Some dating back in 2011 / 2012, that I either dropped or sold poorly. Crypto investment exchange (dot com) was one. I think I had "advisors" too. Combinations like this. Normally not a fan of 3 worders, but held for a short while and dropped. I had "bugbear" at one point, first registered in 1996, has its own unusual meaning. Fancy trader (fancy diamonds business), red trader (popular colour, paired with a meaning of bear market trading), owner today wants Low X,XXX. Some regret, but I won't cry too hard
I renewed these for around 4 years, then felt 'metaverse' was going nowhere, that all changed quickly with the 'Meta' (Facebook) rebrand and the NFT and crypto space embracing 'the metaverse' now these domains are taken in multiple extensions.
I let a domain expire, but someone BIN purchased it on Afternic for $1K. Luckily, the domain was still in redemption stage, so I was able to get it back and sell it. I had to pay the redemption fee but still made a good profit.
Acht.tv 8 in German, was later picked up and sold by another member of the .tv subforum here at Namepros for $10K.
When .xyz launched I was not a big believer not going to Monday morning Quarterback like I saw these big Swetha sales coming, But I did register 3 for the heck of it, Encryption, Cryptography and FantasySports.
Sold way too cheaply, 7599.com, Sayy.com, XEF.com.