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
