Warren Buffett Shares Biggest Investing Mistakes — $433M Deal That Cost Berkshire Billions And Trillion-Dollar Tech Stocks He Missed

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Warren Buffett, the CEO of Berkshire Hathaway BRK BRK.B)), is renowned in the world of investing and leadership. With Berkshire valued at around $990 billion, his annual letters to shareholders are highly anticipated for insights into markets and governance. In this year's letter, he admitted to past mistakes, and reconfirmed his commitment to transparency and lifelong learning.

Buffett on Mistakes and Leadership

In his letter, Buffett emphasized the need to address mistakes quickly. He referenced his late business partner, Charlie Munger, who coined the term "thumb-sucking" to describe the danger of inaction when faced with errors. "Problems can't be wished away – they demand immediate action," he said. 

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This kind of honesty appears to be rare among CEOs. Many corporate leaders avoid using words like "mistake" or "wrong" in official communications and instead downplay setbacks. Buffett has made those words a staple in his letters, and that's what makes him accountable.

Buffett's record isn't perfect and he knows it. One of his biggest blunders was the 1993 acquisition of Dexter Shoe Company for $433 million in Berkshire stock. The deal ended up being worth billions in shareholder value, and he later called it the "worst deal." Another costly mistake was investing in ConocoPhillips at the peak of the oil prices, which resulted in significant losses.

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He also misjudged IBM, and missed the opportunity to invest in Amazon and Google in the early days. He now calls those "errors of omission." Those are valuable lessons for investors who worship Buffett.

Beyond investing mistakes, Buffett acknowledges management mistakes. He has admitted to errors in evaluating executives and calls poor leadership choices "a bad marriage". To ensure a smooth transition, he has named Greg Abel as his successor. According to The Economic Times, Abel's ability to balance operational excellence with strategic foresight makes him the natural choice to lead the company forward.

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Investors like Bill Ackman are confident Abel can unlock more value within Berkshire's businesses and drive better operational efficiencies. Berkshire Hathaway has $334.2 billion in cash, the most ever, and Buffett says it's because of high stock prices. According to The Wall Street Journal, this huge war chest will allow Berkshire to buy during a market downturn.

However, some analysts say this large cash position means there are no good investment opportunities or Berkshire is being too cautious. As noted by Merrill Lynch, holding too much cash could lead to lower long-term returns. Some say deploying capital into undervalued assets, even in a high-valuation market, will yield better results than sitting on the sidelines.

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