To be honest he didn't even live right up to his means. He had a $500,000 nest egg at one point. That's a lot better than I could ever do. I think it was really the decision to leave the workforce that ended up crippling him in the long run.
I live in one of the cheaper (livable) areas of Los Angeles and a $500k "nest egg" would last me, my wife and my daughter 7 years at our current burn rate. My daughter is not in school, there are not eight of her, and none of us are keeping up with the Joneses next to the Huntington Gardens. Lemme just throw a Street View on this sucka real quick. That's some Greene & Greene shit up in that place. The Joneses be light speed, yo. It was the decision to stay the fuck in LA that crippled him in the long run. I know a guy who wrote on Veronica Mars. He didn't get staffed one year when it got canceled, and he took a long look, knew that statistically he wasn't likely to get staffed for 3+ years after that (if at all) and went back to investment banking. A dispassionate eye on the problem would reveal that our friend was in LA because of Tom Arnold. That's bad mojo. With a clear eye, one would think "Well, I had my fun. Time to hie my family back to Paramus where our burn rate shall drop by seventy percent and remember my stories while they're still pleasant." That's why I'm still here - I keep getting hired. As soon as I have no financial ties to this place I'm a fuckin' fart in the wind.
That's about 3 years longer than I would have guessed given where you live and your penchant for the drink.
Ha! Was thinking about it in the hot tub (don't start - yesterday involved lots of stairs and lots of Simon Cowell) and I realized it isn't that bad. a half mil would last us ten years at our current burn rate, or twelve or so if we cut back to the bone. But, again, no Greene'n'Greene in my zip code. San Marino is where people in Beverly Hills wished they could afford to live.
Yeah, by the sounds of it, he was actually a little ahead of the game compared to most people with his savings-to-costs ratio, -again, I don't think most people in his position would have predicted not being able to even get hired at Trader Joe's. Still, the blame rests squarely on his shoulders in every way imaginable.