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Less than three years after going public, Google is confronting one of the more confounding consequences of its phenomenal success: a potential brain drain if its earliest – and richest – employees quit after earning the right to cash in the last of the stock options that made them millionaires.

Hundreds of the 2,300 Googlers hired before the Internet juggernaut went public in August 2004 are hitting their fourth anniversary. When they do, they’ll be free to cash in the final portions of their pre-IPO options, worth an estimated $2.6 billion before taxes.

So far, the exodus has been limited to “handful of people,” said Stacy Savides Sullivan, Google’s chief culture officer and a 43-year-old pre-IPO millionaire herself. “We anticipated more because we think it would only be natural. We worry every day about this and hope we can stay ahead of it.”

Senior executives have viewed this problem as a significant risk and have been taking aggressive and innovative steps to retain early employees, including mixing in other forms of stock compensation and rolling out a first-of-its-kind in-house market this month that will enable workers to sell even “underwater” options. Google also is working on softer issues, from conducting an annual “happiness” survey to outright coddling of critical talent.

Still, Google executives know some people will leave anyway. Some will move on because their jobs no longer seem challenging. Others will quit to start a restaurant, found a nonprofit or build a dream house.

Despite the mind-boggling dollar figures, Google’s story is no anomaly. Every Silicon Valley start-up that dishes up stock options to lure workers faces a similar predicament if their initial public offering is successful.

“This is what any of these companies struggle with,” said Steve Patchel, a tech-industry pay consultant in Watson Wyatt’s Santa Clara office. “There are all these moving parts. Nobody can ever get it perfect.”

Google’s story is also a case study of how companies must learn to manage overnight millionaires who think more like “volunteers” because they’re no longer motivated primarily by pay and can quit at any moment. Google’s pre-IPO crew, for instance, is sitting on $2 billion worth of options that have vested already and can be cashed in at a moment’s notice. And it doesn’t count the riches they took off the table last year alone by exercising more than 6 million options with strike prices ranging from a penny to the $85 IPO price.

Their good fortune can stir jealousies as less-fortunate later hires park their Hondas next to a cube-mate’s Ferrari, then head into the office to shoulder an equal share of the workload.

And when the stock price tails off after years of explosive growth, somehow companies like Google must reformulate their mix of pay, stock and perks to retain those already wealthy workers and attract new recruits since options won’t continue to have a big payoff.

For now, though, hundreds of Google’s pre-IPO crew are still bound with “golden handcuffs.” Under Google’s vesting rules, employees typically earn the right to cash in 25 percent of their options when they hit their first anniversary, then the rest in monthly chunks over the next three years.

For example, if Google gave an employee 10,000 options in 2003 – a figure some experts say is on the low side – at Thursday’s stock price of $471.51, the typical pre-IPO Googler’s shares are worth an estimated $4.7 million, before taxes, according to Google’s options data on Dec. 31, 2006.

In that case sticking it out until their fourth anniversary would be worth about $98,000 a month, $3,200 a day or $400 an hour. That’s on top of their regular salary and any other options, restricted stock or bonuses.

That kind of money will make anyone rethink their lives. With that in mind, Google also has drawn up lists of its most valuable pre-IPO “old-timers” and is pressing managers to keep tabs on their mood swings and professional goals. These workers are encouraged to speak up if they want to tackle a new job, work part-time or take a leave before they start feeling burned out, for example.

“We always have to be understanding where their heads are at,” Sullivan said.

Google has already lost some key early employees. Among them are Doug Edwards, the marketing guy who named the “Adwords” advertising product that is Google’s golden goose, and Charlie Ayers, the chef who concocted the secret sauce of yummy food and old-fashioned fun that became a hallmark of Google’s corporate culture.

“There’s the notion that it’s not as much fun and that you don’t have to stay there if you don’t want to,” said Edwards, who resigned in 2005, shortly after his boss left. “You start looking for excuses and they are not hard to find.”

Ayers said he always planned to leave Google after his options vested. “I joined Google for one reason,” he said. “I wouldn’t work that hard for anyone else ever again. I would only work that hard for myself.”

Ayers is writing a cookbook, working as a consultant to various companies and preparing to open a restaurant in Palo Alto, the Calafia Cafe, which will feature a locally grown, organic menu, similar to meals he whipped up at Google.

So far, most of the pre-IPO Googlers are hanging in there even after the initial grant that made them rich has vested. Susan Wojcicki, who joined Google shortly after the founders moved out of their first home in her Menlo Park garage, says she loves building new products. It is no coincidence, of course, that her title is vice president, product management.

Wojcicki says she stays because Google is a stimulating environment and because she has been able to comfortably balance her family with her job. “It’s always been exciting, but this time is as exciting if not more exciting than it was in the past,” she said. “I have personal goals about what I want to achieve at the company, things I want to build.”

Sullivan can relate. Hired on when Google had only about 50 employees, her first stock options finished vesting in 2003, though she said she didn’t mark the milestone because her husband handles their finances. People ask her all the time why she bothers to keep working.

“I know this sounds corny, but I still have fun here,” Sullivan said, then adds a remark that cuts to the heart of Google’s challenge.

“That’s the only reason I stay. If it weren’t enjoyable, I would leave.”


Contact Mark Schwanhausser at mschwanhausser@mercurynews.com or (408) 920-5543. Contact Elise Ackerman at eackerman@mercurynews.com or (408) 271-3774.