17. Steven Comfort – HotWired into the first online ads

Steven Comfort started life — as so many ad tech pioneers did — as a media planner and buyer in NYC for agencies such as DMB&B and Messner Vetere. Inspired by his grandfather, who founded his own successful agency via the G.I. Bill after World War II, Comfort abandoned dreams of playing professional baseball and embraced traditional media, little knowing that a confluence of time and place was about to insert him into the epicenter of the first ads on an entirely new medium, the internet.

As Comfort tells Marty & Jill in this reflective episode, he was tasked by Vetere management to compile a “cheat sheet” to new media testing opportunities (primarily in nascent cable systems such as Time Warner in Orlando). During his researches, he heard about Wired magazine’s plans to launch a website and cold-called them for more info. Shortly thereafter, he had a “mind-blowing experience” (his words) as Wired co-founder Jane Metcalfe showed him QuickTime and the imagery-plus-sound-plus interactivity possible on the new browser-based media.

(For a compelling oral history of the birth of Wired check this out.)

Wired issue from Oct 1994 announcing HotWired

Settling the rumors, Comfort admits the first online ad was sold “by Jane.” And it wasn’t – as widely believed – just an ATT ad but rather a “twelve-way tie” among the first advertisers on HotWired.com, Wired’s new online venture, all of whom went live simultaneously.

Comfort then joined Wired and moved to San Francisco, a move he doesn’t seem to regret, and rode the dot-com boom to its peak and down again. What was that like? “It felt like college,” he recalls, but he believed in Wired’s mission – and also their office building neighbor Organic’s – and it’s persisted.

After Wired, Comfort joined a startup that was acquired by Yahoo, and then a number of high-flying (and less high-flying) media and content companies such as Monster, NexTag, YuMe and Radius. Currently, he provides go-to-market consulting services for tech companies and is based in the Bay Area.

(For more on the layout and approach of the original HotWired site, check out this cool site.)

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