DuckDuckGo is a big one in the stupid naming area. They own duck.com, they suggest using "Duck It" (which kinda works IMO) and they still choose to use the ridiculous "duckduckgo" branding. It's stupid but it's honestly the main reason I'm not using it. That and their crappy duck logo.
Apparently Google owned Duck.com ever since it acquired Duck Corp. in 2010[1], and only 2-ish years ago transferred the domain to DuckDuckGo.
However, Duck is rather generic-sounding and will require $$$ in ad-spend to get name recall. Even though it's awkward, DuckDuckGo is certainly memorable, sometimes that works in a product's favour.
I wish they would be wise and rebrand too.