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Andy Nulman, co-founder and CEO of Play the Future, poses with fortune cookies outside his offices in Montreal, August 8, 2016.

Christinne Muschi/The Globe and Mail

Andy Nulman, 56, is chief executive of Montreal-based Play the Future, which creates prediction games for brands, and former co-founder of Just for Laughs.

I've dedicated my life to avoiding uniformity. I've never had an average day. Frankly, I wake up every morning waiting for someone to throw me a curveball. My business partner, Parisa Foster, doesn't answer her phone if she doesn't recognize the number. I'm the polar opposite – I'm waiting for that random phone call, that unknown e-mail, that chance encounter that will send me off in new directions.

I got my first job at 16. I had just finished high school and saw a tiny ad in a newspaper called the Sunday Express that they were looking for two people to work all day and night on Saturdays in their sports department. I was way more a rock 'n' roll guy than sports at 16, but I loved writing and journalism and this was a way in the door, so I applied. At the interview, I noticed a layout sheet on the sports editor's desk and I told him I was an expert since I had worked with them putting together my high school yearbook. The truth was that I had worked on the yearbook for one single, miserable day but details like that didn't matter now that I was inside his office. I wasn't leaving without that gig and would do or say anything to get it. I did. Two weeks later, I wrote my first ever article. It was on Peter Frampton, who had come to town. I lied to the editor and said that I'd already written a piece for college, but the truth is I hadn't been to college yet and had never written anything in my life. Three months later, at the age of 17, I became the newspaper's entertainment editor, and held that job full time while going to school part time and I still worked in the sports department every Saturday for six years.

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You can never let your guard down. What I learned at Just for Laughs is no matter how prepared you are, something will go wrong. That's just the nature of the beast. When everything is perfect, there is a power failure. You have to know that it's going to screw up and deal with it, so you can't freak out when it does. In the late nineties, we did a huge tribute to Roseanne Barr and the Hollywood Reporter ran a tribute to her. I then get a call from Roseanne's plane that they are turning around and she isn't coming because they wrote something she didn't like. I told their manager that she will look like an idiot for turning around and that I can't control what someone writes, so she showed up. The same thing happened with John Candy in the late eighties, when he decided a month before the show to pull out. As I was on the phone, I climbed on the ledge of my building and said, "John, I'm on the ledge of my building. You can hear people screaming. If you don't come back, I'll jump." He agreed to do the show. I was only three floors up.

People have an inherent need to predict the future. It's the reason we read horoscopes and play the lottery. Play the Future is like fantasy sports. Rather than just predict the outcome of a sporting event, you predict every event. How many times will Trump's facts be wrong in today's speech? When this interview comes out, how many vowels will it have? We've built it into a marketing tool so users can predict Canadian Tire sales or Via Rail on-time records. I got the idea 28 years ago reading the prediction issue of the National Enquirer and whoever says if they were right or wrong and if aliens will ever land in the White House.

This is my fourth career. I've been a journalist, comedy-festival builder, mobile-media pioneer and now future player. What's important to me is that each one is diametrically different from the other. If there is one constant in my life, it's striving for innovation, challenge and the new … to do something that's never before been done, even if it's only never before been done by me.

What haven't I learned? I learned so much that for seven years straight, I wrote a weekly blog about the lessons I learned, mroe than 1,000 in total. Some of my favourite lessons are: Anything you do just for money will ultimately fail. Everybody loves change until you change something. "Nice" is worse than "bad" and beware the person who doesn't like balloons.

When I was a kid, I wanted to be a garbage man. I'm not being facetious or silly; it was my first-ever career goal. As a four-year-old, my room window faced the street, and I remember being mesmerized by these wild guys waking me up twice a week. They were raucous and loud, they yelled and threw things around with reckless abandon, they dangerously climbed on and hung off a large moving vehicle in a savage, urban choreograph. What a gig. Who wouldn't want to do that?

The best and worst advice I ever received are the same: "Forget it, it can't be done." I've been told that so many times, and rather than deflate me, it inspired me. "A kid can't work at a newspaper." "What the hell is a comedy festival?" "Nobody will ever pay for mobile content." And now it's, "Where's the business model in prediction?" If I just listened to all the advice instead of been motivated to prove it wrong, I'd be an unhappy, unaccomplished, bitter man today.

To be very honest, I'm a terrible manager. I'm a decent leader and can rally a team together, but when it comes to day-to-day management, my approach is that people should fix their own problems. I have no problem leading people into battle but in terms of actually managing them, I let people manage themselves. There is a goal and there is the outcome, and we need to focus on what we are going to do to make sure it gets done. My management style is that you need to figure it out.

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Today's failure is tomorrow's story over beers: In Thru the Out Door came out in 1997. I sold it to the CBC. It was the world's first all-gay comedy show, with all gay cast and writers. For me it was a big Kum Bah Yah moment. It was so risqué and ahead of its time. The complaints almost shut down the CBC switchboard. I thought it was going to be an Earth-shattering, groundbreaking phenomenon that would go on and on, but it was too early and was a disaster. They showed it once and never showed it again. I watch it now and love it.

As told to Leah Eichler. This interview has been edited and condensed.

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