📸 Photo

Richardson met Bozeman and gave a forty-five-minute presentation. He was ready to write the check before she was done.

It was a route that many other companies had taken and, at the time, a promising one: A mysteriously large number of Conway’s angel investments got larger venture funding down the road. Yet by late 1999, it seemed remarkably easy to get a blessing from Conway—an unimposing middle-aged man in glasses who came across more as an agreeable frat boy than as one of the most important men in the Valley.

Conway’s technology career started right after college, when he went to work for chip manufacturer National Semiconductor Corp., soon emerging as head of sales for the company division that sold chips to car-makers. Denied a raise, he left for a nine-person start-up called Altos Computer Systems, where he went on the road making sales calls. When the company went public in 1982, Conway’s 2 percent stake was suddenly worth $5 million. Three years later, as Altos was slumping, Conway quit, spending his time on charity efforts and advising other start-ups, always taking a piece of the equity for his services. After briefly returning to Altos and helping sell it to another firm, a deal that netted him $2 million, Conway was itching to get back in the game full-time. He bought a majority stake in a computer-instruction firm called Personal Training Systems, took over as CEO, and resolved to either make it big or sell it. Building the struggling company proved hard, but at long last, as the company was running out of money, Conway pulled off another lucrative sale.

While trying to peddle Personal Training, Conway came in contact with more and more rising Silicon Valley stars. One was Kim Polese, a core developer of Sun Microsystems’ Java programming language. He thought she was an up-and-comer, and when he read that she was starting a new company named Marimba Inc. he pestered her with uninvited advice for more than a year until she relented and allowed him to invest in the company’s second financing round alongside VC kingpin Kleiner Perkins, which had backed Sun, Netscape, and Amazon.com. “He was very pushy,” Polese told author Gary Rivlin for his 2001 book about Conway, The Godfather of Silicon Valley. But he was pushy “in an inoffensive way. In fact, in a rather charming way. That he cared about the human side was very clear.” In fact, the human side was Conway’s obvious