> Sears had everything. Global supply chain, check. Top notch distribution operation, check. System and infrastructure to take orders and handling billing, check. Name recognition and established customer base, check.
I've never understood this line of thinking. I worked in engineering at Sears, and I left the company in 2000. So I was there when Amazon was getting big, and I quit Sears to go work for a company in Redmond Washington.
Sears just didn't have the engineering manpower. When I'd wander around the Sears headquarters in Hoffman Estates, I saw tons of people working on marketing, clothing, and advertising. There weren't a whole lot of people working on the Sears website.
From my perspective, in 1999 our engineering team was mostly concerned with whether the cash registers worked (Sears was ahead of the curve when it comes to the sophistication of their registers) and whether customer service worked (we had over five thousand customer service representatives working out of a series of Regional Credit Card Operation Centers AKA RCCOCs.)
Competing with Amazon isn't trivial; even in 1999 Amazon employed thousands of people.
More importantly, Amazon lost a ton of money to get where it is today. In 1999, Amazon lost something like thirty cents on every dollar that they sold.
As someone who actually worked at Sears, it's inconceivable to me that Sears could have stomached the idea of losing that kind of money. And I don't see any scenario where they'd make the kind of investment in people, even if they could find them.
https://www.nytimes.com/1999/11/28/business/amazon-s-risky-c...