Earlier quoted context omitted.
It may be a way of filtering out older workers without having a policy as such.
That is totally possible, but I recognize this as an interrogation tactic. Your resume is a showcase of your best accomplishments. Short of clearance-level interviews with your family and friends, people in C-level positions ask for transcripts from 20 years ago because it's the only intelligence concerning your failures they can get their hands on (your previous employers won't ever attest on-record that you sucked)…
This firm clearly put a huge amount of stock in education. They were 4 blocks from a major CS university, and a significant number of staff were recent grads. I suspect the CEO had a masters which only adds credence to their belief in the education system.
On top of that, they knew how much I was making ($x), how much I was asking for ($x + $50,000), and ended up offering me more ($x + $150,000). That's not the kind of thing you do when you're trying to dissuade someone from taking a job with you. Especially when the offer is 100% cash (company was private and they offered no equity).
I strongly suspect that this person came from a bubble of education, and just didn't understand how you could be a poor student and then successful outside of academia.