When Blunders Become Billions: My 'Embarrassing' Investment Mistakes That Paid Off Big

In the unpredictable world of investing, we often hear about the triumphs, the brilliant insights, and the perfectly timed moves. But what about the moments of doubt, the decisions that felt utterly wrong at the time, yet somehow blossomed into significant victories? Today, I want to pull back the curtain on two such 'embarrassing mistakes' from my own portfolio – decisions that flew in the face of conventional wisdom, left me questioning my sanity, and ultimately, made a lot of money.

My journey through the stock market has been anything but linear, and these two particular instances stand out as powerful lessons in conviction, patience, and the art of ignoring the noise.

They serve as a testament to the idea that sometimes, the best investment decisions don't look like them at all when you're making them.

Mistake #1: Not Selling Google (GOOGL) – The Perpetual 'Overvaluation' Paradox

Ah, Google. Or rather, Alphabet. It’s a company that has consistently been deemed 'overvalued' for what feels like an eternity.

For years, financial commentators, analysts, and even my own internal voice whispered that Google's valuation was stretched, its growth slowing, and that it was high time to lock in profits. Every earnings report that showed slight decelerations, every market correction, every new competitor on the horizon felt like a sign to exit this 'obviously' overextended position.

The 'embarrassment' wasn't just holding a stock that many considered ripe for a fall; it was the persistent internal battle against what felt like common sense.

Logic dictated that I should sell, take my gains, and reinvest in something 'safer' or 'cheaper.' Yet, something held me back. Perhaps it was a deep-seated belief in the company's innovation engine, its ecosystem dominance, or simply the inertia of a long-term holder. Whatever it was, I stuck with it.

And what happened? Google continued its relentless march upward.

Despite the cyclical dips and the constant 'overvaluation' narrative, the stock delivered substantial returns year after year. The 'mistake' of not selling became a highly profitable act of omission, teaching me a profound lesson: sometimes, true quality, even at a seemingly high price, justifies long-term conviction.

Market narratives about 'overvaluation' can often miss the forest for the trees when it comes to truly exceptional companies.

Mistake #2: Buying Palantir (PLTR) – The Contrarian Bet on a Controversial Tech Innovator

My second 'embarrassing mistake' involved a far more audacious and controversial move: initiating a position in Palantir (PLTR).

When I bought into Palantir, it was a poster child for speculative growth, a 'meme stock' darling for some, and an overhyped, unprofitable enigma for many others. The company's unique government contracts, its opaque operations, and its lofty valuation in the direct listing phase drew immense skepticism.

The common refrain was clear: 'Stay away from this one, it's pure speculation!'

Buying Palantir felt like walking into a financial minefield. It was embarrassing to admit to peers that I was taking a significant stake in a company that many seasoned investors were openly deriding. The 'mistake' here was going against the overwhelming negative sentiment, ignoring the warnings about its high P/S ratio and its perceived lack of clear profitability path.

Yet, beneath the noise, I saw something compelling: a powerful, enterprise-grade data analytics platform with sticky, mission-critical applications for both government and commercial clients. I believed in the long-term vision, the unique technology, and the massive, untapped market potential, even if the near-term financials looked challenging.

The market, in its unpredictable wisdom, eventually recognized the value.

After a period of volatility, Palantir's stock surged dramatically. My contrarian bet, which felt like a reckless gamble at the time, transformed into one of the most significant wins in my portfolio. This experience underscored the power of independent research, conviction in a company's fundamentals despite popular opinion, and the willingness to take a calculated risk when others are fearful.

The Unconventional Wisdom of Profitable Blunders

These two 'embarrassing mistakes' weren't just lucky breaks; they were profound learning experiences.

They taught me that investment success often isn't about perfectly timing the market or slavishly following consensus. Instead, it's about:

• Conviction in Quality: Sometimes, holding onto a truly great company, even when it appears expensive, can be a winning strategy over the long run.
• Challenging the Narrative: Don't let popular sentiment dictate your decisions entirely.

  Dig deeper, understand the business, and form your own educated opinions.

• Patience and Long-Term Vision: Both Google and Palantir required patience. Short-term fluctuations and criticisms can obscure the long-term growth trajectory.
• The Courage to be Contrarian: When everyone is telling you to zig, sometimes the most profitable move is to zag, provided you've done your due diligence.

These stories aren't an endorsement of reckless investing, but rather a reflection on how sticking to your guns, even when it feels uncomfortable, can lead to extraordinary outcomes.

My biggest 'mistakes' turned out to be some of my best decisions, proving that in investing, as in life, growth often happens outside your comfort zone.