Our next guest, Paul Ollinger, is a nationally-touring comedian, writer, and podcaster. After 20 years in digital sales positions for companies like Yahoo! and Facebook, Paul retired at age 42, only to find himself bored, missing his work friends, and annoying his wife. After three years trying to find himself, he resumed his pursuit of the comedy dream that has taken him all over North America, opening for top comics like Daniel Tosh, Dave Attell, Norm Macdonald, and many more. Bob chats with Paul about:

• The psychological aspects of retiring early.
• Having money doesn't mean you will be happy forever.
• The pitfalls of comparing your finances to others.
• Monitoring your spending habits.
• Saving lives with philanthropy.

To learn more about Paul, visit his website or check out his Crazy Money podcast where he explores the connection between money and happiness. Facebook: @PaulOllinger Twitter: @Paul_Ollinger Instagram: @paul_ollinger