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?