alt Hacker News> Every post was a gamble because it could have been wrong
Symbolic differentiation is a deterministic algorithm. There is no reason for his posts to be a gamble. I'm sure there was a lots of interesting trial and error in developing good question and answer pairs, but once he posted the question he knew what the answer was already.
As I understand, he was specifically targeting problems that symbolic math software had given up on. He was only using symbolic software to solve the similarly shaped problems first, which allowed him to be fairly confident in his conjecture, as he became quite keen on how to slip his way from the output of symbolic math software from one solvable formula to a closely related formula that broke the software.