In 1974, at the age of 13, Michael J. Cooper won his first sailing championship in Toronto. And at this very young age he quickly learned that if you’re good at something, people treat you better. You become influential.

But the real lesson came when he and colleague Jason Lester started making money by cleaning and taking care of other people’s boats. What Michael learned was that different professions seemed to attract, or perhaps cultivate, different personalities.

The doctors weren’t the best customers. They weren’t that engaged. And they weren’t that personable. The lawyers were marginally better, but even then they weren’t like the business people. The business people were engaging and overall better customers.

But then, in Michael’s words, you got to the real estate people. Now, they were charismatic. These are the people that Michael wanted to hang around. They were funny and interesting. They were the people that young Michael admired. His career wasn’t a direct line to real estate, but this early experience would later impact its trajectory.

Like David Wex (previous BARED post), Michael started out as a lawyer. He went through law school and loved every minute of it. He found it conceptually fascinating. It was a different way of thinking. But after his first day working in a firm, he said to himself: “I can’t believe lawyers do this for a living!”

He quickly discovered that his personality wasn’t a good fit for law. Michael framed it to me in the following way: “I asked myself, was I going to be an airline pilot or a baseball player? As an airline pilot, like a lawyer, my job would be trying to be 100% mistake proof. However, as a baseball player, I could make audacious plays, only be right 30% of the time, and still be considered excellent.”

He wanted to be a baseball player.

I would argue that most entrepreneurial minds think of themselves more as baseball players than as airline pilots. Billionaire Mark Cuban has famously said: “All that matters in business is that you get it right once. Then everyone can tell you how lucky you are.” Nobody remembers all of the failures.

So Michael decided to go back to school, get an MBA, and figure out a way to do the most exciting thing possible – which in his words was “ABL, baby!” (Anything But Law!)

In order to complete his MBA and not put himself deeply in debt, he decided to “pull a George Costanza.” Meaning, he continued to work full-time, but he also enrolled at the Schulich School of Business full-time. He would simply come into the office in the morning, put down a cup of steaming coffee, and then take off to class.

Anything but law, baby.

Upon graduating and upon reflecting on his childhood experience cleaning boats, he decided that real estate was the most exciting thing he could get into. So he drafted up a bunch of letters and sent them over cold to 10 different real estate developers. His offer was that he would work for free. (He had the ability to do this because of his clever George Costanza-like employment moves.)

As luck would have it, he ended up getting a job with a man whose boat he had washed as a teenager. It was a man by the name of Walter Zwig. Walter Zwig had a 50-year real estate career in Toronto. He was responsible for developing over six million square feet of space in 13 downtown Toronto office towers, before eventually selling his portfolio to Olympia & York Properties; the legendary Toronto-based development company started by Paul Reichmann and his brothers. It was alleged to be largest development company in the world before going bankrupt.

Michael started in 1986 and he would eventually work for Walter until 1993. However, Walter didn’t want him to work for free so he started him at $1,000 per month.

Michael would cut his teeth with Zwig and eventually go on to develop office properties such as the Dynamic Tower at 1 Adelaide Street East, the Zurich Centre at 400 University Avenue, and the Atrium on Bay at 595 Bay Street. It was a small and flat organization without titles and Michael was able to learn a lot.

But then the early 90’s hit and everyone went broke. The industry went into dormancy.

However, as luck would again have it, he got a call from Ned Goodman who felt that there were great opportunities emerging in the market. (Ned also appeared in my BARED post about David Wex.) Michael had met Ned’s son, David, while he was looking for office space and Michael had greatly impressed him.

Michael had brought David to five office buildings. Two of the buildings were owned by Zwig, but three of them weren’t. However, Michael knew that with the current economic climate, the buildings now had more debt on them than they were worth. So if the Goodman’s needed the space, he could simply buy the debt at a discount and take it over. Michael was showing buildings that his company didn’t own and he had a damn good reason why.

On January 4, 1994, Michael, Ned, and Walter sat down for lunch at the Victoria Cafe in Toronto’s Financial District. The agenda was to figure out how to merge both Goodman and Zwig’s businesses into one and capitalize on what was starting to happen in the real estate market.

However, Walter said that he was too old to join. He was out. But he encouraged Michael to seize the opportunity. In 1994, Michael Cooper became co-founder of what would eventually become Dream Unlimited Corp. He was 32 years old at the time.

Remember, if you’re good at something people treat you better.

Since 1994, Dream (TSX: DRM) has grown to over 1,000 employees and over $15 billion of assets under management in North America and Europe. They provide asset management services for 4 funds listed on the Toronto Stock Exchange and they have operating businesses that span master-planned communities and condominiums to renewable energy infrastructure and retail centre development.

But what is not necessarily obvious from the above numbers is that, alongside Dream’s incredible growth, Michael also became one of “the real estate guys” that he admired so much as a young teenager cleaning boats. After sitting down with Michael to learn about how he got to where he is, I can honestly say that he is one of the funniest and most charismatic people I have ever met. He is the kind of guy you want to do business with and then go out drinking with afterwards.

Perhaps not surprisingly, when I asked Michael if he had any advice for young aspiring developers (which I know is a lot of you readers), he quickly suggested that people study the classics. Speech. Drama. He said: learn how to connect with people.

Because as a developer, your job is to conceptualize what the future could be and then get other people to believe in that same vision. Michael describes navigating all of the constraints on building as one of the most creative things you can do. And in a market like today where you have to be willing to pay the most for a piece of land, it’s the best ideas that win.

That doesn’t sound like a lawyer or airline pilot to me. That sounds like a real estate guy with one hell of a batting average.

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This is the second post in my blog series called BARED (Becoming A Real Estate Developer). A big thanks to Mariane for helping to coordinate this piece. More posts to come in the following weeks. Subscribe to stay in the loop.