Remember filing for student loans? I do. It was a nightmare, and I completely shanked it about twice. The student loan office was comically inept in trying to help me, a kid with virtually no organizational skills and zero financial education. Christopher Jacobs, the extremely British CEO of Communally, knows where I’m coming from. “There’s a joke about FAFSA (Free Application for Federal Student Aid),” Jacobs says. “It’s easy, as long as you already have your doctorate.”Jacobs should know.