Kevin O’Leary told a podcast host he stayed married because losing two thirds of your wealth is “the stupidest thing you can ever do”

Shark Tank star Kevin O’Leary has a blunt take on divorce: it is one of the worst financial decisions a person can make, and staying married even in an imperfect relationship is the smarter economic play. The 71-year-old entrepreneur, who has been married to his wife Linda since 1990, made the comments during an appearance on The Diary Of a CEO podcast. He did not hold back on the numbers.

O’Leary told the podcast host that if you are happy 51 percent of the day with your spouse, you should stay with them. As reported by UNILAD, his core argument was simple: splitting up means paying the person you are divorcing and also paying the government a third through capital gains taxes and the forced liquidation of assets. He put it plainly: “You are going to wipe out up to two thirds of your wealth.”

O’Leary went further, suggesting that it took a lifetime to build a nest egg and that anyone considering divorce should think carefully before dismantling it. He also argued that sometimes the person pursuing the divorce is the source of the problem, and they might be better off simply staying single rather than entering another economic union.

The financial reality of divorce is more complicated than most people realize

The tax consequences of splitting up are often overlooked in favor of the emotional side of a separation. As detailed by Schwab, most US states follow equitable distribution rules, dividing assets based on factors like the length of the marriage and earning potential, while nine community property states including California and Texas split marital earnings down the middle. Cash transfers between spouses under a divorce decree generally avoid gift taxes, but selling a home or liquidating a brokerage account can trigger significant capital gains liability, and real estate exemptions require proving the seller lived in the property for two of the past five years.

Brokerage accounts carry their own complications, with after-tax value varying widely depending on how long assets have been held and each spouse’s tax bracket. Assets held for a year or less are taxed as ordinary income at rates up to 37 percent, while long-term holdings attract lower capital gains rates.

Retirement funds like 401(k)s and pensions require a Qualified Domestic Relations Order to avoid early withdrawal penalties and unwanted tax hits, adding yet another layer to the process. Amid Trump’s $1.8 billion anti-weaponization fund renewing debate about tax settlements and government money, O’Leary’s warning about handing the government a third of assets during a divorce reflects a concern that applies well beyond celebrity finances.

O’Leary has always been vocal about practical money habits. He and Linda built several businesses together, including O’Leary Wines where she serves as vice president of marketing, and he famously kept his own wedding low-key by hosting friends at home with pizza and beer to avoid going into debt. Those savings went toward Softkey Products, the company he eventually sold to Mattel for billions in 1999.

A billionaire who lost a $45 million crypto investment after a deal soured illustrated the point O’Leary has long made: once money is committed to a bad economic decision, recovering it is rarely straightforward.