Why Kevin O'Leary Won't Leave His Kids an Inheritance

Kevin O'Leary has built enough wealth to make work optional for his children. Instead, the famed investor is not giving them an inheritance. The money will instead go to charities and an intergenerational trust that skips over his kids.

While I often disagree with O'Leary's heavy-handed approach, his reasoning makes a lot of sense. I'm a married mother of two children who will likely inherit nothing. They're getting an excellent start in life, and each has a college savings account. I will help them pay for higher education, but I refuse to imperil my retirement or go into debt to do so.

Children entering adulthood need a loving family, not fat checks. O'Leary believes they also need financial incentive to work hard and get off on the right foot. His approach begs questions: How much should we leave our children, and when does support risk becoming harmful?

Guaranteed wealth kills ambition

O'Leary's objection is not simply that inherited wealth might be wasted (it's usually squandered by the third generation). He believes eliminating financial risk deprives children of struggle that drives self-development.

"You curse a child when you de-risk their lives," says O'Leary.

He's got a point. Seeing your kid struggle is not the same thing as watching them suffer. I want my kids to learn to manage setbacks, but not inflict deliberate harm, and offer more emotional support than fiscal aid.

The cutoff comes after college, not childhood

Having a college degree is no longer the key to lifelong financial success. But paying for your child's education, from birth through college, like O'Leary, can be an excellent start. Especially if you're guiding your child to a pragmatic, marketable degree.

As O'Leary began teaching his children about money from the age of four, he gave all the foundational tools they needed to make it.

His mother established the same expectation

O'Leary credits his philosophy to his mother, who told him her financial support would end after college. She strongly disliked entitlement, and believed parents should prepare children for independence.

My children, now ages 8 and 5, hear a similar message. I've repeatedly told them I will help them acquire the credentials they need to earn their own money, after which assistance will come in the form of a free lumpy couch to crash on.

Education itself is an inheritance

You don't need O'Leary's fortune to borrow from his strategy. Funding tuition, vocational training, or another path toward employability provides better lasting value than a fat inheritance. A debt-free education is a phenomenal head start in life.

Without student loans, a child can take a lower-paying job, internship, or volunteer opportunity for resumé "pedigree" – prestigious bullets that will give them a bankable leg-up for years to come.

Milestone support may offer another middle ground

Inheritance planning does not have to be a choice between leaving everything or leaving nothing, or stopping all support after college. Some parents help with specific milestones, such as a first home, graduate school, or the birth of a child.

Some may give "inheritance" help while they are alive, so they can see their children succeed and offer guidance. Others may use an estate plan to release funds at certain ages or for designated expenses.

The goal is determining what kind of help reflects your family's values.

A generous inheritance is not automatically harmful

O'Leary's conclusion is not for everyone. An inheritance may help an adult child buy a home, care for family members, or take a worthwhile career risk they otherwise could not afford.

Financial security does not automatically destroy motivation, just as financial hardship does not automatically build character. Much depends on the recipient and family structure.

The right amount depends on the child

Fairness is another conundrum. When planning your estate, you want to deal equally. But what if one child lives in Washington, D.C. and does humanitarian work, while another owns their house outright and makes twice as much?

And pre-death gifting, in the form of tuition, poses ethical considerations too. One child may get a full ride or go to community college while another goes to Harvey Mudd College (with an annual cost of attendance of $104,512).

Equal financial gifts and equal inheritances are inherently unequal. Children do not have the same needs, ambitions, or abilities.

But giving consistent, universal guidance may help. My children have similar ambitions and inclinations – probably because I give them the same lectures about college costs and salary forecasts.

"You can be whatever you want" – but with caveats. "If you're a balloon-twirling cookie baker, I'll love you. But let me paint you a picture of the kind life you'll be able to afford."

Talk about the plan before it becomes a surprise

You don't have to settle on, or declare, an amount today. But talk. Inheritance conversations are just as important as the amount itself, especially if the amount will be $0.

Children who grow up expecting one outcome and discovering another after a parent's death may interpret it as punishment, favoritism, or a final character judgment.

If you will leave your kids (or your kids' kids) money, establishing a trust with provisions for different contingencies can help protect funds from being squandered.

Bottom line

Kevin O'Leary's estate plan provides his children with advantages, but no income, compelling them to hustle.

Middle-class families may lack his financial resources, but should still consider O'Leary's approach as they reflect on what legacy they want to impart.

An estate-planning attorney can explain which tools may fit, and help transform good intentions into clear instructions that can be formally carried out.

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