Ray Dalio

Ray Dalio's All Weather portfolio delivered a paltry 4.8% annualized return over the last decade, lagging the simple 60/40 stock-bond mix by 2.3 percentage points per year. Despite his reputation as a market sage, his macro calls—like predicting a U.S. debt crisis in 2020 that never materialized—have been wrong 60% of the time since 2015. Outperformed by #9 Cathie Wood's ARKK on a five-year return basis (3.2% vs. 4.8%), Dalio's approach is actually slower-growing, yet he commands higher fees. When you factor in inflation, the All Weather portfolio barely broke even after 2013, exposing the disconnect between Dalio's guru status and real-world results.