Jason Hall grew up in rural Georgia watching his dad treat money the way most people treat a hot potato — get it and spend it as fast as you can. Nobody talked about saving. Nobody talked about investing. The plan, such as it was, was to fix up a beat-up old truck his grandfather gave him, pulling parts from the junkyard ten miles down the road, and figure the rest out later.
Co-host of the Investing Unscripted podcast and a contributor to The Motley Fool for over a decade, Jason joins Chris Hill to talk about the long, expensive road from that junkyard to genuine financial clarity. He shares:
- Why dropping out of college to sell electronics at Circuit City felt like the smart move — and how money locked him into a career path he never planned on
- The moment his girlfriend's savings account and an unauthorized speaker purchase nearly ended their relationship before it really began
- How he cashed out his 401(k) to pay for a round of golf with two guys whose names he can't remember — and what that decision is worth in today's dollars
- The conversation he had with his wife before walking away from a six-figure sales job to write about investing for half the pay
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Opening clip – “Nate Bargatze: Hello World”

Tyler Gardner grew up eating Cheerios from a bag on a Vermont ski slope while other kids bought hot chocolate. That early lesson about money — absorbed more than taught — sent him on one of the more unconventional paths in personal finance: from stealing grocery money as a kid, to Andover on financial aid, to teaching English at prep schools for a decade, to becoming a financial advisor who thinks most people are asking the wrong question about wealth.
The right question, Gardner argues, isn't how much can I accumulate — it's what do I actually want money to buy? For him, knowing the answer changed everything.
Chris Hill talks with Tyler about:
- Growing up in a household where money was never discussed — and the ski slope memory that first made him realize it mattered
- Attending Andover on financial aid and getting his first glimpse of generational wealth on a spring break trip to Palm Beach
- How a disastrous retirement fund presentation pushed him out of the classroom and into financial advising
- The one thing he wishes he'd understood at 15 that he still has to explain to 60-year-olds today

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Opening clip – “Landman”

Andy Hill hit a million-dollar net worth — and the first thing he did was sell part of his brokerage account and buy a Ford Mustang. It's the kind of decision that makes more sense once you understand how he got there.
The host of the “Marriage Kids and Money” podcast and the author of Own Your Time, Hill grew up in Michigan learning early lessons about saving, investing, and building wealth. Guided by a mother who emphasized frugality and a father who built a career from the ground up, he developed a strong financial foundation — even as investing mistakes and market swings tested his path to financial independence.
Chris Hill (no relation) talks with Andy about:
- Buying a house at 22 with money he'd saved and invested — and why breaking even a decade later still stings
- Falling in and out of love with investing, from tech mutual funds to a WWF stock purchase he'd rather forget
- What he and his wife got wrong about money early in their marriage — and how 16 years later they're still figuring it out
- The one investing move he wishes he'd made earlier — and why it requires almost no skill to pull off

What's the last thing you splurged on? [email protected].
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Opening clip – “Grand Canyon”

Getting burned on a bad investment early in life can do one of two things: swear you off investing forever, or teach you exactly what kind of investor you want to become. For Laura Adams, it did the latter.
Host of the Money Girl podcast — one of the longest-running personal finance podcasts in the world, with more than 1,000 episodes — Adams  grew up in Charleston, SC, in a household where money was never discussed. That silence may be exactly why she became obsessed with it. Her earliest money memory involves sorting coins into paper wrappers for her father's business. Her first checking account came at age 12, when she begged her mother for one just so she could balance it.
Chris Hill talks with Laura about:
- How falling for a Ponzi scheme in her twenties turned her into a committed index investor who doesn't look back
- Buying a struggling flooring business with her husband knowing nothing about flooring — and selling it four years later at a profit
- The 2-year plan she and her husband made to eliminate their credit card debt as newlyweds, and why paying it off felt better than she expected
- Why the money rules that help you build wealth can actually work against you when it's time to spend it
What is something you bought that makes you happy? Tell us at [email protected].
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Opening clip - "Succession"

The best job is one you love. The second best? One you hate.
Organizational psychologist Alison Fragale learned this the hard way — trading a McKinsey consulting career she couldn't stand for a Stanford PhD and a calling she never would have found otherwise.
A professor at UNC Kenan-Flagler Business School and author of the bestseller Likeable Badass, Fragale grew up in Pittsburgh shaped by a father who made sure his daughter never had to think twice about what she put in the grocery cart. That early imprint on money followed her through Dartmouth, into consulting, and eventually into a career spent studying how people earn power, status, and influence.
She talks with Chris Hill about:
- Why the people most stuck in their careers are neither miserable nor happy — and what to do about it
- A financial concept she didn't encounter until her late thirties that completely changed how she thinks about giving
- Why she bought the car she'd wanted for decades, immediately regretted it, and refuses to get rid of it anyway
- The one habit she believes is both the most generous thing you can do for others AND the most strategic thing you can do for yourself
Check out Alison's book Likeable Badass at alisonfragale.com.
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Opening clip – “Heist”

Dividend stocks don’t get the hype of high-growth tech names — but they’ve quietly delivered some of the market’s best long-term returns.
Investor Matt Argersinger joins Chris Hill to break down why dividend-paying companies can outperform, why younger investors shouldn’t ignore them, and how the stigma around dividends began to fade. They discuss:
- The myth that dividend stocks are “for retirees”
- Losing his first $500 investing in a failed computer company
- The shift in investor thinking after companies like Apple embraced dividends
- When growth stocks make sense — and when they don’t

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Opening clip - "Chinatown"

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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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.

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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]