Business

How Leor Massachi Conquered The Startup World And Became The Co-Founder Of His Company Dandy By Age 20

Published

5 years ago

April 3, 2021

We’d like to introduce you to Leor Massachi: a 23-year-old carrying the titles of co-founder, Chief Product Officer, and Chief Marketing Officer for a tech startup named Dandy. Massachi had been interested in business since he was in middle school, so it only made sense that he decided to pursue a business-related program at the University of Southern California after graduating high school.

Although his major was in real estate development, Massachi’s true passion always lied in learning about the realm of technology and how multifaceted it could become when starting a business. He became obsessed with the idea of entrepreneurship to the point where he began interviewing successful executives on a television segment he came up with for his school’s newscast called “Word Hard, Play Hard”. Massachi would also constantly find himself dreaming big and taking notes of “cool ideas” for potential business endeavors on his phone so he wouldn’t forget them down the line. Then, once he got to USC, he was able to learn directly from the experts about the dos and don’ts of launching a tech startup. Along the way, Massachi networked with a number of successful entrepreneurs that gave him some of the advice he still applies to his business today.

In 2018, Massachi and his partner, Daniel Newman, came up with a concept for a dating application while chatting in their dorm room at 1 AM. The app was brainstormed to be completely different than your average Tinder or Bumble; the college seniors noted that they didn’t want users wasting time while they waited for the other person to reply. Instead, the app would work instantaneously for all users. At 8 pm every night, the app would go “live” for 10 minutes and users would make the attempt to log on and find a match. Once two users “liked” each other, they would be automatically transferred into a three-minute message-based chat where they could get to know each other in real-time. If they both decided to move forward when the call was over, the application would provide each user with their match’s phone number.

The concept was unlike anything the market had ever seen, and the two seniors knew they were onto something big. But with great originality also came significant challenges. The two entrepreneurs hired top-tier engineers to work on the product due to its complicated synchronous nature. If too many users logged on at the same time and overwhelmed the server, the entire application could crash. Therefore, it took numerous rounds of trial and error to have the servers reach an optimized stage that could handle the load of thousands of users.

And despite the innovative concept of the product, however, Massachi knew the idea and design of the app alone would not be enough to get the users to participate in the launch. He began to brainstorm ways of marketing the product while remaining under the extremely limited budget he and Newman were paying out-of-pocket. They had to be resourceful and minimalistic with their spending while still making enough of a statement to gather brand recognition. An entire discussion of ideas later, they decided to buy hundreds of yard flamingoes that resembled the outline of the app’s logo and disperse them amongst the USC campus overnight with flyers that read “you’ve been flocked!”. People responded extraordinarily well to the marketing tactic, and just like that, Dandy gained over a thousand users overnight.

Eventually, Massachi was designated as the company’s CPO and CMO while Newman took care of logistics as the company’s CEO. “When things started becoming a bit more stable and the app began taking off, we decided to divide the workload based on what we were best at,” Massachi said. “I focused on the development of high-level product concepts and marketing strategies for Dandy because my natural way of thinking was: ‘how can I penetrate the market in a different and effective way that will still prioritize remaining as resourceful and low-cost as possible,’” he added. “Since I tend to lean more toward working creatively than logistically, it just made sense this way.”

In February 2020, the Dandy app went through some major rebranding after news of a possible pandemic began to consume the media. The company founders gathered in an emergency meeting to discuss the possible consequences of what a nationwide lockdown could mean for students who were still in the prime years of their college experience. They understood that the consequences could force students to leave campus and have classes resume virtually, along with the hopes of establishing new relationships going right out the window. But Massachi and Newman came up with a plan to fix that. They introduced the idea for Zoom University: a live two-on-two video chat application that would be aimed towards recreating the way millennials and Gen Zs formed new connections and relationships online. Since each user went live with a friend, the sense of comfort and trust allowed the product to run far more smoothly than the nerve-racking one-on-one video chats from Dandy’s early stages.

Massachi’s marketing tactics for Zoom University were more digitally-focused than those for their previous product. This time around, the CMO utilized a cutting-edge social strategy that involved having hundreds of TikTok creators tell their audiences about ZoomU in their own organic way. “We wanted the content to be as authentic as possible, so we let the creators do it however they felt was most relatable to their community. It was a win for them because they were able to use their own creativity and brand personality to talk about the product, but it was also a win for us because people received it as a genuine endorsement rather than as some random ad,” Massachi explained. As it turned out, the CMO’s approach was immensely effective. One of the influencers’ videos uploaded to Tiktok ended up going viral overnight, and in a matter of 48 hours, the video was viewed over 2.5 million times. Zoom University ended up adding hundreds of thousands of users to their waitlist as a result of that one video.

A couple of months after its launch, Zoom University surpassed a user mark of 100,000 and it even gained a spot in the Top 10 Social Networking Apps on the App Store. That alone was a dream come true for Massachi and Newman. But the work didn’t stop there. Since August of 2020, the two co-founders have been in the process of developing yet another new project alongside some big investors. Details cannot be discussed quite yet, but they have shared that they will be implementing all learnings and feedback from their prior products into perfecting this new endeavor.

Bearing in mind their monumental milestones, you’re probably wondering how these fairly young business owners have time for anything else besides attending to their ever-evolving business. But they actually happen to heavily prioritize the balance between work and social life. “I’m very mindful. I try to live every day like it’s the weekend,” Massachi said. “Occasionally, I’ll go biking, I’ll eat good food, I’ll meditate, or I’ll hang out with friends. Taking a break helps me reset so that I can continue coming up with fresh, new ideas once I’m back to work. I’ve gained a lot of knowledge along the way on how to manage this heavy lifestyle, but I’m also still learning as I go. That pretty much goes for everything when you’re involved in a startup.” Massachi adds that he is eager to wake up every morning and think of new product ideas to improve people’s everyday lives; products that will not only provide high efficiency, but will also be meaningful enough to bring joy to its users.

Business

Royal York Property Management And Nathan Levinson On Building Stable Rental Portfolios In A Volatile Market

Published

2 days ago

December 11, 2025

Matthew Wiles

Across North America, Europe, and much of the world, rental housing is caught between two pressures. On one side are tenants facing record affordability challenges. On the other side are landlords seeing operating costs, interest payments, and regulatory complexity move in the opposite direction.

Recent analysis from Canada’s national housing agency shows how tight conditions still are. The average vacancy rate for purpose-built rentals in major Canadian centres rose to about 2.2 percent in 2024, up from 1.5 percent a year earlier, but still below the 10-year average despite the strongest growth in rental supply in more than three decades.

At the same time, higher interest rates have pushed up the cost of acquiring and financing rental buildings, which has slowed transactions and made many projects harder to pencil out.

In this environment, the question for landlords and investors is less about chasing maximum rent and more about building stability. That is where Royal York Property Management and its founder, president, and CEO Nathan Levinson have drawn attention.

From a base in Toronto, Royal York Property Management manages more than 25,000 rental properties, representing over 10 billion dollars in real estate value, and operates across Canada, the United States, and parts of Europe. Levinson also sits on a Bank of Canada policy panel focused on the rental market, where he provides data and on-the-ground insights about rent trends and landlord stress.

For many smaller property owners, his model has become a reference point for how to treat rental housing as a structured financial asset rather than a side project.

Rental housing under pressure from both sides of the balance sheet

In many countries, the basic rental story is the same. Construction of new rental housing has climbed, yet demand still runs ahead of supply in most major cities. In Canada, overall rental supply grew by more than 4 percent in 2024, the strongest increase in over thirty years, while vacancy rose only modestly.

At the same time, borrowing costs have moved sharply higher compared with the pre-pandemic period. Research shows that elevated interest rates have reduced the profitability of new multifamily deals and slowed investment activity, even as structural demand for rental housing stays strong.

For small and mid-sized landlords, that tension shows up in a simple way. Mortgage payments, taxes, insurance, and maintenance rarely move down. Rents move up more slowly, and in many jurisdictions they are constrained by regulation or market realities.

Levinson’s view is that this gap will not close on its own. Landlords who want to stay in the market need more predictable income, tighter control of costs, and clearer systems for dealing with risk.

A property management model built for volatility

Royal York Property Management did not start as an institutional platform. Levinson’s early clients were owners of single condominiums, duplexes, or small buildings who were struggling with irregular rent payments, surprise repairs, and complex rental rules.

Instead of handling each property ad hoc, he built a standardized operating model that treats every door as part of a wider portfolio. Each unit sits on a centralized platform that records rent, arrears, lease expiries, maintenance tickets, and legal actions. Owners see real-time statements and performance metrics rather than waiting for year-end reports.

That structure, combined with an internal maintenance and legal team, is designed to handle stress rather than avoid it. When markets are calm, the system may look conservative. When conditions worsen, it is what keeps owners in the black.

“Execution is everything” is how Levinson often frames it in interviews.

Turning rent into a more predictable income stream

The feature that first drew many investors to Royal York Property Management is its rental guarantee program in Ontario. Under this model, landlords receive their rent even if a tenant stops paying. RYPM takes responsibility for legal proceedings, arrears recovery, and re-leasing the unit, while the owner continues to receive income.

Independent profiles of the company describe this as one of the first large-scale rental guarantee frameworks in the Canadian market, and note that the firm manages tens of thousands of units under this structure.

The guarantee itself is closely tied to local law and does not transfer directly into every jurisdiction. The underlying logic, however, is straightforward:

Treat unpaid rent as a recurring and manageable risk rather than an occasional shock.
Price that risk into a clear product instead of handling each case informally.
Use scale, legal expertise, and data to keep default rates low and resolution times shorter.

For landlords who are facing mortgage renewals at higher interest rates, having a more stable rent stream can be the difference between holding a property and being forced to sell. That is one reason rental guarantee models have started to attract interest from investors outside Canada who are watching RYPM’s approach.

Using technology to see risk earlier

Behind the guarantee and the day-to-day operations is a technology stack that tries to surface problems before they become crises. Royal York Property Management’s internal platform uses data from payments, maintenance, and tenant behavior to flag risk signals and operational bottlenecks.

Examples include:

Tenants who move from on-time payments to repeated short delays.
Units where small repair tickets point to a larger capital issue ahead.
Buildings where complaint volumes suggest service gaps or staffing problems.

Rather than treating these as isolated events, the system aggregates patterns across thousands of units. That allows management to decide whether a problem is individual, building-specific, or systemic.

Levinson has also pushed this data outward. As a member of the Bank of Canada’s rental policy panel, he provides anonymized information on rent collection, defaults, and renewal behavior, which feeds into broader discussions about financial stability and housing policy.

The same data that protects a landlord’s cash flow in one building helps central bankers understand how higher rates are affecting thousands of households.

Why the Canadian case matters for global landlords

Several recent reports underline how closely rental markets are now tied to national economic performance. Tight rental supply and high rents are feeding inflation in many economies. At the same time, higher borrowing costs are discouraging new construction, which risks prolonging shortages.

This feedback loop is especially hard on small landlords. Many own only one or two properties and have limited room to absorb higher mortgage payments or extended vacancies. Analysts in Canada and abroad have warned that some owners are at risk of default as their loans reset at higher rates.

In that context, the Royal York Property Management model offers three lessons that travel across borders:

Standardization protects both sides. Clear processes for screening, rent collection, maintenance, and legal steps reduce surprises for owners and tenants at the same time.
Risk pooling is more efficient than one-off crises. Handling arrears, legal disputes, and vacancies inside a structured system is less costly than improvising each time.
Operational data belongs in policy conversations. When policymakers have access to real rental data rather than only mortgage statistics, interventions can be better targeted.

It is not an accident that Levinson’s work now sits at the intersection of private property management and public financial policy.

What everyday landlords can borrow from the Royal York playbook

Most landlords will not build a 25,000-unit management platform. Many will never interact with a central bank. The core ideas behind Nathan Levinson’s approach are still accessible to smaller owners that manage a handful of properties.

Three practices stand out.

First, treat every rental unit as part of a simple portfolio. That means using a consistent template to track rent, arrears, expenses, and vacancy days for each property, then reviewing it on a schedule instead of only when something goes wrong.

Second, write down the rules for risk in advance. Late-payment steps, repayment plans, documentation standards, and maintenance response times should exist on paper, not only in memory. Royal York’s experience suggests that clear rules reduce conflict, because everyone knows what will happen next.

Third, invest in service as a protective layer. Multiple independent profiles of RYPM point out that faster response times and transparent communication reduce tenant turnover and protect building condition, which in turn supports long-term returns.

For landlords and investors trying to navigate today’s volatile rental markets, the message from Royal York Property Management and Nathan Levinson is surprisingly simple. You cannot control interest rates or national housing policy. You can control how organized your portfolio is, how clearly you manage risk, and how consistent your operations feel to the people who live in your buildings.

For many, that shift from improvisation to structure is what will decide whether their rental properties remain a source of wealth or turn into a source of stress.