Twice the Career in Half the Time

Career DNA: Greenstein is an information omnivore. Each week, he chews through about 2,500 emails and 10 hours' worth of trade-magazine reading. He meets monthly with the World Wide Web Artists Consortium in New York, an organization of hip Internet players, to get the latest scoop on new software tools. (He's been involved in various leadership positions since the consortium's founding in 1994.) For Greenstein, staying ultra-informed is a career imperative: As an evangelist at Microsoft, he's a major proponent of tomorrow's technology. He learns Microsoft's software when it's little more than a glint in a developer's eye, and then he teaches its inner workings to companies that will use it to build other applications. Among other marquee projects, he has helped Web developers create the preloaded content channels in Microsoft's Internet Explorer 4.0.

Says Greenstein: "My job is to know about the next big thing before it happens."

Observation: In 1996, Greenstein joined Netcast Communications Corp., a pioneering company that planned to deliver broadcast-quality music, news, and sports over the Internet. As director of operations, he oversaw the technology infrastructure: the data center, the Internet connections, the hardware - all of the tools that developers would need to create product. Greenstein was the startup's number-five hire, and although the company's future was uncertain, he had no doubts. "They had a great concept and a really great business plan," he says.

But venture capitalists were skeptical of Netcast's business model, which relied on content gathered from other companies. Netcast also burned a big chunk of its available cash by building a spacious office that would have let the company grow physically - but that left little in the coffers to let it grow financially. One investor backed out, and others quickly followed. The founders laid off the staff for three and a half weeks but then tried to keep the business running until they could get a bridge loan. Once they got the loan, Greenstein recalls, they asked members of the senior staff to take pay cuts until the cash flow improved.

"Even at that point, I believed we would succeed," Greenstein says. "But Netcast's plight certainly made it easier for me to consider another offer."

Results: Greenstein was snapped up by Microsoft a few weeks before Netcast finally closed shop. (This past July, Broadcast.com redeemed Netcast's business model when it recorded the most successful IPO ever - after adopting a similar model.)

Conclusion: A setback can sometimes put your career in fast-forward. Though Netcast did not survive, Greenstein doesn't think of his experience there as a failure. In a job that coupled immense freedom with overwhelming responsibility, he learned how to fend for himself.

Microsoft didn't care that Netcast failed: All that mattered to the software giant were Greenstein's skills. "I've proven to any future employer that I can take risks, manage uncertainty, and come back for more."

Coordinates: Howard Greenstein, hgreenstein@hotmail.com

Hypothesis: Experience is a leader's most valuable asset.

Subject: Miles Walsh, 46, independent CEO-for-hire

Career DNA: Walsh is a self-described "executive gunslinger." He gallops into a company and stays just long enough to generate triple-digit growth, a successful IPO, or whatever goal he's promised its board of directors. Then he rides off to find another company that needs a guy in a white hat. Walsh does more than swap jobs - he swaps entire industries. He's held top jobs at companies that specialize in hardware, software, Internet technologies, catalog sales, and electronics. Walsh says that he's the victim of a short but ferocious attention span.

"I can get up to speed quickly and get significant results, but then I get bored with whatever industry I'm in," he admits. His most recent heroic role was at Flycast Communications Inc., a Web-advertising network where he was president and CEO. When he joined the company in April 1997, it had lost a round with venture capitalists, it had burned through all but 60 days' worth of cash, and it was woefully behind schedule for shipping its premier product. Four months later, the company had secured more than $7 million in venture capital, it had delivered a product, and it had landed more than 100 customer contracts.

Observation: As a frequent industry hopper, Walsh is an outsider who needs to get on the inside - fast.

In 1994, Walsh had joined Macromedia Inc. as VP of marketing. The multimedia software company had an alarming image problem: Most potential customers couldn't tell pollsters what the company did, let alone name its flagship multimedia products (Director and Authorware). After work one day, Walsh gathered a group of eight seasoned Macromedia veterans for pizza. His goal: to brainstorm a marketing plan.