Evan Kaplan is a risk-taker in the best sense of the term. He eschews the predictable course, pushes himself beyond what's comfortable, and never limits his possibilities. It has spurred him to climb mountains–and climb corporate ladders. His capacity for challenge is a particular asset now as he leads Aventail Corporation, the Internet connectivity company he co-founded, amid a volatile business world.

Interviewed on "Information Technology Leaders," Kaplan describes himself as a nonconformist, starting when he was a college student and he bucked the family trend to study business. In his eventual business career, Kaplan often took the unconventional route: He landed one promotion by asking his employer to take a chance on him, and before one last-minute interview with a high-tech company, he crammed from a Byte magazine article to get up to speed. Nevertheless, his combination of confidence and conceptual intelligence–"being a quick study"–always won people over.

"Information Technology Leaders," produced by the University of Washington’s School of Business, presents multi-faceted portraits of the people filling the top IT positions at major corporations such as Microsoft, Boeing, and AT&T Wireless Services. The revealing interviews show that personal characteristics often play an important role in the unpredictable career trajectories of this industry.

Kaplan, a New York native, started testing himself early. After high school, he traveled alone through Europe. Initially reluctant even to go camping, he took a course that sparked his passion for the outdoors. That led him to college in the Pacific Northwest and to a job with Outward Bound, leading groups through the wilderness.

Solely responsible for 13 youths on a snowy mountainside, Kaplan developed his leadership skills–"what it takes to get people going." But he soon felt drawn to business, the field of his father and both grandfathers. He went back to school for a master's degree in organizational development. Then he landed a human resources job at Eldec, an aerospace company, "something I had no experience with," he admits. Kaplan chuckles at the memory of his first day, when he leaned over a desk to shake hands with a new colleague and his tie fell into a coffee cup. But he quickly proved himself, and worked his way to the revenue side of the business. Eldec saw an emerging leader in him and not only promoted him to project manager but also sponsored his Executive MBA at the University of Washington, where he was the youngest person in the program.

In 1990, Kaplan sensed the aerospace field was flagging. He left Eldec and looked for his next challenge. A friend at Walker Richer & Quinn (WRQ) got him interested in the company, which created connectivity products. Once again, Kaplan was undaunted by his lack of familiarity with the industry. He joined WRQ and "learned how to be a marketing person" for new product lines.

After four years of steady promotions, Kaplan was passed over for vice president. It was a learning experience–"Being taken down a notch can be good for you," he notes–and it helped him realize that WRQ's corporate culture was no longer a good fit. He wanted a more ambitious, aggressive environment. Soon, he would create one for himself.

Aventail was born in 1996 after friends came to Kaplan with an idea for helping organizations conduct business over the Internet. He quickly realized he was "wired" for building the new company–that "this was a journey that could challenge me emotionally, spiritually, and intellectually." Starting out with 11 people working out of his home, he assembled a top-notch team that eventually grew to 120. After a few years, Kaplan took Aventail in a bold, new direction: operating extranets for companies. The company grew swiftly, doubling staff.

Recently, Aventail has suffered the economic downturn in the tech market, forcing Kaplan to lay off 20 percent of his workforce. But he says tough times haven't dampened Aventail's spirit, which he proudly describes as "not scared of the general adventure."

Now in his 40s, Kaplan is a matured, sanguine version of the plucky young guy bent on summiting the business world. But he's not slowing down; leading a rebounding Aventail and serving as an advisor to several local groups keeps him busy. In fact, he says, "I feel like I'm hitting my stride in a different way."

Produced By: Christopher Redner

Contact Make It Timeless Inc. to find out how your company can be featured in our television programs.