Re: Dumb
He could easily have gone legit, but made the same money? Not so sure.
Also, it's a lot harder to get a high paid job in tech than most think. Talent is only one piece of the puzzle. A lot of the time you have to have the right paperwork too.
As probably quite a few people here can probably attest if they've ever stood in for a fired CTO...you're only good enough to make the seat safe, you probably aren't good enough to be proudly displayed on the exec team page on the website.
"Studied at Oxford and successfully steered X,Y,Z companies over a 20 year span" sounds a lot better than "Appointed at short notice because we were fucked and dug us out of the shit after our last crap CTO".
I've stepped up in loads of situations where CTOs have either been fired, they fucked off or were just incompetent and I've not yet been offered the position permanently. Granted I'm only 37 and quite baby faced so I probably don't look old enough to appear wise yet...but still.
The way I see it is there's this weird grey area when you start aging as a techie where you're too old for mid level hands on engineering roles, but too young for a senior role.
The elephant in the room is qualifications as well. I've been working in tech since I was 17, 14 if you count the tech support I was doing for small businesses, family friends and the like before that for pocket money. Experience doesn't count for shit if you don't have the right academic creds most of the time. There are exceptions, but they aren't very common.