I don't think he's claiming to be a humble person, just humble about his role within his own company. It's not necessarily a contradiction for him to claim that he's really good at being a humble boss.

If you truly believe you're awesome, I'm not sure it's beneficial to sit around and wait for someone else to recognize it. People won't ask you to contribute to the conversation; they'll assume that if you have anything to say, you'll speak up.