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Seems like you were merely doing what we all do in uncharted territory: Calibrating oureslves by testing the extremes then using that as a foundation to refine our future.
Good luck, no reason to be down on yourself.
Jason, as he'd probably readily admit, hasn't "made it" on this scale yet. That's what makes this post so courageous. At some point, Jason will be raising money for 42floors and a potential investor will ask him about Flightcaster. He won't be able to spin the story of Flightcaster in a way that makes him look like a dot com hero. I'm impressed that Jason put this out there.
> I'm not going to let my fear of failure drive my decisions next time around. If we fail, we fail. A startup failure won't affect how my family sees me, how my friends see me, or how my girlfriend sees me. And I'm never again going to let the possibility of failure affect how I see myself.
I feel like this is a lot easier to say after having a success, especially if that success put some money in the bank. Having a healthy fear of business failure is a good thing, as it allows you to see the potential negative outcomes. It's the fear of failure in life that negatively affects decision-making, and it seems unreasonable to expect someone with no history of success and no comfortable safety net to avoid succumbing to that.
You see it as mostly luck and I'd agree with that, start-ups are a big lottery. But there is also skill involved and without that skill you'd get nowhere, you need both, skill and luck.
I hope you'll do 42floors in a way that makes you feel more confident about the outcome. Regardless of how you feel today, 20 years from now you'll look back at this first company you were a part of and you'll see it as the best school you ever went to.
Don't knock it, you made it further than most.
I used to worry about the exact same thing. I wonder if every YCer has this fear.
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 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.
Clarification: they weren't just aggregating and presenting data: they were processing large piles of numbers to predict the friggin' future. And they didn't just curve-fit to do it.