It's one of those new-fangled "crowd sourcing" design services where you can pay a few hundred bucks to host a design contest for, say, a logo, and designers will submit their entries and then you select a few and you get a few revisions and then eventually you pick a winner and they get the bucks. 
 
Their "silver" logo design package is $500. You submit a few details about what you're looking for and hopefully the contestants will actually listen to your requirements and design something great around it. Or maybe not. Here's the dilemma. If you offer a "guaranteed prize," you're going to get more designers and maybe the better quality ones, but there is no money-back guarantee. You're paying the $500 no matter what, even if all of the submitted designs are crap. If you need the money-back guarantee, you're not offering a guaranteed prize and so it's likely that fewer designers will want to take part (and they're likely to be the less experienced ones). 
 
I'm looking for a new company logo and I've been browsing a few "pro" logo designer's websites and I have to say, I'm always a little disappointed by their portfolios. It seems like everyone has this generic style these days and all of their designs look the same. Maybe it's a consequence of them all using Illustrator and all utilizing the same techniques. So I figure maybe if I go with 99 Designs, maybe I'll end up with something a little more unique simply by virtue of the number of designers who are let loose on the project. 
 
Then again, I'm kind of a little uncomfortable with this whole crowd sourcing idea. While it sounds kind of cool for the customer, I can't help but feel bad for the designers who put loads of work into a contest but end up with diddly squat. Yeah I know, that's the nature of the game, but I'm quite soft in the head, so there it is. 
 
Thought(s)? 

$500 isn't a lot for that type of work actually.  I've done branding and logos for a few companies (including my own) and there can be quite a bit of work involved - a lot just to REALLY understand what the requester is asking for.

Oh yeah, and you have to hope they didn't use any copyright images in their logo.
 

Out of curiosity, what ARE you looking for in a logo?

Graphic design has about as much perceived value as music or photography these days. I studied it 1976-80 but went a different route after college. My good friend Tim has been a logo designer for the last 35 years, working all over the world (Intel Inside and Logitech were just 2 of his), now he struggles to find decent paid work.
 
Time was, designers would be paid just to pitch for work, but that's long, long gone.

I guess I have no idea what I'm looking for in a logo other than some speculative descriptive words. Part of my problem is that I'm infernally fussy and picky and truth be told, have a very narrow stuff that I "like" when it comes to visual aesthetics. A lot of the time when people say they think stuff is awesome I'm like "meh." But I'm also terrible at getting visual ideas from my head to paper (or even describing them). So the fear with working with one designer is that I'm just going to hate everything they come up with but be afraid to tell them. I can't even point to one logo in existence and say "That! Design me something like that!" So 99 Designs has a lot of appeal for me in that respect, in that there's an element of anonymity - I don't have to tell all those people "I hate your design," I just don't shortlist them. But at the same time I feel bad for them. Truly pathetic, right? I basically need a good slap 

jamesg1213
Graphic design has about as much perceived value as music or photography these days. I studied it 1976-80 but went a different route after college. My good friend Tim has been a logo designer for the last 35 years, working all over the world (Intel Inside and Logitech were just 2 of his), now he struggles to find decent paid work.
 
Time was, designers would be paid just to pitch for work, but that's long, long gone.

I think to make money out of it these days you have to do the whole kit and kaboodle - logos, web design, business cards, GUI's, postcards, leaflets, t-shirts etc.  One of the reasons why 99 Designs is becoming so popular with amateur designers is that there is the chance the company you design a logo for will want to continue to work with you for their additional branding needs. Once a business has gotten a logo they love, they're going to want to retain some kind of aesthetic coherence across the rest of their company designs. And if the designer is successful at that then they're going to get more work through word of mouth. So it might be a good way for amateur designers to get a foothold (and some kind of portfolio going). 

sharke,
 
You sound just like the kind of customers I avoided when I had the T-Shirt printing shop.

I like that song
 
99 Designs on the wall, take one down, pass it around.... etc.

bapu
sharke,
 
You sound just like the kind of customers I avoided when I had the T-Shirt printing shop.

Just wait until it gets to the revision stage. I'll be taking out life insurance....