Money Unplugged with Chris Hill Skin in the Game: Why Your Investments Should Match Your Convictions (Brian Stoffel)
Apr 24, 2026
Brian Stoffel, co-founder of Long-Term Mindset and former middle school teacher turned investor. He recounts a Taleb-inspired experiment showing that stocks he actually owned beat those he only praised. Listens to antifragility, seeks companies that thrive under stress. Talks about his unconventional path from Iowa classrooms to Costa Rica and why conviction matters in investing.
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Double Your Time And Cost Estimates
- When estimating time and cost, double both numbers as Brian's father advised to avoid underestimating projects.
- Brian recounts his dad's specific rule: whatever you think it will cost and how long it will take, double both figures.
Grinnell Basketball Shaped Investing Style
- Brian credits Grinnell College basketball's high-scoring, analytic approach for inspiring his Rule Breaker investment mindset.
- He describes coach Dave Arseneault's system that emphasized rapid threes and setting picks after shots, which taught unconventional thinking.
Prioritize Shared Frugal Values
- Live well below your means and prioritize shared financial values in a partnership.
- Brian and his wife, both teachers, intentionally saved and didn't make maximizing net worth their primary goal.
