Gateway 2000’s descent from awesome to bad ads in the 90s (Part II) • Buttondown

Such Bad Tech Ads

August 4, 2026

Gateway 2000’s descent from awesome to bad ads in the 90s (Part II)

What started as endearingly bootstrapped marketing descended into soulless corporate sales.

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PC Computing Jul ‘93 via Archive.org<br>Party hats and sunglasses on animals are the fart jokes of advertising. Somehow lazy and effective, shallow yet infectious, and definitely not too tasteless for Gateway 2000 or its wunderkind president.

"I've used soap dishes as ashtrays in the best hotels in the world,” Ted Waitt bragged during one of his New York Times interviews, explaining in another article that he picked his 1990 Porsche Carrera-C4 because it was “the only car I could find that would go 160 miles an hour in the snow with the top down." Restraint didn’t rocket him or his company to $1 billion in sales over six short years. And it was never a part of the marketing strategy.

The 486 Fest spread pictured above was eleven pages long. It had 28 wildly unnecessary “Party Reason” subheadings, more than a dozen barnyard puns, and a photo of all 2,000 Gateway 2000 employees in front of the cow-spotted headquarters in Sioux City.

“When I worked at PC Magazine in the early 1990s, Gateway 2000 regularly ran 8-to-12-page ad inserts, often featuring cows, cornball jokes, or both,” Lance Ulanoff wrote earlier this year. And that was never more apparent than the months following the company’s eminently unexpected IPO.

Byte Nov ‘93 via byte.tsundoku.io<br>Gateway had opened its first international headquarters in Dublin one month before this ad, selling mail-order computers in Britain (propped up by marketing in local, region-specific magazines), and working on plans to expand into other parts of Europe.

The “pilgrimage” was not without, uh, trials and tribulations, however, and Waitt’s prayers were not answered (this time, at least. He did go on to fund the expedition that successfully unearthed the Gospel of Judas in the Egyptian desert but I digress). The hope was that an IPO would buoy some of the unexpected costs from crossing the Atlantic. A gamble that minted one of America’s first tech billionaires.

“Gateway hit the market at $15 a share. It shot up, then dipped and is now double the original trading price,” according to one article two-years post offering. “Forget that Waitt owns only one suit (a bad-fitting one, to boot), typically sports blue jeans and seldom wears socks, when he hit Wall Street, he blew away any notions by investment bankers that they were dealing with a rube.”

By December of 1993, Gateway was running cheesy 26-page Christmas ads in Byte and had expanded from a manure-ridden livestock exchange building to the Nasdaq stock exchange.

Byte Feb ‘94 via byte.tsundoku.io<br>A few not-so-obvious things worth noting about this ad include (but are not limited to!):

The cosmic ennui of the woman standing at one o’clock.

The creepy ogling of Mr. Sunglasses.

The massive downer of dedicating the page to a dead customer.

The historical context that these two pages (along with the 13 others in this ad buy) ran when Gateway 2000 was more corporate and plagued by customer complaints than ever.

Sure, the company was hoping to crack the corporate buyer market, but a public SEC filing claimed that, until that happened, “over 50% of the Company's business is believed to be attributable to either previous buyers of Gateway 2000 PCs or new customers referred by previous buyers.” So, in an effort to shore up its base, technical support headcount was doubled, its one-year warranties were tripled, replacement parts were bumped up to one-day deliveries, and the phone lines were open 24 hours.

Still, What’s Luck Got to Do With It cited a market research study from around this time that claimed 87% of potential buyers knew little to nothing about Gateway 2000, hence the spray-and-pray approach to increasing brand awareness. But surely they could have done better than Julius Caesar getting stabbed (while buying eucalyptus lip balm?) because “Sometimes it’s hard to know who to trust,” preceded a few pages earlier by the Leaning Tower of Pisa guy opining that “Mama-mia! What’sa matta me! That’sa last time I buy a kit from the Towers-R-Us catalog.”

"We get horrible marks from the marketing-guru types," Waitt told Inc. Magazine a few years earlier. "But it seems to work." By 1995 Gateway 2000 had purchased additional manufacturing facilities in Virginia and Malaysia, and scooped up an 80% stake in one of Australia’s largest computer retailers–revenues were up to $3.7 billion.

PC World Feb ‘95 via Archive.org<br>This faux soap opera nails all of my criteria for a Bad Ad. There are a full 230 words wasted on Simone’s “bouts of...