The Team. The more time that I spend building companies (Securemote, Linuxcare, Sputnik, Technorati, and now Offbeat Guides), the more I realize that the single biggest risk is in picking a great team. Get a great team that works together, and you can resolve almost every other problem - competition, product, market, financing, etc.

Pick a poor team, and you can have all the advantages in the world - lots of money, little competition, a killer product, a huge market, and the company will find a way to screw it up.

This was probably the biggest eye-opener for me when I moved from CTO jobs to CEO. It's all about the people, and how everyone works together. Learning leadership skills was incredibly important for me to be able to build and inspire teams.

I've seen both sides of this at all the companies that I started. In my experience, it's far and away the most important factor in a company's success or failure.