From the Googleplex to the wine bar

While some ex-Google employees are still grinding away as angel investors and entrepreneurs in the tech industry, it's occurred to some others that they're wealthy enough to do whatever they want.

Sometimes, it's not easy to leave the Googleplex.

Even for the many millionaires among the search giant's pre-IPO employees, there's great appeal to a workplace that prizes creativity and rewards its employees with everything from free food to dry cleaning. Of course, there's also the cachet of working at one of the hottest tech companies in the world, a virtual Shangri-La for the geek set.

"Worldwide, people know Google, and it has an impact on their life, and being a part of it makes you feel famous," said Bonnie Brown, Google's masseuse-turned-millionaire.

Maybe that's why so many of the employees who were there before the initial public offering of Google stock are still at the company when they no longer need to work. In fact, nearly all the original executive management team is intact--except for departing CFO Georges Reyes and former engineering lead Wayne Rosing, who's now on a Chilean mountaintop setting up what may soon be the world's most powerful telescope. On Monday, Google topped Fortune's list of "100 best companies to work for" for the second year in a row, thanks in part to its ability to mint millionaires.

Nonetheless, they're starting to leave and they're pollinating Silicon Valley and beyond with little bits of Google culture. From the venture capitalist who said leaving the search giant was "like breaking up" to the developer of sustainable real estate who still has lunch with Google co-founders Larry Page and Sergey Brin when he flies into town, they all say the formative years at Google taught them to think big.

On Tuesday, CNET profiled several ex-Googlers who've left to start companies such as the micro-messaging service Twitter. This second installment in the two-part series looks at Google employees turned entrepreneurs and do-gooders.

Ray Sidney
Former software engineer,
now developer of sustainable real estate

As one of Google's first software engineers and one of the first to leave (about 18 months before the IPO), Ray Sidney could be considered the company's first retiree. He met the Google guys in September 1998 through a friend who was dating Brin. He signed on later that year as an engineer when there were still "four employees in half a house," as Sidney tells it. He was a Harvard mathematics undergraduate and held a doctoral degree in mathematics from the Massachusetts Institute of Technology.

After about four years retooling the Google search engine, Sidney felt he needed a break to recharge from long days in the office. But once out of the office, he didn't want to return. In 2003, he moved to Stateline, Nev., and a year later, the IPO made him wealthy enough to not worry about work anymore. "It gave me the freedom to do anything," he said.

In the years that followed, Sidney, 38, became a triathlete, an amateur pilot, and a benefactor to local and national environmental causes. He's donated $1 million to help launch a public bus service in Douglas County, near Lake Tahoe, and another $250,000 to replace a South Lake Tahoe track that was once used as training ground for runners competing in the 1968 Olympics. A longtime environmentalist, Sidney bought a house near Tahoe (where Google once took its annual ski vacations) that generates power from solar panels and solar heating that he installed. He also drives a Highlander Hybrid SUV and has donated "big money" to the X Prize Foundation's upcoming Automotive X Prize, a contest to build a 100-mpg vehicle.

Although he didn't intend to start a business, Sidney founded sustainable real-estate company Big George Ventures last year after buying 100 acres of land in Carson Valley from the U.S. Bureau of Land Management. With that property and one employee (his friend and flight instructor), Sidney aims to build affordable, eco-friendly single and multifamily homes, made with sustainable materials like ICF (insulated concrete forms) that are designed to keep the houses warmer in winter and cooler in summer. Still in the planning stages, he's also meeting with scientists this week in MIT's urban-planning group to get more cutting-edge ideas on sustainable building. If zoning permits, he hopes to have the homes built within the next few years.

"A lot of real estate developers are about the bottom line. To me, it's not critical to squeeze every dollar out of the land," Sidney said. "This project is about doing what's good for the planet, what's good for the locals, and what's good for the company."

Bret Taylor
Former developer of Google Maps,
now co-founder of Friendfeed

In 1998, Bret Taylor was a freshman at Stanford University in the computer science department when Brin and Page were building up Google, but he never met them. Five years later, he crossed paths with the search gurus when joining Google as an associate product manager. Over four and half years at Google, Taylor helped launch products like Google Local, the Google Developer Network, and Google Maps, for which he won a founder's award that could have been worth a million for him and his co-worker Jim Norris.

Taylor said he didn't strike it rich at the company, comparatively speaking, considering the cost of living in the San Francisco Bay Area. Yet he's able to afford a house in Los Gatos with his wife.

In June 2007, Taylor and Norris left Google for Benchmark Capital's entrepreneur-in-residence program. Four months later, the two launched a beta of a site called Friendfeed with former Googlers Sanjeev Singh and Paul Buchheit, who were the developers behind Gmail. With RSS and Atom feeds, Friendfeed lets members share things like news articles, song preferences, and photo updates from across the Web, fostering what Taylor calls "water cooler" discussions in a closed environment. It's like Facebook, but without the poking or virtual gifts.

"We want to solve an information problem using social solutions and make it easier for people to discover content on the Web," Taylor said.

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