You failed once so you knew what failure was like. Then you wanted to succeed once (as you defined it) so you took the shortest path possible to reach success. Now you know what thats like.
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.
There's a distinct writing style among today's tech entrepreneurs that becomes hard to stomach. Many blog posts have this authoritative and overly confident tone. It's only after an entrepreneur experiences success that they admit how they "did everything wrong." (see Suster, Mark) This pattern makes sense; as a startup CEO you need to always be selling. Once you "make it" it's hard to disabuse people of the notion you are competent.
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 really appreciated how candid this article was, but I don't find it very applicable to me.
> 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.
Fear of failure, though, can become fear of success -- which, when you think about it, is nothing more than fear of failing harder at the next level. There is a difference between prudence and paralysis, between taking reasonable risks and recklessness. And sometimes it's really hard to tell the difference between a comfort zone and a rut when you're in one.
Knowing when to quit is actually a big plus. Plenty of people go for broke and end up with absolutely nothing. So don't berate yourself for 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.
> By this time, we'd gotten into Y Combinator, one of the greatest startup handicaps ever created. If I couldn't succeed with YC's help, than I was truly incapable.
I used to worry about the exact same thing. I wonder if every YCer has this fear.
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.
With all this "I failed, I took risks, I hit the bottom, but now I'm awesome" type post mortem advice in the entrepreneurship community, I'm wondering how much of a survivorship bias we're seeing here. "Risk" isn't risky because it always pans out.
You are pretty tough on yourself for being afraid of failure. I feel that the fear is somewhat natural. The difference is how we respond to the fear. It sounds like you are figuring things out pretty well. Good luck on your next venture :)
[+] [-] tsunamifury|14 years ago|reply
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.
[+] [-] forgot_password|14 years ago|reply
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.
[+] [-] 0x12|14 years ago|reply
[+] [-] BrandonM|14 years ago|reply
> 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.
[+] [-] stan_rogers|14 years ago|reply
[+] [-] 0x12|14 years ago|reply
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.
[+] [-] breck|14 years ago|reply
I used to worry about the exact same thing. I wonder if every YCer has this fear.
[+] [-] hyperbovine|14 years ago|reply
[+] [-] callenish|14 years ago|reply
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.
[+] [-] amirmc|14 years ago|reply
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.
[+] [-] starpilot|14 years ago|reply
[+] [-] alexshye|14 years ago|reply
[+] [-] Hisoka|14 years ago|reply
[+] [-] alnayyir|14 years ago|reply