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> They were Amazon before Amazon, but just didn’t realize it.

They did realize it (well, they obviously didn’t have Amazon as a reference, but...). And they enjoyed it for a long time. But, as has happened many times to firms very successful in one set of conditions, they failed to adapt to changing conditions.

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except arguably they should have it in their DNA to adapt. How does the company built on mail order not adapt to the new mail order reality.

They were caught flatfooted between being Wal-Mart and Amazon.

Sears had shifted so firmly into retail by the 80s. Then Wal-Mart ate their lunch on low price retail logistics.

Then Amazon came along, and solved last-mile delivery of catalog sales.

Perhaps Sears/Kmart could have filled the Target niche, and leveraged Sears' brand portfolio rather than selling them off to make crushing interest payments.

They invested heavily in Prodigy, when that failed, management thought the internet was a fad and didn't invest or even try. By the time they tried, they were way behind Amazon.

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