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? info@moneyunpluggedpod.com.
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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
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Opening clip - "Succession"