Real stories.
Relatable money struggles.
Financial insights for all.

EPISODE 37

OCTOBER 17, 2025

Growing up with five siblings, Paul Ollinger vividly recalls the lengths to which his "frugal" parents would go to avoid spending money. While getting his MBA at the Tuck School of Business at Dartmouth, he discovered his love of stand-up comedy after he’d taken out $80,000 in student loans. Paul shares:

  • How he ended up as an executive at Yahoo and Facebook

  • Why the opposite of broke is not rich

  • An expensive item he bought that his friends just didn’t notice

  • The 1 thing about money that “never stops”

Comedian Paul Ollinger on Being a Facebook Executive & the Hilarious World of Estate Planning

Sign up for occasional updates.