Two thoughts come to mind: 1) I wonder if they would have got the domain via the first contact if they had offered $250k, or even $125k there and then (ie no t

Two thoughts come to mind: 1) I wonder if they would have got the domain via the first contact if they had offered $250k, or even $125k there and then (ie no trademark route). When people email me about domains "asking if I'm interested in selling" it's usually because they are looking to pay $500 range. If it's worth $250k to you, use a lawyer and then the other person knows you're serious. I would have thought almost all unused domains are for sale at $250k. 2) No one seems to be thinking about the risk here, which is that they invested a lot of time, effort and money into the Groupon brand (inc trademarking it) but they didn't own the domain. That seems like quite a risk because, despite common assumption, you are not entitled to a domain just because you own the trademark (the other party could have other circumstances). Mr A R Mani legitimately owned and held armani.com until they had to privately buy him out and this dude could say he was building a community for roof-top gardeners (Gro Upon.com). Put up a dummy site for that and their case is tough.