How to avoid the biggest mistake in investing: expert

Three financial commentators reveal the decisions that cost them millions of dollars, and hope others can learn from their errors.

| More on:
A group of disappointed board members.

Image source: Getty Images

You’re reading a free article with opinions that may differ from The Motley Fool’s Premium Investing Services. Become a Motley Fool member today to get instant access to our top analyst recommendations, in-depth research, investing resources, and more. Learn More

If you were asked what your biggest investment mistake was, you'd likely think of a stock that almost shrunk to $0.

But one expert reckons that would not be your biggest error.

US financial expert Brian Feroldi, in his Long-Term Mindset newsletter, revealed some of the startling mistakes he and his fellow commentators have made over the years.

"In 2009, Brian Stoffel sold Alphabet Inc (NASDAQ: GOOGL) for a split-adjusted US$10 per share. He's missed out on 820% returns — a mistake costing tens of thousands of dollars," said Feroldi.

"In 2007, Brian Feroldi sold DexCom Inc (NASDAQ: DXCM) for a split-adjusted US$2 per share. He's missed out on 5,800% returns — a mistake costing hundreds of thousands of dollars."

Those are painful enough, but the third error was a whopper.

Brian Withers sold Netflix Inc (NASDAQ: NFLX) shares in 2010 for a split-adjusted US$20.

"He missed out on 1,500% returns. Because it was his largest position, this mistake cost him millions of dollars."

Loss aversion

What do these massive mistakes have in common?

They were all bad selling decisions rather than buying errors.

And the same motivator was behind the sale of all three shares — loss aversion.

Loss aversion is the psychological phenomenon that sees humans trying a lot harder to protect what they have than to gain the same amount.

"Stoffel sold Google because he couldn't believe that he'd made a quick thousand dollars. Feroldi wanted to lock in a small profit while he could," said Feroldi.

"Withers — sitting on 20-bagger returns — was worried about losing all he'd gained."

Look at the business, not the stock

According to Feroldi, each expert was so anxious about losing capital that "we lost sight of what actually mattered".

That's the long-term potential of the businesses.

So the three Brians are urging all long-term investors to learn from their mistakes and do exactly that.

"If we had looked at the businesses instead of the stocks, we'd likely have stayed put," said Feroldi.

"Holding great companies for long periods of time isn't easy. But, selling a future mega-winner early is one of the most costly investing mistakes that you can make."

Should you invest $1,000 in Dexcom, Inc. right now?

Before you buy Dexcom, Inc. shares, consider this:

Motley Fool investing expert Scott Phillips just revealed what he believes are the 5 best stocks for investors to buy right now... and Dexcom, Inc. wasn't one of them.

The online investing service he’s run for over a decade, Motley Fool Share Advisor, has provided thousands of paying members with stock picks that have doubled, tripled or even more.*

And right now, Scott thinks there are 5 stocks that may be better buys...

See The 5 Stocks *Returns as of 6 March 2025

Suzanne Frey, an executive at Alphabet, is a member of The Motley Fool’s board of directors. Motley Fool contributor Tony Yoo has positions in Alphabet. The Motley Fool Australia's parent company Motley Fool Holdings Inc. has positions in and has recommended Alphabet and Netflix. The Motley Fool Australia's parent company Motley Fool Holdings Inc. has recommended DexCom. The Motley Fool Australia has recommended Alphabet, DexCom, and Netflix. The Motley Fool has a disclosure policy. This article contains general investment advice only (under AFSL 400691). Authorised by Scott Phillips.

More on Investing Strategies

Cubes placed on a Notebook with the letters "ETF" which stands for "Exchange traded funds".
ETFs

If I could only buy 1 ASX ETF, it would be this one

This ETF simply covers all bases...

Read more »

A woman sits in a cafe wearing a polka dotted shirt and holding a latte in one hand while reading something on a laptop that is sitting on the table in front of her
Dividend Investing

Here's what CBA, Fortescue, and BHP investors are paying for their dividend DRP shares

The recent market fall means investors using dividend reinvestment plans will pick up more stock for lower prices.

Read more »

A young woman dressed in street clothes leaps happily in the air with the focus on her bright red boots that are front and centre for the camera.
Dividend Investing

I think these 2 ASX income stocks offering big yields are a buy

These stocks offer impressive yields and upside, in my view.

Read more »

Hand holding Australian dollar (AUD) bills, symbolising ex dividend day. Passive income.
Growth Shares

Got $2,000 to invest? These ASX shares could rise 30% to 60%

Analysts are tipping these shares to rise strongly from current levels.

Read more »

Three business people join hands in strength and unity
Blue Chip Shares

2 strong ASX 200 blue chip shares to buy after the market selloff

Analysts have good things to say about these blue chips.

Read more »

Middle age caucasian man smiling confident drinking coffee at home.
Dividend Investing

Buy and hold these top ASX dividend shares  for 10 years

Analysts think these shares could be top long term picks for income investors.

Read more »

A man holding a cup of coffee puts his thumb up and smiles while at laptop.
Growth Shares

Macquarie tips these ASX growth shares as buys

The broker is feeling bullish about these top shares. Let's see why.

Read more »

A man slumps crankily over his morning coffee as it pours with rain outside.
Dividend Investing

Why is the New Hope share price sinking 6% today?

Why are investors heading to the exits? Let's find out.

Read more »