Hitting up 99 Designs is like throwing spaghetti at a wall in hopes that something sticks, well that's an almost apt description. I guess the biggest difference is that you are hiring N-'designers' who probably aren't very skilled at their craft so they have to lock into gladiatorial combat for mere dollars to each make a noodle and throw it at the wall for you. They won't care about your identity, and the quality of what you get will largely depend on how good you happen to be at scoping an illustration project and wrangling amateurs to get results.
With this method you will have some sort of graphic to slap on a site or slather on a t-shirt, but you will be extremely lucky if it stands the test of time or even stands out in your market. A good logo is one thing that sets apart the amateurs from the professionals. Facebook knew this and that's why they went to Cuban Council (http://www.cubancouncil.com/).
You could just find a designer/firm who's work you admire, see if they do identity work, speak with them about your brand, and collaborate with them (they will guide you if they are any good at what they do, and they will always have your best interest at heart) to create something everyone (including your customers) will love.
Sadly, OP's description of "Startup" logo design is what is currently popular, and many people don't realize that this is not how the best logotypes/icons are made.
The quality of what you receive depends on the quality of information you provide to any designer or firm. Our suggested process for a bootstrapped startup provides a solution for how to formulate a thought out design idea and get you going in the right direction at no cost.
In reply to your comment about Facebook: Zuckerburg knew minimal about 'design' so he did what so many other startups in the Valley do. Go to the big design firms. This solution works well for startups in the position to hand over the big bucks. Different solutions work depending on startup condition, status, and/or funds available.
This process may work best for startups with limited resources and limited funding. Even if you dont like the initial work you receive from 99 designs or any other design marketplace, two important things can happen:
1. You'll be a better judge for what works and doesn't work for your startup.
2. You're design idea will strengthen from concepts created by these designers at a price you can afford to pay.
When we wrote the article, we were totally backing a graphic designer first and foremost. Hands down, having a personal graphic designer is the best route to go. But it's definitely not the only.
I think 99designs is great. If you don't like the logos they shoot out, there's 100% money back guarantee, and a lot of people feel like they're logo is in good hands in the competition format rather than just pinning their hopes on one graphic designer. If they see something that they love, then they can stick with it. If not, they lose some of their time, but they get their money back. No harm done. And I think that's where 99designs shines. In ways, it's a safe route to go, especially for starting out.
For sure on the point you made though, we think that collaboration breeds the best logos. I'm checking out Cuban Council, and these types of logo designers and firms are ones to strive toward. Thanks for the insight man!
He blogs about the process, the concepts of branding, what to expect etc. In general David has been a good source of logo design info for the past several years.
Let us wield pasta metaphors together in the fight against poor design process recipes: spaghetti against a wall is the exact analogy I use when asked about 99designs or other spec sites ;)
With this method you will have some sort of graphic to slap on a site or slather on a t-shirt, but you will be extremely lucky if it stands the test of time or even stands out in your market. A good logo is one thing that sets apart the amateurs from the professionals. Facebook knew this and that's why they went to Cuban Council (http://www.cubancouncil.com/).
You could just find a designer/firm who's work you admire, see if they do identity work, speak with them about your brand, and collaborate with them (they will guide you if they are any good at what they do, and they will always have your best interest at heart) to create something everyone (including your customers) will love.
Sadly, OP's description of "Startup" logo design is what is currently popular, and many people don't realize that this is not how the best logotypes/icons are made.