Comedian Kurt Braunohler explains how what seemed like a huge waste of money actually turned into a valuable investment.
How Andy Kindler learned to love his credit card debt.
Writer Simran Sethi looks back on how her family's upbringing changed her life.
Actress and musician Alicia Witt decides to teach her father a lesson about handling his cash
Stand-up comedian Jimmy Pardo explains how sometimes you don't choose your dreams, but they choose you.
Alex White, one half of rock band White Mystery, tells us about life on the road running a business with her brother.
Comedian Carol Leifer discusses what she learned from her father about spending small and dreaming big.
For recording engineer Steve Albini, it's about work but not profit
For Hari Kondabolu, the board game Monopoly was a lesson about life.
North Carolina-based author and humorist Celia Rivenbark talks about how her parents shaped her views on money as an adult.