Failure is part of the maturing process in the startup world. If you haven't failed, you aren't trying hard enough, or you aren't  "pushing the envelope" far enough. I have always said "Success is a terrible teacher. Success masks over flaws that may hurt you later."

Roger Ehrenberg - the co-founder of Monitor 110, wrote a story on the lessons he learned from this recently failed startup. [found via Fred Wilson] He lists "seven deadly sins" that lead to their demise.

• The lack of a single, "the buck stops here" leader until too late in the game
• No separation between the technology organization and the product organization
• Too much PR, too early
• Too much money
• Not close enough to the customer
• Slow to adapt to market reality
• Disagreement on strategy both within the Company and with the Board

In my opinion, there are two key reasons Monitor 110 failed; first, no clear CEO leader, and second, too much money. Trying to run a startup as a group of friends or make decisions by committee will never work. Too much money allows you to waste time, ignore danger signals, and continue down a wrong path for too long.

More Lessons - But here is the story of GameClay, another startup failure at the other end of the spectrum. They didn't raise any VC money...and still failed. [Found via Jeremy Liew]

1. If your idea starts with "We're building a platform to..." and you don't have a billion dollars in capital, find a new idea. Now.
2. It's a marathon, but it's a marathon made of sprints
3. Initial conditions matter. A lot.
4. Developing in a vacuum never works.
5. Beware the chicken and the egg.
6. Prototype any 3rd-party libraries that you'll be depending upon, before you base your product on them.
7. If you're doing anything other than building your project and getting users, it's premature.
8. The product will take longer than you expect. Design for the long-term.
9. People have an incentive not to crush your dreams. Take everything they say with a grain of salt.
10. Know your limitations.

Building a startup is the most difficult, and most rewarding, thing anyone can do. Sometimes you can even make some money at the end of it all. There are so many things that can go wrong it is a miracle when a startup actually makes it.

It is important to celebrate our successes, learn from our failures, and value them equally. Failure is important, because success is a terrible teacher.