Couples rarely argue about dollars and cents. More often, they're arguing about security, freedom, priorities, and the future they want to build together.

Ross Anderson, CFP, is the co-founder of Craftwork Capital and co-host of the podcast Check Your Balances. He talks with Chris Hill about growing up in a family of entrepreneurs, what it’s like sitting across from couples who are miles apart on money, and how digging himself out of debt changed the way he thinks about money. They also discuss:

• Why he couldn’t wait to get his first job at 14

• Entering the financial industry at exactly the wrong time

• The innocent budgeting question that raises a red flag

• How Together We Bake is changing lives—one cookie at a time

We think about wealth as a finish line — hit your number and the anxiety stops. Blair duQuesnay, a financial advisor at Ritholtz Wealth Management, says it's almost never that simple.

Her clients (ultra-high-net-worth families) aren't worried about running out of money. They're worried about screwing it up.

Blair talks with Chris Hill about growing up in a Southern family where money was never really discussed, transferring colleges to study finance (after starting as a dance major), and writing The Belle Curve, her newsletter on money, markets, and wealth, as well as:

• Having a front-row seat to the 2008 financial crisis while working in an office right next to Lehman Brothers

• Starting her own RIA and having to wait tables to make ends meet

• What she wishes she had understood about risk earlier in her career

• The $400 phone call she would like to take back

Jesse Cramer had two engineering degrees and a stable, well-paying career designing hardware for an aerospace company. Then one day, about six months into his first job out of college, he looked at his 401(k) statement and saw $11,000 sitting there. That single moment sparked an interest in investing and compound interest that eventually pulled him out of engineering altogether and into a career managing other people's money.

Jesse talks with Chris Hill about:

• Why he kept a full-time engineering career for years after that moment

• Starting a finance blog after colleagues kept asking him 401(k) questions at work

• What surprised him most about managing real money for clients versus just writing about it

• The hot tub purchase he still regrets and what it taught him

Alison Kosik spent years reporting live from the floor of the New York Stock Exchange for CNN—and for most of that time, she wasn't investing a dollar of her own money. She could explain the market to millions of viewers, but couldn't bring herself to trust herself with her own finances.
Alison talks with Chris Hill about:

• How her parents' fights about money affected her financial confidence as an adult

• Taking a $13,000-a-year TV job in Corpus Christi and sleeping on a piece of foam to pursue her journalism career

• The divorce that finally pushed her to start investing with confidence

• Why she didn't truly believe in the power of compounding until recently

• Check out Alison's book, What's Up With Women and Money? How to Do All the Financial Stuff You've Been Avoiding, wherever books are sold.

We all outsource some part of our financial life — taxes, investments, retirement contributions, etc. But it turns out you can outsource the small stuff too! Even if that means leaning on the person sitting next to you at a blackjack table. 

In this holiday weekend solo episode, Chris Hill covers:

• A favor to ask of you — why do you listen to Money Unplugged, and what do you get out of it? (Email: info@moneyunpluggedpod.com)

• One thing every guest on this show, every Marvel superhero, and even America itself have in common

• What two very experienced friends taught him about knowing when to ask for help

Paula Pant grew up watching her mother spend six hours going between four different grocery stores, coupons sorted by location, all to save a few dollars on milk and bread. Frugality wasn't a choice in the Pant household — it was the operating system. It took years for her to realize that nobody had ever asked what all that time was actually worth.

Host of the popular podcast Afford Anything, Paula talks with Chris Hill about that early lesson and how she unlearned it, as well as:

• How getting rejected by Taco Bell at 15 led to a career in journalism (eventually)

• Why frugality can be its own trap

• What freelancing taught her about the real relationship between time and money

• Her framework for building wealth, and why mindset comes before tactics

Joe Saul-Sehy co-hosts Stacking Benjamins, one of the most popular personal finance podcasts in the world. But before that, he was a financial advisor with a secret — and a marriage the secret was about to put to the test.

In the conclusion of his two-part conversation with Chris Hill, he shares:

• What he was hiding from his wife when they got married — and how long it took him to come clean
  - A phone call with the IRS that flipped his entire relationship with debt

• How a CPA with the heart of a teacher became the person who finally helped him understand his own finances

• One habit that changed how he thinks about spending forever

Joe Saul-Sehy is the co-host of Stacking Benjamins, one of the most downloaded personal finance podcasts in the world — but long before he was giving financial advice to millions of listeners, he was making every money mistake in the book.

In this first of a two-part conversation with Chris Hill, Joe traces the roots of his complicated relationship with money, from a childhood defined by financial silence to the early adult mistakes that shaped everything that came after.

- What a Huffy bike taught him about emergency funds (before he knew what an emergency fund was)

• The moment a letter from American Express changed everything

• Why the most important money lesson he ever received had nothing to do with money

• The decision that turned a successful financial advisor into a podcaster — and what it cost him to get there

John Wordock spent decades working for the biggest names in financial journalism — Bloomberg, CBS MarketWatch, The Wall Street Journal, Dow Jones. He interviewed Jack Bogle, and Mike Bloomberg personally sent him to Washington DC to build a broadcast bureau.

John knew everyone worth knowing in the world of money. And then he put his savings in index funds and stopped thinking about it. Chris Hill sits down with John to find out what three decades inside financial news actually taught him about his own relationship with money, as well as:

• How his money story began in blue-collar Maine

• Why knowing all the right people made him less likely to tinker with his portfolio

• How he and his wife, both journalists, built a financially independent life and sent three kids to college without student loan debt

• The one purchase he still regrets (due to terrible Bluetooth)

Hannah Cole grew up watching her father, a successful architect, call family meetings at the dinner table whenever the economy turned. Belt-tightening conversations. No explanation of how bad things actually were. Just anxiety, and a dad in a bad mood.

Cole spent her early career as far from the world of money as she could get — a master's degree in painting from Boston University and years as a working artist in New York City. Then reality intervened. And when she finally sat down with an accountant for the first time, he opened the meeting by asking, "So when are you gonna get a real job?"

That question changed everything.
Today she's a tax expert, the founder of Sunlight Tax, financial education firm built specifically for creative people, and the author of Taxes For Humans. She talks with Chris Hill about:

• Why the feast-or-famine reality of artist life turns out to be one of the best teachers of financial discipline

• The two competing messages she received growing up about money and passion

• What it actually means to make peace with money

• How reality TV can be a counterintuitive teacher of good money habits

Joseph Moore grew up in rural South Carolina, the son of an electrician who worked during the day and went to school at night. Money wasn't discussed in his house (there wasn't enough of it to make conversation).

Today, Moore is a historian and author of the national bestseller How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t) who achieved financial freedom in his mid-40s. But the path there was anything but straight: a detour through seminary, a near-financial disaster in 2008, and a decade spent asking the question that would define his career — where does our financial advice actually come from? Chris Hill talks with him about:

• The $56.56 mortgage payment that haunted his grandfather and shaped Moore's relationship with debt

• Why developing a "peasant mentality" about money is not all bad

• How marriage, more than almost anything else, predicts financial success

• What the animated movie Ratatouille gets right about wealth and talent

For nearly two decades, Marc Goldman was the voice of the Marine Corps Marathon — running marketing, communications, and sponsorships for one of the most prestigious road races in America. Five years ago, he walked away from that stability to launch Event Voice, his own announcing and event strategy business. In this conversation, Marc and Chris Hill explore:

• Why the pandemic became the catalyst for a career leap Marc had been quietly building toward for years

• How he thought through the financial reality of trading a steady paycheck for the uncertainty of solo entrepreneurship

• A money philosophy he and his wife established on their 1st date

• The way "Die With Zero" by Bill Perkins changed how he thinks about saving, spending, and the purpose of money

• What it's like to announce the Berkshire Hathaway 5K in Omaha, where runners arrive from every corner of the world united by their faith in Warren Buffett

Ben Carlson has a simple philosophy when it comes to money — and life: less is more. He writes it in every book he signs. It sounds obvious, but most people never actually live it.

He’s the co-host of Animal Spirits and author of the brand-new book, Risk and Reward: How to Handle Market Volatility and Build Long-Term Wealth.
Chris Hill talks with Ben about:

• The lesson his late brother Jon taught him about risk and money

• Growing up in Michigan with frugal parents and a dad whose only financial advice was "never carry a credit card balance"

• What it was like to sit in the room during the 2008 financial crisis and watch the smartest people he'd ever met choose fear over opportunity

• Why he gave his wife a PowerPoint presentation about investing before they got married — and how far she let him get

Dan Caplinger has spent most of his career helping people understand money — first as a tax and estate planning attorney, then as a longtime writer at The Motley Fool.

But the financial lessons that shaped him most started long before any of that: skipping school lunch to save a few dollars, counting coin rolls with his mom, and learning the hard way that a $60 Pac-Man game isn't what a nine-year-old thinks it is. Chris Hill talks with Dan about:

• What the billable-hours model of law firms taught him about misaligned incentives

• How he and his wife structured their finances before getting married

• One change he would make to the US tax code

• The money lesson he wishes he'd learned at 19