Ray Dalio tripled his money at 12 on his first stock pick — then a bad call left him borrowing $4,000 from his dad

Ray Dalio's first investment at the age of 12 was in Northeast Airlines, which went bankrupt and then was acquired by another company, tripling the value of Dalio's investment. This early success in the stock market sparked his passion for investing. However, Dalio's confidence in his ability to navigate the markets proved to be a double-edged sword.

After losing money on subsequent investments and learning the difficulties of being right, he adopted the principle "Pain plus reflection equals progress." This mindset was crucial as he later predicted a U.S. depression during an ongoing recession, resulting in significant financial losses and forcing him to borrow $4,000 from his father.

Despite these setbacks, Dalio's experience taught him the importance of humility, diversification, and dealing with uncertainty, which have remained central to his investment philosophy.