Wednesday, August 06, 2025

Wired, A Love Story (2)

(Second in a series.)

By the time I joined the HotWired team in late 1995, I'd already been working in media for almost 30 years. This was not necessarily a good thing in the eyes of my new colleagues, who were busily upending the analog media world I came from with a digital alternative they considered superior.

“Content wants to be free” was a standard rallying cry at HotWired, which was not yet two years old and was undergoing a massive growth spurt fueled by corporate advertising revenue. We were hiring people almost as fast as we could; I joked to friends that our interviewing strategy was to lock the door behind candidates so they couldn't leave once they were inside. 

In point of fact. nobody wanted to leave -- if you were Gen-X and into creative media work in the mid-1990s, this is exactly where you wanted to be.

As for me, I was twice as old as most of the other employees, and my career had been almost entirely in the alternativemedia, not the mainstream. From my days in the underground press to SunDance to Rolling Stone to the Center for Investigative Reporting and from New West to Mother Jones and public radio plus other stops along the way, I had pretty much remained outside of traditional journalism institutions.

But in all those jobs I did adhere strictly to the values and standards of traditional journalists.

My new colleagues were early-stage writers and reporters and editors and designers and photographers and engineers and interface experts and audience research specialists and several other categories of workers, almost all of them in their mid-to-late 20s.

I was sort of like their weird uncle.

They all used a techno lingo unfamiliar to me, with terms like web browser, domain name, interactivity, bandwidth, interface, pixels, TCP/IP, url, html, coding, style sheets, IP address, network domain and on and on -- so many strange words that I scribbled them down on a scrap of paper and kept it in my pocket exactly as I did with foreign language phrases when visiting non-English-speaking countries overseas.

After a few months, I finally got around to asking someone what all of these words actually meant. He smirked and quipped: "Don't worry what they mean; just sprinkle them liberally into your speech and your market value will triple."

As I pondered that, the daily political site my team produced called The Netizen began to flourish. We rapidly built a large audience during the early months of election cycle 1996, which attracted the interest of Wired's co-founder and CEO, Louis Rossetto. 

He had a reputation as an articulate visionary but a difficult boss; many employees seemed fearful of his intensity. He was a fierce advocate of libertarian political views, a lifelong Republican, pro-corporate and dismissive of leftist ideas. 

So when Rossetto first summoned me to a private meeting I really didn't know what to expect. Most of my previous work had appeared in left-leaning publications, and he probably assumed my politics were defined by that. Maybe he wanted to suss me out.

From our very first meeting, the Louis I got to know was quite different from his image. He was smart and opinionated, true, but also quiet-spoken, thoughtful and happy to debate the issues of the day with me. Most importantly, he was committed to remaining open-minded about how we covered those issues in The Netizen.

That kind of tolerance was essential if I was to remain part of the Wired organization, which I already knew I wanted to do. Louis and I quickly developed a mutual trust that allowed us to argue through the various sides of the issues we were covering and agree to disagree when we could not reach a consensus.

Meanwhile he never interfered in my actual editorial choices, though they often differed from what I knew he would have preferred.

The ultimate test came when one of our cantankerous Netizen columnists decided to write a piece savagely critical of Wired itself. He decided to lambast the institution and everything it stood for in his daily column. 

Talk about biting the hand that feeds you! This surely would be too much for Louis to handle, I thought.

As the hit piece was about to post, as a courtesy to Louis I let him know what was coming. His response was shocking and refreshingly direct: 

"Let him rant!" 

We ran the piece unedited. 

For me, that moment confirmed that Rossetto was committed to his principles, which started with free speech for everyone.

Looking back on that incident, I realize that by then dealing with bosses other people considered difficult was becoming something of a habit for me; after all, I'd studied under one the masters, Jann Wenner at Rolling Stone. Others may have feared these men and their outbursts, but I genuinely liked them and developed a deep fondness for both Jann and Louis that lasted well past my jobs with them.

A few months after the “Let him rant” episode, Louis suddenly summoned me to his office again for an unscheduled meeting. Again, I assumed there must be bad news of some sort, but instead he surprised me by saying he wanted to move me to the top of the org chart as V.P. of Content Management for all of the websites in the HotWired network.

I was content producing The Netizen and hadn't sought this role at all but of course I agreed to it, especially because it came with a hefty raise. (And at home we had another baby on the way.) 

In my new role, dozens of people now reported to me, including my former bosses who seemed stunned by the change. 

If I was going to head up this brilliant, unruly band of web revolutionaries, by acting as “the adult in the room” (as some called me), I was going to have to be always switched to “on.”

(To be continued)

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