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If I own a reasonably successful business, and want the prestige / vanity of something like "Since 1953", could I buy a small / failing business in some small town and merge the companies? Would my company now technically be running since 1953?

I have companies in both Japan and the US. It's a fun though experiment at the very least. I don't think I'd ever execute on something like this, but a software development agency "since 1876" would be a great conversation starter.

Yes, this is exactly what the people behind Abercrombie & Fitch did.

They had an idea for a college brand of clothing and repurposed an old, dying hunting brand in the company lineup to give the new brand authenticity and a nice number to follow “est. “ in their branding.

There was actually an intermediate incarnation. After closing its high-end hunting/fishing store in Manhattan (gunsmiths on premise, fishing lures for a particular type of fish on a particular stretch of Western river) and going bankrupt, a Houston-based outfit made them a more generic "yuppie-ish" sort of store with connections to hunting mostly as an image thing. Then they were sold and developed into their current form.

In my opinion that would only count if the small company from 1953 bought out the larger company. Since in that case it is the older company absorbing the younger one.

In your example the younger company is absorbing the older one, so the old ceases to exist.

Sure, but brand recognition is still much more important than the founding date.

Brand recognition cuts both ways. Sometimes companies deliberately sunset their brand. For example, Foot Locker today is actually a successor corporation to Woolworth which was an example of what used to be called five and dime stores.

Or you could just put "since 1953" on the sign and not buy a company and few people would know any better. Equally disingenuous, probably not much less legal either.

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