Kevin O'Leary Says You Should Never Do These 6 Things With Money

Kevin O'Leary built a reputation on Shark Tank for telling entrepreneurs exactly what was wrong with their pitch, no matter how much it stung. He brings the same energy to retirement planning. Ask him what people get wrong about their money in their 60s and 70s, and he doesn't hold back.

O'Leary's retirement warnings are to take care of yourself, save with discipline for decades, and don't assume anyone or anything will bail you out. He learned some of it the hard way. After selling his company Softkey for $4.2 billion in his mid-30s, he retired completely, then was bored out of his mind within a few years and went back to work. Here's what he says are the money mistakes retirees should avoid.

Carrying credit card debt into retirement

Asked what struggling Americans should do to get their finances on track, O'Leary's answer was unequivocal. He tells people to pay off their credit cards immediately. Credit cards destroy opportunities to grow wealth, he says. The math is simple. Credit card interest compounds fast, and it doesn't care whether you're collecting a paycheck or living on a fixed income.

That advice gets more urgent close to retirement. A balance that felt manageable during your working years gets a lot heavier once your income shrinks and stops growing. O'Leary treats debt elimination as something to finish before retirement starts, not something to manage alongside it.

Treating Social Security as a paycheck

O'Leary has said it's a mistake to count on Social Security as a retiree's main source of income, and the numbers back him up. The Social Security Administration's own trustees project the OASI trust fund will be depleted in late 2032, at which point it would only cover about 78% of scheduled benefits unless Congress acts.

His point is that betting your retirement on a single, government-run income stream like Social Security, one that's already facing a funding shortfall, is a fragile plan. O'Leary pushes people toward building multiple income sources, including savings, investments, and maybe part-time work, with Social Security as one piece rather than the foundation.

Retiring before pricing out health care

A 65-year-old retiring today can expect to spend $172,500 on health care throughout retirement, according to Fidelity's most recent Retiree Health Care Cost Estimate. And that figure doesn't include long-term care. O'Leary's standing advice not to retire until you can actually afford it applies directly here, since health care is one of the biggest and most underestimated costs in anyone's retirement math.

Medicare doesn't kick in until 65, and even after that, it doesn't cover everything. Premiums, deductibles, prescriptions, and dental and vision care all add up outside what Medicare pays. O'Leary's general rule is to throw out your retirement plan entirely if the numbers don't work, rather than retire on hope that health care costs will somehow be manageable.

Counting on a windfall instead of saving consistently

Most Americans, O'Leary says, have homes and closets cluttered with things they don't need. He asks, "Why do you have 40 pairs of shoes? You only wear two. Why are there 16 jeans here when you only wear 4?" His advice is to stop the needless and impulse purchases and redirect that money toward savings instead.

O'Leary says that this habit matters more than any single payday. His approach treats consistent saving, not a future inheritance, lucky investment, or bigger paycheck, as the thing that actually builds retirement security. Saving is a habit you can count on, rather than a windfall that might never arrive.

Assuming the government will be there to catch you

O'Leary has long argued that self-reliance isn't optional when it comes to retirement, and that people shouldn't structure their finances around the assumption that a government program will fill whatever gap their own savings leave behind. The trust fund that pays retirement benefits is already projected to run short within the next decade, so it makes sense to be as self-sufficient as possible.

While you shouldn't ignore programs like Social Security or Medicare, you should treat them as a backup, not a strategy. Building enough of your own savings means that a shortfall in either program doesn't derail your plans.

Quitting work completely with no plan to stay engaged

O'Leary tried full retirement once, at 36, after selling Softkey. He retired for three years and was bored out of his mind. He now says he has no plans to stop working, telling CNBC, "I don't know where I'm going after I'm dead, but I'll be working when I get there too."

Working is not just about money, he has said. People don't understand this until they stop working. Work defines who you are. It gives you social interaction, a sense of purpose, and, in his words, helps you live longer. His advice is to have a real plan for staying engaged before you do decide to retire.

Bottom line

O'Leary's retirement philosophy boils down to the idea that security comes from decades of discipline, not a lucky break or a safety net you didn't build yourself. Skip the debt, price out the real costs, save consistently, and have a plan for your time as well as your money. Anything else is wishful thinking that leaves you in a dangerous position.

Yet, according to the Federal Reserve's Survey of Consumer Finances, the typical household just a decade out from retirement, aged 55 to 64, has only around $10,000 saved in a retirement account. Making smart money moves for seniors requires you to plan ahead, especially when it comes to clearing debt and putting aside money for your senior healthcare costs.