If he's a seasoned trader I don't think he's making money by playing with his own stock right now. He's constantly selling at the bid or at the ask when it's lowered. I doubt he's shorting TYTN for all the reasons I've stated the last couple weeks.
Maybe he's made some bad deals the last year and needs the money? Or is trying to refi some real estate and is under water? We don't know but even the best traders get caught off guard when facts change