Position Sizing – The Most Overlooked Skill in Investing

In Episode 19, we explore the underrated art of position sizing - the skill of knowing how much to invest in any single stock, ETF, or asset. You’ll learn why “how much” often matters more than “what,” and how concentration vs. diversification impacts both your upside and your risk. We discuss simple position sizing frameworks for beginners, as well as more advanced methods used by pros, like Kelly Criterion and volatility-adjusted weighting. The episode also covers common mistakes — like going all-in, averaging down blindly, or spreading yourself too thin. Smart position sizing is what keeps you in the game when things go wrong and multiplies gains when you’re right.