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Kevin O’Leary, best known for his direct style and business acumen, recently opened up about his experience working with Apple co-founder Steve Jobs. In a video posted to his Instagram account on May 26, 2025, O’Leary recalled Jobs’ intense focus and work ethic.
The Learning Company, with which he was associated, developed educational software for Macintosh computers in the early 1990s. O’Leary, who has built a reputation through Shark Tank as a sharp and often blunt investor, described Jobs’ behavior as “abusive” but highly effective.
“He would email me at 2:30 in the morning and expect a response in five minutes, and that I'd give it to him. I mean that guy was unbelievable,” O’Leary said. He added, “He didn't let anything get in the way of the four or five things he was going to get done that day.”
Inside Shark Tank investor O’Leary’s encounters with Jobs and Musk
In his Instagram video, Shark Tank’s Kevin O’Leary elaborated on a concept he called the “signal-to-noise ratio,” which he credits as a key lesson from working with Steve Jobs. He explained that Jobs, though difficult and “not a nice guy,” maintained extreme focus on immediate tasks.
O’Leary recalled quarterly meetings in Cupertino during which Jobs harshly critiqued team members, including product managers, who were sometimes left in tears.
“He just didn’t give a sh*t because he had to get done those five things,”
O’Leary said, referencing Jobs’ daily task list. According to the Shark Tank investor, this obsessive focus led to extraordinary results. Jobs worked 18-hour days and demanded instant responses, often communicating in the early morning hours.
O’Leary emphasized the results of such behavior, noting the success Jobs achieved by refusing to allow distractions. O’Leary also compared Jobs to Elon Musk, noting that Musk had an even higher signal-to-noise ratio.
“He’s 100 percent signal, zero noise,”
O’Leary said, recalling how Musk would instantly disengage from any conversation he found unproductive. Though both leaders have been criticized for their intensity, O’Leary underscored their ability to block out distractions to achieve results.
“Look at what he’s achieved,” he said of Musk.
O’Leary’s investment philosophy, personal milestones, and business principles
In a separate interview with the Financial Post published on December 18, 2024, Shark Tank star Kevin O’Leary shared further insights into his business mindset, investing background, and views on achieving financial freedom. O’Leary, whose net worth is estimated at $400 million, stated that true financial freedom begins with $5 million in the bank.
“It’s the minimum and it’s very, very, very hard to get,” he said.
Despite his wealth and success on Shark Tank, O’Leary said he no longer works for money, citing a principle taught by his mother:
“Never brag about money or you won’t have any.”
He credits much of his early financial knowledge to his mother, Georgette O’Leary, who secretly amassed wealth by investing 20 percent of her weekly income in dividend-paying S&P 500 stocks and telecom bonds. She followed strict rules: no more than 20 percent in any one sector, and no more than 5 percent in any single stock or bond.
O’Leary’s first major liquidity event occurred when he sold Softkey Software Products Inc. to Mattel Inc. for $4.2 billion in the late 1990s. He and his co-founders chose to continue working even after the windfall.
“From that point on, it really wasn’t about money,” he said. “It was the pursuit of things that I’m passionate about.”
One such venture is WonderCare, a watch insurance product launching in the U.S. He explained that as a passionate watch collector and horologist, it combines both personal interest and investment. Another initiative he’s backing is a large-scale AI data center in Alberta, which he’s funding himself.
O’Leary advises young investors and entrepreneurs to master the discipline of filtering signal from noise.
“If you can keep that ratio 70:30, you’re going to be successful,” he said.
He applies this philosophy daily, emphasizing that too much noise leads to failure.
“When you’re all signal, you get a lot of social criticism because you’re not the nicest person.”
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Shark Tank airs every Friday on ABC at 8 pm EST.
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