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
Why do YOU listen to Money Unplugged? Tell us at info@moneyunpluggedpod.com.

Want to invest like the pros? Try TIKR for free at tikr.com/unplugged.

Opening clip – “Moneyball”

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.

Discover Mar Mar, the chili garlic flavor that goes on everything. Go to ilovemarmar.com and use the promo code “MONEY” for 10% off.

Opening clip – “Wall Street”

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
Opening clip – “The Color of Money”

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
Got a question for the show? Email info@moneyunpluggedpod.com.
Want to instantly improve your cooking? Go to dizzypigbbq.com and use the promo code “MONEY” to get 10% off your 1st order.
Opening clip – “Sex and the City”

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
Discover Mar Mar, the chili garlic flavor that goes on everything. Go to ilovemarmar.com and use the promo code “MONEY” for 10% off.
(And if you want the recipe for Chocolate Mar Mar ice cream that Chris made just email info@moneyunpluggedpod.com)
Opening clip – “The House”

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
Want to invest like the pros? Try TIKR for free at tikr.com/unplugged.
What's your biggest money regret? Tell us at info@moneyunpluggedpod.com.
Opening clip – “The Dark Knight”

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)
To read more from John, check out his Substack!
Discover Mar Mar, the chili garlic flavor that goes on everything. Go to ilovemarmar.com and use the promo code “MONEY” for 10% off.
What's your favorite movie or TV series about money? Tell us at info@moneyunpluggedpod.com.
Opening clip – “Moneyball”

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
What's the last thing you splurged on? Tell us at info@moneyunpluggedpod.com.
Want to instantly improve your cooking? Go to dizzypigbbq.com and use the promo code “MONEY” to get 10% off your 1st order.
Opening clip – “The Big Short”