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Very enlightening series of posts and also very very well written, IMHO. I couldn't help admire your clarity of thought and your lucid writing style while reading. You mention your remark to your family about screwing up: If I were your father, despite that you have indeed failed, I would be proud of having a son who is so capable of taking all that has happened in an admirably mature way and is so capable of dissecting, analyzing, reasoning about and also relating them with such clarity of thought. Don't worry, FWIW, for me these series of posts very clearly indicate that you have the basics to be successful eventually; so don't despair and keep trying.
Your "mistakes" sound more like what people say during an interview when they get asked about their "faults".
From reading the series the only failure seems to be you.
'Just keep on throwing. Even if you're a complete idiot, eventually you'll hit the bulls eye.'
Good luck and thank you for your openness.
That's a.. different way to look at what a startup is or is not doing. Thanks.
"At the end of the day though, I still believe he and I could have been a great a team and could have pulled this thing off."
I had a great friendship ruined because I felt this way. We did a business together and things didn't work out. I rationalized that a second time would be different -- that the first business wasn't the right fit, we'd learned from our mistakes and so forth. When we did another business the EXACT same problems showed up. We were great friends but lousy business partners. Now, do to the second business (but not the first) we are no longer friends. Maybe your situation is different, but I thought I would share.
I have read the whole series, and its about time I've shared something.
Have you read the poem "If" by Rudyard Kipling? If not, go google it out.
I am working with four of my friends in a startup for ten months. We all quit our jobs ten months ago with a dream to "build something people want", obviously we were (and are) greatly inspired by Paul Graham. Details (and bad days) aside, we have developed a simple web application that we are hopeful about trying at YC winter 2008.
I live in Bangladesh, and living the startup life (and dream) is more tough than in USA (or other places).
I completely agree with you on the following points:
1. Conviction
2. Talking to people about what you are doing
3. Leadership and decidability. I remember a quote from another startup postmortem that they lacked "a leader to say that the buck should stop here".
You didn't mention the mental support you got from your family and girlfriend, which I believe is a very important bolster for a startup. My girlfriend is pissed off at my startup thing. She says she can't take such uncertainty. I could be more productive if things would be otherwise. My parents are giving me wonderful support, without which I couldn't last long.
I believe, and still believe, someday I will build something that will establish my entity in the Internet. Pray for me. I wish you good luck, and success.
I wish you luck with your application, let me know how it goes. Uncertainty is extremely difficult and I think most people would prefer to settle for a clear situation that isn't all they'd hoped for than to aim bigger but risk disappointment. I'm sorry your girlfriend is stressing you out... but on the other hand it's good to have that other perspective. It's easier to convince yourself of something than other people, so, think of it as a challenge!
"If you can trust yourself when all men doubt you
But make allowance for their doubting too,"
Startup days are full of waves of elation and frustration. But I will hang on.
Thanks for your note.