MW What investors can do about seller's remorse - and how to decide when to buy a stock back

By Weston Blasi

Regret selling a stock or asset too early? That's something that happens to billionaires, too.

That feeling when you realize you sold your Nvidia shares way too early...

Sometimes, you only recognize an investment's value once you let it go.

Take tech billionaire Mark Cuban, who sold a majority stake in the NBA's Dallas Mavericks to the Adelson and Dumont families in 2023 at a $3.5 billion valuation. Recently, NBA insider Marc Stein reported that local investors have expressed interest in partnering with Cuban to buy back the Mavericks, likely at a higher price.

While there have been no formal or public movements on a Mavericks sale, Stein's report illustrates how even billionaire investors aren't immune to second-guessing selling an investment, also known as "seller's remorse." Indeed, Cuban told the "DLLS Sports" podcast last fall that while he didn't regret selling his majority stake, he regretted how he sold the Mavericks - saying he "would've put it out to bid" instead.

"Seller's remorse" is generally defined as a feeling of anxiety or regret after making, or after promising to make, a sale. It's the opposite of "buyer's remorse," or feeling regret after making an investment or purchase.

"It's the regret that comes from underestimating the emotional component of selling," Bernadette Joy, a financial educator and money coach, told MarketWatch. "When you're selling, you might also be changing what identity, control and optionality looks like for you."

Joy, who has written several financial books including "Crush Your Money Goals," believes this recent situation shows that feeling regret after exiting any type of investment can happen to even the most experienced investors.

"Even though Mark Cuban is a billionaire, I think a lot of people can relate to this," she said. "They had an asset - whether it's a business, a property - sold it, and then thought, 'Oh, maybe I shouldnt have done that.'"

Of course, most investors have not sold an NBA team for billions of dollars. But let's say that an investor bought Nvidia stock (NVDA) in 2020 at roughly $6 dollars a share, and then sold their investment when Nvidia hit $32 a share one year later. That's a great trade - until you see that Nvidia is now one of the biggest companies in the world, and was trading at $187 a share as of Thursday.

In fact, American billionaire investor Stanley Druckenmiller admitted in a fall 2024 Bloomberg interview that selling almost all of his Nvidia stock too early - for somewhere between $800 and $950 (pre-stock split) - was "a big mistake," and that he was "licking my wounds from a bad sale there" and looking to buy in again if the price dropped.

This can also happen with real estate - such as selling your home for a big profit only to see its value spike years afterward, making one question if they timed their sale correctly.

What to do if you're feeling seller's remorse over a stock

Even if you are suffering seller's remorse, buying that asset back might not be the answer.

"Before buying anything back, pause and ask one disciplined question: 'If I had cash today and had never owned this, would I buy it at this price?'" Joy said. "If the honest answer is no, the regret is emotional, not financial. If the answer is yes, then it becomes a forward-looking investment decision, not a backward-looking mistake."

It's only with hindsight that investors can know for sure if they sold at the right time, at least when it comes to valuation - so it can also help to audit why you sold it in the first place, Joy noted.

"There are only a few valid reasons to sell: Your goals changed, the fundamentals changed, you needed liquidity for a higher-priority use, the position size or risk was too high," she said. "If those conditions are still true, buying back is usually a mistake. If they are no longer true, then a re-entry can be rational."

There are other factors at play when reassessing if investors sold at the right time. It's possible that Cuban, like many other investors, knew he would make a decent return on investment by holding on to the Mavericks longer, but thought he could make even more money elsewhere with that capital.

"Liquidity is freedom, and it's possible Cuban thought the money he made from selling the team could make more money elsewhere," Joy said. "Usually, people don't sell unless they are using it for something else."

The Mavericks' current owners released a statement last week that "the team is not for sale." Cuban declined to comment for this article.

Exiting an investment to deploy capital elsewhere is one reason to sell, but other factors - like reducing portfolio risk, diversifying, or major life changes such as getting married, having children or moving - can also play a role.

And keep in mind that an asset going up in value after you sell it doesn't necessarily mean it was a bad decision to sell at the time.

"Several years ago, I sold a paid-off home," Joy said. "I was traveling a lot, I was barely home, I didn't want to live in the suburbs anymore. That house I sold for $500,000 is now worth $700,000. I was able to take the money from the property and use it in other investments, and have more financial freedom."

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Risk is always part of investing, even for the most experienced traders. And one of the golden rules of investing is just how difficult it is to time the market.

"It's a fact of finance that investments carry risk - a lot of this is luck," Corey Frayer, director of investor protection at the Consumer Federation of America, told MarketWatch about timing investments.

Seller's remorse happens to everyone - even billionaires. But Frayer believes the best way to build sustainable wealth is not to stress out about the right time to sell an asset, or the feeling of regret with seller's remorse. Instead, it's to think ahead and focus on your decision-making process.

"What's important for investors is to think about the long term," Frayer said. "If you have a long-term strategy in mind, the process of building a nest egg is more important than any individual transaction."

Joy agreed: "Oftentimes, people will sell based on what's going on with them at the moment, and not thinking far enough ahead."

-Weston Blasi

This content was created by MarketWatch, which is operated by Dow Jones & Co. MarketWatch is published independently from Dow Jones Newswires and The Wall Street Journal.

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February 19, 2026 16:25 ET (21:25 GMT)

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