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I've hooked up with a Seattle programmer named John DeRosa, and we're in the early stages of developing a Web product. We aren't sure where it will lead, if anywhere, but we think the concept is strong and we decided to apply for a start-up incubator-like program in Mountain View, Calif., called Y Combinator.
This was a total long shot. They get more than 1,000 applications twice a year, choosing 50 or so fledgling projects for three months of guidance in launching a business. Most of their applicants are hackers young enough to be our children, some of them still in school. I think our idea has huge potential, but it is somewhat unlike what Y Combinator has backed in the past, so we were a little out of place from the start. The application process was not difficult, however, so we thought what the hell.
Well, we didn't make the cut, but the rejection was more than thoughtful — it was downright insecure!
We're sorry to say we couldn't accept your proposal for funding. Please don't take it personally. The quality of the applications continues to increase with each cycle, and since there's a limit on the number of interviews we can do, we had to turn away a lot of genuinely promising groups.
Another reason you shouldn't take this personally is that we know we make lots of mistakes. It's alarming how often the last group to make it over the threshold for interviews ends up being one that we fund. That means there are surely other good groups that fall just below the threshold and that we miss even interviewing.
We're trying to get better at this, but it's practically certain that groups we rejected will go on to create successful startups. If you do, we'd appreciate it if you'd send us an email telling us about it; we want to learn from our mistakes.
Y Combinator Staff
Having been in a position myself to deliver bad news via mass e-mailing, I was curious to know how well I've handled similar rejection messages. Thanks to the fact I have an archive of all my personal and professional e-mail dating back to 2002, I was able to find out.
I did OK, I think, but these aren't quite on par with "I probably should have chosen you but for some reason I didn't":
Dear applicant,
Thanks for your interest in Seattle Weekly. We have selected interns for summer 2005, and I'm sorry to say you were not among them. As you know, the competition is very keen in this job market, and even very talented people did not make the cut. You are in good company.
Our next internship period is this fall, roughly September through December. If you are available then, please send us fresh material and we'll put you in the running. Attached for future reference is our recently adopted internship policy.
Sincerely,
Dear applicant,
It pains me to write that, but there are more than 250 of you, and I don't know a more personal way to let each of you know that you weren't a finalist for our editorial-assistant opening.
We were impressed and astonished by the quality of the applicant pool.
We'll keep your information on file and hope you'll think of us again when we have another opening. Best of luck in whatever you do.
Sincerely,
Dear applicant,
Examining the flood of applications for our editorial-assistant opening was challenging, but we've made a decision and I'm sorry to say you aren't the person we were looking for. Please keep us in mind next time we have an opening.
Sincerely,
An applicant replied:
Chuck,
I'm nominiating you for prospective employer of the year for sending out replies! :-)
Dear Crosscut applicant,
Please forgive the mass mailing, but I wanted to let you know that we've filled our deputy editor job. I want to thank you for applying. You were in a very strong pool of applicants, which was heartening. If we have a future opening at Crosscut, I hope you'll apply again.
We wish you the best and thank you for your interest in Crosscut.
Sincerely,
Crosscut applicant,
I'm sorry for this impersonal update, but there are very many of you ...
We've found our part-time editor. I'm sorry you weren't the right person for this job, but you are in very talented company and I hope you'll consider applying to Crosscut again in the future, as we grow.
Thanks for your interest, and I wish you the best.

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