Skin in the Game: Why Your Investments Should Match Your Convictions (Brian Stoffel) episode artwork

EPISODE · Apr 24, 2026 · 29 MIN

Skin in the Game: Why Your Investments Should Match Your Convictions (Brian Stoffel)

from Money Unplugged with Chris Hill · host Chris Hill

What if the stocks you believe in the most are the ones you actually own? Brian Stoffel spent years as a teacher before stumbling into investing — and one experiment changed everything. After reading Nassim Taleb's Skin in the Game, he went back and coded 300 of his own articles into two buckets: companies he wrote about positively that he owned, and companies he wrote about positively that he didn't. The results were striking. The stocks he owned outperformed the market. The ones he didn't own underperformed — by a wide margin.Brian talks with Chris Hill about what that experiment taught him about conviction investing, why he looks for companies that get stronger under stress, and what his unconventional path (from rural Iowa to DC classrooms to Costa Rica) taught him about the relationship between money and the things that actually matter in life, as well as:- The reason he actively avoided money for most of his early life- A mistake with whole life insurance he made as a 1st-year teacher- What Nassim Taleb and a small Iowa college basketball team have in common- Why he doesn’t “fight the universe”Find more from Brian at LongTermMindset.coWhat’s your favorite movie or TV series about money? Tell us at [email protected] Markets is the best wrap-up of the day on Wall Street. Sign up for FREE at BrewMarkets.com/moneyOpening clip – “Heist”

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What if the stocks you believe in the most are the ones you actually own? Brian Stoffel spent years as a teacher before stumbling into investing — and one experiment changed everything. After reading Nassim Taleb's Skin in the Game, he went back and coded 300 of his own articles into two buckets: companies he wrote about positively that he owned, and companies he wrote about positively that he didn't. The results were striking. The stocks he owned outperformed the market. The ones he didn't o...

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Skin in the Game: Why Your Investments Should Match Your Convictions (Brian Stoffel)

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