Chances are it is short-sighted to keep trying to make the NFL and collect only minimal paychecks. If he never makes an NFL regular season roster and has to find a job in a different career, it might be a bad decision in retrospect. It reminds me of 30+ year old minor league baseball players who hung around a bit too long only to never play in the major leagues. If he had started a career in something else 10 years earlier, he'd likely be a lot better off. He's probably young enough that it may not matter, but I certainly don't see an annual tryout as hugely successful compared to other QBs who have won Super Bowls or have become stars in the business world.