I remember that what became NewEgg opened a brick and mortar store for (mostly) software and such (some hardware) in the suburb of Seattle that I lived in at the time, then a year or two later shifted entirely to online. They pivoted //hard// and made it work.

I don't think Sears could have done quite that, but keeping the catalog and 'order to the store for free (long time) shipping' / 'delivery to home with paid shipping' would have been a much better move and SHOULD have been within their grasp to understand and execute on. All the more so if a customer could look at clothing styles and options and order slight variants or harder to get sizes from the catalog.

Tiger Direct did the same. They had a brick & mortar in the Western Chicago Suburbs - Naperville or Aurora, I think. Never stepped foot in there, despite being a easy weekend drive from them. Everything I ever bought from them was online.

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.

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.