This as-told-to essay is based on a conversation with Irwin Simon, the chairman and CEO of Tilray, based in New York City. It’s been edited for length and clarity.
My career started 40 years ago as a life insurance salesperson. I didn’t do that for too long because I didn’t like selling something to someone who ultimately had to die to get it.
I then became a salesman for an electronics company and later a brand manager for Häagen-Dazs Ice Cream in Canada. I moved to New York to work for Häagen-Dazs, which felt like getting my MBA in business.
I next worked on an incredible brand called Grand Met (now Diageo), and then for SlimFast, where I got fired. The best thing that happened to me was getting fired. It makes you go back and rethink your career and yourself.
I started a company, the Haines Celestial Group, in the natural and organic food and personal care industry. The company grew to make billions in revenue.
In 2019, I took over a company called Aphria, which later became Tilray, and became its chairman and CEO that March. Tilray is a pharmaceutical, cannabis-lifestyle, and consumer packaged goods company, with products across medical and adult-use cannabis, craft beer, spirits, beverages, and hemp foods.
Here’s what a typical day in my life looks like.
I wake up at about 4:30 a.m.
When I wake up, I get out of bed. I don’t lie in bed and read emails and newspapers. I also pray every morning. I’m a big believer in spirituality.
I’ll see if there are any texts, emails, or WhatsApp messages about anything urgent while I’m getting going.
I’ll then read The Wall Street Journal, The New York Times, and The Washington Post. I also look at some online stuff to see if the press is saying anything nice or nasty about me.
On Tuesdays and Thursdays, I box at a gym. Every day that I’m home, I take my dog to Central Park, even on days when I’m boxing. We walk anywhere from three to four miles.
After the walk, we go back home, and I have my coffee
I make my own coffee every day because I don’t like going to get coffee. I have a paper cup that I take with me — I try to use it three to four days a week. I make ground coffee with cinnamon — I don’t need fancy coffee.
I’ll have a little cereal and some bread with a little peanut butter. I don’t sit down and have a full breakfast. I’ll do some calls from home and some work because no one’s there to bother me.
I then walk to the office after breakfast
I work seven days a week, 24 hours a day. I go into the office at least four days a week when I’m not traveling. On Friday, I like to either work from home or from the Hamptons.
I’ll typically take calls and meetings while I’m walking to the office. When I get to the office, I have meetings all day. I catch up on reviewing numbers and going through things.
Isa Zapata for BI
I never go to lunch
We buy lunch for our 2,800 team members, who are mostly in the office, so I have lunch with them here. I’ll have a salad and soup.
My afternoons are the same as the mornings. It’s meetings, team calls, and I’m booked until the evening.
The big thing is, as a CEO, it’s OK to be criticized. It’s OK to be wrong, and it’s important to get feedback. I hate being surrounded by yes people.
If you’re not having fun, you’re not enjoying your work. If you can’t have fun while you enjoy your work, I feel bad for you.
I leave the office between 6 and 8 p.m.
When my wife is away, I have flexibility and freedom, but I try to either do a business dinner or have dinner with people on my team. I recently had dinner with my medical team, for example, talking about medical cannabis legalization.
After dinner, I enjoy watching sports and some Netflix — I love movies. I also turn on CNN or another news channel because I like to stay up to date on everything. I also scroll the Journal, the Times, and the Financial Post.
I’ll hang out with my dog while watching and reading, and power down after the workday.
Some things could derail my day
If there are challenges or something happens within the business, I have to spend more time discussing it — that could derail my day. I also have four children, and they always come first if something is going on with them.
At the end of the day, I always ask myself, What did I accomplish today? Did I really accomplish and feel good about it, or not? What did I learn today?
I like to go to bed much earlier than I used to these days at 10 p.m.
Sleep is so important, and for me, I need seven hours of sleep a night.
I put my phone away on Sundays while I’m watching Meet the Press or working on personal businesses I’m involved with.
I make phone calls to my family, try to keep up with my siblings and friends, and fit in a personal life. CEO is a title, but you are a human being first.
