I am not saying he made good choices but it's hard to picture all that many well balanced people working when they don't need to.
Let's say you are 18 and make 20k / month and that's the tip of the iceberg you are going to get another 50+ million by the time your 40 even if you do absolutely nothing. Do you really think you would aim for an office job? What's your ROI for "wasting" one of the few thing you can't buy time? Are you going to do a startup when you already have more income than your lifestyle requires?
PS: As soon as you realize you don't need to live in an expensive area and most expensive items are more about status than quality you realize money quickly has significant diminishing returns.
I wouldn't aim for a traditional office job with that kind of money, but I'd want to be doing something. He could go to graduate school, write a novel, start (or at least join) a non-profit.
With a trust fund that can support him indefinitely, he certainly has nothing to lose in taking a job. If it turns out to be a hideous waste of time, he can quit.
One of the intractable unfairnesses of the work world is that those who need or rely on their jobs are destined (all else being equal) to be less successful in their careers, because they can be trapped into a dead-end and because they do have a reason to fear the boss. Your friend, on the other hand, didn't have that problem. He can take a job and, if it turns out to be a waste of his time, quit^ and do something else.
(^ I am not, of course, suggesting that he ought to quit just because a job gets difficult. What I'm saying is that the biggest danger of the career minefield is stagnation and unrecognized toil, in which case one really is wasting one's time in going to work, and your friend had an inexhaustible "get out of jail free" card.)
Let's say you are 18 and make 20k / month and that's the tip of the iceberg you are going to get another 50+ million by the time your 40 even if you do absolutely nothing. Do you really think you would aim for an office job? What's your ROI for "wasting" one of the few thing you can't buy time? Are you going to do a startup when you already have more income than your lifestyle requires?
PS: As soon as you realize you don't need to live in an expensive area and most expensive items are more about status than quality you realize money quickly has significant diminishing returns.