The century-long interplay between technology and retail suggests Walmart is screwed. Its efforts to morph into an online retailer by buying Bonobos and will end up making the company seem like Michael Jordan playing baseball—what made it great at one thing doesn’t translate to another.

At the same time, Amazon is marching through the retail sector with the ruthlessness of General Sherman taking out Georgia, remaking shopping in its image. When the company said it will buy Whole Foods, we could imagine the combination resulting in futuristic drone-delivered Veganic Sprouted Ancient Maize Flakes, even though Amazon has said almost nothing about what it will do with the high-end grocer. (Please, at least introduce a new meat called Amazon Prime Rib.)

Long before Amazon, tech shaped retail, and that history gives us a hint of what’s to come. Start back at the founding of Sears, in 1893. For its initial 30 years, Sears was solely a mail-order company, relying on the U.S. Postal Service and railroads for delivery. But the automobile was emerging as a new technology that would change society and alter the way people shop. There was now a relatively easy way to go to a store many miles away and bring items home. Sears’s big innovation was to build big stores that catered to customers arriving in cars. It opened its first store in Chicago in 1925 and built stores across the country as the economy boomed in the two decades after World War II, luring shoppers who would drive in from newly built suburbs. By exploiting the tech of automobiles, Sears reigned as the nation’s largest retailer into the 1980s.

In 1962, while Sears was winning the car era, Sam Walton opened his first Walmart, in Rogers, Arkansas. Over the next dozen years, he opened 125 stores in rural areas ignored by big retailers like Sears. Walmart wasn’t an especially innovative retailer then, but another society-altering new technology was emerging: computing. In 1975, Walmart leased an IBM machine and started to collect data from all its stores. By the early 1980s, bar codes and systems to glean information from them were perfected. Walmart built huge centralized computing and wrote software to run its operations in ways established retailers couldn’t yet imagine.

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