I know there is a temptation to look back on events with hindsight and pound your chest shouting, "Mea culpa, mea culpa!" But it is a misplaced notion in your case.
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.
I disagree. I think a better description is risk tolerant. Pretty much everything in a startup is about risk mitigation e.g. Talking to customers early, building the minimally viable product, hypothesis testing etc.
Entrepreneurs are more tolerant of that risk to begin with and as they prove the market/product, more people have an appetite to get involved, and you can build a business.
If an entrepreneur is really risk seeking then as soon as she's reduced the unknowns, she'll lose interest.
You are right that it is a better term, and I should have used it. I disagree that there is no link between being risk tolerant and risk seeking, though. It would be an interesting study to see if entrepreneurs engaged in high risk sports such as sky diving more frequently than others.
While it might be interesting to do a comparison of extreme sports and entrepreneurship, I don't think we could draw any meaningful conclusions (neither one depends on the other).
You might find the following article interesting, published in Nature in 2008. The researchers compare entrepreneurs with managers (controlling for age etc). It doesn't really make the same distinction I did in my previous comment (re risk tolerant vs seeking) but it's relevant nonetheless. The paper is: Lawrence et al The Innovative Brain (http://dx.doi.org/10.1038/456168a) and slightly off-topic comment Hermann Hauser (http://dx.doi.org/10.1038/456700c)
...this risk-taking performance in the entrepreneurs was accompanied by elevated scores on personality impulsiveness measures and superior cognitive-flexibility performance. We conclude that entrepreneurs and managers do equally well when asked to perform cold decision-making tasks, but differences emerge in the context of risky or emotional decisions.
I'd argue that there weren't so much risk-seeking but the willingness to place bigger bets would indicate risk-tolerance (that's my interpretation, anyway)
If you don't have access to the journal, I've dumped them both in the following pdf. It'll be there for at least the next week but no guarantees beyond that (if you're reading this and it's gone, email me for a copy)
http://dl.dropbox.com/u/486678/InnovativeBrain.pdf
Aside: So sorry to see notify go. I'd probably never have seen this comment if I hadn't got an email about it.
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.