There have been a few times where I sold domain names for less than I wanted to sell them. The majority were sold as parts of bulk deals that wouldn’t happen without those specific domain names, and I wanted to close the deals at the time, so I included them. I can’t say that I’ve regretted any deals done in the past, but there are a few domain names I’d love to have back in my portfolio.
With the economy performing poorly and many domain owners looking to raise capital (who isn’t?), now might be a good time to repurchase some of these domain names, perhaps at an even better price than you sold them.
The first thing to do is to check to see if the owner has spent time or money on developing a website on the domain name. If not, you may be in luck, especially since the domain name probably isn’t earning as much revenue as it once was. Send the domain owner an email asking if he would consider re-selling it, and make him an offer.
There will be a fine line between lowballing and trying to get your domain name back for its adjusted market value. Just be cautious, as you don’t want to lowball one of your former clients, as this might lead to future lowballing on his part. I’ve recently bought back a few names that I had sold within the last few years, and now might be a good time for you to do the same.