Jul 29, 2026
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Add us on GoogleKevin O’Leary has built a career on being direct. But the Montréal-born investor says the sharpest career advice he has ever received came from someone he considered brilliant, if not difficult to work with: Steve Jobs.
Speaking with fellow Shark Tank investor Robert Herjavec on “The School of Hard Knocks,” a business interview series, O’Leary recounted how the late Apple co-founder told him “there’s only three things you have to get done every day.” Everything else — the emails, the meetings, the notifications — was just noise getting in the way of what really mattered.
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O’Leary said he pushed back at the time, telling Jobs he had no reason to take advice from someone so hard to work with — Jobs’ response was simple: trust me.
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Signal versus noise
Separating signal from noise became central to Jobs’ leadership at Apple, especially after he returned as CEO in the late 1990s. At a widely cited 1997 appearance at Apple’s Worldwide Developers Conference, Jobs argued that real focus means saying no to good ideas, not just bad ones — a philosophy that led him to cut dozens of low-priority Apple projects and narrow the company’s focus to a handful of categories, setting up its eventual turnaround.
That same discipline shaped O’Leary’s own career. Born in Montréal in 1954, he co-founded the software company SoftKey Software Products in Toronto in 1983. SoftKey grew by buying up rival companies throughout the 1980s and 1990s, eventually renaming itself The Learning Company. Mattel bought the business in 1999 for a reported US$3 billion to US$4.2 billion (~C$4.2 billion to ~C$5.9 billion) in a deal that proved disastrous for Mattel but made O’Leary very wealthy.
O’Leary became a household name in Canada first, joining the panel of CBC’s Dragons’ Den in 2006, three years before he crossed over to Shark Tank, the American version of the same format, in 2009. Both shows built his “Mr. Wonderful” persona: a straight-talking investor obsessed with cash flow and allergic to distraction.
Herjavec, 63, who founded and sold cybersecurity companies before joining Shark Tank, told the hosts he’s never met a genuinely wealthy person without a clear sense of purpose. O’Leary agreed, adding that the wealthiest people he knows aren’t chasing money for its own sake — they’re chasing a mission, and the “three things a day” habit is how they protect the time to do it.
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How the ‘3 things a day’ rule holds up against the research
The Jobs anecdote lines up with a growing body of research on attention and focus. Gloria Mark, a professor at the University of California, Irvine, found in her research for the book Attention Span that it takes people roughly 23 minutes, on average, to fully refocus after being interrupted — whether that interruption is a phone notification, a chat message or a colleague stopping by.
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Canadian data suggests those pressures are just as real north of the border. Statistics Canada’s first Canadian Survey on Working Conditions found that half of Canadian managers reported frequently working to tight deadlines — nearly 20 percentage points higher than workers in jobs that typically require only a high school diploma. More than one-third of managers also said they regularly do unpaid work on their own time just to keep up.
Set against that backdrop, O’Leary’s routine sounds almost defiantly simple.
Lessons for Canadians trying to get more done
O’Leary’s advice isn’t really a productivity hack — it’s a way of protecting the handful of decisions that actually affect your income and your business. A few ways Canadian readers can put it to use:
- Choose three priorities before opening your inbox each morning. Treat everything else as a distraction to manage, not a task to finish.
- Batch check email and messages at set times instead of reacting to every notification as it comes in. Grouping these checks together frees up longer stretches of uninterrupted time.
- If you’re building a business or a side hustle, ask yourself whether today’s task actually grows your income — or just feels productive. There’s a difference, and it’s easy to confuse the two.
- Block off at least 30 minutes of focus time before the day’s meetings start eating into it. Even a short window of uninterrupted work can move the needle more than a morning full of quick responses.
The habit costs nothing to try — and for anyone working to build wealth on top of a full-time job, it may be worth more than another budgeting app.
-With files from Melanie Huddart
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Dave Smith is the VP of Content at Wise Publishing and Editor-in-Chief at Moneywise and Money.ca. His work has also been published in Fortune, Business Insider, Newsweek, ABC News, and USA Today.
