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Kevin O'Leary Sounds Alarm on Rich Kids' Upbringing: 'They Become Lost in a Sea of Mediocrity, It's a Disaster for Them'

Bibhu Pattnaik
August 23, 2025

Kevin O’Leary has divulged his five most important tips on wealth management and life.

What Happened: O’Leary, who sold his software company to Mattel in 1999 for a staggering $4.2 billion, shared some valuable advice.

His five crucial tips are: stop squandering money, concentrate your efforts, listen more than you talk, address financial matters early in a relationship, and instill self-reliance in children.

Speaking with the Insider O’Leary said, “Stop buying $7 coffees. Don’t pay 40 bucks for lunch. Make it yourself. Ask yourself every time you’re about to buy something: Do I really need this?”

O’Leary underscored the necessity of financial prudence, cautioning against frivolous spending. He further highlighted the importance of investing, stating that an individual earning $70,000 annually could retire a millionaire if they consistently invest 15% of their monthly income in a diversified portfolio from their late 20s until the age of 65.

O’Leary emphasized the power of active listening, calling it a “superpower.” “You have to learn how to shut up,” he added.

Also Read: Kevin O’Leary Advocates Entrepreneurship Over Consulting to Students: ‘Why Would Anybody Burn All Those Hours While Someone Else Makes Money?’

“It’s akin to having your ear to the rail and hearing the train coming down the track that’s going to run you over,” O’Leary said, adding, “To know to get off the track. That’s what listening does,” O’Leary continued.

Regarding productivity, O’Leary suggested identifying three primary tasks each day and focusing on their completion. He also encouraged employees who find themselves in disagreement with their company’s direction to explore other job prospects.

He also suggested discussing financial matters by the third date and signing a prenuptial agreement before tying the knot.

Lastly, O’Leary cautioned against the “curse of entitlement” for the offspring of wealthy parents, recommending teaching self-reliance to evade a “sea of mediocrity.”

“The risk in their life has been removed. They’ve been guaranteed a free ride for the rest of their lives. They become lost in a sea of mediocrity. It’s a disaster for them,” he said.

O’Leary’s advice comes from a place of experience and success, making it invaluable for those seeking to improve their financial situation and life management skills.

His emphasis on financial prudence, investing, productivity, communication, and self-reliance are key principles that can guide individuals towards a prosperous and fulfilling life.

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