It's a really bad place from which to seek funding, YC or not. Sachin overemphasizes the Chicago financing community, but it's worth knowing that most VCs, even outside Sand Hill and Waltham, aren't going to be happy funding a company in Chicago.
And they're right. It's easier to flip a company in San Mateo, where a bizdev meeting is just a 15 minute drive to Palo Alto, than it is in Chicago where the same meeting is a 3-day trip arranged 2 weeks in advance.
It's just not easier enough to matter for a founder, who is so unlikely to get a real round in the first place, and then so unlikely to get the B round, and then so unlikely to wind up with something that can be flipped at a huge profit, that this is just not something worth optimizing for. That's hyperbole, of course, but not by much.
If you have data that proves that I've overemphasizing how bad financing is here, please provide it. I am more than happy to consider additional data. Being able to provide a HOWTO that's more than "for God's sake, move to the Valley" would make me thrilled.
I think there's more to it than this point, but I'll the easy argument to articulate here is, "you can get funded as a company domiciled in Chicago by a firm or investor that isn't local to Chicago".
Well, sure. But I believe that the traction/revenue/user bar to do so is much higher here than it is in a more robust funding environment. Also, it's much, much harder to get a deal syndicated here.
And they're right. It's easier to flip a company in San Mateo, where a bizdev meeting is just a 15 minute drive to Palo Alto, than it is in Chicago where the same meeting is a 3-day trip arranged 2 weeks in advance.
It's just not easier enough to matter for a founder, who is so unlikely to get a real round in the first place, and then so unlikely to get the B round, and then so unlikely to wind up with something that can be flipped at a huge profit, that this is just not something worth optimizing for. That's hyperbole, of course, but not by much.