Thank you for the advice, frankly I would love to work for Matasano, they are arguably one of the premier security firms in the country. However, I have difficulty placing myself in the top-tier category they are in (plus they are not in San Francisco). I honestly don't know if I could write a network protocol fuzzer without relying on SPIKE or Scapy off the top of my head in an interview.
As far as Square goes, I feel I have 0 chance there. I would love to work there as well but no computer science/Math degree, spotty work and residence record and entirely self-taught. I get the feeling that doesn't jibe with their culture and I would just be wasting their time and mine.