What would be the point of penetrating YC? There isn't much useful intelligence to gain from a startup accelerator. Things might change now that there are a lot of foreigners in the program, but even then, it's a relatively small group of people.

As much as people on this site like to think they're important, I highly doubt that anyone here (with the exception of the infrastructure/security people) matters enough to the intelligence community for anything more than your run-of-the-mill passive wiretapping/eavesdropping that all Americans are being subjected to.