He reportedly graduated HS in 1994 and Springfield College in 1998. So any involvement he had with the Patriots back in the Tuna SB days (as well as his supposed involvements with bob sled teams and hockey teams and arena teams) had to have been some sort of summer jobs or internships. I would guess he is around 31. He seems to have landed in Foxboro sometime in 1999-2000 and was canned in January 2003. So his 10 years in football claim is at best disingenuous.
Holley just had to break off the football talk for a baseball interview, but he was about to probe why as an employee you would tape your conversations with your boss. His point was you would do it to in some way be prepared to take him down. He was mentioning that in football, unlike in other jobs, there isn't really an HR department function where you can go and claim for example your boss is not being nice or talking nicely to you... And it's true, when a coach is mad at someone's performance, the conversation usually starts with something like "hey, mf, what is wrong with you...". That is the culture in the NFL. And if you can't take the heat, you move along to a kinder, gentler line of work. So it's not a stretch to assume Matt was taping in anticipation of a dead end career, either to have something he could point to as the rationale for his lack of success or something he could perhaps one day or in some way use against the employer be blamed for it.
The fact that his existence and his claims were apparently not news to some in the sports news business, even though they basically ignored him for quite a while absent substantiation, would lead me to believe they knew he existed because he told them things about the evil management team at Gillette over a period of time while he was transitioning to the golf industry (where lots of mediots spend their free time) here in NE. The undercurrent of how Patriots management was needlessly hard on poor employees mantra has long existed among those who had issues with Belioli's information management policy.