Eric Sink posted a follow-up to his MSDN article Make More Mistakes.  In it he refutes the popular notion that his own personal wealth helped SourceGear through the many mistakes he made.  The notable quote:

“Regardless of the scale of your business, the central point of my article still applies:  "Make all the non-fatal mistakes that you can -- don't make any of the fatal ones."  Only you can figure out what might be "fatal" for your particular situation.  Smaller firms should take smaller risks.  Bigger firms can take much bigger risks without placing the survival of the company in jeopardy. 

Either way, choosing to take no risks at all is an excellent algorithm for avoiding success.”

In case you are wondering why I posted this, it’s all about risk management.  The same basic principles apply regardless of whether it’s a project or a small business.