Escapees and wanderers have their mysterious allure, but among those who have contributed most to American mythology are the dreamers who ventured into the open spaces in order to fulfill a destiny that was thwarted in their present circumstances, but who became builders of new communities in which they found fame, made fortunes, and tried to establish some purer place. In doing so, they ended up carving the virgin terrain into physical and cultural shapes that in some cases enriched the lives of their descendants and in others became the borders that confined their lives.

I’m Feeling Lucky:
The Confessions of Google
Employee Number 59

by Douglas Edwards
Houghton Mifflin Harcourt, 432 pp.

The best parts of I’m Feeling Lucky: The Confessions of Google Employee Number 59, Douglas Edwards’s intermittently interesting account of five years spent at Google during its start-up years (some of them not yet a decade past), are those that capture the excitement of being among the explorers and builders who have ventured forth into the new century’s new world. Its enormous success aside, Google is a particularly apt company to watch during this period; Google, at root, is a search engine, and, with other search engines like Alta Vista and Inktomi and so on, it performed the function that Lewis and Clark and Captain Cook and other explorers performed in previous centuries, namely, mapping the unknown world.

While it is true, reading an account of encountering Pacific aboriginals will always read more dramatically than accounts of the crises confronted during a tech company’s growing years (“Here, attach this cable to that server—now!), we have to take the new world as we find it. Besides, some of these tales can be quite exciting. For example, things got pretty touch and go the day a cornerstone deal between the established Netscape and the up-and-coming Google went live. Suddenly a Mississippi of search requests swamped Google’s servers, which nearly caused a systemic breakdown, which was avoided only when Larry Page, cofounder of Google with Sergey Brin, boldly ordered that Google stop responding to search requests from people coming to the Google site, and handle only requests coming from Netscape, until more server capacity could be brought on board. This averted paralysis preserved the all-important business relationship and enhanced the young company’s credibility. Okay, it’s not wrestling a bear, but then, what is these days?

One of the limitations of this memoir is that although Edwards was an early hire at Google, and certainly had close contacts with key players and witnessed some privileged moments, there was always a kind of cognitive membrane between him and key people at Google. Edwards was a journalist for the San Jose Mercury News who was hired to serve as Google’s online brand manager. He was, as he often reminds us, a word guy, the person who wrote screen copy and messages to consumers and other suspiciously unquantifiable material. The big men on Campus Google were its engineers, the code writers and software designers and hardware architects who designed and built the search engine. After them were the business people, the people who figured out how to turn all these bits and bytes into money. After them, and probably after the staff chef, and almost certainly after the staff masseuse, were the wordsters.

There is throughout the book the sense that if Page and Brin thought that what Edwards was doing was important, he wouldn’t be doing it. Page and Brin would be dealing with it, or at least an engineer would be. The reader feels just a bit marginalized, as though one had entered a drawing to have dinner with Keith Richards and ended up in second place, having nachos with Ronnie Wood. It is, moreover, difficult to gauge just how valuable Edwards was to the organization. We assume he made a useful contribution—he was kept around long enough for him to hit the jackpot when Google went public—but it would seem to auger poorly for anyone’s status in any company if the co-CEO felt comfortable saying, as Sergey Brin did at one meeting in 1999 during Russia’s war with Chechnya, “I have a good idea. Why don’t we take the marketing budget and use it to inoculate Chechen refugees against cholera? It will help our brand awareness and get more new people to use Google.” A worthwhile cause, certainly, and who among us would not give his salary if it would mean saving a child’s life? Note, however, that Brin did not offer even a sliver of the engineering budget to rescue the refugees.

Far and away the most interesting people in Edwards’s book are Page and Brin, the brilliant researchers who developed the Google search program as undergraduates at Stanford, and who, by placing a premium on technological excellence and shrewd, patient business dealings, then led the company into other wildly successful Internet services and technologies to become the world’s top tech company. On the face of it, they are a pair of admirable and still-young geniuses (both were born in 1973). “If we can’t win on quality, we won’t win at all,” Page said at one marketing meeting; as a consumer, it’s hard not to applaud an attitude like that. “Don’t be evil” is the famous, if unofficial, motto of the company, coined by engineer Paul Bucheit, and again, one has to admire co-CEOs who are bold enough to affix that phrase, as infinitely fungible as those words may be, on a bull’s-eye on their backs. For all that, though, they still seem to have a bit of that undersocialized quality that seems to be characteristic of hard-driving visionaries. It’s true that Edwards doesn’t report either of them saying “I drink your milkshake,” but one wonders if that is because he was never in the inner sanctum with them and the engineers and the masseuses.

“Larry and Sergey,” Edwards writes, “for all their opacity and all their antipathy to traditional thinkers, were easy to approach and easy to like.” Okay, but Edwards doesn’t expend very much energy capturing them in their “easy to like” mode. Mostly he portrays them as iconoclasts, highly demanding and willing to use applied anxiety as a management technique. To their credit, Edwards never depicts them as mean or abusive, which bosses so frequently can be, but they do display the overweening self-confidence that high school quarterbacks, teen heartthrobs, mid-level royalty, and others who have never known defeat often possess. There’s the moment, for instance, when Edwards, after a contentious debate with his bosses, said, “Larry, I realize that more often than not you’ve been right about things,” and Page, with the uninflected tone of a robot encountering data that does not compute, responded, “When were we ever wrong?” There’s Edwards’s introductory interview, in which Brin—who was wearing roller hockey skates at the time—not only asked Edwards his college GPA but, for the decisive query, challenged him to take five minutes and then “explain something complicated to me that I don’t already know.” There was the time Brin had his secretary summon Edwards to help load the boss’s scuba gear into his car, and Brin and Page’s habit of praising an idea with the withholding phrase “That doesn’t seem too sucky” and of rejecting an idea with the alienating phrase “That’s not very Googley.” There was the time when Google CEO Eric Schmidt was conducting an off-site meeting with mid-level managers in a country club conference room while Brin, wearing spandex bicycle shirt and shorts, periodically attempted to make a battery-operated remote-controlled flying saucer hover over Schmidt’s head; there was also the time a staff engineer came up with Gmail, and they insisted on releasing it on April 1 because it would be amusing to see the press grapple with whether or not it was a joke.

Perhaps they had poor upbringings; perhaps it comes with being visionaries. The good news is that there is hope for Brin and Page. For example, if you Google the phrase “Am I being a jerk?” you get about 33,900,000 results in a tenth of a second; presumably at least of few of them would be useful.

“I’ve been asked if Larry and Sergey were truly brilliant,” Edwards writes. “I can’t speak to their IQs, but I saw with my own eyes that their vision burned so brightly it scorched everything that stood in its way. The truth was so obvious that they felt no need for the niceties of polite society when bringing their ideas to life. Why slow down to explain when the value of what they were doing was so self-evident that people would eventually see it for themselves?”

Virgin spaces are seldom settled by the mild-mannered; they need zealots, criminals, and iconoclasts who are willing to go where no one has gone before and hew out of the jungles and deserts the neighborhoods the rest of us will live in. It is a good thing that they have confidence in their visions, and we ought to offer them honor and gratitude and reward. But we should also be careful. John Winthrop, standing on the deck of the Arabella in 1630 and calling for the Massachusetts Bay Colony to be “a shining city on a hill” would recognize a kindred spirit in Google’s “Don’t be evil.” But within six years, rivalries with other settlers and various tribes led to the death or captivity of 700 members of the Pequot tribe. Sooner or later, somebody goes too far.

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Jamie Malanowski

Jamie Malanowski is a writer and editor. He has been an editor at Time, Esquire and most recently Playboy, where he was Managing Editor.