Oh boy. She might even be able to get him to take his helmet off if she did that. However, it's people like Jessica and AI's like Baroths that have made him extremely paranoid. While quite a bit of his personal fortune is stored on a regular data base, he keeps most of it in a secure, standalone server, inaccessible from anything but direct access. He also keeps hard copies of many of his most important files. When it comes to his finances and gear, he could teach the Thalmor a thing or two about paranoia. He can even cut his suit off from any wireless intrusion by removing the receiver from his helmet, although it's capabilities are lowered considerably.