We recently changed the name of our company and one of the implications was that we needed to create a new logo for the company.
The name of the company is iglloo (igloo.com was taken, big surprise, but we managed to grab iglloo.com) and when we chose that name I immediately envisioned us having some kind of cute logo, although nothing specific came to mind.
For some reason, we thought it would be pretty easy to create the imagery that goes along with the values what we want our brand to represent (in a nutshell we build apps, primarily for iPhones and iPads), but we quickly learned that creating something "real" out of our vague thoughts, was not an easy task.

We tried a few concepts but the designs that we got were too literal. We kept getting images of igloos.
Things like this:


Which is cute, but not more than that. We were looking for something sophisticated, simple, and fun.
I had envisioned a simple textual logo, with an igloo incorporated somehow as part of that textual logo.

So we decided to open a contest on 99designs. 
If you aren't familiar with 99designs, it lets you setup a contest for any graphic work you need. For example, you can create a contest for designing a web page and offer a $300 reward to whomever designs the best page for you.
Lots of designers hang around 99designs looking for projects to work on and they may see your project and submit a design, hoping it will win the contest and they'll get paid.

Similar to the X Prize (and the original Orteig Prize which Charles Lindbergh won in 1927 for flying non-stop from New York City to Paris), the idea is that the sum of all the effort put in to the competition by the participants is greater than the value of the prize.

Essentially you get tons of people working for you for free and one of them gets overpaid a bit for their effort.

Sounds like a great concept, especially for things like graphic design.
I heard from a few people about different results on 99designs, some were really happy and some didn't like the quality of the work they got there. So we decided to go with the cheapest option there ($299) and give it a try.

Within a week we got 38 designers who submitted about 140 design concepts for our logo.
Some were WAY off and a few were quite close to the concept we had imagined and tried to describe to the designers, but none of them really stood out. We were basically looking for a stroke of genius.

Here are a few of the designs that were kinda of the concept we were looking for (some after refinement based on our comments to the designers):









In our opinion, none of them were really spectacular/genius enough and we were pretty disappointed with the results.

At that point we pretty much gave up on the contest, didn't award a winner, and went on with our day to day business (still using the old brand). The rules at 99designs are that if you don't pick a winner you don't have to pay. We were definitely willing to pay full price for the design, if there was something that we liked.
I must say, the support team at 99designs did a great job. They were very accommodating, they offered to extend our contest longer because we hadn't decided on a winner yet (contests are typically for 1 week) but we still didn't get good enough results.

At that point I even tried to create the logo myself and came up with this idea:


I actually really liked the concept (I guess I'm just in love with my own ideas) but the problem was that it doesn't scale. At small sizes that little igloo image is totally not clear.

After about 2 months the logo issue came up again and I went back to 99designs to see the old submissions, maybe looking at them again would give a different perspective. Still nothing spectacular.

Since 99designs offer a refund if you don't pick a winner, I sent them an email and asked how I get the refund. They replied that they can only refund within 60 days and that more than that had passed.

They did offer to reopen our contest and basically start over. So we reopened the contest, again for 1 week.
This time we got WAY fewer submissions. I'm not really sure why (I asked their support and they didn't have any good answers). They also offered to give us their PowerPack for free which basically gets you better listings in their directory along with a few other tweaks so it stands out (usually $85).
The PowerPack didn't make any difference, we just got a few random submissions, nothing even close.

Then while looking at all the different submissions I suddenly ran across this design from the original contest:

I never really noticed it because it "wasn't what we were looking for", we were looking for some kind of genius twist as part of the textual logo.
But this was interesting.
We showed it to a few people around the office and everybody pretty much liked it.

I asked the designer for the meaning of the icon and this is what he sent in reply:
The meaning of the icon according to the designer


Ok, I can live with that.

We then went back and forth playing around with different fonts and stylings, these were among them:

At this point I was just exchanging emails with the designer, going back and forth about different things like the dot above the i, what L's to use, etc... According to 99designs, during the handoff process you can ask for some changes but the designers aren't obligated to do anything. Beehive, the designer who created this logo, was very responsive and helpful. 

After about a day of mixing and matching different elements from different fonts (and trying to keep it from looking like a Frankenstein-ish mess) we finally came up with the final design!

It wasn't what we had originally envisioned in terms of the concept, but it does the job.


And without further ado, here is the official new logo for iglloo:






So do I recommend using 99designs?
To an extent. While looking around there at different projects (I was looking to target designers who created things I like) I saw some pretty good designs.
My feeling is that it's kind of a crapshoot, with relatively good odds.
You may be able to get something really good for not a lot of money but you may leave disappointed.

If you can afford $299 then I would give it a try.
I think logos are particularly difficult to design (the story behind the Conduit logo is quite long too) but if you are looking to design a website you'll probably be able to get good results (although 99designs may be a bit more expensive than just buying a template and customizing it a bit).