Lets say you're an average joe and you own a site. The site gets bigger and bigger each day...when do you start thinking about the trademarking your name? What if someone does it before you just because they know its not trademarked and they see that your site is huge and your name isnt trademarked? are you screwed then?
When to start "trademarking" your name depends on whose jurisdiction you're talking here. In the US, you have to use the term in commerce. If the public sees the word "shelby" and thinks you're the one marketing that product or service, then you might have it. Check with an attorney who specializes on this to be sure. Your 2nd question isn't necessarily a lost cause depending on circumstances, but try to be hush hush about it.
I Had a complete nightmare trying to register a tradmark. I paid for a preliminary search done by the patent office which came back clear, so i filed and application and paid another fee. Another search came through clear again, the mark was published, then about a week before it was due to go through, I had opposition to the trademark. The company had a name which had part the same words as mine, but was not registered in the class I had applied for. To cut a long story short I hired a solicitor who said I had a good chance but then changed their mind after further info was provided by the other party. I cancelled the filing it cost me about £1500 including patent fees. I wrote a letter to the patent office complaining - they refunded their fees £350. If I had to do it all again I would do my own search, use the mak with TM (not bother registering it you can claim prior mark even if it is not registered) and only register it once I knew it would make money. But then thats my opinion I am sure lots of people will disagree
Yes, here in the States it is the same; part of the registration process is a period during which the mark is published and other parties can object to your use. If the search is done thoroughly beforehand, you hopefully won't run into any objections, but you could, and if you do, that's when you either hire a lawyer or cut your losses and drop it.