Bought a 4 letter .com 20 years ago for a business I started. It cost $5000. My wife did not love the idea but I assured her that even if I went out of business, I could resell the domain for a handsome profit. I have taken a lot of business risks but for me this one was a no brainer.
I promptly went out of business, losing about $80,000 more.
A few years later, someone pretending to be an entrepreneur with a general demographic profile like my own pretended they were starting a new company and wanted to buy the domain for $200,000. I did a cursory background check and figured out that they were fronting for a much bigger company. The truth is, $200,000 was just fine with me. But their appeal to my perceived vanity was insulting. I ended up getting $350,000 for the domain name. I’m unable to disclose the domain name because of an NDA.
The process has always been childishly simple because I used escrow.com. Before selling that domain name, I had purchased a business website using escrow.com so I knew it worked well.
I have sold a few other domain names for up to $15,000. I do have a stock of a few hundred other names I have not done a good job selling.
A few people have called me and asked me for domain names with a good sob story. I gave them away for free and nothing was ever done with the domains except to end up parked. I’ve changed tactics and when others tried to get domain names for free I told them to put up a website using WordPress and once I’d seen their initiative I would be happy to give it to them. No one has ever completed the task.