Kevin O'Leary has spent decades building businesses and investing in entrepreneurs, but he says one of the most important financial lessons people learn has nothing to do with the stock market or investing strategies. For parents, it starts at home.
“You shouldn’t entitle your kids. You shouldn’t give them money for nothing because that’s not how life works,” O’Leary says on an episode of the The Jaime Catmull Show.
Must Read
A dad of two, he encouraged his children to work and earn money on their own from an early age.
For O’Leary, learning how to earn money is just as important as learning how to manage it. He says children often develop a different understanding of responsibility and independence when they work toward a goal themselves instead of having success handed to them.
His approach at home was simple: college first, then independence.
“I did provide for education," he says, adding that support ends at graduation. "When you get out of school? Nothing.”
O’Leary says many parents continue financially supporting their children well into adulthood, and data has shown this to be true. According to a Pew Research Center study, 59% of parents with children ages 18 to 34 provided financial assistance in 2024, highlighting how common it has become.
That's one reason why he believes independence helps people build confidence, discipline and responsibility.
Where People Are Refinancing Their Student Loans Today
According to O’Leary, some of the most important financial lessons come through experience — whether that means getting a first job, managing spending money or understanding the actual effort required to earn something. He says he believes work ethic is one of the most valuable lessons parents can teach.
Decades of building companies and investing in entrepreneurs have confirmed for O’Leary that the core principles behind financial success remain relatively straightforward: discipline, hard work and understanding the value of money.
While technology and the workplace continue to evolve, he says he believes those lessons are timeless. O’Leary says many people focus heavily on financial outcomes later in life without teaching the habits that help create those outcomes in the first place.
And in his view, those lessons begin at home — long before someone earns a full-time paycheck or starts building wealth on their own.
