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Dundee CEO David Goodman does stand-up comedy in his spare time for kicks – and to raise money for charity through the annual Humour Me event, sponsored by his company.

Jennifer Roberts/The Globe and Mail

24/7 Executives is a series of stories on high-performing professionals who are as serious at play as they are in the conference room. See the other stories here.

It was the perfect set-up. (Actually I'm not that smart. I only realized it was a perfect set-up after the fact.)

The place was a stately if generic, 21st-floor meeting room overlooking Toronto's Yonge Street at the offices of Dundee Corp. David Goodman, the president and chief executive officer of the holding company, was talking about his hobby performing stand-up comedy.

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So I asked him to picture a friend trying stand-up for the first time. And the friend is going, oh my God, I'm so nervous. To reassure him, you tell the friend to sit back and think about ...

Mr. Goodman didn't take the bait. There was no joke about imagining the audience in underwear (maybe that could create a different set of problems). No, Mr. Goodman responded earnestly, "If it's something you want to do, you gotta do it. It's that simple. Just go do it."

This was the more serious, aspirational side of Mr. Goodman. At 51, he came back to head Dundee nearly a year ago, after a stint at Bank of Nova Scotia. He had been head of Scotiabank's global asset management, after the bank had bought Dundee Wealth where Mr. Goodman had been president and CEO.

He originally joined Dundee, the company created by his father, Ned, as a partner, vice-president and portfolio manager in 1994. He went on to become CEO and president of Dynamic Funds in 2001, before heading Dynamic's parent Dundee Wealth in 2007.

Under his new leadership, Dundee Corp. is trying to become more transparent to investors in terms of explaining its various holdings in numerous business sectors, from agriculture and real estate to oil and gas. The aim is also to organize the company in a way "that maximizes profitability in finding common objectives" between Dundee's various divisions.

But Mr. Goodman isn't all business. He's not a walking-talking annual report. He sees humour as essential to business life – helping competing interests find commonality – as him punctuating his gags with a half-laugh, half-exhalation.

As in, when recounting the first time he tried public comedy many years ago: "My brother was getting married for a second time. It was a tense evening and I got up to make a toast. I said, 'It's not every day that you get to toast your older brother on his wedding. It's often, it's just not every day.'"

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A few minutes later, another gag: After his older brother's wedding (he also has two younger brothers), Mr. Goodman took a week-long workshop in stand-up at Humber College in Toronto. A musician friend had recommended it. "To put it in proper perspective, this course was taught at the campus of Humber College that used to be an insane asylum," he said. (Humber's Lakeshore Campus has some buildings once part of the Lakeshore Psychiatric Hospital.)

Stand-up scratches an itch Mr. Goodman has had since he was a kid growing up in Montreal, imitating skits from the original Saturday Night Live with his older brother and listening to comedy albums from favourites such as Steve Martin in his King Tut days, back "when stand-up comics filled stadiums with 20,000 people," he said.

"Whenever something funny happened, or whenever we said something funny," he and his brother would say, "You know what? That's going in the act. But we never had an act! I got a commerce degree and a law degree [McGill and the University of Ottawa, respectively]. He got a geological engineering degree and an MBA. We both got married really young. We each had a whole bunch of kids. And I woke up one day, and I was 40, and the act never happened.

"I didn't want to let that dream die unfulfilled. So I enrolled myself in the Humber College course and went for it."

Although he had experience speaking in public in business, the experience of delivering three to five minutes of comedy in front of 100 to 150 people was entirely new. "It was electric. The first time you perform in front of a real crowd, and there's real people there ... and a celebrity there whose name I now forget," Mr. Goodman laughed.

"For me, it started as a hobby or a passion, where I kept trying to see how far I could take this thing," he said. "So, I started going to the open mics in and around Toronto, trying out my material, trying out my new stuff. And I was ridiculous, because I would go out with eight pages of type-written notes. That's not funny!"

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He was heading Dynamic Funds by then. He didn't have time then to properly prepare. "That's why I had to bring the notes. I didn't have the time to commit to memory anything I was doing," Mr. Goodman said.

Still, he kept trying, one or two nights a week, pulling out his notes after work, reading them twice, and then hitting the open mic nights.

"It was good because it helped with my weight control. I wouldn't eat dinner that night because I was so nervous. I couldn't eat anything before going on stage, and I'd been working for 12 hours, so I was really tired.

"All I would do was have a grande Starbucks and go on stage for five minutes. It was exhilarating and thrilling and fun. And after doing that I auditioned for Yuk Yuk's. And the advice I was given was, don't quit your day job," he said, "which I didn't."

The parallels to the day job though are myriad, from taking risks to recovering quickly from mistakes, to the entrepreneurial spirit comedians have in creating an act from scratch. "In business, in life, to be able to laugh with your partners, it's a bonding experience," he said.

In recent months, since taking over Dundee Corp., Mr. Goodman has had to push stand-up to the side, even though the walls of his corner office are covered in photos of him with famous comics. Dana Carvey, Russell Peters, Steven Wright. Some have appeared as part of charity events he has held.

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In October, Dundee will sponsor the fifth annual Humour Me event, where Bay Street executives try to deliver their best gags (much of the humour is in the trying) to raise money this year for Sunnybrook Hospital in Toronto. Professional comics judge the executives and choose a winner. A headlining comedian is also due to perform. Last year's event raised $1.2-million for the Hospital for Sick Children, also in Toronto.

"Part of the magic of the evening is watching these people step waaaay outside their comfort zone, and waaaay outside what you'd perceive to be normal for a leader of a company," Mr. Goodman said. "I think it's an important thing to do, because it demonstrates humility, which is part of humour."

Truth be told, he's quite shy himself, he admitted. He wasn't the class clown. He even thought twice about performing under his real name. And at the end of the interview for this story, he let out a quiet "phew." He's not big on boasting about his hobby, but likes to talk about it if it helps his charity causes.

So, don't think of comedy as being some kind of double life, he said. He plays piano, too, and takes it just as seriously. But "I wouldn't say that that means now I'm three people!"

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