I love seeing Joshua Schachter went from a ridiculous domain (Del.icio.us) to the new trend of simple, fantastic and probably expensive domains.
(Talent acquisitions may defy this to an extent, but that just goes to show how valuable great people are, and in particular the value of many great people who work well together)
> If you're at all optimizing based on what will be
> valuable when you sell your company for scrap
2. It's still a cost/benefit analysis, but the fact that you may be able to recoup the costs factors in to mitigate some of the risk of sinking too much money into the name.
3. Who says that you can't resell the name, and rebrand if it's a failure?
4. The name has resell value for a reason.
5. If I buy a car based on resell value, have I also 'already lost?'
As for 5, this is different than the normal car buying case. You're driving a treacherous trip to buried treasure with limited resources. If you make it, you won't care what the resale value of the car is, and if you optimize for anything other than making it, you won't.
I don't necessarily object to buying a good name. Depends how good for how much. But if you think about it in terms of what you can sell it for, you're heaping value onto the name that you're never going to realize to justify spending it on something easy like a short, shiny name instead of something hard like hiring
A good name is always helpful, and unless you are having cash-flow problems, sinking money into the name is a perfectly decent investment that is unlikely to lose a lot of value.
As you say, if you have funding and make a large pivot, keeping the old name isn't a bad idea. It's a win-win, and because of that it's not as risky as people's gut reactions tell them.
One particular high scorer was already registered but unused so I tried to buy it. The domain owner had others, offered jig, which was WAY better than what I was trying to buy. So I did it.