Kevin O’Leary, Barbara Corcoran and Robert Herjavec all avoid mixing money and family. Why retirees should do the same

“Something I learned from my mother decades ago is that entitlement is a curse."

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Kevin O’Leary, Barbara Corcoran and Robert Herjavec all avoid mixing money and family. Why retirees should do the same
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When it comes to retirement security, Shark Tank's Kevin O'Leary, Barbara Corcoran and Robert Herjavec have it made, amassing multiples of the $1.46 million nest egg many Americans believe they need to retire comfortably.

According to The Street, real-estate maven Corcoran, 77, is worth an estimated $100 million. O'Leary, 72, who became a millionaire when he sold his software company Softkey to Mattel for $4.2 billion in 1999, is worth $400 million. Tech security pro Herjavec, 63, is worth north of $300 million.

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Notably, none of them have retired, even though they have the money to do so. They keep on investing, building both their wealth and their brands as celebrity millionaires — followed by millions of people of all ages, including older Americans.

But all three Sharks have advice that retirees in particular would do well to heed: avoid mixing money and family.

"Money complicates relationships, relationships with your friends, family … so when you don't have a lot of money, things run smoother," Corcoran told CNBC Make It.

Here's what these sharks do to prevent money conflicts with family, and why that's especially important for retirees who may not have the level of wealth that they've achieved.

Sharks don't loan money to family members

Herjavec made his position on money and family clear in a social post, saying he keeps business and family separate. All his adult children have successful careers, but he hasn't hired any of them or partnered with them on business ventures.

"I will never lend money to family and I won't invest with family," he said. "I will give money to family if they need it and there's a good reason."

O'Leary follows the same playbook and applies the strategy with immediate and extended family members who come to him for cash.

"I don't want to loan anybody money. I don't want anyone to owe me or to drive a wedge in my family," he told Business Insider. "So, instead, I'll agree to a one-time gift."

He makes it a generous gift and does so happily, not expecting repayment. Then he shakes on it and tells the recipient they are never to talk about the gift — or ask for more money — ever again.

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Where this came from

This story was reported and first published by Yahoo Finance on 16 September 2026. HUE Legacy Ventures did not write it.

Carried in full with attribution and a link to the original. Rights remain with the publisher, who may request removal at any time.

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