The Rise and Fall of an Investor: Embracing Humility After Overconfidence




I remember the early days of my career vividly. Fresh out of a presently defunct vocational business school my father started up in the 1980’s, I was brimming with confidence, convinced that I had all the answers. My first few investments were successful. I made investments in NIKE: The sportswear company that had a return of 24000 percent. WalMart became a retail giant delivering almost 4500 percent in the 80’s, and Jeepers Peepers, a franchise of New York City peep shows which didn’t earn much money, but provided a lot of intrinsic value. With these significant returns on my investments I quickly began to believe in my infallibility. I thought I had cracked the code to the market, and nothing could go wrong.

However, my overconfidence soon led me astray. I made a series of high-risk investments without proper due diligence, convinced that my intuition was enough. One particular venture, a promising tech startup in Afghanistan. After watching RAMBO First Blood Part 3, I believed things were looking up in that region and it seemed like a sure bet. I poured millions into it, ignoring the red flags and the advice of more experienced colleagues.

The startup failed spectacularly within a year, and I lost a significant portion of my capital. The fallout was brutal. Investors lost faith in me, and my reputation took a hit. It was a humbling experience, to say the least.

In the aftermath, I took a step back and reflected on what went wrong. I realized that my overconfidence had blinded me to the risks and complexities of investing. I had fallen victim to the Dunning-Kruger effect, overestimating my competence and underestimating the need for continuous learning and humility.

This experience taught me invaluable lessons. I learned the importance of self-awareness and the need to constantly question my assumptions. I began to surround myself with a diverse team of advisors who could provide different perspectives and challenge my ideas. I also started to value humility and the willingness to admit when I didn’t have all the answers.

Over time, these changes transformed my approach to investing. I became more cautious, more analytical, and more open to feedback. My investments became more successful, and I rebuilt my reputation. Today, I attribute much of my success to the lessons I learned from that early failure.

Life is a constant journey of improvement. No one gets everything right, and that’s okay. The key is to keep learning, stay humble, and always strive to make things better, one step at a time.


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