Your Money Guide on the Side31 Maalis 2025

On Playing to Win (The Asymmetry of Opportunity)

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Jess Inskip where we answer the question, How do I fight against misinformation? Most people spend their lives trying not to lose. The wealthy? They play to win. In this solo episode, Tyler Gardner breaks down the asymmetry of opportunity—why one big win can outweigh dozens of small failures, and how our fear of loss keeps us from seeing the upside that could change everything. Tyler takes you from Disney’s acquisition of Pixar to Jeff Bezos’ “regret minimization framework,” unpacks the psychology of loss aversion, and explains why Monte Carlo simulations, the Kelly Criterion, and even barbell investing can help you make better decisions in life and money. You’ll also learn: Why we overweight risk and underweight opportunity How only 4% of public companies have driven all net market gains (ASU study) What venture capital teaches us about failure and power laws Why the S&P 500 has never lost money over any rolling 20-year period (Fama/French) The exact 3-question framework the wealthy use to evaluate high-stakes decisions Whether you’re building a business, investing for your future, or just trying to get out of your own way, this episode will help you rewire your decision-making process and start playing for upside. 🧠 It’s not about taking reckless risks—it’s about taking the right ones. 📈 Learn how to structure your decisions like a builder, not a hedger. — For more insights, visit tylergardner.com, and subscribe to Tyler’s weekly newsletter for 3 actionable financial ideas every Sunday. Follow Tyler on all platforms @socialcapofficial (IG + YT) and @socialcap (TT)

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