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

Such Bad Tech Ads

May 18, 2026

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

The company known for both some of the best and some of the worst ads in 90s computer magazines.

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Byte Nov ‘88 (special edition issue) via Vintageapple.org<br>We’re doing it folks. We’re diving into one of the most infamous computer advertising rabbit holes of all time: Gateway 2000.

It will take a few issues (I plan to intersperse regular, non-Gateway issues between them) and will include a bunch of not-bad ads, like the one above, to show how much respect and goodwill Gateway 2000 managed to set fire to in a relatively short timeframe.

“Computers from Iowa?” is a legendary advertisement. It is mentioned in nearly every account of Gateway 2000’s absolutely bananas rise to 90s dominance and I have nothing negative to say about it (the poor contrast on the text seems to be a scan issue rather than a design one).

The question in the heading and the visuals behind it are intriguing without being inscrutable. And, in the span of a glance, you know exactly what’s for sale and how Gateway 2000 is different from the competition. Heck, only a few pages before this one another advertiser was selling the same 286 for $400 more.

To understand their subsequent misfires, you need the full context of just how phenomenal these freshmen outings were. This ad’s copywriting and cattle, for example, is not the product of some agency or stock photography. The words and the animals came directly from the farm of Gateway 2000’s CEO, the ponytailed long-term billionaire boyfriend of Ghislane Maxwell, Ted Waitt.

When his grandmother, “Momo,” pledged a $15k CD for Ted to start the company in 1985, “We were so uncreditworthy that the bank would only lend us $10k,” according to one interview. Waitt and co-founder Mike Hammond had to literally rent a computer to write the business plan they presented to the bank. Not owning a computer and asking for a loan to sell computers is hysterical, like trying to sell cars as a bicycle tour guide.

Years down the road, Andy Grove, the chairman of Intel Corp., would tell the New York Times that "If anybody had walked into my office and described his business plan – location-wise, look-and-feel wise – I would have thrown him out." And Gateway seemed to agree with that sentiment as years went on, trading their scrappy on-location and DIY marketing for outside agencies and try-hard trash, which we’ll get to in later issues. First, we have to examine how far Gateway had to fall.

PC World Nov ‘89 via Vintageapple.org<br>In 10 years of copywriting I don’t think I’ve written a headline as wonderful as the one above. That’s really their father’s farmhouse, where they actually worked, making $100,000 in the first four months of business!

By the time this campaign appeared in print, they were bringing in $12 million per year, with the entire operation running out of “Sioux City’s 100-year-old Livestock Exchange building, paying $350 a month in rent. The cow manure was cleaned from the building, and Gateway’s new offices were furnished with used furniture.”

A year after the Outstanding In Their Field spread, Gateway 2000 had sold another $70 million worth of computer hardware over phone and fax (and the occasional BBS enquiry), spending a paltry 2.5% of revenue on marketing and paying employees $5.50 an hour. Ted reinvested every penny into growing the company and went as far as spray painting their logo on computer boxes instead of ordering them custom made.

The whole time, Waitt was intimately involved in the company’s ads. In 1990, he hired a couple of local creatives and an advertising manager who recalled how, “Once, so jet-lagged he was practically hallucinating, Waitt blurted out a fully formed idea for the "PC Saloon" ad.”

PC World Jul ‘90 via Vintageapple.org<br>What a perfect counterargument to my complaints that elaborately costumed and staged ads almost always do more harm than good! In deliciously few words, this ad communicates everything a buyer needs to (literally) make the call. And, for those who are willing to give it more than a few seconds of attention, there are plenty of subtle gems.

Obviously, that’s Ted Waitt front and center. I believe that’s Mike Hammond in the blue suit on the left, and Norm Waitt, in all black on the right. “The others at the table, including a frustrated young man and an older, stodgy businessman, were meant to represent various Gateway competitors. ‘It was a bit of an in-joke,’” advertising manager Barb Gross told Inc. magazine in 1991.

There were other, more traditional ads from Gateway 2000 in the 1990. But Waitt only seemed...