All episodes of The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network

The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network · 2026-04-05 · 68 min · 13,450 words

TIP805: Stock Market Maestros w/ Kyle Grieve

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You're listening to TIP. The world's best investors are wrong more often than they are right. Let that sink in for a minute. The elite investors profiled in today's episode had a median hit rate of only 49%. This means they actually lost money on the majority of their picks.

However, they have also dramatically outperformed the market. How is this even possible, you may be wondering? They made a lot more money on their winners than they lost on their losers. Today, we're going to look at key lessons from the book Stock Market Maestros. I honestly think this book will help reshape just how you think about portfolio management because it does an exceptional job of showing why treating your winners and losers

is vital to investing success. The problem that most investors have is that they optimize for finding the next great stock pick. But the real edge to investing lies in how you manage what's already in your portfolio. Specific strategies for how you enter and size a position, how long you hold it, and how to exit properly are more important than finding your next great idea.

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