It's a warning sign when startups have the cash to invest in a domain name before they have traction. Talk about putting the cart before the horse.
You can't say the same for a similar amount of put into high end office furniture, for example.
webvan.com still exists as part of amazon.
pets.com points to petsmart.com
An untainted domain is an asset, which is why there are many squatted domains. A tainted domain is a liability.