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

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
Opening clip – “F1”

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

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Why do smart, capable people still avoid looking at their finances?

Chris Hill talks with Nick Wolny, personal finance writer and author of Money Proud, about the emotional side of money—why avoidance is so common, how early experiences shape financial behavior, and what actually helps people face their finances without shame. They also discuss Nick’s initial career path in music, following where "money is moving", as well as:
Closing the Wealth Gap - Why certain communities fall behind on savings and how "service journalism" can spark better financial habits.
The Pivot - How to identify where the money is moving in the economy and adapt your skillset to higher-paying industries.
Business Acumen vs. Marketing Hype - Lessons learned from the "dangling carrot" of expensive online courses and how to avoid being “in the red" in your first year of business.
Illegal Money - The thrilling documentary TV series (currently streaming on YouTube) that looks at money through the lens of organized crime.

Opening clip – “Jim Gaffigan: Comedy Monster”

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We’re kicking off the new year with one of our most popular episodes of 2025. When Dan Pink was growing up in Ohio, money issues in his home were like a cloud that caused “an endless drizzle” over his family. Despite having written a string of #1 New York Times bestsellers, his earliest encounters with finance still play a big role in Dan’s conservative approach to money. Sitting down at his kitchen table in Washington DC, he shares:
- Taking a VC approach to lemonade stands
- The economic reason behind his decision to attend law school
- Why a poor financial decision helps him sleep better at night
- An “absolute waste of time” he finally got rid of

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Chris Hill shares some holiday wishes before handing the show over to the late, great Louis Armstrong for his reading of Clement Moore’s classic poem, A Visit From St. Nicholas.
Opening clip – “Scrooged”

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We’re back with more holiday-themed conversations on topics only loosely connected to money! Motley Fool senior analyst Bill Barker and Bill Mann, Chief Investment Strategist at Motley Fool Asset Management, share:
- Regrettable holiday purchases
- Songs we enjoy despite popular opinion
- Our individual Mt. Rushmores of holiday movies
- The legend of the Sourtoe Cocktail (Yes, really)
Opening clip – “Elf”

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Enjoy awesome holiday music you WON’T hear on your local radio station.

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Santa has run his company for centuries. It’s arguably the most admirable business in the world. But is it profitable?
Motley Fool senior analyst Bill Barker and Bill Mann, Chief Investment Strategist at Motley Fool Asset Management, break down the company’s revenue streams and discuss:
- Why KGE’s logistics are “state of the art”
- The relative negotiating power of Santa's elves
- How cryptocurrency may be boosting the bottom line
- Mismatched holiday-themed buddy cop pairings (Yes, really.)
Opening clip – “Money Train”

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You don’t start your own newspaper business when you’re in grade school unless you have entrepreneurship running through your veins. Fortunately for David Simnick, he had parents who indulged his ventures from an early age. Now the co-founder and CEO of Soapbox Soaps (one of the fastest-growing companies in America), David shares:
- The military career he came close to pursuing
- Early business ventures that failed
- How “money is a fuel to go after what really matters”
- Why he unabashedly loves his Shop-Vac

Opening clip – “Billions”

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Happy Thanksgiving!
Need a little break from your family & friends?
Take a walk or go for a drive as Chris Hill reveals how a listener email led him to spend an entire day in Atlanta with the Teachers Retirement System of Georgia. Plus, he shares:
- 3 big Thanksgiving traditions in the U.S.
- How two approaches to charitable giving (that have come up on the podcast) tie in to one of his favorite organizations, the Waterville Area Soup Kitchen
- Tina Fey’s opinion of the only true reward in life

Opening clip – “Wall Street”

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