You describe your first attempt at a startup as a failure. It should be seen as a learning experience. Entrepreneurs tend to be risk seekers, which is why they take the chance on a startup to begin with. I would guess from your description of your actions with FlightCaster that you were far more risk averse the second time around, from which I conclude that likely you learned that you took too many heedless risks the first time.
Would there have been an exit with FlightCaster if you had taken more risks? Possibly not. Perhaps the level of risk you took on was exactly what was needed. The nature of life is such that you will never know.
It is good that you keep in mind how lucky you are, though. Many good people lose out while making all the right decisions. After all, even with a 95% likelihood of success for a particular action, 5% of people will still lose. And there are an awful lot of bets you need to win in order to get a startup off the ground.
So make sure you learn the lessons you can from the past, but keep it in perspective. Otherwise you will put too much emphasis on things. I wouldn't trust a person to run a company who didn't fear that it might fail, but fear is self-fulfilling if you let it. Striking a balance between the two is the key, and each experience you have helps you find it.