My YC application, one week later

Last Tuesday, I submitted my YCombinator Winter 2010 funding application. Since then, I've thought about it a lot. Not too much, I don't believe, because it asked a number of questions that were important for me to think about, but enough that I have now have an opinion on what I submitted.

My new opinion is tempered by my understanding that I am my most severe critic, yes, but I feel it's still an honest look back.

My opinion is that I screwed up.

Not in the idea. Not in submitting the application. Not in the process of better defining what I want to do with the project.

I screwed up in waiting for so long to apply, not only with waiting until 2010 to apply, but also with waiting until Tuesday to finish up the application. I had viewed the application a while before it was due, had saved the questions to my desktop, had viewed them daily and thought about them. I didn't, however, write everything up, ask for feedback from various people, and hit SUBMIT until Tuesday.

Aaaaaaaand.... I screwed up with some of my answers.

In particular, I tempered my answers with spins I felt YC would want to hear.

Which was stupid.

Really.

Why? Well, I don't know what they're looking for 100%. If I did, I'd be running my own startup fund. I know what has been posted, I know the tenacity part. I know the multiple founders love each other part. I know the smart part. But I don't know the secret sauce, so why would I not put down what I really wanted to say?

Take, for example, the question, "Please tell us about the time you, kitt, most successfully hacked some (non-computer) system to your advantage."

My conversation with Kris about this question went something like:

"Well, I could tell them about X."

"Wasn't that illegal?"

"Uh, yeah. Well what about Y?"

*blink* *blink*

"Yeah, okay, maybe that was a bit illegal, too... Okay, I can tell them about W."

"You sure you want to admit to that one?"

"I'm sure I don't. What about Z?"

"Really? Did we not just discuss this? Illegal?"

"B?"

"Not really a hack."

"C?"

"Seven years aren't up yet."

"Crap."

Okay, it wasn't that bad. And not that anything that was outrageously illegal. Going 66 miles per hour on a freeway with a 65 miles per hour speed limit isn't outrageously illegal, but it is illegal. It's not morally outrageous either, but you don't really go around bragging about it on blogs (well, unless you want it to be used against you in a trial, but that's a different post on a different blog by a different person).

So, yeah, I came up with some happy positive thing I did that enabled me to succeed even though I lacked the talent to do "the right way" (in particular, I won the track team's MVP award my senior year in college, even though I wasn't the best athlete, who was usually who won the award ). It was a safe example, I played the system to my advantage, but I didn't really *hack* the system the way I would have preferred to say if I hadn't been tempering my answers.

Unfortunately, that wasn't the only question I held back with. I'm sad to say I screwed up on question, "If you've already started working on it, how long have you been working and how many lines of code (if applicable) have you written?" which is followed by the question, "If you have an online demo, what's the url? (Please don't password protect it; just use an obscure url.)"

I tried to play off just how obsessed I've been in the past with this project. It's hard to say, "Wow, this project consumed my every waking thought for three months straight, and most of my thoughts for the next six, and I still don't have something ready." I was more worried about having spent so long on the project without having a working demo.

I shouldn't have been. I'm not tackling an easy problem. That hard part means it may take a while to solve. Rather than try to hedge my answer, I should have just let my work speak for itself and sent them the link.

What I didn't screw up with on the application form was, however, the single founder question (answer: yes). There's a good chance I shot down any chance I had of being in the program with that answer, but I know that was the right answer. I could have asked Mike Gull or Kris or a host of other people to sign on with me. Could have. No matter how uncomfortable I feel about my answers in the other questions, this one is the one I know is right, even if it causes an immediate dismissal of my application.

Probably helps that I've already started a couple companies, the current of which lasted the five years that most companies fail (Yay me!) and rather know how much help I'm going to need to make this new idea really successful. A "the more you know, the more you realize how much you don't know" sort of thing.

So, I shot myself in the foot for this funding program before I even started. This will be okay, because I have a Plan B. It's a different way to the end. It's a harder way (meeting weekly deadlines, focusing on only the single project, letting go of everything else, generating exposure), but the endpoint it not barred from me.

Because, really, in this area, the only true failing is not trying hard enough.