there. The hardship fostered an intense self-reliance, which daughter Joy has as well. Covey tired of frenetic Internet life and left Amazon voluntarily in 2000, She spent her time raising her son, Tyler, and showing that high-powered corporate women can indeed lead a rich life beyond a business career: She got her pilot’s license, threw herself back into extreme sports–Alpine rock climbing, Utah skiing, kiteboarding–and deployed her Amazon wealth into environmental and other causes. She served as Treasurer of the Natural Resources Defense Council and on Harvard’s Advisory Board. “I’m not retired,” she told me after quitting corporate life. “I intend to have two or three more careers.” The world has lost an amazing person in Joy Covey. We will miss her greatly.