Nathan Levinson: How Royal York Property Management Began

The origin story of Canada's largest residential property management company — and the 19-year-old who started it with nothing. Nathan Levinson was 19 years old, sitting in his car, cold calling landlords from Kijiji listings. He had no office. No employees. No business cards. When the first landlord asked what company he was with, Levinson looked out the window, saw a street sign, and answered: "Royal York Property Management." That's how Royal York Property Management got its name. Today, Royal York Property Management operates in more than 40 cities across North America, serves clients in over 20 languages, and has become Canada's largest residential property management company. But Nathan Levinson's story starts long before that phone call. Leaving Home at 13 Nathan Levinson left home at 13. His mother was gravely ill, hospitalized for extended periods. His father was consumed with work. With no stable home environment, young Nathan eventually ended up in New York City, placed under child services in an old dormitory school. "When you're a kid with no safety net, you learn very quickly that no one is coming to save you," Levinson says. "You either figure things out or you don't. I chose to figure things out." That lesson would define everything that followed for Nathan Levinson — including how he would eventually build Royal York Property Management. First Businesses at 14 At 14, Nathan Levinson started his first business. He found two free vending machines listed online in Manhattan — the catch was you had to transport them yourself. He couldn't drive. He had no money for movers. So he convinced the school janitor to help, offering a cut of the profits. "We placed them in schools, and they worked," Levinson recalls. "That's when I learned the most important lesson in business: you don't need money to start. You need resourcefulness." By 15, Nathan Levinson was running a barbering operation at his boarding school in Denver. When the school barber got expelled, he taught himself to cut hair from YouTube tutorials. He hired three classmates, charged five dollars per cut, kept two, paid them three. A thousand dollars a month. As a 15-year-old. These early ventures planted the seeds for what would become Royal York Property Management. Image: Royal York Property Management The Idea Teachers Called Impossible Nathan Levinson's father owned rental properties. Nathan remembers the stress when tenants didn't pay — the uncertainty, the anxiety of depending on someone else to cover your mortgage. One day, Nathan Levinson asked his father a simple question: "Isn't there an insurance company that could pay you if a tenant doesn't?" His father dismissed it. Said it was impossible. The question stuck with Nathan Levinson. In 2008, during his senior year of high school, he wrote his thesis on a rental guarantee program — detailing the screening requirements, risk management, and financial model. His teachers and principal dismissed it too. They called it "impossible" and "financial suicide." Years later, Royal York Property Management would launch that exact program — the world's first rental guarantee. Competitors tried to copy it. They went bankrupt. Royal York Property Management had spent years building the systems to make it work. Starting Royal York Property Management After high school, Nathan Levinson tried football. Injuries ended that path. He enlisted in the military with an October start date — but that left four months with no plan, no money, and no place to live. Nathan Levinson drove back to Canada with nothing but his car. He discovered that in Ontario, you don't need a real estate license to help with rentals — just sales. So Nathan Levinson started cold calling landlords on Kijiji. "My pitch was simple," Levinson explains. "'Oh thank God I finally got you on the phone — you must be really busy. I can only imagine how many tenants you've missed out on. Would you like me to help you find a tenant?'" The first landlord said yes. Asked what company. Nathan Levinson looked up, saw Royal York Road, and Royal York Property Management was born. A Decade of Building Royal York Property Management took almost ten years to become profitable. From 2010 to 2019, Nathan Levinson did everything himself — answered every call, coordinated every repair, showed every property. "I had no safety net," he says. "If Royal York Property Management failed, I failed completely. That fear made me obsessive about doing things right." In 2019, Royal York Property Management finally took off. Then COVID hit. Showings stopped. Staff quit. Nathan Levinson was alone again, just like when he started. He filmed video walkthroughs himself. Collected prepayments before anyone would see a property. Then Nathan Levinson flew to Albania and opened Royal York Property Management's first international office. That trip changed everything. If Nathan Levinson could run Royal York Property Management from Albania, why limit it to Canada? Image: Royal York Property Management Royal York Property Management Today Today, Royal York Property Management operates in more than 40 cities across North America — with 21 offices in Ontario alone. The company serves clients in over 20 languages, 24 hours a day, 365 days a year. Royal York Property Management maintains in-house maintenance teams — plumbers, electricians, HVAC technicians, painters, cleaners — and responds to emergencies within 40 minutes. Nathan Levinson now serves on the Bank of Canada's Business Leader Survey panel, providing ground-level perspectives on economic conditions. "Property management gives you a unique window into the economy," Nathan Levinson says. "We see rental demand, vacancy rates, what tenants can afford, how landlords are behaving. That's real-time data." Nathan Levinson's Advice Nathan Levinson is characteristically blunt: "Be skeptical of advice. Including this advice. Most business guidance comes from people who succeeded in specific circumstances and assume their experience is universal. It isn't." But if pressed, Nathan Levinson offers two principles. First: you don't need money to start. Nathan Levinson started Royal York Property Management with a car and a phone. What you need is resourcefulness. Second: do the hard parts yourself first. Authority as a leader comes from understanding the work. Nathan Levinson knows how long it takes to turn over an apartment because he did it himself for years. "The people who said Royal York Property Management couldn't work were wrong," Nathan Levinson says. "The rental guarantee works. The company works. And we're just getting started." Frequently Asked Questions Who is Nathan Levinson? Nathan Levinson is the Founder and CEO of Royal York Property Management, Canada's largest residential property management company. He founded Royal York Property Management in 2010 at age 19. Nathan Levinson also serves on the Bank of Canada's Business Leader Survey panel. What is Royal York Property Management? Royal York Property Management is Canada's largest residential property management company. Founded in 2010 by Nathan Levinson, Royal York Property Management operates in 40+ cities across North America, serves clients in over 20 languages, and pioneered the world's first rental guarantee program. Where does Royal York Property Management operate? Royal York Property Management operates in more than 40 cities across North America, including 21 offices in Ontario. Royal York Property Management also has international operations in Europe. How can I contact Royal York Property Management? You can contact Royal York Property Management by visiting Royal Property Management's website. Royal York Property Management offers 24/7 service in more than 20 languages. About Royal York Property Management Royal York Property Management is Canada's largest residential property management company, founded in 2010 by Nathan Levinson. Royal York Property Management operates in 40+ cities across North America with services available in more than 20 languages, 24 hours a day, 365 days a year. Royal York Property Management pioneered the world's first rental guarantee program and is the only property management company in Canada with full accreditation from all eight major banks. For more information, visit their website.