

“Buying Things Is Usually Stupid” with Joel Stein
Jan 29, 2025
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.
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Early Money Memory
- Joel Stein's earliest money memory involves his mother suggesting he donate a portion of his allowance.
- This created a strong feeling of sadness and pressure between his security and doing what felt right.
Basement ATM
- Joel's family had a vending machine business with a cash box in their basement.
- He could take money as needed, as long as he tracked it, essentially a personal ATM.
Silicon Valley Wealth
- Joel's first encounter with extreme wealth was in Silicon Valley.
- He found it surprising that many tech millionaires bought sports cars but lived in modest apartments.