Joel Stein, a cultural commentator and author with sharp insights on money and status, joins the discussion to scrutinize our relationship with wealth. He shares humorous anecdotes about spending habits, including renting luxury cars and mingling with billionaires at Burning Man. Stein challenges the idea of 'having enough' and questions the secrecy around income. Through witty observations, he critiques the absurdity of status symbols and reveals why his so-called 'irresponsible' financial choices may resonate with many.