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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.
"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 to retire a millionaire.
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.
“You’ll become very productive and a very valued employee,” he said. Filtering out the noise helps you to “avoid 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: “Get another job.”
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."
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."
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."
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The job market might be weakening, but that doesn't mean your career has has to.
There are steps you can take to level up your work — and that might be more important than ever.
It's not just that some companies are being slower to hire. Workers tend to hold greater responsibility for the shape of their careers than they did five to 10 years ago, when employers often played a bigger role, Lisa Walker, a managing partner at the executive search firm DHR Global, told Business Insider.
"You have to be vigilant about managing your own career," she said.
Here are three ways you can level up your career, according to workplace experts.
Sean Barry, the vice president of talent acquisition at Allstate, told Business Insider that workers should try to become more proficient in artificial intelligence.
He said the technology will place a premium on new skills for many people. Creating appropriate prompts for generative AI wasn't something many people talked about just a few years ago, Barry said.
"It's critically important now," he said, adding that workers who are better at this will likely get ahead in their careers.
One way to improve your AI skills is simply to use it. Start by trying out chatbots and seeing what works.
It's become a cliché to say that AI won't replace you, but someone who knows how to use it will. Yet, there are areas where AI might replace humans, which is why a better understanding of how AI works can be beneficial.
That's advice Sam Altman, the CEO of OpenAI, has given: If you're worried that AI will take your job, get better with the technology.
Kiki Leutner is cofounder of SeeTalent.ai, which is developing tests run by AI that would simulate tasks associated with a job to help the hiring process. She told Business Insider that, traditionally, employers tended to use such tests for more senior roles only where it was worth the money and effort. Or, Leutner said, a company might give a software developer a coding task to measure proficiency.
Leutner said GenAI can let employers test far more job seekers and across a broader range of roles than would otherwise be practical. Plus, she said, AI-run assessments can collect insights that previously were difficult to capture, such as how someone might interact with others.
Success in such areas often involves the soft skills employers say they're seeking, and that some bosses sometimes say too many workers lack.
You might feel too busy at work, yet carving out some time to help others can help you, too. A study from the University of Oxford found that volunteering proved more effective in boosting worker well-being than other interventions.
It's especially beneficial if it involves using your skills to assist others, according to Leila Saad. She is the founder of Catalyst Lane, a consulting and operations strategy firm. Previously, she was CEO of Common Impact, a nonprofit that connects companies and their workers with other nonprofits.
While head of Common Impact, Saad told Business Insider that many nonprofits lack the resources to meet all of their operational needs. So, when workers with that expertise can help, it benefits both the organization and the worker, she said.
"It feels good to give back skills you've honed over your entire career," she said.
That often trumps something like showing up for a one-off event like painting a school or planting trees, Saad said.
Beyond that, she said, workers — and their employers — can benefit if the employee might develop additional skills through volunteering.
Jennifer Schielke, the CEO of the staffing firm Summit Group Solutions and the author of the book "Leading for Impact," previously told Business Insider that volunteering — even after something traumatic like a job loss — can help those newly out of work gain perspective.
"If you have time to volunteer, go do it," she said. "Go get some encouragement by sitting alongside someone who has it worse than you do."
Side hustles get a lot of attention when they're lucrative, yet there can be other benefits. They can be limited to weekend jobs, so workers' weekdays aren't too full. In other cases, side hustles might relieve burnout.
They can also make workers feel empowered.
Daniel Zhao, the lead economist at Glassdoor, told Business Insider that workers in some industries might feel stuck in their 9-to-5 roles because of lackluster hiring. That might be one reason more workers are picking up side hustles.
"Workers are much more willing to experiment nowadays," Zhao said. He pointed to rates of entrepreneurship, which he said "skyrocketed" during the pandemic.
Zhao said it's good news that entrepreneurship rates remain elevated following a "fairly weak" 2010s and said it indicates America's entrepreneurial spirit has recovered.
"Not only is that an opportunity for people to supplement their income on the side, but it also opens up new opportunities, new ideas, new technologies that can potentially boost the economy in the long run," he said.
An earlier version of this story appeared on November 30, 2024.
Do you have a story to share about your career or your job search? Contact this reporter at [email protected].
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