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'Shark Tank' star Kevin O'Leary shares 5 pieces of blunt life advice: 'You have to learn how to shut up'

23 August 2025 at 09:00
Kevin O'Leary
Kevin O'Leary is an investor on "Shark Tank."

J. Scott Applewhite/AP Photo

  • Kevin O'Leary shared five pieces of life advice with Business Insider.
  • The "Shark Tank" investor warned against wasting money, getting distracted, and talking too much.
  • "Mr. Wonderful" said new couples should talk money on the third date, and kids need to fly the nest.

Kevin O’Leary, the "Shark Tank" star who sold his software company to Mattel for $4.2 billion in 1999, shared some harsh advice on life and wealth in a recent interview with Business Insider.

Known as "Mr. Wonderful," O’Leary offered five nuggets of wisdom: Stop wasting money, focus your efforts, listen more than you speak, have the money talk on the third date, and ensure kids learn to fend for themselves.

Think before you spend

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

"Look in your closet at all the clothes you don't wear," he added. "It's all crap you don't need, and that crap could have been earning you market returns of anywhere from 8% to 10% over your entire lifetime."

O'Leary said that, if historical returns continue, someone earning $70,000 a year who invests 15% of their monthly income in a diversified portfolio starting in their late 20s and continuing until 65 can expect toΒ retire a millionaire.

Focus on 3 things you need to get done at work each day

Workers should ask themselves what three things they need to get done each day, and not allow anything to distract them from completing those tasks, O'Leary said.

β€œYou’ll become very productive and a very valued employee,” he said. Filtering out the noise helps you to β€œavoid getting sucked down that vortex” and falling short of achieving your most important goals, he added.

O'Leary had some blunt advice for anyone who disagrees with the direction their bosses are taking the company in: β€œGet another job.”

Listen more, it's a 'superpower'

Many entrepreneurs have "huge egos" and "love to hear themselves talk," O'Leary said. But when they're talking, they're not listening to the market, their customers, their investors, or their employees, he said.

"You have to learn how to shut up," he said, describing listening as a "superpower."

"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."

Talk about money on the third date

New couples should talk about money early on, when both sides are clearly interested in one another but aren't yet blinded by love, O'Leary said.

"You get to a third date, after the second drink, bring up money," he said. "That's Mr. Wonderful's advice, and I'm always right."

He recommends couples sign a prenup before getting married as that "forces you to do due diligence" and find out if your partner is buying drugs, racking up credit-card debt, or comes from a bankrupt family.

"Nobody wants to deal with this stuff when you're in the euphoria of courtship," he said. "But it's the reason you're going to get divorced if you don't get it right."

Children need to leave the nest

O'Leary warned about the "curse of entitlement" that can bedevil the kids of wealthy parents.

He recalled his mother's words to him at his graduation: "The dead bird under the nest never learned how to fly." When he asked what that meant, she explained that she had supported him all the way through his education, but there would be "no more checks," and he would have to fend for himself.

O'Leary added that some rich kids were "screwed up" by being funded for too long, meaning they had "no reason to launch."

"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 emulated his mother's approach with his two children, providing for them from birth through to the last day of their education. He recalled telling them, "Full ride, but after that, you'll become a dead bird if you don't figure it out."

Read the original article on Business Insider

A wedding therapist says you shouldn't get engaged if you haven't talked about these 5 things with your partner

A woman twists an engagement ring around her finger.
You should be discussing kids, finances, and sex with your partner before getting engaged.

Grace Cary/Getty Images

  • Many couples don't talk about their long-term life together until after they're engaged.
  • Wedding therapist Landis Bejar said delaying those conversations can be a mistake.
  • She recommends talking about children or handling finances before getting engaged.

When you get engaged, your first conversations with your partner are likely about wedding planning and giddy daydreams about spending your lives together.

After that excitement settles, though, many engaged couples start discussing the kind of life they want to live together from a practical perspective, from their financial future to whether they want kids.

Those conversations are important, but a therapist told Business Insider that couples should have those discussions before getting engaged.

You shouldn't wait until you're engaged to discuss life-changing topics with your partner.
A couple laughs together as the man pulls out a small box wrapped in a bow.

Janina Steinmetz/Getty Images

Landis Bejar, a wedding therapist and the founder of AisleTalk, told Business Insider that for many people, a proposal marks the beginning of a life together.

However, she said that waiting to talk about important topics until you have a ring on your finger can lead to problems, as you may discover you and your partner want different things as you talk.

"When you start to feel serious about one another, it's time to start talking about those things," Bejar said. "You want to make sure that you're not just on the same page about life in the moment that you're meeting."

"Breaking off an engagement feels different than breaking up for a non-engaged couple," she added.

You should discuss kids before you agree to spend your life with your partner.
A man and a woman look down at a baby with love in their eyes.

ROC CANALS/Getty Images

Bejar said that early in your relationship, you should discuss whether you want childrenΒ and what having children would look like for you and your partner.

"How many? What are your views on parenting?" Bejar recommends asking. "How were you parented? What were your experiences being parented? What were your relationships like with your parents growing up, and how are they now? What do you envision would be your ideal version of that if you do want to become a parent?"

Bejar also said spending time with children as a couple can be helpful before you take that step.

"If you have a sibling or a friend with kids and they need some time away and they trust you with their kids, spend some time with them," she said. "It can invite some really fruitful conversation about how you handle the stress of that."

It's also important to talk about money as a couple.
A young Asian couple planning family finances together at home.

Chong Kee Siong/Getty Images

"People really don't like talking about money," Bejar told Business Insider. "Money feels very, very taboo."

She said it is crucial to discuss money with your significant other because your personal finances impact nearly every aspect of your life, even if you don't plan on combining your money with your partner when you get married.

"You want to get on the same page because there's a lot of variability about what partners' expectations are or how they handle their money," she said.

"I really like to start premarital counseling with questions like, 'What does money mean to you? How was money talked about growing up in your family?'" Bejar added.

For some, money offered a sense of security, or it could have been a huge source of stress or even trauma.

"That's all going to impact the way that you talk about money, the way you feel about money, the way you spend money, the way you invest money, and the way you save money," Bejar said. "All of that is really rich with story and emotion and behavior, and it can very easily be swept under the rug as not relevant in your relationship."

You might have different expectations of the roles your families will play in your life together.
An older Black woman sitting with two young children, laughing and interacting with multi-generation group in backyard.

Johnny Greig/Getty Images

As Bejar told Business Insider, having in-depth conversations with your partner about your "families of origin" can help you understand not only your partner's upbringing but also the vision they have for their family in your life.

"As you shift from being a child of your family versus creating your own family, how do you integrate those two identities?" Bejar said.

Bejar said you might want to talk about how often you expect to see your in-laws throughout the year and how involved you anticipate them being with your children if you plan on having them.

Plus, if either of you plans on having your parents live with you someday as they age, you should discuss that with your partner, as that would have a dramatic impact on their day-to-day life in addition to your own.

"You want to have a sense of where you guys stand on that and whether that's going to be something that creates challenges along the way," Bejar said. "We're not coming to a compromise right now, but maybe it'll be something that we need to compromise on in the future."

Cultural and religious differences can become sources of stress if you don't talk about them early in your relationship.
Two men sit in bed and talk together.

Zinkevych/Getty Images/iStockphoto

As Bejar told Business Insider, even if you were raised in the same culture or religion as your partner, your upbringings could have looked quite different.

"As you're combining a family together, you want to talk about how you formed your own cultural or religious identity," Bejar said. "If you do want to have a family, talk about what sort of values you'd like to bring in from your own upbringing. Do those conflict with your partner's experience? How does that look when you're talking about it with kids?"

Bejar also said wedding planning might be easier if you discuss your religious and cultural backgrounds early in your relationship.

"It actually comes up a lot with weddings because sometimes, you have a couple who might not be actively day-to-day practicing within their religion or their cultural background or their ethnicity," she said. "But a wedding is a big life milestone where you would infuse that."

Finally, you shouldn't assume you and your partner will automatically be on the same page about sex.
Two sets of feet poke out from underneath a comforter on a bed.

Frank and Helena/Getty Images/Image Source

Although sex might seem like an intuitive aspect of a relationship for some people, Bejar said she encourages her clients to talk about intimacy expectations if they're considering getting married.

"You want to talk about how you feel good sexually with your partner. You want to talk about what doesn't feel good," she said.

For instance, one person might want to have sex more often than the other, and being open with your partner about your needs can help ensure a difference in sex drive doesn't lead to conflict.

"You want to have open lines of communication about sex," Bejar went on to say. "And you want to have open lines of communication about what to do if things change. How can we talk about that?"

When you spend your life with someone, things will inevitably evolve, so establishing a "culture of communication," as Bejar puts it, can prepare you and your partner to take on those changes in stride.

Read the original article on Business Insider

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