Why would I mention Sears? Because in a different timeline they would have dominated online sales and brick and mortar. They could have been doing an online catalog with Prodigy, the popular online service they co-owned, but instead ignored the opportunity. Eventually when the Sears catalog go too expensive to print, they quit offering that. Making them into nothing better than Kmart or Target with worse customer service at J.C. Penny prices.
So, i too have given considerable thought to Sears, and how it seems obvious in retrospect that they could have been Amazon. I'd submit a few points that go beyond 'thick-headed managers who couldn't see the future'...
1. In fairness, I agree that the Sears Catalog, and the traditional order-by-mail model could have been kept as an online thing - browsing and searching, with the result being a printout of the order forms that then ultimately got mailed. That likely would have been a good move, but they discontinued the Sears Catalog in 1993...the same year AOL went public. Internet access was still a rare novelty at best. Moving the catalog online, and having the handful of people who *did* have an internet capable PC browse it on their 28.8k modems, probably was not the market size that would have justified the expense.
2. Sears was in the middle of an overall shakeup at the time; the 'buy once, cry once' market that Sears catered to (Craftsmen tools and Whirlpool appliances were legendary for both being expensive and lasting decades until the end when they cheapened both) was being upended by Wal-Mart, Home Depot, and JC Penney, all of whom beat Sears in price in exchange for longevity. Consumer preference was shifting from "having a $3,000 stove that lasts a lifetime" to "having a new $800 stove every few years", and Sears wasn't in a great place to make that shift. At the same time, Sears was shifting to being more of a real estate company than an actual department store, and it was the real estate investments that helped Sears last as long as it did.
3. Even if Sears waited until 'the time was right' to become an online retailer...they still have the problem of getting people to shop online. There were some enthusiasts who were willing to roll the dice on eBay ("that worldwide garage sale", as Weird Al so eloquently put it), but it really was Amazon that made buying online with a credit card something people were willing to do. The thing is, when Amazon first started, they weren't an everything-storefront. They sold books. They sold books *cheap*. They used their venture capital money to sell $29.99 books for $17.99. They grew as fast as they did *because* they spent the first several years putting every cash infusion into subsidizing purchases for customers. When Amazon started, people were still wary about shopping online. As time progressed, and credit card companies added in Cashback/Airline Miles rewards incentives while *also* adding fraud protection...it was only then that buying things online became mainstream. Sears couldn't have done the same thing, because they simply were too established to subsidize online purchases the way Amazon did.
4. The internet is the way it is now because a whole lot of things were disrupted at the same time. It's incredibly easy to look back and say "see how Sears was in the perfect place to shift to eCommerce?"...but if it were that obvious, then why was IBM's Google Glass predecessor as much of a complete dud as Google's attempt decades later? Amazon's Just Walk Out grocery store idea was also thought of by IBM in the 90's, and neither of those multibillion dollar companies, each of whom spent a fortune on the development, were able to make that work, either.
It's 1993, and you're in charge of Sears. You're already straddled with debt from your real estate hedging, and you've got Wal-Mart fueling consumer shifts away from your business model. A genie comes to you and gives you a coin to toss. Heads, you bet the farm on eCommerce and win, ensuring Sears' dominance of the 21st century reflects their dominance of the 20th. Tails, you bet the farm on eCommerce and it works just as well as the IBM ideas that didn't work then an didn't work now, and you go down in history as the CEO who sank the unsinkable ship. Are you flipping that coin, or are you going to try and weather the storm?