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should I register every domain name that comes to mind?

This would be better served as a survey question hoping that the wisdom of crowds knows something that I don't. So the question is this:

I have a unique business idea at least once a week and the foundation of that initial business idea could be a simple blog or wiki and an eCommerce store. There is something to be said about integrity when all of the brand's assets are tagged with the same custom domain. It invokes some sense of trust.

On the other hand... 1 idea a week, 52 custom domains a year, and 52 new web sites to manage content for. Well, depending on the registrar that could be another $520 in ICANN fees accumulated annually meaning $1040 on year 2. And then there is all the attention and content that each property would require. ... that's 52 web servers, 52 email servers, 52 custom domains... and so on.

But the real downside is what happens when the domains start to expire and what happens to gmail and other assigned accounts. If you have some sort of round robin authentication going on then this could get ugly and fast.

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