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”