I think it reflects different life phases. I did the "risk it all" approach when I was 19, when "risking it all" meant potentially being back to living at my parents and going back to university.

These days I wouldn't do that, because I have a kid and a mortgage, but I don't regret doing it at 19 - it taught me a hell of a lot of things that I'm not sure I would have if I'd only tried the cautious approach, and it still I think affects how I do things (e.g. it taught me that as much as testing and validating is important, sometimes it's better to just dive in, try, and fail fast - which is right depends how much you're risking and for what; you just need to actually assess your risks first).