Most consumer technology companies are founded by young or youngish men. They’re funded by men who live in the same world.

They do best when making stuff for themselves. Take Vindigo. The original service, a Palm-based city guide, was made by smart dorks who didn’t like not knowing where to go in the big city. With Vindigo in hand, that tribe still wouldn’t know the latest underground bars, clubs, and restaurants, but they’d have directions (and, crucially, reviews to parrot) for the places that had already surfaced. Creators and audience understood one another, and it’s still one of the best mobile phone applications available in the US, though little known, and underused these days.

Juno, like Vindigo, hired the kind of people who later graduated to jobs at Google. Juno’s requirements were strict, but not sensible. Unbelievably, SAT scores counted. Experience didn’t. Ivy League GPAs were verified, but common sense wasn’t. This would have worked if the service were based on spotting tiny arbitrage opportunities, like their hedge-fund parent company. Instead, Juno provided free, dial-up email to millions of people who had never before used the Internet. The idea was audacious, and in theory the numbers worked.

However, Juno employees worked in a glass tower 26 floors above Times Square—opposite MTV, and in the same office as P. Diddy, back when he was Puff Daddy, and Every Breath You Take played in every elevator. Those microscopic glitches our hedge fund brothers searched for? That was about the scale of our intimacy with customers. All we knew was, we were doing them a favor—hey, it was free—and that the product they bought most often from our daily bombardment of direct-sales ads was religious clip art.

This was just proof that they were weird. And most likely hadn’t gone to Yale.

A switched-on French colleague railed shortly before he left that it seemed everyone wanted to “do strategy,” and nobody wanted to go to the warehouse to figure out the best way to get these people the religious clip art they had paid for. Solving the technical challenges of serving ten million people was (rightly) valued, but learning about their lives was not. We spent our energy on odd things—getting fervent about serial commas in intranet articles, or designing “error message” advertisements to trick people into upgrading to paid services. Or “doing strategy.” (As Joel says, “no one at Juno owned anything. They just worked on it.”)

Well, that was extreme, and that was ten years ago. Still, it’s left me with an interest in figuring out how people make things for people who aren’t like them. Walking around the Yahoo! offices in Sunnyvale last spring, it was clear that, though they still call it a campus, that internet generation is older now. The majority are the thirtysomething dorky guys I’ve always liked. And Yahoo!—like Google and others—has done well with the services that matter most to their staff as users: Autos, Finance, Personals, Instant Messenger, Video, Maps…

Where I get interested is in the efforts of tech founders and organizations to move beyond their tribe. In their efforts to hire, or at least get to know, people who are different. The Yahoo team I worked with last spring are little on the margins—“a bunch of moms,” they called themselves, maybe ten years older than the surrounding engineers. They’re designers, in a technologists’ world. And they wanted to work for customers that Yahoo hadn’t yet talked to. So they found some, visited them, and picked their brains. They made prototypes together, big looping sketches that filled walls. They spent time showing them how older services actually worked—even instant messaging is always new to someone. Eventually they gathered a bigger group—sixty representatives—from this tribe that doesn’t surf the web all day. For ten days, they lived at Yahoo!, while the “bunch of moms,” their engineering allies, and some executives with big ideas listened, answered, explained, and asked. There was no fancy method, just people getting to know one another, then sketching, building, and testing ideas together. They produced good work. Also some Princess Leia skits, but that’s another story.

The “just moms” were curious, self-deprecating, and tenacious as Borat. It’s to Yahoo’s credit that passionate entrepreneurs have a place to live, and room for a real life to draw from. I hope they succeed.

If you don’t take the time they took to explore unfamiliar ground, it’s hard to sound real. Here’s what today’s Valleywag pulled from an article on a recent launch—Yahoo’s Food portal, as it happens.

Just Wait Until Forbes Writes About Yahoo! Sex

• “Brown has been working with food for most of the Internet’s history.”
• “Yahoo! media and entertainment head Lloyd Braun hired Brown because ‘[Braun] identified “food” as something he wanted to do.’”

• “‘He saw the food marketplace as under-served.’”

(For the record, this is what real sounds like: Meetup’s Scott Heiferman on his stint at McDonalds.)

Is it fair to say most tech founders think they’re smarter than everyone else? I hope so. They need that shell of arrogance to weather all the doubts and threats and blows to come. (And besides, they’re often right about being smarter.) That belief is probably a necessary condition for facing startup odds.

It’s also a conviction that limits their reach, from what I’ve seen.

What I look for now are the ones who, in action and conversation, can make others feel more smart, valued, and heard, not less. Staff, family, friends, and allies first—they’ll need them, to get through the brutality of birthing something new. Then customers. Mena Trott has that quality, as far as I can tell with an outsider’s eye. That’s why her new blog/community service, Vox.com, addresses with such warmth and respect people who aren’t visible to the Valley tribe.

Of the six billion people in the world, it’s amazing how many still fall into that category.

I’ve been re-reading George Dyson’s wonderful essay on Google, “Turing’s Cathedral“. You should read it.

Few know how to ask good questions—of computers or of each other. And fewer still know how to listen, in a culture that babbles or sits slack-jawed. John Battelle has some free advice on the subject for the MacArthur Foundation.

I’m a new customer at Bank of America. Though Citibank has bought billboards all over San Francisco to advertise their unsettling belief that money isn’t important, they have only one or two actual branches. This forces me to use other banks’ ATM machines, for which I get charged two dollars. Still, I stayed loyal until they turned me down for a small overdraft facility with a form letter that said, in block capitals, ‘YOU ARE NOT A PERMANENT LEGAL RESIDENT.’ Yes, I’d noticed. It hadn’t stopped them giving me an automatic overdraft for years, which I’d never even used.

Feeling rejected, I walked across the street from my office and opened an account at Bank of America. This branch exuded ugliness, from the low, dark building, to the ancient, grubby Windows terminals, to the tacky welcome kit. Though I missed Citibank’s shiny ATMs, pride kept me there even as the terminal crashed three times on the young Relationship Manager who was setting up my account. “Your first check will take three weeks to clear,” she said. That seemed fair enough.

Then I tried to confirm receipt of the credit card and debit card that arrived two weeks later.(They are almost identical, and butt-ugly. I’m not sure how customers with poor eyesight are supposed to manage.) On two separate calls, I had to sit through a six-minute pitch for an identity theft protection ‘service,’ which I didn’t want. There was no indication that my card had been confirmed until right at the end, so each time I was trapped with a robot huckster. “Welcome to Bank of America,” she lied.

Then I went to the branch and deposited a pair of checks. Since I was a new customer, the teller told me, they were going to place a ‘Hold’ on them for three weeks. I asked how long this policy would apply, and he consulted a more senior employee. I’d be on ‘probation’ for six months, she explained.

Probation? These people are getting automatic delivery of my paycheck.

I told the poor young clerks that these experiences were not what I’d hoped for as a new customer. They looked stricken. ‘We can’t do anything. Corporate doesn’t listen to us. Maybe if customers told them they’d do something, but we have no way to tell them. Maybe you should try to find out who to complain to.’ They had no idea who that might be. “Corporate?” they bleated.

Bank of America, are you listening? You’re toast.

Ten years ago, I experienced the internet only through paper. It was reverently capitalized back then, like the Electric or the Motor-Car, and for those who visit but don’t yet live there, it still is.

I was working at Hodges Figgis bookshop in Dublin while my future ex-husband finished his thesis on delivering video through noisy channels. I’d had little chance to use computers, and was hazy about his post-graduate research. When I found the first issue of Wired, it didn’t occur to me it might have any connection to his work. Wired burbled with the promise of this World Wide Web, and I pored over it with the fizz of discovery, even though the typography was maddening. More than once I had to trace with my finger some distressed fuschia font as it wobbled from a lime-green background to the purple overleaf. I felt like a dyslexic with a treasure map.
(more…)

The poet who sits next to me at work taps out strategy documents with a brisk two-fingered peck. She never learned to type, she says, because she feared ending up a secretary. When I started out, just a few years after her, I’d taught myself to touch-type but was determined not to admit to the slightest knowledge of mark-up language or web development. At the time, London was so desperate for those skills that I thought it would mean spending ten years adding tables to online annual reports. Then when the rest of the world figured out that a marquee tag wasn’t, in fact, rocket science, my wages would drop from fifty to five quid an hour, and I’d have learned nothing interesting or saleable. I thought it was better to pretend to be the person who could tell those guys what to do.

That was a mistake. I may spend more time typing than tweaking web layouts, but I still wish I could do a better job.

When my blog comments broke last week, I took it as a sign that I should support technology startups—the clan I come from—and upgrade to the paid version of Movable Type, the software that runs this site. It took an evening of tense FTP negotiations with my database before I managed it. Since I first installed it two years ago, Movable Type’s parents, Six Apart, have taken out most of the non-expert instructions and introduced dead-end navigation on their support site. Presumably, we poets are now supposed to use their subscription service, TypePad.

(At lunchtime, sneaking out to a tag sale at Red Dot on Fourth Street, I was star-struck to notice that the Six Apart office is kitty-corner from mine. Their front door is appropriately unglitzy.)

Now a recent burst of posts is forcing me to look at this site again, and it’s painful. I’ve never liked this typography. The serif font of the body copy works badly on screen, and the kerning always seems a little off. Photos are not so much placed as abandoned. The site doesn’t validate against web standards, because I galumphed all over the templates when I was learning two years ago, leaving open tags and half-digested hacks strewn about. It’s not fully accessible to disabled readers, and it probably degrades like a sloppy drunk on phone browsers.

The navigation is clumsy. As the months go by, the sidebar gets more and more cluttered with archives and content categories, but Movable Type doesn’t make it easy to summarize old posts on flexible sub-pages. (I’ve already stripped off the blogroll, which was hopeless outdated.) I’d like to use this site as an outboard brain, but haven’t found a good way to keep track of all the lists and clippings from my magpie mind—book blurbs, heroes, playlists, web subscriptions, recipes, fleeting obsessions (sweet Kalamata olive jam!), and Things I Love/Hate About San Francisco.

I’d like to turn comments back on for old entries, now that I have a better way to manage them. So many people wash up here from Google searches that I’d like to give more context on old posts, at least to the visitors who aren’t looking for “schoolgurl loleeta knickers.” Trackbacks need de-spamming. I should offer more and better syndication choices, and an accessibility statement to be proud of. I want to find a spot for the podcasts I promised Bernie. I want to make a site that’s elegant and clean enough to merit a colophon.

My curse is that I know enough to know what’s failing, and not enough to fix it without a week to read up, noodle, steal and swear. I sketched a layout and a list of design requirements in my notebook (those who can’t, brief) and then wandered around to see who does this well. Shirley Kaiser, over at Brainstorms and Raves, say, or my Brooklyn friend Michael Barrish. (Michael, I miss you.) La Dooce. Dean Allen, still. Or Leslie Harpold, who says of design, function, and web standards that “pretty is as pretty does.”

Spare change for a frustrated, incompetent aesthete? Advice, sympathy, sample stylesheets, and donated archive templates gratefully accepted.

My blog comments have been broken for a week, and I don’t know how to fix them. This makes me sad. Spammers had already made me close comments on old entries, and I miss the random stuff that used to come in from people stumbling on old posts through Google searches. Until I reinstall Movable Type, you can always email me instead. dervala [at] dervala [dot] net.

I was a gadget geek. Then a paper purist, haughty about the toys that tethered the unenlightened ones. Now I’m a gadget geek again.

Truth is, for all my Zen posing, my pared-down life wasn’t a conscious renunciation of what the Quakers call “cumber”. It was just that I kept losing shit.

I lost my Sony laptop. Two cellphones. A digital camera. A Palm PDA. A film camera (or three, if you count the ones I owned with my ex.) A few wallets. An iPod, given to me by Meetup. On my way to an interview for my new job at Stone Yamashita, I abandoned my IBM laptop on the A train platform at JFK—perhaps acting out a fear of San Francisco.

Mostly, I shrugged. It’s just stuff. I didn’t feel rich enough to replace it, so I took each loss as one less thing to fret about. My co-workers made fun of my gadget-repelling forcefield. My friends and family complained that they could never call me, but that was okay; I find a whining phone no better company than a mosquito.

But the stuff crept back into my life. Meetup kindly gave me another iPod. Hooked by that touch-me iPod, as groovy as Courreges go-go boots, I bought a Bose Dock so that it could live out loud. I celebrated my new job by replacing the lost laptop with a matching iBook, proud that I’d finally earned a product designed in California. When I got there, Stone Yamashita trumped it with a sleek 17” PowerBook that made the iBook feel like an Etch-a-Sketch.

Before the move, I’d given in and bought a pay-as-you-go cellphone on eBay so that I could wrangle movers and realtors. Then Stone Yamashita handed me a BlackBerry that I clip to the strap of my backpack for full dorkish effect. It hasn’t helped my email twitchiness, though its clunky Canadian icons annoy me whenever I take a digital hit.

Yesterday we moved to new offices, just down the street on Brannan and Fourth, where the dotcom ghosts walk. It must have been wrenching for a small, cultish company to leave ten years of stories in the old loft we’d outgrown. To ease and celebrate the change, the partners handed us champagne and Shuffles, and fifty grown-up faces lit with glee.

I used to wander Brooklyn with a notebook, a pen, and a secondhand paperback. Now I schlep two laptops, two phones, and two iPods through SoMa (though I draw the line at listening to music in public: I can’t be in two places at once.) In the words of Mr. David Byrne, �How did I get here?”

Most social software acts more like a gawky thirteen-year-old than like Emily Post. I write customer service email for a living, so I’m touchy about software corporations telling me how fabulous a job they’re doing.

Spare me and show me, kids.

Frank is my Friend? That’s what my mother called menstruation when I was twelve.

Most of my toys were stolen from storage while I was away: laptop, cellphone, Palm organizer, digital camera, jewelry, journals, and CDs. More were stolen from my backpack while traveling, or worse, misplaced, like my Buddhist paraphenalia, by the guardians in whose care I’d left them.

I can finally laugh at how cross I was to learn that my meditation cushions and little altar were thrown out by the friend who had asked for them as a keepsake. A bodhisattva he was, the careless fecker, slicing through my spiritual materialism. These weren’t just cushions, you see, in spite of their kapok-and-cotton manifestation. They were zabuton, and they were fifty bucks apiece. Hand-stitched by chanting monks and stuffed with their shaven hair, I suppose. I had bought them from a special website three years ago, when I was bent on following the upper-middle way. Now I sit on the floor in my lower-middle neighborhood, and brood about attachment. Mine.

Of all the things I lost, I miss the cellphone least. I used to design software for cellphones, so they feel like work, and now that I pay my own way the billing plans confuse and worry me. You would think I’d like phones, given that their main function is to put off decisions, but that’s cancelled out by the multiple calls that every meeting now requires.

Sadly, these days I’m too rarely untethered to need a cellphone. I’m on my fifth startup, and startups don’t change. That means I’ve spent the summer at a desk, Sundays too, or at my volunteer gig for a change of desk. So it was last Friday when I finally missed having a phone. My friend Amy had asked me to a showing of Spike Lee’s 25th Hour under the Brooklyn Bridge. I met Amy in Mexico last year, and she is one of my favorite Brooklyn people, the kind that always has a scheme for something to do. But I live online and she lives on the phone, and so our arrangements to meet can be awkward.

The movie started just after sunset and I was late when they valet-parked my bike. No Amy. I searched the park for a small woman with two deck-chairs and couldn’t see her. I did bump into Michael, whom I’d hired some years ago to work on cellphone applications with me. I knew I could count on him to lend me a phone, but didn’t want him to think his old boss had hit the skids. So I nosed around again during the opening credits, squinting in the dusk as Edward Norton did something with a dog a few blocks from the same park. Finally I sat on the grass by myself.

After the film I stood at the back and scanned every face leaving, but there was still no sign of Amy. I collected my bike, and wandered around DUMBO looking for a payphone. But DUMBO is one of those fake neighborhoods where people pay huge sums to live in old factories, and there are no payphones and no bodegas. Eventually, I biked up to her apartment in Brooklyn Heights, sure by now that she’d suffered a terrible accident and was lying on the bathroom floor while I’d watched Edward Norton for two hours.

Amy answered the door in her pyjamas. She’d given up on me and left an hour into the movie to go home to The Curious Incident of the Dog in the Nighttime.
“What did we do before cellphones?” she said sleepily.

Well, we said more than “See you at the park.” We said “Let’s meet at the popcorn stand at twenty past eight.” But we’ve been trained out of these habits, and now we need our walkie-talkies.

Another guest entry from Ranger Tim: