Mad Money's Jim Cramer reveals 5 “boneheaded mistakes” he’s made over decades of investing so you can avoid costly errors

Buffett has confessed to a fair share of glaring gaffes. The same goes for Jim Cramer. The Mad Money host and author recently opened up to CNBC Make It about some of his biggest errors (2). He says learning from these “boneheaded mistakes” helped turn him into a better investor. And they can arguably help us, too, if we analyze them properly.

1. Holding losers for too long

We’re often taught to be patient, stand by our convictions and ignore outside noise. However, sometimes events happen that warrant reevaluating an investment case.

Cramer learned this lesson with Bausch Health (NYSE:BHC). When investors dumped the stock after it fell short of its profit forecasts and faced earlier-than-expected patent expirations, he shrugged it off as ignorant panic-selling. Cramer admitted that he opted to believe the company’s PR rather than investigate the warning signs — and said it cost him “a fortune.”

Holding losers for too long is one of the most widely cited blunders an investor can make (3). Nobody likes to take a loss, and this emotion can overshadow rational thinking.

Ideally, investors should objectively analyze every holding after a setback. Before buying and becoming emotionally involved with a certain portfolio choice, it’s also wise to establish a list of criteria to stay invested and potentially consider implementing a stop-loss order, which instructs the broker to automatically sell the stock if it falls to a specific price. The latter option especially makes sense with companies that have great potential and downside risk.

2. Overconfidence

Cramer fell into the trap of believing that historically well-run and legacy brands are immune to economic and political risk. But Estée Lauder (NYSE:EL) proved him wrong.

When COVID-19 hit China, Estée Lauder’s biggest market, Cramer said he assumed management would adapt and the company would bounce back as it had always done — it didn’t. Management had no response to dwindling demand or the Chinese government’s subsequent crackdown on luxury goods, and it took the stock plunging from US$370 to somewhere in the region of US$90 for Cramer to wake up and clue in.

Overconfidence and failing to respond when fundamentals shift are common errors. In a survey conducted by deVere Group, 38% of the high-net-worth respondents claimed their biggest mistake was banking on history repeating itself (4).

How can you avoid this? A good starting point is recognizing that brand strength isn’t always enough to survive setbacks, while a lack of response and downplaying major threats should be treated as red flags, even from executives with historically fantastic track records.

3. Panic-selling

Another classic mistake is panicking at the first sign of danger.

In 2023, Cramer bought Oracle (NYSE:ORCL), believing investors were undervaluing its prospects. Everything was going smoothly, he said, then other parts of the business started disappointing, analysts became bearish and an angry Cramer lost sight of why he bought the stock in the first place and dumped it — just weeks before it rebounded off encouraging AI-related developments.

That said, major developments warrant reevaluating an investment. In this case, there was no evidence to suggest the long-term drivers that convinced Cramer to buy were under threat.

Cramer let a fear of loss cloud his long-term strategy. To prevent this from happening, it can help to impose a cool-off period before pulling the trigger. Remind yourself why you invested in the first place and do your own research rather than be driven by external noise.

4. Blindly following advice

Billionaire hedge fund managers are renowned for voicing their opinions on how to invest money, and people often take the bait because they work for prestigious companies — and they’re moneyed.