Business
Interviewing Jimmy Boss on a new talent acquisition platform on Instagram: Outsiders
Hello Mr. Boss! First of all, I would like to thank you for agreeing to answer our questions, it’s a real pleasure for us to have you today. For those who don’t know you yet, could you introduce yourself? Who are you, where are you from and what are you doing now?
Hello, my name is Jimmy, I have lived in London for over 3 years but I’m now living in Paris and I do a lot of things
My 3 main activities are:
- The management of artists for 4 years now within my agency SDW Management
- The production of artists within my music label SDW Records
- I now offer training for young emerging artists who want advice on how to get started and develop in music
What I like a lot about your journey is that very often you went to fight to get the opportunities you wanted, even if that meant being refused dozens and finding devious methods to get there. Do you have to be relentless to succeed in this industry according to you?
Yes, you have to be determined and combative. In 2006, during a studio session in Paris, I met an R&B producer who told me how he had succeeded in placing one of his compositions on Alicia Keys’ album. He knew that she had booked 4 days of studio in Paris, he showed up at the studio 1 week before, he begged the sound engineers to let him attend the session. After a good ten refusals, they finally accepted.
Then, he tried several times to listen to his production during the session, but to no avail because of a manager mounted like a mirrored cabinet who was standing in the way. Then at the end of the session, he followed him down the street, then got into a taxi to follow him to his hotel. And in front of his determination, the star ended up asking what we let him pass, he could put his CD in the car and she just loved it!
Where many would have stopped at the first refusal, or might never even have tried, he showed courage and fighting spirit and even today the royalties he receives from this single piece allow him to live quietly in a 90m square in the heart of Paris without worrying about tomorrow.
I am convinced that any talented artist who presents a successful project is able to make a living from his music if he finds the right business model suited to his music and consistent with his values and if he is sufficient combative to face the trials that await him.
Remember that it only takes a song, a meeting, an opportunity for everything to change. For my friend it was a chase in Paris…
Industry-wide, there are a lot of conscripts, but few are chosen … What do you think are the 3 biggest shortcomings of musicians who are getting into the world of music today?
The first that many lack is the lack of knowledge in our industry.
Because a lot of people have learned music by themselves, we think we can learn marketing and business by myself too, but I think that’s impossible. Since a pencil needs to be held by the hand to write, I needed a mentor to hold my hand to build myself.
And of all the artists and producers that I have had the chance to meet or rub shoulders with, I know of none that has been built alone, without the support of a third party more experienced in this industry.
The second defect that I come across a lot is the inability to look in the mirror.
Every artist believes that his creation is the best in the world, just as any parent finds his child to be the most beautiful. The public will have the final say. An artist unable to seek and / or accept feedback is doomed to failure.
The third is the lack of a plan.
That is to say, they are able to invest several thousand euros and several months or years in an album, but have no plan to defend it. They refuse to invest in clips and a substantial marketing budget to promote them. Which leads them to say “Well, it didn’t work, I’m doing another one …”.
Besides, with your experience and that of artists and contacts, for you is it better to remain independent or seek the signature in label in the long term?
The Majors have an incredible strike force, for sure. But the real question is: is it better to be top priority or number 97 on a list of 100?
If you become the No. 1 goal of a Major, then you should sign on the spot. If you are not sure, then abstain and use other methods to develop your visibility alone. In any case, when you have reached a sufficiently interesting level of visibility, the record label box will have to be considered with reflection because at the risk of repeating myself, the majors have an incredible striking force.
In addition to your musical activities, you offer training in the music industry. Can you tell us more about your Successful Artist program? Who is it for and what is it about?
The Successful Producer and Artist Training is precisely the kind of training that I would love to take when I started because it would save me a lot of time and money.
When I had to book my first studio session, I had no idea of the rates charged, when I had to hire my first press officer, I had no idea who was good, who was bad and how much cost, etc., etc. In fact, at each stage, we either know what to do, how and with whom, or we go there in luck luck and intuition. With my Training, more chances. Everything is under control.
It is aimed at all artists in auto production or all producers in the making who wish to live from their music, professionalize and develop their visibility. Anyone who makes music, but comes up against a glass ceiling when it comes to selling it. The problem very often comes from a lack of method or the lack of tools and network. The training provides them with the answers they expect.
Where did you want to become a Music Business trainer?
In fact I always did. I’ve always been the guy you call when you have a question or problem.
I had already given my advice to many artists and producers before even thinking of creating this formation, I did it naturally and with pleasure because I feel that we are all fighting the same fight. One day a singer said to me, “You should write a book to guide future generations of artists who are coming.” It resonated with me.
At the same time, I was already taking online training in marketing, business management and personal development. It tilted, I thought rather than a book, why not condense all my knowledge and all my experience in an audio visual training accessible by everyone from anywhere in the world. And the project came to life.
What are your plans after that ?
I am currently working on the creation of a Music Business convention which should take place at the end of September 2020 in Paris. This convention will bring together many recording professionals as well as a few legendary producers who will come to share their experience on stage and during a cocktail party at the end of the day. I will have the opportunity to talk about it again.
Through your journey, we note how training has been a development engine for your projects. What resources do you recommend for musicians and producers outside of online programs to better understand the music world?
To better understand the music industry, I don’t really have it because I learned everything either in the field, or by interviewing more experienced professionals.
However, I learned a lot from the university that I went to in London specialized in music business when I started.
Given the trends of the past few years, what do you think the music industry will look like in 10 years?
From what I know artificial intelligence will be a thing but I can’t say no more about it.
Where can we find you if we want to know more about your services or your news?
Either on my website http://www.jimmyboss.com or on instagram @outsider
Business
Royal York Property Management And Nathan Levinson On Building Stable Rental Portfolios In A Volatile Market
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.
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