One Fateful Phone Call: How I Ended Up At Wired

Living at the cutting edge of technology in the early ’90s required either a magical token forged of copper and silver, or the capacity to memorize a ridiculously long string of numbers. Either the token or the code would connect you to a vast telecommunications network driven by immense computers housed in bunker-like buildings scattered around the world.

Labor Day 1992. I squeezed into a pay phone behind the oldest bar in California, The Iron Door, pride of Groveland, California – the “gateway to Yosemite.” I never could remember my access code, but I did have a token – also known as a quarter – which I slipped into the pay phone, then dialed my voicemail, a state of the art service that cost me an extra five bucks a month. Back then everybody used voicemail, it was an asynchronous lifeline to the rest of the world.

I’d been offline for the long weekend on a backpacking trip in the Sierra Nevada, on a vision quest of sorts. I’d graduated from J-school earlier that year, and I was struggling. I was 25 years of age, had just quit my plum but depressing job at the Los Angeles Times, and was in the midst of a messy breakup with my girlfriend of seven years. In short, I was lost.

I had no one to blame but myself. That job at the Times was a brass ring, and here I was throwing it away. But even in the early 90s, it seemed obvious to me that newspapers were dying. I had written as much in my Master’s thesis – a dense and unreadable study of the impact of digital technology on the publishing industry. The lifers at the Times were sallow, smoking ghosts, and I had no desire to join their downward spiral. I quit the week before Labor Day.

During school I worked as a freelancer, producing desktop-published newsletters or writing pieces for tech magazines with names like Corporate Computing. Tech magazines back then were big, boring, and rich: They paid five dollars a word for stories about how large companies were adopting new computer networks to “drive efficiencies” and “empower executive decision making.” Not exactly Pulitzer material, but it paid the bills. Without a salary at the Times, it was back to freelancing, at least until I figured something else out.

This was not the future I imagined for myself after earning a Masters in Journalism from UC Berkeley. I wanted to write game-changing masterpieces chronicling how technology would change the world. But for now, Corporate Computing wanted a profile of a company that made gear for airport luggage systems. It was due in two weeks.

I needed the money. I had tens of thousands in student loans, and another $15,000 in credit card debt piled up wooing a woman in New York, a television producer who was entirely out of my league. My big plan, crystallized in the mountains over Labor Day weekend, was to move to New York, continue the wooing, and – naturally – land endless assignments from Vanity Fair, GQ and The New Yorker. But first, I needed cash for the trip.

***

A few days in the wilderness had cleared my mind, but it was time to check back in with reality. Maybe the voicemail gods had thrown me something interesting while I was in the backcountry. You never know.

Amongst the messages from friends, colleagues, and random PR firms was an enigmatic voicemail from a man named Louis. Louis said he was from a company called “Wired” and wanted to know if I could meet this week. He didn’t leave a lot more context than that.

I almost deleted that voicemail – “Wired” sounded like some kind of computer networking company. I didn’t know if I had it in me to write another piece about LANs, WANs, or routers. But there was something about Louis’ voice – detached, a bit hoarse, soft but confident – that made me wonder who this guy was. I wrote his number down and made a note to call him when I got back to civilization.

I almost forgot to make that call, because the next day I purchased, with a nearly maxed out credit card, a one-way plane ticket to New York. I was broke, but I had to see how it might turn out with that stunning producer at CBS News. Plus, I wanted to cover the story that had captivated me since I first set eyes on the Macintosh in 1984. Getting the chops to properly tell that story – how digital technology would impact society – was the rationale for going to grad school in the first place. If I could sell that narrative to New York, I reasoned, I’d have a chance at making some kind of dent in the universe.

In the pre-Internet days, there was one way to become a “real” writer (at least as far as I was concerned): Get your byline in glossy magazines published by Conde Nast – the apex predator of New York media. Of course the editors at Conde had no idea I existed. But I was an optimist with a freshly minted Masters degree. I had five years of bylines in … MacWeek and PC User and Corporate Computing! OK, maybe that wasn’t much, but I had chutzpah and blessed ignorance and a brief, if miserable, stint at a respectable newspaper. So what if The New Yorker or Vanity Fair had never run a piece on the impending digital revolution? I was sure – well, kind of sure – I could convince them to let me try.

But before I left, I remembered to call Louis back. On the phone he explained that he and a few other lunatics were starting a new magazine called Wired. It would be based in San Francisco, it would launch early next year, and it’d be – and here Louis became animated – the bible of the digital revolution.

That phrase stuck me dumb. I told Louis that all through grad school I had wanted to create exactly such a magazine – I called it “the Rolling Stone of technology” – but I’d failed to convince my Faculty mentors that the idea was worth pursuing. “Cool!” Louis said. Would I be interested in interviewing for the position of Managing Editor?
***
To say I was unqualified to be the Managing Editor of anything would be severely understating the case. I had worked at a trade publication for a few years, but I’d never really managed anything. But I was excited about the job – and Louis wasn’t put off by my lack of experience.
We met at Wired’s first office, a top floor walkup in a disheveled warehouse off South Park in San Francisco less than a mile from Rolling Stone’s first headquarters. “We’re still fixing it up,” Louis explained, gesturing to the back half of the floor, which was an unlit farrago of musty detritus. MacWeek, the startup magazine I worked at prior to graduate school, had been based nearby, but I never ventured into South Park, which at the time was a scruffy habitat for junkies and drifters. Two decades later, it would become the epicenter of San Francisco’s tech-driven reincarnation – the birthplace of Instagram, Uber, Twitter – and Wired.
Tall, slender, with rock star hair and a conspiratorial air, Louis Rossetto initially struck me as both charming and a little weird – but I was used to weird, having covered the menagerie of characters orbiting Apple and the tech industry in the late 1980s. He was 15 years older than me, which made me nervous – why would anyone that old want to hire a kid out of graduate school? He motioned us over to a beat up sofa facing the windows overlooking Second Street, and we began a conversation that changed my life.
The rock world is full of colorful stories about how bands got together – Mick Jagger and Keith Richards met at a bus stop, Jimmy Page recruited Robert Plant after hearing him sing at an obscure college gig outside Birmingham. No matter how bands meet, they never really form until one player says to the other – “hey, come over and let’s jam.” Playing together is the only way to test the indefinable chemistry that turns random session musicians into a cohesive band like Led Zeppelin. I didn’t know it at the time, but on that early Fall day in San Francisco I was auditioning for a spot in Louis’ band.

Louis had funding lined up from people I respected, including Charlie Jackson, the founder of Silicon Beach, a well known software company, and Nicholas Negroponte, the director of MIT’s Media Lab. I had devoured Stewart Brand‘s The Media Lab: Inventing the Future at MIT, as far as I was concerned, Negroponte was a god. “He’s in the Wired braintrust,” Louis told me. “So is Stewart.”
A braintrust? Who else was on the Wired bandwagon? Louis reeled off a few more names: John Perry Barlow, the tech-savvy lyricist for the Grateful Dead. I’d seen his posts on the WELL, an early online community started by Brand and his cohorts at the Whole Earth Catalog. I mean, this guy wrote Estimated Prophet! Danny Hillis, an engineering genius who had invented parallel computing. Esther Dyson, one of the smartest early tech analysts who also ran PCForum, one of my favorite tech conferences.
“Oh,” Louis added with what I would learn was a trademark sly smile, “we’ve also got Kevin.” And indeed, there was Kevin in the flesh – an elfin man with mirthful curiosity in his eyes. Kevin Kelly was a compatriot of Brand’s and the editor of Brand’s Whole Earth Review. Kevin had recently agreed to become Wired’s first Executive Editor, and he joined us on the sofa. The next 90 minutes gave me a taste of the kind of music the three of us might make together.
Each of us was obsessed with technology, its impact, its world changing potential, its magic. That initial conversation demonstrated how each of us “fit” – the roles we’d play as Wired came to life. Louis was the enigmatic frontman with attitude and a knack for turning phrases, Kevin the idea guy, painting fantastical melodies like a tripped out lead guitarist. Then there was me. My job was to hold it all together – a classic role for a drummer, it turns out.
I was beyond sold. If Louis would give me the job, I was in. I told him I was heading to New York that week, but didn’t let on that I only had a one way ticket. “That’s great,” he said, “because Jane is in New York, and you should meet her as a next step.” Jane was Louis’ romantic and business partner, the manager of our newly forming band. We met two days later and it went well. The next day I got a call from Louis – the job was mine.

I excitedly told the woman I was pursuing that I’d accepted a job in San Francisco with a startup magazine. Now came the big ask: Might she want to quit her job at CBS, and move to California with me?

This post is something of a departure for me – the result of a friend asking me “how did you end up at Wired, anyway?” Let me know what you think.

You can follow whatever I’m doing next by signing up for my site newsletter here. Thanks for reading.