December 1987 was no time to be raising money for a startup. Computer engineer Len Bosack was trying to attract funding for a young enterprise called Cisco Systems (CSCO). But the stock market had just crashed and the Dow Jones industrial average had plummeted 40% since October. Gun-shy venture capitalists either didn't get the newfangled technology or deemed it too risky.
Making matters worse, Bosack was running low on the savings he had used to bootstrap the business, and competition was gaining steam. It wasn't until this 75th meeting that he found a receptive audience. The willing financier was Donald Valentine of Sequoia Capital, a venture capital firm in Silicon Valley. On Dec. 14, two months after Black Monday, Sequoia invested $2.5 million in Cisco. "Valentine's reasoning was pretty simple," recalls Bosack, now CEO of telecom gear-maker XKL. "It doesn't matter what they are. They are selling stuff in a bad market. With a little bit of capital and more experienced help they should be able to do better."
Better is just what Cisco did. By the time of its initial share sale three years later, in February 1990—during a recession—the maker of telecom networking equipment was worth $224 million. Within a decade, Cisco Systems had become one of the world's most valuable companies.