How a little luck (and a lot of leverage) helped an investor work his way up Toronto’s property ladder

Brad Nathan is the 48-year-old president of Lynx Equity, a company that buys businesses from people who are about to retire. When he first got into real estate, he was motivated by the simple desire to own a home and not pay rent. Today, his real estate ventures are his passion. He rarely sells a property once he has acquired it; he’d rather collect rent. In his free time, he enjoys riding around the city on his bike in search of unique places to buy. “If I won the lottery tomorrow, I’d go back to doing the same thing on Monday,” he says.

The first purchase

Woburn Avenue (near Yonge and Lawrence) Purchased for $255,000 in 1996 Sold for $675,000 in 2011 Brad’s first property was a two-bedroom detached home. He made the $50,000 down payment using money saved from working various jobs, like selling monogrammed shirts to car dealerships. His parents also loaned him $10,000.

The rebound

Price Street (near Yonge and Roxborough) Purchased for $425,000 in 2005 Now rents for $3,100 a month After breaking up with a girlfriend, Brad was looking for somewhere new to live—ideally close to his gym at Yonge and St. Clair. He found this condo: a loft with unusual rounded living and dining rooms. He financed the purchase by remortgaging his Woburn property, then lived in the unit for about five years before he decided to rent it out.

The holy of holies

Pape Avenue (near Danforth) Purchased for $420,000 in 2008 Now rents for $2,200 per month Brad found this condo for a friend who was looking for an apartment to rent. With a trusted tenant already in the bag, the purchase was a no-brainer. The unit is in a former church with high ceilings, exposed brick and a fireplace.

The homestead

Crescent Road (near Yonge and Roxborough) Purchased for $2 million in 2013 After a few years of living at his various properties, Brad found this three-bedroom Rosedale suite, situated inside a former single-family house that had been split into two condo units. He was drawn to the backyard, which had a circular pool bordered by white columns. Brad made a $500,000 down payment and paid the balance by leveraging another property. He now lives here with his girlfriend, Ashley Manis, who works in marketing at Lynx Equity.

The fixer-upper

Christie Street (near Davenport) Purchased for $940,000 in 2014 Now rents for $9,000 per month This place was a “dump of a convenience store,” Brad says, but he saw its potential. He financed the purchase by mortgaging his Crescent Road property and invested $500,000 in renovations. He planned to rent to a marijuana dispensary, then thought better of it before opening day.

The bottom line

Brad grossed $420,000 when he sold his first house. According to his bank, the present-day value of all the properties he still owns (including some not shown here) is roughly $11 million.