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Advice needed, past experiences wanted on selling domains

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Spex

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So I bought a couple of names at a drop recently because I figured they could be attractive to a couple of local presences here.

First one is a one-word slogan used by a local, non-profit organization here. After some preliminary searches, it doesn’t appear to be TM’d and it’s super generic so I don’t ever foresee having any problems. My question is…

i) How hard is it to deal with a non-profit organization? In a case like this, should I sit back and wait for them? Because approaching a non-profit and trying to sell something feels a little sleazy.

Second domain is a last name. But a local business here is called name+service (think of something like smithgarage.ca). Since it’s a last name, I don’t see a problem (although a quick search shows another company using that name, but it’s an American company that doesn’t have a Canadian presence.)

This business has been around for as long as I can remember and has never referred to itself as “name”, always “name+service” but I’ve heard people call it “name” when talking about it, so my domain would probably not confuse the general population if they went for it.

My questions are…

i) How would I pitch this domain? Should I suggest that they simply buy the name and using it to forward visitors to the main www.nameservice.ca site? Should I suggest that it can be used for a rebranding campaign should they feel the need to explore that route?

ii) Should I sit back and wait for them? If so, should I park it or buy some cheap hosting package and put up a for sale sign and contact info and nothing else?

iii) Am I dreaming here and the odds that an established company will go for the shorter name are actually closer to 0%


If this hard to follow, let me know and I try to clarify things. Also, I would love to hear from anyone who has been in this situation before.

Thanks
 
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