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.

Stefanie Olsen
Stefanie Olsen Staff writer, CNET News
Stefanie Olsen covers technology and science.
10 min read
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 News.com 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.

Aydin Senkut
Credit: Courtesy
Aydin Senkut
Aydin Senkut

Aydin Senkut
Former Google sales manager,
now venture capitalist

Aydin Senkut, a self-described type "A" personality, started at Google in November 1999 as employee No. 63. At Google, he worked 16-hour days, helped launch the company's first 10 international sites, and signed historic search ad-distribution deals like AOL in the United Kingdom and Fujitsu in Asia.

With some work fatigue and a significant change to his bank account, he took a leave from the company in 2005 to spend time with his family. He officially left Google in April 2005, an emotional break he likened to splitting up with a longtime girlfriend. Now running his own investment company called Felicis Ventures, he's backed as many as 35 companies, including Buzzlogic, Meraki Networks, and Mint.

"I want to make a name for myself on my own," Senkut said.

Senkut is a strong presence among ex-Googlers. He shares an office with Google veteran Georges Harik. With his wife, he is a benefactor to the University of Pennsylvania, which has a scholarship in his name, and to the University of California at San Francisco for research in the fields of longevity and cancer.

Lisa Rhorer
Credit: Courtesy
Lisa Rhorer
Lisa Rhorer

Lisa Rhorer
Former marketing manager,
now sommelier

Many old-timers trade on the Google name as they pursue new ventures in technology. But for Lisa Rhorer, leaving the search giant meant starting from scratch in a world where search didn't mean much--food and wine.

When Rhorer, 40, was recruited to Google in September 2002 and hammered with 12 interviews, she had already worked for 13 years at companies like Silicon Graphics and Oracle. Google offered her the ability to create her own job as its first marketing person in the sales department, and that entrepreneurial role eventually led her to believe she could start her own business--especially after the IPO. In October 2004, Rhorer left Google to pursue the stress-free life of meditation, boxing classes, and adventure camps.

After some time off, she set out to learn wine "from the ground up" with the ambition to open up a wine bar. She went to school at the California Culinary Institute in St. Helena, Calif., to become a sommelier, worked around Silicon Valley in wine bars in San Jose and Los Gatos, and then signed on as the wine buyer for the Los Altos Whole Foods.

She recently quit Whole Foods to prepare for the opening this spring of her first "green" wine bar on Village Lane in Los Gatos. The eco-hangout, funded solely by Rhorer, will sell sustainably made, sustainably grown wines and locally sourced meats and cheeses. The bar, called Cin-Cin Winebar, has eco flourishes like bamboo floors, a reclaimed black-walnut bar top, and in the mold of Google's cafeteria, biodegradeable paper products and straws.

"Google taught me that you can work really hard on one thing and still have a worldly view," she said.

Chris Sacca
Credit: Google
Chris Sacca

Chris Sacca
Former Wi-Fi negotiator,
now investor

For Chris Sacca, a trained attorney from Georgetown University and an avid skier, leaving Google after nearly four years as its wireless dealmaker was a tough call, considering his run of high-profile experiences. One year he represented Silicon Valley speaking at Oxford University and the next he was battling AT&T and Verizon in a multibillion-dollar wireless spectrum auction. But once his shares vested last fall, he longed to be back at a smaller company (he started at Google in November 2003 when the company had more than 500 employees) where he could be more of a jack-of-all trades, writing business plans or helping conceive of services like Google Talk. He decided to make the leap into angel investing in December.

While still at Google, he tested the waters of tech investing by putting money into companies like Twitter and Photobucket, which sold to News Corp. Now Sacca plans to raise a venture fund that's smaller than a traditional fund, with assets less than $100 million.

He said traditional funds don't take into account that it's much less expensive to develop software these days and a big fund typically tries to force too much money on start-ups. For that reason, he envisions working with smaller companies that don't necessarily need human resources or an office. Investing like this "is the easiest way to approximate the kind of experience at the early Google--there's always cross pollination," he said.

Dave Watson
Dave Watson

David Watson
Former software engineer,
now aspiring musician

David Watson figured it was time to leave Google when he couldn't leave home without his guitar pick. Apparently, enough money in the bank can put things into perspective.

Watson, 30, who has a computer science degree from the University of California in Santa Barbara and sounds more like a surfer than an engineer, joined Google in April 2000 when it still had fewer than 100 employees. In roughly six years at the company, he worked on everything from Froogle to Google's search appliance to the search engine itself--and he opened Google's office in Bangalore, India. Watson left in March 2006 to pursue his dreams in music.

Two years later, Watson is funding construction of a music studio in Oakland, Calif., that will be an incubator for young musicians in the Bay Area. The studio should be finished this summer. With luck, the yet-to-be-named music studio will deliver up the next Green Day or Watson himself. Since he left Google, he has been formally studying the blues and North Indian classical music, and he plans to work at the studio as a junior producer, songwriter, and musician.

As for the connection to Google, he said that the studio will approximate his early experience at the search giant, when it was a tightly knit group of people who collaborated on ideas. "I feel like Google upped my game. It was great to do what you wanted," he said. "Music making is a lot like engineering--it is a creative task."

Ron Garret
Lead engineer on first release of Adwords,
now filmmaker and investor

Ron Garret was a researcher for NASA's Jet Propulsion Lab before he joined Google in June 2000 as employee No. 104. He never actually left his home in Pasadena, Calif., near JPL, when he took the job. But he flew to Google every week to help develop the first release of Adwords, Google's wildly successful ad platform. (Google rival Overture Networks, which was first to commercialize search, didn't respond to Garret about a job.) After the September 11, 2001, terrorist attacks, air travel become more difficult for Garrett and he left the company after just more than a year, enough time for his first batch of shares to vest.

Garret said he made enough money so he doesn't have to pay the mortgage and he works part time as a venture capitalist with a small Santa Monica, Calif., firm called Funk Ventures. Garret still lives in Pasadena with his wife, and one day while walking his dog he met a homeless man who had lost his wife and kids in a drunken driving crash. That experience inspired him to make a movie about five homeless people living in Santa Monica called But for the Grace of God. In his words, he was the producer, cameraman, director, cinematographer, and chief bottle washer on the film. After editing it, he plans to take it to the film festival circuit in June.

"There seems to be a very prevalent feeling that all this money we've made must be put to socially responsible use," said Garret, who keeps up with former Googlers through several private e-mail lists. "They're all looking for causes--probably because we're all techno-geeks."