Why aren't you doing this live?

In 1995 I was hired by the New York Music Festival as a registration admin.

That's the part that never makes it into the retrospectives, so let me start there. Just the guy processing badges, assigned to a desk in the office of a chain-smoking music director with a temper. I was about ready to quit when someone invited me to the first meeting about the festival's website.

Somewhere in that meeting I asked the question that changed my life: "Why aren't you doing this live?"

Michael Dorf looked at me. "You know how to do that?"

"No. But we're in Manhattan, the new media capital of the world."

"If you can make it happen, go for it."

So I went and made it happen. Zero budget. I recruited a team of forty volunteers and partners: engineers, artists, people I found because in 1995 Manhattan, if you asked loudly enough, the people who could do impossible things showed up. We wired fifteen nightclubs to the World Wide Web and put a live, multi-venue music festival on the internet, the web's first. The New York Times wrote it up before opening night. Time covered it. And MTV News sent cameras, which found me in "Web Central" on the first night, mid-crisis, troubleshooting the network, one of the only times I've ever been on camera for something I built, and only because I happened to be fixing the story while it was being filmed.

Watch on YouTube

Careers launched off that week, deservedly; it took a lot of people to make it work, and the retrospectives are full of them. I'm not in the retrospectives. Partly that's how history works: journalists quote the people they can find, and I never wrote my chapter down. This page is me, thirty years late, writing it down.

For a season after the festival I was a minor prince of the New York new media scene. Everyone wanted to build something with the person who'd just wired Manhattan. I did a trial run with Adeo Ressi at his first web agency (I could recognize a mover when I met one), and then Apple called, and I had to choose. I chose Apple. Adeo sold that agency a few years later for [Ian: ~$85M? verify; public reports cite Methodfive→Xceed, 2000, ~$88M]. I'll come back to what I think about that.

Apple's Interactive Music Group was about ten of us, building toolkits for CD-ROM. Here's my favorite part.

On my second day in Cupertino, I overheard a new colleague on the phone with the Emmys, walking them through a technical plan for their first webcast. I knew that plan intimately, because it was mine. An acquaintance consulting for the Emmys had picked my brain in New York about how to webcast a live event, and my answers had traveled west faster than I had. So I did something the registration admin of a year earlier wouldn't have done: I walked over and said, "That's my plan. Send me to be your Apple rep there."

Day three, I was approved. I showed up at the Emmys and was handed a coax cable and a computer: "Put this on the internet."

I did. The crew I worked with that weekend became friends, and then became the people I recruited to Apple to build out the Macintosh Music Network, Apple's move from CD-ROM entertainment to live streaming. I designed and built a roadcase rig and installed it in five music venues across the country, delivering remote-controlled video and CD-quality audio back to [Ian: MCC, spell out (Music Control Center?)], where we encoded RealAudio and early streaming formats, with a concurrent [Ian: “IJ” channel, spell out]. Nightly live music from wired clubs, years before anyone said "livestream." My email address was webguy@apple.com. In 1996, that was the whole job description the internet had for what I did.

Then I drew up something bigger. With a colleague who was writing the video streaming architecture for Apple's videoconferencing software, I sketched a content distribution network on overhead transparencies, because that's how you pitched executives in 1996, and presented it up the chain.

"Not our business," they all said.

I said "OK," and went back to work. I still have the slides. At that same moment, Mark Cuban was building the very same idea in Austin; it became broadcast.com, and Yahoo paid $5.7 billion for it in 1999. Apple, of course, eventually decided that streaming media was very much its business.

The project didn't die from being wrong; it died from being early inside a company in freefall. This was Apple at 2% market share, in the chaos of constant reorganizations just before Steve Jobs came back. Our little group got absorbed into a senior director's org along with the eWorld castoffs and swelled to fifty or seventy-five people. Satjiv Chahil, the marketing VP whose air cover we lived under, was out when Jobs returned, and our before-the-wave project went with him.

So here is the honest accounting, the one the LinkedIn version of a career never includes. I stood at three or four doors that other people walked through to fortunes: Dorf and Rasiej built enduring institutions off the festival; David Pakman, brilliant, and a better student of getting ahead than I was, turned that summer into a career that runs through Venrock; Adeo built toward his eighty-five million; Cuban shipped the slide deck I couldn't get greenlit. For a long time I told myself the difference was luck, or politics, or my own insecurity, and insecurity was real, and it cost me.

But that's not the whole truth. The whole truth is that at every fork, I chose curiosity over capitalization. I followed the interesting problem instead of the equity. That choice had a price, and I've paid it. It also built a particular kind of life: I got to make the record, host the show, run the remote company before remote existed, throw the 24-hour ad agency for nonprofits, fight for a forest, and now build civic infrastructure with tools that finally caught up to how I always wanted to work. Curiosity compounds too. Just not in Yahoo stock.

What I'd tell the registration admin: keep asking the impolite question in the meeting. But write it down after. The work deserved a witness, and the witness was standing right there the whole time, holding the coax cable.

I was there. Here's what I saw.