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Stop That Bus (I Want to Get On)

What if the feeling you’re feeling when that Peninsula-bound luxury shuttle rumbles by isn’t resentment or hatred? What if it’s envy? The ballad of the left behind.

In the past year, there have been rounds of news stories about how the industry is either sanguine or downright gleeful about the fact that it’s made up of young people. Many venture capitalists and company executives say straight out that young people have more energy and time (no pesky family responsibilities) and are just plain smarter (thanks, Mark Zuckerberg). The entrepreneur Vinod Khosla has been quoted as saying, “After 45, people basically die. They keep doing what they were doing before, and it’s the worst thing that can happen” to a tech business. Khosla later put his comment in a larger context (that experience can count for something). But still, it’s less than encouraging to a middle-aged woman with a liberal arts degree.

Even those working to bring more women, African Americans, and Latinos into the tech fold hesitate when asked about age. “Age is a barrier to entering the tech industry, even more so than gender,” says Michele Weisblatt, executive vice president of Women in Technology International, an advocacy and consulting group. “It comes down to dollars and cents. A company can mold a younger person and at the same time pay her less” than an experienced worker.

Cliff Palefsky hears this all the time. A prominent San Francisco employment attorney, Palefsky often represents tech workers who have been let go after years of service. “I spend 80 percent of my time as a psychologist, dealing with people in the throes of losing a job,” he says. “Their concerns are, honestly, to do with money. They wonder, will I ever get another job? They’re not so much worried about the existential question, am I on the Ferris wheel of life?”

“How old are you?” Palefsky asks me bluntly. I’m a bit taken aback, but given the clientele that he deals with every day, I shouldn’t be. “54.”

“Oh,” he says, “you have plenty of time to move on.”

As I’m sure I do. I’m not, for some reason, worried about never working again. What I am worried about is the precise nature of that work. I want to be where the action is. To Palefsky, that’s a nice ambition, but it’s too existential. His main objective is to help his clients once again put food on the table, not to find them stimulating, ennobling jobs that will enrich their souls.

Fred Turner, however, gets my mental state—or at least sees my angst as something more than an idiosyncratic (and admittedly privileged) state of mind. “Technology is brilliant at turning products into symbols of youth,” says Turner, an associate professor in Stanford’s communications department who writes about the history and culture of tech. “We see the conflation of cultural desires—like youth, progress, optimism—with technologies. The industry has made itself a symbol of youth.” Part of the allure of an industry built on constant change is that it never grows old.

Turner gently nudges the now-familiar age question toward me. “I don’t know about you, but I’m 52,” he says. “I’m guessing that like me, you’re entering that stage where being part of technology might represent a way to hold on to one’s youth.” His words cut close to the bone. I suddenly feel very naked.

“This all has a deep human component,” Turner continues. “American culture values the young, and the technology culture is very American. Also, there’s that terrible imperative: If you’re not running on Internet time, you’re falling behind.” He keeps talking, but I’m hardly listening: I’m stuck on what he’s just said. My tech angst doesn’t derive from concern that I’m too slow to code or too proud to slide down the org chart, or even from a desire to leave old media for new. The root problem is that I’m too old to be young. Which may have less to do with my actual age than with, as Turner sees it, an industry built on accelerating obsolescence. This goes for products—the tablet usurps the desktop; the smartphone crushes the camera—and it goes for people.

I meet up at a café with a friend who escaped from magazines to a lifestyle website. She’s happy that she got out, but she tries to clear up any rosy view I might have of the startup life. Hour-by-hour deadlines, pivots in tactics every other day, a tech team that works all hours just for the fun of it—she doesn’t even have time for a cappuccino before heading back to her cubicle.

“I feel old,” she says. She’s 35.

With the help of Google Maps, I drive down to Google headquarters in Mountain View and thread my way into the campus. Looping around, looking for Building 43, I pass the turnaround where the Bus lands. And there one waits, taking on employees for the ride home at the end of the day. Seeing the workers toting their backpacks onto the Bus, the big Playskool-colored shared bikes leaning in racks, and the campus of gleaming glass-and-steel buildings surrounded by well-kept plantings, I feel like I’m visiting a prep school for rich, popular kids.

I’ve been dipping around the website, a huge networking marketplace where you can find virtually any affinity group—backpackers of the East Bay, lovers of classical guitar, Wiccan allegiants. I get alerts about all things tech, as well as recommendations for 100 groups within 50 miles of my neighborhood. Overwhelmingly, they have “startup” or “entrepreneur” in their title: Lean Startup Circle (4,794 members). Startup Mind SF (3,255). Not Another Startup (225).

Tonight, it’s “Startup Grind: Silicon Valley Hosts Vinod Khosla.” As a cofounder of Sun Microsystems and a longtime venture capitalist, Khosla is one of the Valley’s most revered entrepreneurs. He’s also the man who said that you’re dead, idea-wise, after 45. More than 250 people are expected at the Googleplex event.

Many meetups are all about drinking and networking, but here, most people pass up the pizza and stake out seats as close to the front of the room as possible. The audience mix is young, but includes some middle-aged men and women who, I gather as I eavesdrop, have been part of the Valley for some time. Startup Grind’s maybe-30 founder, Derek Andersen, sits on a chair next to Khosla and asks the crowd what they want to hear about. “What’s hot for investing?” someone shouts. “What about agriculture?” “How do you scale from small to midsize?”

Khosla—cropped gray hair, an artist’s long, thin hands—is a highly entertaining contrarian, and I instantly like him despite his ageist remark. He kicks off the discussion by asking, “Who here wants to do a startup?” Many hands are raised, but not all. “Why are you here if you’re not going to do a startup?” he asks, smiling but serious. “It’s the only useful life to live.”

Khosla has refined his philosophy into inspirational sound bites: “Most people are limited by what they think they can do, not what they can do.” “There’s no courage if you’re not scared.” “Think big, act small.” He even tacks toward the evangelical: Most startups “need this religious belief in your idea,” he says, “so you’ll survive long enough to get lucky.” The whole session boils down to this: Take risks. Don’t be afraid to fail. Start something.

It’s good advice, but it’s also obvious, especially when spoken in the well-honed patois of the techno-titan. Instead of sitting in the ’Plex on a sweet summer evening in this blessed Valley, we could easily be in a big chain hotel’s windowless conference room, taking in a Donald Trump–endorsed seminar called “Think Yourself to Riches.” Google’s magical unicorn castle is a very posh office park, but still an office park. The fundamental promise isn’t Zuckerberg fame and bazillions, but that you, like Khosla (who is 58, by the way, and definitely not dead), can work your way to success if you don’t accept failure. It’s a promise as old—yes, old—as Benjamin Franklin and the American Dream.

Looking around at the intent audience, I think about a conversation I had recently with Linda Oubré, dean of San Francisco State University’s College of Business. She describes her students, many of whom come for the entrepreneurial and technology programs, as “nontraditional—first-generation college, single moms, military vets.” Their stories are fascinating to her—and to me. “They have no anxiety about technology,” she says, “just an assumption that it will be part of their lives.” For Oubré, the seductiveness and hype of the industry are its least valuable aspects. “What’s more interesting is that many of the students say, ‘I want to have an impact on the world.’” A number of them are working on a project to bring laptops to children in poverty. “It’s easy to build a computer,” she says. “But a $20 computer? That takes innovation.”

When Khosla finishes talking, audience members line up to ask him questions. First is a twentysomething named Chris who identifies himself as an art school grad and furniture maker. An outsider, maybe, like me. When the meeting breaks up, I seek him out. Turns out, Chris Tolles is 27, is getting his MBA, and has already been involved with a handful of startups—including one that developed a simple light-reflecting dish to boil water in fuel-deficient regions. And he’s working on his next invention.

“I got bitten by the social enterprise bug,” Tolles says. “Many people just want to be in charge, make some technology, sell it, maybe sell the company. I want to see a problem and solve it, then know enough to make it happen.” He finishes, “There’s a lot of noise around this startup world. But the startup isn’t the point, is it?” No, I think, it’s not.

Next Monday on the bike, I still feel a pang when the Bus drives by—but only a small one, and this time it’s not envy I feel, but impatience. That tech angst? Over it. The age thing? Nothing to be done about it. Let the Google job be “On fire!” Let the Bus sail on. I might be too old to be young, but show me a 25-year-old who’s reinvented magazines, survived sinking corporations, and rewritten her own job description. I’ve already been my own startup, half a dozen times. I just need to figure out how to do it again.


Originally published in the October 2013 issue of San Francisco

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