"Listening to the market" — Shark Tank star Kevin O'Leary shares what career he'd pursue outside of finance

Kevin O’Leary, famously known as "Mr. Wonderful" on Shark Tank, is a finance and business tycoon. With decades of entrepreneurial experience and a net worth of $400 million as of September 2024, O’Leary has become a household name for his strategic investments and sharp business acumen.

On December 26, Kevin shared a video on his Instagram page (@kevinolearytv) discussing his views on what he would do if he was not involved in finance:

"'what would I be doing?' What I'm always doing, I'm listening to the market.” He added," I'm a salesman, I sell stuff. So I'm looking for pain points, problems people are having, finding solutions, and marketing and selling them."

He shared that while finance remains his primary focus, the key to success lies in always listening and observing.

On his Instagram, Kevin frequently provides financial tips and insights, offering guidance to his followers and aspiring entrepreneurs.

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Kevin O’Leary has been on Shark Tank since 2009

O’Leary has been a part of Shark Tank since its debut in 2009. He was a member of the initial panel and is renowned for his direct approach to businesses and incisive criticism.

During the first season, fellow shark Barbara Corcoran made fun of him by calling him 'Mr. Wonderful.'

According to Sharkalytics, O'Leary has made investments in 40 companies throughout 131 episodes. Among his most notable transactions are his investments in Wicked Good Cupcakes, which achieved $10 million in sales just three years after his $75,000 investment, and Plated, a meal delivery service that generated a 1,346% return when it sold for $300 million.

O'Leary maintains that his strategy on Shark Tank isn't about being tough, even though he is financially savvy. He stated to the Business Insider:

“Maybe people think I'm bullying them. That’s not true. I'm the only guy there who tells the truth all the time."

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Net worth and investments

In O'Leary's early days as an entrepreneur. He established Softkey Software Products in 1986, a business that completely changed the market for educational software.

Softkey dominated the market because of its aggressive acquisition strategy, which ultimately resulted in its $4.2 billion 1999 sale to Mattel.

O'Leary's career and wealth skyrocketed as a result of this deal, solidifying his standing as a prominent businessman.

O'Leary's estimated net worth as of 2024 is $400 million. His portfolio spans multiple businesses, including O'Leary Fine Wines and O'Leary Ventures, a private venture capital firm, in addition to his investments on Shark Tank.

His investments in Shark Tank include a variety of products, including the fingerprint-accessible padlock BenjiLock and the cat DNA-testing business Basepaws. O’Leary attributes a significant portion of his success to female entrepreneurs.

“This is real data: 75% of my returns have come from companies run by women,” he told CNBC Make It.

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The cost of risk

O’Leary’s career hasn’t been without its missteps. On Shark Tank, he’s celebrated for his wins, but off-camera, he has acknowledges his losses as well.

“No matter how you feel, and how optimistic you are, in the moment of making an investment, you have no idea of the outcome,” he told CNBC Make It.

While he’s reluctant to name his worst investment for legal reasons, he recounted losing $500,000 on a failed venture. He advised:

“The lesson is: Listen to your gut, because that is your experience [talking].”

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Shark Tank airs every Friday at 8/7c on ABC.