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I think amazon got to play by different rules though, it would be a very different thing for an established company like Sears to reinvest all of its profits into growing its digital platform in the 90s, 00s, or even now. There is no way investors would have stayed on for that ride.

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Exactly this, the CEO of a publicly traded company would have to answer to the board of directors and investors. That would add resistance to spending lots of money on something unproven. Publicly traded tech companies get much more freedom in this regard. Plus just the amount of institutional cruft (technology, policy, procedure, personnel) in a large/old company like Sears.

You're correct, although it should be said in view of recent events, that the path they took didn't play all that well with investors either. But you're right, most investors aren't interested in the 20-year timeframe.

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