I think the way to look at cases like these is to recognise organisations aren't monoliths, but a mass of individuals each tugging in their own direction. Clearly, there were inventors, progressives and visionaries within these companies that correctly predicted future trends and were trying to steer the ship to capitalise on them, but for some reason, other voices drowned them out.

And that right there is why a good CEO can make or break a company. They don't have to be experts in everything, but they need to be good enough to tell which of their experts working for them to believe, or to bring in outside expertise when needed.

Completely agree. I think the darker side though is that successful individuals must not only have good ideas, but advocate for their ideas effectively. I still haven't figured that one out, personally

Sears I think hurts the most. I used to love looking through the catelogs as a kid. It felt so futuristic.

All they had to do was have the foresight to move that model onto the internet. They had the supply chain, warehousing, etc. They may have even been able to have done their own logistics, since every city had a Sears. Kinda how Walmart does deliveries now.

And as you mentioned...they got crushed by a bookseller :(.

The problem for Sears was that mail-order was killed off by malls and big box before web-orders took off. Sears was losing 150M a year on catalog in the early 90s. If they didn't invest in malls and strip malls, they'd have been out of business before web shopping was significant.

Amazon was the right size to grow with the market. Amazon didn't even start selling clothing until 2002.

Which is why I always find Service Merchandise the more interesting case study than Sears. Service Merchandise was an "upstart" trying to hit Sears where it lived in the 90s and basically was the American vanguard of what today we tend to call the Ikea model (and which Amazon keeps hinting they might do at some point): (relatively) big just-in-time fulfillment warehouses with attached showrooms.

Service Merchandise hit some weird bad luck in early franchising (and franchising may have been the wrong choice/it's own bad luck) and accidentally got somewhat region-locked into the US South East, but the business model was from today's perspective ahead of its time, directly addressed that "mall shopping need" while still keeping what made catalogs and drop shipping useful (and relatively efficient just-in-time logistics).

It would be an interesting "game" to play 20/20 Hindsight with those companies -- knowing what we know now, how could they have successfully navigated into the new world.

Sears seems like it could have transitioned if it didn't have its head up its ass. The death of film means Kodak would have to constrict and double down on printing, and simultaneously expand their general chemistry efforts into new markets (which I believe they did but too little too late).

Amazon was never a bookseller.

How a company that was focused on their legacy customer relationship system and logistics operations lost out to a company that was focused on building the future of customer relationships and logistics is a lot less difficult to understand.

> Amazon was never a bookseller.

I remember it differently. Also, actual history is different too.

> Bezos finally decided that his new business would sell books online, because of the large worldwide demand for literature, the low unit price for books, and the huge number of titles available in print.

https://en.wikipedia.org/wiki/History_of_Amazon#Online_books...

Yeah, they sold books, I didn't say they didn't. The couple paragraphs above the one you link talk about Bezos wanting to participate in the internet business boom and then the ones you link talk about commerce.

Selling books was never the ambition, it was only the path.

That was their MVP of retail. IIRC, they never hid their ambitions to expand their market.

I'm not sure what your point is? They still sold books and only books at the time

Yes they only sold books at that point because it was the easiest thing for them to sell (thus the MVP). IIRC they did not hide their ambition to go beyond that.

The point is that doesn't make them a bookseller!

That's literally the definition. It kind of does.

Time to stop digging.

Not my internet points!