the scene cut after obediah says "the best thing about tony is also the worst thing: he never stops working" and it cuts to tony at a casino... its played for jokes and its very much meant to emphasize how little tony cares for "serious" awards/work, but the camera cuts to a wider shot and theres litterally like 100 people watching him play this game.
"hes always working"
I wish we knew more about pre-cave Tony, because I wonder if that tony considered public apperances as a chore the same way later tony did, and if that tony would rather be in his workshop.