Brian Feroldi grew up in Rhode Island as a born saver — the kind of kid who hoarded his lunch money candy rather than eating it, just to watch his collection grow. His dad was a CFO. His mom raised money for the ALS Association. Nobody sat him down and explained how investing worked. That part he had to figure out on his own.
A financial educator, YouTuber, and author of the book Why Does the Stock Market Go Up?, Brian joins Chris Hill to talk about the long road from money-illiterate college graduate to one of the most-followed investing educators on the internet. He shares:
- Why he chose his college major purely to save $5,000 a year in tuition — and why the classroom demographics sealed the deal
- How 40,000 miles a year on the road became an unlikely PhD in business and investing, while his coworkers listened to Howard Stern
- What Charlie Munger understood about incentives that most investors still get wrong — and why stock-based compensation at most public companies is completely broken
- Why he regrets his MBA (and it’s not because of the money it cost)

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Opening clip – “Neal Brennan: 3 Mics”

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

What's the last thing you splurged on? info@moneyunpluggedpod.com.

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Opening clip – “Landman”