It sounds like you're the kind of guy with the contacts and skills necessary to make deals, Why not skip YC and go straight for a large angel or VC investment? A large part of what YC brings is business knowledge and contacts for hackers, you probably have that covered.
And while I'm dishing out arbitrary advice, it sounds like #1 is not trying to hire people as good or better than he is. Specific Ruby experience probably isn't as important as the brains and attitude of the hacker. You're going to have to bring anyone up to speed, just make sure they are worth the effort.
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It sounds like you're the kind of guy with the contacts and skills necessary to make deals, Why not skip YC and go straight for a large angel or VC investment? A large part of what YC brings is business knowledge and contacts for hackers, you probably have that covered.
And while I'm dishing out arbitrary advice, it sounds like #1 is not trying to hire people as good or better than he is. Specific Ruby experience probably isn't as important as the brains and attitude of the hacker. You're going to have to bring anyone up to speed, just make sure they are worth the effort.