Dr. David Brumley has spent his career teaching computers how to hack, going from handling security incidents at Stanford to training some of the world's best hackers at Carnegie Mellon, mentoring a top competitive hacking team, and building picoCTF to introduce younger students to the field, all while insisting that any security warning his systems produce come with actual proof, like a working exploit, rather than just a vague alert. He carried that same hands-on approach from winning DARPA's Cyber Grand Challenge with Mayhem into his work today, where he studies how far AI can go in finding and exploiting software bugs, work that now shapes how the industry measures AI's hacking abilities, even as he continues investing at Rain Capital.