I was really just a hard-core geek, if you will, in 1996, and was building websites as a hobby. I started doing a lot of web design and development and built my first website on the now-defunct GeoCities platform.
Don't drag candidates through weeks of endless interviews. Don't flake out on interviews. At DeveloperAuction, we often have offer letters prepared in advance, so we can hand them to great candidates as they are leaving the office.
On April 1, 1998, I launched Webmaster-Resources.com, and I remember that date specifically because it was the date that the price of a two-year domain name registration dropped from $100 to $70, and considering I was funding this out of my allowance, that $30 made all the difference.
If I go to a conference and someone tells me that they learned how to develop websites on Sitepoint and now they're a CTO at a company earning almost $200,000 a year, that lets me know that I'm doing the right thing.
I never really felt like my age stopped people from wanting to work with me. I was speaking at conferences and lecturing at universities at 18, and I think that was mainly because web developing and management was a really young industry.
A poor logo doesn't mean a business will fail, and a good logo doesn't mean it will succeed - it just helps. Ultimately a good logo is something that people recognize instantly and relate to.
The main thing that 99designs is about is choice. It's a fantastic model that eliminates risk for small business owners and puts designers on equal footing.