From Childhood Entrepreneur To Business Leader

Nathan Levinson has always had an entrepreneurial streak in him, even as a kindergartner, turning a profit shoveling driveways. Forced to be self-reliant as a runaway and then in foster care, Levinson continued to hone his business acumen as a teenager.

Now, he’s made a name for himself as president of Royal York Property Management, a Toronto-based firm that Levinson founded in 2010. He quickly grew the business and for the last six years, Royal York has been rated the top property management company in Ontario.

The firm now has 17 office locations servicing 40-plus regions across the province. To date, Royal York has leased and managed more than 22,000 rental properties, valued at more than $10.1 billion.

Levinson shares his journey, his successes and his love for philanthropy.

Tell us about your youth and how your experiences shaped your passion for entrepreneurialism—and your drive.

When I was growing up, as young as 5 or 6 years old, I became interested in entrepreneurship. It started with a massive snowstorm that hit the region, and I quickly organized my friends to help shovel snow. We charged $2 per driveway and I paid my friends $1 and kept the rest. This experience was when I first recognized the value of buying time and would become the foundation of my understanding of business going forward.

As I was growing up, I also learned the importance of perseverance and self-reliance. My father was a lawyer and was extremely hardworking, and my mother was often too sick to take care of me, therefore I was often left to my own independence. At 12, I left home and ended up in foster care in New York City.

There, I started my next business, a vending machine company, and I quickly expanded it across multiple schools. These early experiences in entrepreneurship taught me resilience and gave me the drive I needed to succeed in business. It shaped my passion for entrepreneurialism and taught me that success requires innovation, hard work and an understanding of the power of time.

You became interested in property management at an early age. Tell us about that, and how that led to opening your own firm.

My interest in property management began during high school, with the principal as my mentor, who introduced me to real estate by involving me in the management of his own rental properties. Under his guidance, I learned the ropes of property management, such as handling renovations, showings, evictions, rental collections, dealing with contractors and filling properties with tenants.

This experience made me more interested in business than continuing my education, and I decided to apply the skills I had gained during this venture to my own businesses. It also fueled my desire to create tenant-friendly solutions in the real estate market, and Royal York Property Management was born.

What lessons did you learn from your family that enabled you to approach property management differently?

From a young age, I observed my father’s struggles in renting out our basement property. As a full-time lawyer, he simply didn’t have the time to manage tenants and maintain the property, often leading him to leave it vacant. I recognized early on the difficulties that landlords face, especially when balancing another career. This is what inspired me to innovate within the property management field.

Although my idea was initially met with skepticism, I developed the concept of “rental guarantees,” which is a form of insurance for landlords to ensure rent would be paid each month. I used this concept to assess common pain points that landlords face, such as rent collection, property maintenance and stressful tenant living situations.

The lessons I learned from my own family’s experiences made me recognize the importance of mitigating the challenges that landlords often encounter, ultimately leading to more efficient and effective property management practices utilized by Royal York Property Management.

You are also a philanthropist, and you are most passionate about assisting schools with special needs students, as well as organizing anti-bullying campaigns. Tell us about those initiatives.

For some time, philanthropy has been a core aspect of my life and my business philosophy. Inspired by my own challenges as a child, I am passionate about supporting schools and organizing anti-bullying campaigns.

I recently founded the Nathan Levinson Charity Fund, which focuses on helping children who face similar difficulties in school. This charity aims to provide resources for kids who cannot afford therapy, better educational environments or necessary care. My goal is to be the support system for these children that I once lacked.

Additionally, through these initiatives, I am committed to fighting bullying, whether it occurs online, in schools or in the workplace. In my own company culture, I strive to create a safe and supportive environment where young individuals can thrive and have the chance to develop their skills, regardless of their academic background or socioeconomic status.

My philanthropic efforts are dedicated to empowering the next generation, ensuring they have the opportunities and support they need to succeed.