This as-told-to essay is based on a conversation with Canadian businessman and entrepreneur Kevin O’Leary, 71, who gained popularity spending over nearly two decades as the blunt-talking investor on “Shark Tank” sarcastically nicknamed “Mr. Wonderful.” The conversation has been edited for length and clarity.
I grew up in Montreal and Ottawa and received my MBA in 1980. My second business, the software company SoftKey, became successful enough to acquire the educational software company The Learning Company in 1995. Four years later, I sold it to Mattel for $4.2 billion.
I became a venture capitalist, mutual fund manager, and did some Canadian TV, starring on “Dragon’s Den,” a reality series where entrepreneurs pitched ideas to a panel of investors. A few years later, Mark Burnett took me to lunch, as he wanted me to be one of the investors in a US version of “Dragon’s Den,” called “Shark Tank.”
“I’m looking for a real asshole, and you’re it,” he told me. The rest is history.
I’m also acting for the first time, playing a business tycoon named Milton Rockwell in the Timothée Chalamet movie “Marty Supreme,” which is in theaters on Christmas Day.
Here’s what a typical day in my life looks like.
I wake up around 5 a.m. without an alarm clock and bike 12 miles
I don’t need an alarm. Sometimes, when I have to be somewhere, I’ll set it. But it’s just a natural rhythm for me to get up at 5 a.m.
Generally, in business, there are five stories that start in Asia and then come sweeping across the globe. So I get up and watch the different feeds from Europe and Asia so I’m up to speed.
At about 6:45, when it gets light out, I get on my bike and ride for about 12 miles.
I don’t eat breakfast, and I make my own coffee, because it’s stupid to pay for it
I generally work out for about an hour and a half every day. It’s for longevity and mental acuity; I have to do that, otherwise bad things happen.
I don’t eat breakfast. I fast for 16 hours and only have two meals a day. I’ll have coffee in the mornings, but I don’t buy it. That’s stupid. Why would I pay five bucks when I can just make a coffee? I don’t get it.
Every day, I use a ‘signal and noise’ goal technique I learned from Steve Jobs
I used to work for Steve Jobs. Before I sold The Learning Company to Mattel, we worked with Apple a lot to get the Mac into schools. He had this concept of signal and noise. He believed that you needed to do three things, and you had to get them done every day. You need a ratio of at least 70% signal, which are the three things, and the 30% can be noise, whatever is going to stop you from getting the three things done.
In entrepreneurship, and certainly in what I do today as an investor, there is no holiday, there’s no workday — that doesn’t exist. It’s what you want to do with your time. So I pick three things I want to get done that day, and I don’t let anything get in the way until those three things are done.
I’ve given up on emails
I don’t do emails anymore because I get anywhere from 2,000 to 4,000 a day. I’ve tried every system to take the crap out, but over the years, my email address has gotten out there, and so it’s just a constant stream of noise and garbage. As we speak, I see the emails just pouring in. I’m never going to get to them, so I don’t try. So people who need to get a hold of me know that they are going to do that through messaging.
Like my family. We have a family chat. That’s very important messaging for me. It’s perfect for when we are all in the same place. Through the day everyone is doing their own thing, but we figure out through the chat where we’ll go out for dinner.
Lunch is around 1:30 p.m., and I try to get 130 grams of protein
I usually have fish and salad for lunch. Generally, I’m trying to eat 130 grams of protein a day. I do track my diet very closely, so I don’t eat any shit food. There’s no snacking or fast food. You can really change your productivity and how you feel with your energy by just eating a better diet and drinking less. I don’t do drugs, I don’t smoke, but I love wine. And I’m very careful when I drink that.
I love a good nap
A lot of my daily routine has been developed by working with successful people over the decades. I never gave a shit about sleep. I never slept at all. I could work off three hours of sleep, but then I met this CEO, and she said, “You know something, why don’t you try for 10 days getting seven hours and twenty minutes of sleep?”
I tried it for 10 days, and was she ever right. I felt so much better. My energy was up 30%, at least. And I felt like a million bucks in the morning. I felt really good.
So I got into the routine of finding seven hours and twenty minutes, and napping counts. So I nap in limos. I’m able to fall asleep as soon as we start driving. I tell the driver, “Turn off the radio, I’m going to sleep,” so 20 minutes to get there, I grab that 20 minutes of sleep.
Dinner is at 7 p.m., and I try not to drink too much wine before bed
I like to eat around 7 p.m. or 7:30 p.m. A light Steely Dan vibe in the background is pretty good.
I’ll eat protein and have a glass of white wine, a Montrachet. I’ll then move to red, a Burgundy or a Bordeaux. I’ll keep it to two glasses, three max. I really try not to drink three hours before I go to bed. Because that screws up your sleep.
My wife and I generally watch a movie and then are in bed by 10 p.m. or 10:30 p.m.
Shooting ‘Marty Supreme’ messed up my whole routine
I’ve noticed something over the years in the people I invest in. The successful managers, entrepreneurs, founders, they all try something that they may not succeed in. So every time I get an opportunity that’s completely outside my comfort zone, that I’ve never done before, that people tell me I’ll probably fail in, I do it.
I remember the conversation I had with my agent Jay Sures at UTA about doing “Marty Supreme.” He said, “Listen Kevin, you’re going to get offered this role but I want to warn you about something: You’re not a scripted actor, you could shit the bed and destroy your brand that we’re both making millions of dollars off of right now. You’ve got to think about this.” And I said, “Fuck that, I’m doing it.”
But making the movie messed with my routine big time. Over an eight-month period, I worked on the film in New York and Tokyo. Some scenes I didn’t shoot until 3:30 in the morning.
And then there was the amount of takes the director Josh Safdie does. He wanted perfection — beyond perfection — so the takes would take hours. In the beginning, because I’m not used to working in a totalitarian environment, I finally said to Josh, “Listen, this is my 25th take, I nailed it six times.” And he looked at me and said, “You haven’t nailed it until I’ve said you’ve nailed it, do it again!”
I’m used to telling people, “We’re done,” so that was the first thing I learned. But then when I saw the movie, these guys really knew what they were doing; it’s unbelievable.
But I did get my naps in! I have hair in the movie, so I had to be in the makeup chair for hours to put it on and take it off. So there were two to three hours of free sleep there.
“Marty Supreme” is in theaters nationwide on Christmas Day.
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