Agreed on both counts. This guy took a lot of responsible steps: hired an accountant, got a will, began investing, ensured he is prepared from a tax liability standpoint. Not sure how many of us readers here on the Billfold have wills, I don’t (and I should!). He certainly LOVES to gamble, however I am not sure he has a gambling problem, at least not from what he discloses here. Not saying he doesn’t, but I don’t think we have enough info to pass that judgement. He likely spends as much money gambling as people do playing golf (aside from the trip he mentioned to Vegas). I think it’s worthwhile to examine our prejudice around hobbies, or at least what we think should/ought to be considered as one.