not sure why so many people pimp 99designs. It's on the author's "priceless" list, but it's the only tip he spends 6 bullet points instructing how to overcome 99design crap. I tried them once, spent a lot of time collaborating with designers and was not impressed with any of the results. I had to file a chargeback with my credit card company because 99designs refused to refund my money outside their 60 day policy (I was unaware I had 60 days, you have to hover over their money back guarantee to find that out). I could be spoiled, as I've worked with a good designer in the past (http://rohdesign.com/) -- the benefit being more focused attention to your project, albeit for a few more $$, but not really when you factor in the value of your time.
I've been involved in projects that used 99designs.
I would not use 99designs for, say, a whole website.
I would be very wary of design submissions that are stolen or plagiarized from other sources.
But for simple transactional work, like a new logo or wordmark, I think it's the way to go. The fact is, most tech startups probably don't benefit that much from "focused attention" to small graphical flourishes. You are probably not Twitter, and the birdie probably isn't going to make or break you.
Also: how'd you end up needing your money back? Don't you have to accept a design to end up spending money?
You pay first, then get a refund if you do not select a winning design. The benefit of focused attention is not for "small graphical flourishes", rather it takes less of your time so you can move on to other things. This is where I think the 99design concept falls down. It takes less time and energy to work with 1 person vs many, especially when that 1 person has more talent and expertise. 99design is classic penny wise and pound foolish, ymmv as others have stated, sometimes you get lucky (I loose my ass at the craps table, so I tend to stick to black jack).
I used 99designs recently for a logo, and the experience would have been poor except for one huge tip that one of the designers gave me.
As the site is very busy, the best designers might be ignoring your contest. What you can do is visit lots of other contests, and pick out the artists whose submissions you really like. Invite them personally to submit in your contest.
The moment I started inviting the best artists I could find, my contest took off and the logo I ended up with is smokin' hot.
An alternative to 99designs that I've used successfully in the past is BrandStack.com; you can only choose from ready-made designs, but they are high quality and the designers usually are willing to adapt for your branding. They also have Upstack.com which is a similar service to 99designs but you get a little bit more of a warm fuzzy feeling since it's not "on-spec".
