Dark comment: Could this be the perfect opportunity for a genious hacker with enough "fuck you" money (yet doesn't care about their own reputation afterwards) to sneak behind enemy lines (whatever that means), work for nothing, and provide a totally unexpected mentor experience - possibly have them running around in circles and setting up a bunch of startups for failure?
"You're using PHP! That doesn't scale! You'll need Java. I'll show you how."
"You're using Java! Performance will grind to a halt! You'll need PHP. Lemme see that keyboard."
An infamous HackStar, indeed.