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I could always come up with a different URL for the website, but does it make sense to file for a trademark to try and force others to give up the name wholesale, including rights to the URL?

No - not in my opinion.

Have you performed a WHOIS search to see who has the URL's registered? You might be about to wake up an 800-pound gorilla.

Seems like a ton of hassle but I do worry about prospects typing in the name for my business on the web and not finding me.

Are you going to be primarily an Internet-based business or a brick and mortar business that happens to have a website?

Unless you are going to be doing something unique, there probably won't be many people blindly typing your business name with a .com at the end into their browser window. I operate half a dozen sites and none have the same name as my business.

Have you considered changing the name you plan to use so you can get a URL with the same name? It's not necessary to being successful, but some people seem to want the business name and URL to be the same.

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