He gets a random email asking if he's available to talk to the Globe about his pirate license. "Sure, why not?" So he gets on the phone with a reporter who asks him about his interest in piracy, and that's when he mentions that he used to dress up for Talk Like a Pirate Day in high school. "Do you have any photos of you dressed as a pirate?" "No..."
So a couple hours later he gets an email asking if the Globe can take photos of him dressed as a pirate. And when he suggests they do it at the MIT Sailing Pavilion, they ask around and find a photographer who somehow knows the guy who runs the pavilion. So they meet up, and in some down time the manager tells Jacob: "You know, he's a pretty awesome photographer. Everything he does ends up on the front page."
And it did.
edit: I forgot the best part of the story (for me). I was eating lunch with his former roommate when he walks right past us. We both text him. So he comes back and talks to us for a while, then mentions offhand "So I need to go take photos with a reporter for the Globe. By the way, can I borrow your socks?" The next time he passed by he was in full pirate costume.