The wealthiest person I ever dated (he wasn't super wealthy while we were together just doing well, but I just saw him a month ago and he was excited because he CAN retire now but doesn't want to - he's 38) spent TONS of money doing rich people things in the pursuit of wealth, he stretched his bank account very thin over and over doing this.
Going to Sundance, Cannes, Burning Man, TED, etc to network. Spending gobs of money on impressing friends and others he wanted to be friends with. Picking up thousand dollar tabs for groups of people then minorly freaking out the next day.
But spend money to make money. Worked for him. And he got to be super self-indulgent along the way.