You probably haven't heard of Omar Hamoui but his story is definitely inspiring. In 2009 sold his company, AdMob, to Google for $750 Million.
Here is some of his advice:
Don’t be afraid.
Don’t be afraid to fail, don’t be afraid to get fired. Don’t be afraid to make a mistake or change your mind. If you find that you are doing or not doing something simply due to a fear of what might happen, chances are you need to rethink the problem. Fear is an awful guide and people tend to be awful judges of the true “downside”.
One of the most amusing things in the world is watching MBA students at the best business schools in the world fret over their career opportunities as if they will be living out of a cardboard box if they don’t get the right internship.
The best advice I have is that whatever you do, it should be done as you are reaching for a new opportunity, rather than shrinking from a phantom anxiety.
Optimize for the journey, not the destination.
It’s hard to understand this without going through it, but it’s extremely important not to optimize for or aggrandize an exit, or any particular goal represented by a single point in time. The thing is, whatever that goal is, it will be a temporary and fleeting moment, and it simply starts another journey.