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I think the right answer would involve a hack that bent or even broke the written rules but made everyone wealthier (better off) in the end.

I have no idea what Y Combinator thinks about the answer to that question. But if Paul asked me to help out by reviewing some applications, I'd probably send you an email asking how that was to your advantage.

Actually I did something like araneae stated, I started hiding my transcripts in high school and college to avoid drama between my folks because I was NOT a good student -- the formal education system wasn't for me. There was even one point in college where I was failing out, but gamed the GPA system so that they couldn't kick me out.

Anyway, it worked well for me. I didn't get any drama, and I ended up graduating and landing a job with a top 25 software company.

It can also be when you went to to a 3rd party wireless store and got them to add a cheap unlimited tetherable data plan that no one knows about and is in the "depreciated/archived" features section.