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

EPISODE 50

JANUARY 16, 2026

Chris Hill talks with Cullen Roche, investor, author, and founder of Discipline Funds, about why the financial industry continues to misunderstand time, incentives, and risk—and how that confusion shapes the advice people receive.
In this conversation, they discuss:

  • How growing up in a large family influenced his views on ownership and responsibility

  • Early investing losses that reshaped Cullen’s view of risk

  • The role financial media plays in distorting expectations

  • Why many families avoid open conversations about money—and the cost of that silence

Check out Cullen’s new book Your Perfect Portfolio: The ultimate guide to using the world's most powerful investing strategies.

What the Financial Industry Still Gets Wrong About Money with Cullen Roche

Why does so much financial advice feel urgent—yet miss what actually matters?

Sign up for occasional updates.