Antone Johnson, Startup lawyer for 19 years; VP & Director roles in-house; pre-seed through exit and
Ben Hazelwood, Founder of ParkGrades.com · Author has 7.9k answers and 42.4m answer views
Update (September 2015) Two more to add:
Big Tuts. This week a new company announced itself -- Big Tuts. This name is shockingly terrible -- probably the worst name I've come across in 15 years of living in Silicon Valley. Check out what happens when you search for this company on Google: big tuts - Google Search.
G Plus. In 2011, the expert consulting firm GLG launched an online experts service called "G Plus," about two weeks before Google launched Google+. Brutal.
Old answer: When I first came in Silicon Valley about 15 years ago, people talked about how bad the name Inktomi was. The joke was that the company had to spend tens of millions of marketing and ad dollars explaining to people how to pronounce the name. It's pronounced INK ta-mee, even though it looks like Ink TOH mee.
Also, there are some people who think ExpertsExchange looks like Expert Sex Change when it is a URL.