

Humble pie. - ddwoodworth
http://www.humbledmba.com/humble-pie

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tsunamifury
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.

Good luck, no reason to be down on yourself.

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forgot_password
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.

~~~
0x12
I'd rather fund a guy that knows his limits than one that is unrealistically
upbeat and over-confident.

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BrandonM
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.

~~~
stan_rogers
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.

------
0x12
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.

Don't knock it, you made it further than most.

------
breck
> 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.

~~~
hyperbovine
According to Wikipedia, YC has funded ~320 startups. How many can you name?

------
callenish
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.

~~~
amirmc
> _"Entrepreneurs tend to be risk seekers"_

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.

~~~
callenish
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.

~~~
amirmc
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.

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starpilot
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.

------
alexshye
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 :)

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Hisoka
Was FlightCaster acquired mostly because of its user base or because of its
technology?

~~~
alnayyir
Prolly for the engineers like everybody else lately.

~~~
Hisoka
Figures.. their Compete graph shows lack of users, and technology really
doesn't sound that complex...

~~~
rfrey
On the contrary - their tech was extremely complex. There was serious
technology risk in FlightCaster. Jason's co-founder Evan is one of those guys
who exudes technical brilliance: he gives off geek-pheromones that would make
an art history major want to talk algorithms with him for three hours. They
needed all of those chops to do what they did.

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.

