I’m a high school dropout. Here’s how I built an $8-million real estate portfolio

Growing up in Scarborough, when other kids said they wanted to be doctors or astronauts or baseball players, I told them I wanted to be “the owner.” I never knew what that meant, mind you, but that’s what I told everyone. My father, Wayne Sr., probably had something to do with it. He was a developer in Toronto and Port Carling, so our family was always involved in the real estate industry. I suppose I wanted to own properties, just like my dad. Apparently, as a kid, before I was old enough to remember, he would bounce me on his knee and talk about mortgages. Some of my earliest memories are of driving around the city in his four-door Cadillac, doing something he liked to call dream building. I would look on, in awe, as he pointed out his various projects and other fancy buildings.

At the age of nine, I worked on his houses—cleaning, painting, drywalling. I basically did everything except electrical. After the masons would brick a house, I’d get paid 10 cents a brick to pick up the pieces they didn’t want. That’s where I learned the importance of a good work ethic, along with the ins-and-outs of building a house from the joists up. There were some hard lessons, too, like that workers never got paid during their lunch hours—if you weren’t working, you weren’t making money. That’s how my dad operated. He was a very hard-edged guy, but we could always bond over real estate.

As a teenager, there’d always be a copy of Real Estate News in my room. I’d buy books about houses and pore over the floor plans of beautiful mansions, planning where I’d place the furniture in my dream home. I’d look at the newspaper and see Toronto real estate agents like Harvey Kalles, Al Sinclair and Elli Davis—these people were like celebrities. My friends idolized athletes and musicians, but I thought that the top real estate agents, whose names and faces were plastered on billboards across town, were equally impressive. I always wanted to be like them. The only problem is that I never thought I had the intelligence, since teachers were always telling me that I shouldn’t follow my dreams.

When I was 15, my father got sick, and I ended up dropping out of school because I was so lost and unhappy. My education mostly came from self-help books by Tony Robbins and Robert Kiyosaki. Sometimes, I’d find myself driving through the Bridle Path in my dad’s black Corvette, staring at the houses on Post Road. That’s probably where I got my taste for Edwardian architecture. Looking back, it’s clear that I was dream building all on my own.

After I dropped out, I started DJing at small local gatherings. By the time I hit legal age, I was working at clubs in the city like Guvernment, Joker and Atlas, for a promotion company called Brighter Days. I later moved to Japan, where I picked up work as a bartender and a DJ, before heading to the Philippines where I focused solely on music. In 1998, at 23, I came home with $12,000.

I used that money, along with $8,000 from selling my dad’s Corvette, to put a down payment on a $212,000 three-bedroom detached home at Danforth Road and Kennedy. That was my first property and I rented it out, both the top and bottom floor, for roughly $1,800 a month. I used the money I made from my tenants at Danforth to buy a place on Lillington Avenue in Scarborough. It was a less glamorous time. I was driving a big white cargo van around the city. Then, I started delivering mail for Canada Post, which paid about $60,000 a year. Almost everyone who worked there had some sort of side hustle—mine was collecting rent. I combined the money I made from my tenants at Danforth, along with my Canada Post salary, to buy another place on Lillington Avenue. That’s how things got started. After that, I bought some penthouses in Scarborough, a few units in Liberty Village and then some houses in Forest Hill and Lawrence Park. All along, to build my portfolio, I leveraged the equity from my properties, invested the cash from the rental units and used my salary from the post office.

Since getting into the real estate business, I’ve owned 18 properties, everything from condos to detached houses. The most units I’ve ever owned at once is 11. Today, I have a portfolio worth $8 million.

Throughout my career, there have been some real highs. Three years ago, at 40, I quit my job at the post office and got my real estate licence, because I’d always dreamed of being an agent. The job ticks a lot of my boxes: It’s competitive and you really get to help people. It also allows me to spend time with my daughters, Quinn and Stella, who are now 7 and 5.

But there have been some hard times, too. My partner and I decided to split up in 2014. My father died of pancreatitis, at 57, and gave all his properties, which must’ve been worth millions of dollars, to his girlfriend. I’m not bitter, though, because I never thought I was entitled to the money. He left me about $5,000 in cash, his diamond pinky ring and a silver money clip, which is stretched out because he carried so much cash. Of course, he also left behind all of his real estate knowledge, which is what I’m most grateful for.

I know about four things: watches, the Toronto Maple Leafs, house music and real estate. Beyond that, not much. A lot of people think houses are just a financial asset, but I think of them as Quinn and Stella’s education or a better retirement for myself. These days, I’ll drive Quinn and Stella around Forest Hill, where we live. When we pass a nice house, I’ll tell them that’s where the Disney princesses live—and they love it. It’s our own little version of dream building.

– As told to Katie Underwood