Shark Tank’s Kevin O’Leary’s surprising move blazes new trail

Retirement planning remains one of the most aspirational yet elusive financial goals for Americans, as the cost of everyday expenses makes planning for the future difficult.

Kevin O’Leary, the outspoken investor who appears on ABC’s “Shark Tank, has built a reputation for delivering tough love financial advice that cuts through wishful thinking and demands disciplined action.

Related: Shark Tank’s Kevin O’Leary bluntly speaks on Americans’ 401(k)s

Median retirement savings for those aged 45 to 49 is $19,400 and is $24,000 for 50-year-olds, according to the Federal Reserve’s most recent Survey of Consumer Finances (shared by a DQYDJ analysis) — far short of the million-dollar nest egg many envision.

O’Leary also sounds the alarm on the corrosive impact of credit card debt, calling it a “cancer” that quietly drains the potential of 401(k)s and IRAs.

Kevin O’Leary warns Americans on retirement savings

O’Leary cautions Americans on the fact that excessive spending and compounding interest payments are sabotaging Americans’ ability to contribute meaningfully to retirement accounts, especially Roth IRAs which require after-tax income.

With U.S. household debt increasing by $185 billion to $18.93 trillion in early 2025 (according to the Federal Reserve Bank of New York’s 2025 second-quarter Household Debt and Credit Report), the urgency of his message is hard to ignore.

But O’Leary’s advice goes beyond numbers — it challenges the mindset that keeps people financially stagnant. He argues that many remain trapped by magical thinking, delaying action in hopes of a windfall.

For those willing to embrace discomfort, however, O’Leary offers a suggestion and explains a major way he recently took his own advice.

Kevin O’Leary, investor and star on ABC’s “Shark Tank,” recommends people spend 30% of their day outside of their comfort zone to stay sharp.

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O’Leary discusses his surprising new project

O’Leary, in an appearance on Fox Business, talked about a project he’s been working on outside his investment and television occupations that surprised many when it was officially announced.

O’Leary said he is starring in an A24 film, “Marty Supreme” that features the Oscar-nominated Timothée Chalamet and Oscar-winner Gwyneth Paltrow.

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Here is how O’Leary described his word of advice for anyone watching the Fox Business appearance — and how he described his initial communication with the production company for the movie.

If you want to stay sharp, spend 30% of your day outside of your comfort zone. I’ve never done scripted roles before. And when this opportunity came along they said, “Look, we’re looking for a real a-hole guy and you’re it.” And I said, “I don’t know if I should take that as a compliment or not.”

O’Leary explained a bit about the experience.

Working with Chalamet, the A24 people, the director Josh Safdie, the writer (Ronald) Bronstein — what an amazing experience that was. We turned New York into 1952. I closed my eyes when Josh said, “Action,” and I was in New York in 1952. And I’ve got to tell you something. At the end-of-the-day shoots I told everybody, “You go back to 2025. I’m staying here.”

O’Leary said the film opens in theatres on Christmas Day and then he offered a prediction.

“I believe that Timmy will win his Oscar on this one,” he said.

Kevin O’Leary’s key advice for retirement

In addition to working outside one’s comfort zone, O’Leary offers more advice on retirement saving and planning

  • Avoid credit card debt at all costs: O’Leary says credit card debt quietly drains the potential of 401(k)s and IRAs by consuming disposable income through compounding interest.
  • Don’t rely on magical thinking: He warns against fantasies like winning the lottery or receiving surprise inheritances, which delay meaningful financial action.
  • Prioritize Roth and traditional IRAs: O’Leary emphasizes that these accounts are essential tools for long-term security — but only if supported by disciplined financial habits.
  • Early retirement isn’t always wise: He cautions that retiring too soon can lead to boredom and financial strain, especially with longer lifespans and delayed access to Medicare and Social Security.

Related: Tony Robbins sends warning message to Americans on IRAs, 401(k)s

O’Leary encourages people to reach key financial benchmarks early (by age 33) to build momentum toward retirement goals and argues that staying engaged in business or work can provide purpose and fulfillment even after financial independence.

Kevin O’Leary’s 90-Day Number for financial planning 

O’Leary explains a financial plan he recommends that he calls finding one’s “90-Day Number.”

  • Track every dollar spent over a 90-day period — no exceptions.
  • Categorize expenses to identify non-essential or impulsive purchases.
  • Calculate total income versus total spending to reveal surplus or deficit.
  • Cut unnecessary costs and reallocate funds toward retirement contributions.
  • Use the results to adjust budgeting and set realistic savings goals.
  • Repeat quarterly to reinforce discipline and monitor progress toward long-term financial health.

Related: Dave Ramsey has blunt words for Americans on Medicare, Medicaid