How many jobs have you had where the people you worked for “took you aside and gave you advice” on what to do with your earnings and your future?!?? What you do with your future and your earnings is up to you. Also, the percentage of skaters that get a job with the brand they skated for is quite minimal. “So many guys” is NOT as many as you would think. Plenty disappear into obscurity.
I agree with your point that there aren't as many dudes who end up as sales reps or some other inside job. Not every pro can expect to be handed a job after their pro career is over. And, sadly, a few aren't qualified for the jobs
However, I disagree that there is no responsibility of the employer to pull the riders aside and help them plan for a future. My boss is currently giving advice on housing and investments to myself and my colleague and we're all full-on adults.
When the chief finds some 17 year old to exploit and live in his warehouse, its bullshit. He should, at least once a year, check in on finances and offer advice. And, I don't think independent contractors can have retirement plans, but it doesn't take much to bring in a fidelity rep to an office to tell everyone about their future. Will the 18 year olds listen? Probably not, but exposing them is a moral responsibility for a company living off of the young people jumping down stairs and being "cool."
And, yes the experience of being pro would be an amazing experience (although, pro for Zero sounds shitty, not interested in living in a warehouse while Jamie remodels his beach front property), but it is short lived for many and sadly, "I front-side flipped some gnarly gap" isn't going to help someone get a good job outside of skateboarding.