Billionaires don't retire

Kevin O'Leary ($400 million), Barbara Corcoran ($100 million), and Robert Herjavec ($300+ million) all keep working despite having far more than the $1.46 million most Americans need to retire comfortably.

Their shared money rule

All three Sharks follow the same principle: keep money and family completely separate. They say mixing finances with loved ones complicates relationships and creates conflict.

“Money complicates relationships, relationships with your friends, family … so when you don't have a lot of money, things run smoother.”

Herjavec: gifts, not loans

Robert Herjavec refuses to loan money to family or invest with them in business, even though all his adult children have successful careers. He will give money as a gift if there's a genuine need.

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

O'Leary's one-time gift rule

Kevin O'Leary gives generous one-time gifts instead of loans, then makes it clear the conversation is over. He believes loans create entitlement and prevent people from taking risks.

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

Most retirees aren't following this

A 2025 AARP survey found 75% of parents are financially supporting adult children, with a median contribution of $1,400 a year. Of those, 42% said it's causing them financial stress.

The retirement threat

More than a third of parents say supporting adult children is hurting their own finances. Thirty six percent worry it could damage their retirement plan, and 35% report emotional stress from the arrangement.

The loan problem

Fifty six percent of adults aged 50 to 64 and 61% aged 65 or older have loaned money to family or friends and expect repayment. Financial advisors warn this is risky because loans often don't get repaid.

“If you're going to lend money, you should assume that you might not be repaid.”

Tax and legal complications

Gifts of $19,000 or more trigger federal gift tax. Loans of $10,000 or more require IRS minimum interest rates. Withdrawals from retirement accounts for loans may also be taxed.

Run the numbers first

Before lending or gifting money, work with a financial advisor or tax attorney to see how it affects your short-term and long-term security. If you can't afford it, you need to say no.