what's old is new again, they say.
Pets.com is the better example. It was a failure because the market and economics for speciality stores isn't any better with electronic storefronts than with brick & mortar--most people want one-stop shopping most of the time, online or offline. But Sears never tried to go down that route.
These paths to success were right up Sears alley. Yes, they tried and failed with Prodigy. But surely the entrepreneurs on HN understand that failure is often a matter of timing, not of value or market potential. Sears' leadership could have stepped back and asked whether their attempts with electronic retail were a matter of timing or just a hopeless flop. It appears they did neither and simply executed the 1980s-1990s playbook: "focus" on your core business and return everything else to shareholders, who theoretically are better able to allocate funds to experimental ventures. The problem with that economic theory is that it ignores or discounts the value of good will and the intrinsic value of the firm, both of which Sears exemplified, and it neglects the duty owed to the firm as an ongoing concern. Rather than play to win they decided to not play at all. In 1993 such defeatism was hardly justified given their otherwise strong (if declining) market position.