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Maintaining Sound Financials as a Sole Proprietor

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Running a small business is the stuff of dreams for many a sole proprietor who would rather make it on their own than toil away for someone else. Operating as a sole proprietor is just one way to structure a small business. It has its advantages and disadvantages. It also has its challenges, including maintaining sound financials.

The thing about operating as a sole proprietor – or sole trader in the UK – is that the government does not recognise any distinct separation between personal and business assets. Every dime a sole proprietor earns in business income is also considered personal income. It is taxed accordingly. Sole proprietors are subject to fewer write-offs as well. To keep finances in order, sole proprietors have to be a lot more careful in managing their personal finances.

Key Differences for Sole Proprietors

By definition, a sole proprietor is someone who operates their business alone. There are no other employees, with one possible exception: immediate family members. A good example would be a baker who specialises in wedding cakes. They normally work by themself. When necessary, theybring in their spouse and one of their children to help get them through those especially busy times.

Here are some of the key differences for sole proprietors:

  • Legal Entity – A sole proprietor’s business is not a legally recognised entity in the same vein as an LLC, partnership, or corporation. This is definitely important at tax time. It could also prove important in the event of litigation.
  • Tax Structure – As previously mentioned, the government does not recognise separate income for sole proprietor and their business. It is all one and the same. That means sole proprietors pay both the employer and employee portions of Social Security and Medicare taxes.
  • Managing Assets – Assets are not considered business property for the sole proprietor unless they are used exclusively for business purposes. Rented space for the baker would be considered an exclusive business asset. Their kitchen at home would not be.

All of this matters to maintaining sound financials. Sole proprietors have to consider all of these things, and more, and weigh them against non-business financials like paying the mortgage and covering the groceries.

The Budget Is Key

Budgets are important for everyone. They are even more so for sole proprietors. Not only does the budget act as a spending guideline, but it also acts as a fire action sign for a business owner’s financials. In other words, a budget lays out exactly what’s coming in and going out. If expenditures are higher than income, a budget is a warning sign that demands action be taken.

The thing that gives sole proprietors the most trouble in terms of budgeting is planning for business expenses. Like household expenses, there are certain business expenses that are known in advance. But that’s not the case for every expense. Business expenses constantly fluctuate for sole proprietors.

A good way to address unknown business expenses is to take the total from the previous year and then multiply it by the current rate of growth. So, if you are 50 percent busier this year than you were at the same time last year, 50 percent is the rate of growth. You would take last year’s total expenses and multiply them by 1.50 to get an estimate of this year’s.

You would then take that number and multiply it by the rate of inflation to make up for higher prices on equipment and supplies. That final number is the number to use for budgeting purposes. It is a rough estimate of how much you need to set aside to cover equipment, supplies, etc.

Setting Aside for Taxes

The other thing that kills sole proprietors is tax liability. Again, sole proprietors pay both the employer and employee portions of Social Security and Medicare (FICA). That is on top of regular income tax. It is a smart idea to set aside a certain amount for every payment to go toward taxes.

Also bear in mind that sole proprietors have to file estimated quarterly taxes. Payments are made in April, June, September, and January. There are two ways to decide how much to pay:

  • Estimate – Sole proprietors can estimate their annual income and pay taxes accordingly. The federal income tax table indicates the business owner’s income tax while FICA taxes are assessed at a flat rate. Those numbers can be found on the SSA website.
  • Previous Year – Business owners that do not want to take a chance at estimating and getting it wrong can simply pay a total of the previous year’s tax liability. Even if quarterly payments are eventually not enough, there will be no penalty for underpayment the following April.

Sole proprietors required to collect and pay sales tax should be setting aside that portion of weekly receipts to pay the bill. It is very important that a separate sales tax account be set up rather than throwing everything into a general fund. It is just too easy to spend everything in the bank account and then not have enough money to pay sales tax when it comes due.

Planning and Saving

In a nutshell, keeping a sole proprietor’s finances on track is about planning and saving. The budget is a planning tool that acts as both a guideline and a fire sign. Savings enable a sole proprietor to make tax payments on time and, if there is a little leftover, earn some interest.

The one thing sole proprietors should not do is leave their finances to random chance. When business finances are not in order, it is too easy to pass off obligations to the next month, then the next, and so on. A lot of sole proprietors have gotten themselves into tax hell by not keeping their finances in order and then not being able to pay their taxes.

As a side note, transitioning from a sole proprietorship to a partnership or LLC, for the purposes of separating finances, isn’t a good idea unless you’re willing to pay an accountant to keep things straight for you. If you cannot manage your finances as a sole proprietor, you will not be able to manage them as chief officer of the LLC or partnership.

The idea of Bigtime Daily landed this engineer cum journalist from a multi-national company to the digital avenue. Matthew brought life to this idea and rendered all that was necessary to create an interactive and attractive platform for the readers. Apart from managing the platform, he also contributes his expertise in business niche.

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Business

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

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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:

  1. Standardization protects both sides. Clear processes for screening, rent collection, maintenance, and legal steps reduce surprises for owners and tenants at the same time.
  2. 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.
  3. 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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