What's it like to start over in a new city on the day the financial world begins to fall apart? Douglas Boneparth flew into JFK in October 2008 with four boxes and a mattress to buy — and landed in the middle of the Great Financial Crisis. He didn't go home.
Boneparth is a CFP, president of Bone Fide Wealth, and co-author with his wife Heather of Money Together. His path to New York started in the retirement communities of Boca Raton, where as a teenager he and his brother ran a computer repair business charging $30 an hour to teach elderly neighbors how to use AOL. It ended (or began, depending on how you look at it) with him telling his father he wasn't joining the family financial planning firm and buying a one-way ticket north.
Chris Hill talks with Douglas about:
- Growing up the son of a financial advisor who taught him the business of wealth management but assumed the rest would take care of itself
- Why walking away from a family succession plan was the hardest financial decision he ever made — and why he'd make it again
- How he and Heather approached $200,000 in law school debt not as a crisis but as a problem two capable people could solve together
- Why the most reliable path to financial success is almost always the most boring one
Check out Money Together, the best-selling book Douglas wrote with his wife Heather. 
What’s a purchase you still regret? Tell us at [email protected]
Opening clip - "Succession"

Tim Hanson didn’t set out to become a capital allocator.
Today he’s the President and CIO at Permanent Equity, helping steward long-term investments in private companies built to last. But his path to investing included playwriting, early stock picks, and lessons about money that started in childhood. Chris Hill talks with Tim about what separates investing from allocating capital — and why the distinction matters, as well as:
- The first stock Tim ever bought (and what he learned from it)
- How Permanent Equity thinks about holding businesses for decades
- Raising kids who understand ownership
- A surprising purchase that says more about capital discipline than you’d think

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What’s the last thing you splurged on?
Share your story at [email protected]
Opening clip - "Glengarry Glen Ross"

Personal finance isn’t just math—it’s memory, emotion, and lived experience.

Chris Hill talks with MarketWatch columnist Beth Pinsker about why money decisions feel so hard, especially during life’s biggest transitions. Drawing from her work as a journalist and financial planner, Beth breaks down caregiving, taxes, and end-of-life planning in ways that actually make sense.
They discuss:
- How childhood money experiences shape adult behavior
- What financial planners can—and can’t—help with during crises
- Why “bad choices” are sometimes the only choices
- What she learned about profit, inventory, and responsibility while illegally selling soft drinks on the beaches of Atlantic City

Opening clip – “The Princess Bride”

Beth’s new book, My Mother’s Money: A Guide to Financial Caregiving, can be found at BethPinsker.com.

What’s the last thing you splurged on?
Got a purchase you regret and still think about? 
Share your story at [email protected]

Denise Coursey didn’t grow up talking about investing—but she did grow up learning respect for money.
Raised in a blue-collar, union household, Denise became a first-generation college student, took early career risks as a writer and editor, and eventually became a small business owner. Along the way, she developed strong views on scarcity, financial independence, and why “having enough” doesn’t always quiet the money noise in your head.
Chris Hill talks with Denise about:
•Why karate became a lifelong practice—and eventually a business
•Taking creative and career risks without a financial safety net
•How separate bank accounts reduced money stress in her marriage
•Redefining “splurging” as time, not dollars
Opening clip – “Tom Papa: What A Day!”

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More info about Denise's business at VirginiaDojo.com

Send your questions and comments to [email protected]

Money anxiety often starts long before our first paycheck. For Carl Richards, it showed up as “static in the air” growing up around unspoken financial stress—and it shaped everything that came after.

In this candid conversation, Carl reflects on how early experiences with money quietly influence our beliefs about risk, security, and success. From diving for golf balls as a kid to accidentally landing a job in finance, he shares the moments that taught him why money is never just about numbers—and why comparison keeps so many of us from ever feeling like we have enough. Chris and Carl explore:
•Why money stress is often felt before it’s ever discussed
•How childhood experiences shape our financial behavior as adults
•Why hitting a financial “number” rarely brings peace of mind
•Carl’s belief that money’s natural state is flow, not accumulation
•How he now thinks about purpose, profit, and permission in his work
Opening clip – “John Mulaney: The Comeback Kid”

Check out Carl’s new book Your Money: Reimagining Wealth in 101 Simple Sketches
Send your questions and comments to [email protected]

Go to ilovemarmar.com and use the promo code “MONEY” to get 10% off the best chili garlic crunch in America!

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.

Want to find the best stocks and speed up your investing analysis? Try TIKR for free at tikr.com/unplugged

Send your questions and comments to [email protected]

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”

Send your questions and comments to [email protected]

Want to find the best stocks and speed up your investing analysis? Try TIKR for free at tikr.com/unplugged 

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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Email the show! [email protected] 

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”

Looking for a last-minute gift for the book lover in your life? Order a copy of Oh, Christmas Tree today!

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

Email us [email protected]