Money Unplugged with Chris Hill What Do You Actually Want Money to Buy? (Tyler Gardner)
Mar 27, 2026
Tyler Gardner, a former financial advisor and portfolio manager who hosts Your Money Guide on the Side, tells the story of a Vermont childhood that shaped his money views. He explores how silence about money shaped decisions. He shares career twists from teaching to finance. He urges defining what you want money to buy and recounts memorable splurges and lessons.
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Mowing Lawns Gave Early Social Currency
- Tyler's first real income was mowing lawns for $5 which gave him social power among peers.
- He admits he stole grocery money as a kid because having cash let him buy treats and attention from friends.
Palm Beach Spring Break Exposed Generational Wealth
- At Andover Tyler glimpsed generational wealth on a Palm Beach spring break trip that revealed lifestyles far beyond his upbringing.
- That exposure shifted his ambitions toward finance and investment banking as a path to similar wealth.
Bad Retirement Talk Sparked Career Pivot
- A confusing retirement presentation by TIAA‑CREF for faculty pushed Tyler from teaching toward financial advising.
- He self‑studied Tobias, Malkiel, and others, becoming the faculty expert on fees and fund choices before switching careers.
