Michael Batnick’s "Big Mistakes. The Best Investors and Their Worst Investments" contains plenty of teeth-gnashing gaffes made by some of the biggest names in finance.

But the most painful investment miscue he details has to be the following:

"You know Steve Jobs and his partner Steve Wozniak, but the name Ronald Wayne likely means nothing to you. Wayne was the third founder of Apple, but the reason his name is erased from the history books is because in 1976 he sold his 10% stake in the company for $800. Apple is currently worth north of $900 billion!" writes Batnick, a CFA and director of research at Ritholtz Wealth Management, New York.

Cases of poor judgment, hubris, over-confidence and slavish occupation with how the competition is faring have afflicted a Who’s Who of the financial world, from John Maynard Keynes to Benjamin Graham, and including Jack Bogle, Warren Buffett, Stanley Druckenmiller and Bill Ackman.

Buffett and his Berkshire Hathaway partner, Charlie Munger, make investments based on their "circle of competence," which led them to pass on buying into Walmart. But they did buy a Maine shoe company (Dexter).

Batnick tells us that in 1993, "Berkshire agreed to buy Dexter Shoes for $433 million. But it wasn’t just that this business would be worth zero a few years later that was the problem; it was the stock that Berkshire issued to pay for it. The shares were trading for $16,765 at the time of the transaction. Today, at $242,000, the 25,200 shares that they exchanged for Dexter have grown 1350%." That translates into $6 billion.

Buffett said "As a financial disaster, this one deserves a spot in the Guinness Book of World Records."

Bill Ackman and his Gotham Partners co-founder, David Berkowitz, made the mistake of "straying from where their bread was buttered"—classic, old-school value investing—by buying unpopular companies that were not in demand. Although they turned their $3 million start-up investment into $568 million by 2000, they closed the fund in 2002, nine years after it began.

Keynes, the English economist who is credited with building the global monetary system, and who designed England’s financing of World War II and wrote international best sellers, was a driven investor, as well. A currency syndicate he founded in 1920 that shorted French and German money was wiped out with the return of post-war optimism, and his commodity syndicate that invested in tin, wheat and cotton lost its capital when a financial crash decimated the commodity market.

"He suffered from the illusion of control. He thought that by trading so frequently he could control his own destiny and achieve success. He was wrong," Batnick writes.

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