Real Estate Investing Morning Show ( REI Investment in Canada )

Wayne & Gabby Hillier | Canadian Real Estate Investing Coaches / Mentors
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"Real Estate Investing Morning Show" with Canadian investor power couple, Wayne and Gabby Hillier. We talk everything real estate. Joint Ventures, Landlording, Buying/Selling, Financing, Flipping, BRRRR, Multi-Family, Secondary Suites, Condominiums, Agreement For Sales, Rent to Own, Wholesaling. Not to mention, sharing routines and strategies that we've implemented into our lives that have helped us 10X our performance, our drive and our efficiency.

  1. 23h ago

    5 Things to Consider Before Investing Out of Province in Canada

    Investing Out of Province in Canada: 5 Things You Need to Know Should you buy your first rental property in your hometown, or could investing in another province be a better decision? For many Canadians living in expensive housing markets, purchasing an investment property close to home is becoming increasingly difficult. High property prices, substantial down payment requirements, and limited rental cash flow can make it challenging to find properties that generate acceptable returns. But does buying a property thousands of kilometres away create even bigger risks? On today's Canadian Real Estate Investing Morning Show, Wayne and Gabby Hillier answer an email from a 24-year-old aspiring investor living just north of Toronto. The listener wants to purchase his first rental property and has been researching opportunities outside Southern Ontario, particularly Edmonton, Alberta. He asks whether he should start with a property within driving distance, consider smaller Ontario markets like Windsor, Kingston, or Belleville, or take the leap and purchase an investment property in another province. Wayne and Gabby explain the most important considerations for investing out of province, including market selection, cash flow, landlord-tenant legislation, building a local team, and managing rental properties remotely. Why Your Local Market Isn't Always the Best Market Wayne begins with an important question. Why do you want to invest outside your province? Purchasing a rental property close to home certainly has advantages. You understand the area, you're familiar with local neighbourhoods, and you can visit your property when necessary. But convenience should not be the deciding factor when choosing where to invest. Wayne explains that a rental property should be evaluated as a business. If local property prices are too high relative to rental income, the investment may not generate sufficient cash flow to support itself. He uses the Toronto market as an example. A property costing $900,000 could require a $180,000 down payment at 20%. If the achievable rent cannot cover the mortgage, taxes, insurance, maintenance, and other expenses, the property may require ongoing financial support from the investor. Wayne argues that investors shouldn't force a property purchase simply because they want to invest in their own backyard. 1. Understand Your Reason for Investing Out of Province Before researching another city, investors need to understand exactly what they're hoping to accomplish. Are you looking for better cash flow? Higher long-term returns? More affordable purchase prices? A stronger rental market? More favourable landlord-tenant laws? Wayne explains that investing out of province introduces additional responsibilities, so there needs to be a compelling reason to do it. For his own portfolio, the objective is to achieve strong returns while minimizing financial risk. He emphasizes the difference between cash flow and return on investment. Cash flow helps protect the investment during difficult periods. Overall return on investment determines how effectively the invested capital is building wealth. Both matter, but they serve different purposes. 2. Follow the Five Fundamentals of Real Estate Investing Wayne shares the Five Fundamentals he teaches through the REI Masters Mentorship Program. These principles help investors evaluate whether a market and property align with a sustainable long-term investing strategy. Fundamental 1: Cash Flow From Day One A property should generate positive cash flow after accounting for its operating and financing expenses. Cash flow provides a financial buffer when unexpected problems arise. Fundamental 2: Profit Without Relying on Appreciation Wayne prefers investments that can generate acceptable returns even if property values don't increase. Investors should not rely exclusively on the hope of selling for a higher price. Fundamental 3: Strong Landlord-Tenant Legislation The legal environment matters. Investors need to understand their rights and obligations, including procedures involving unpaid rent, tenancy termination, dispute resolution, and eviction. Fundamental 4: A Great Tenant Profile Properties should attract the type of tenants an investor wants to rent to. Understanding the neighbourhood, local employment opportunities, rental demand, and suitable property types is essential. Fundamental 5: Long-Term Growth Potential Wayne also wants properties in markets with strong economic fundamentals and potential for future appreciation. The goal is to combine current profitability with sustainable long-term growth. The 5% Rule Cash Flow Test Wayne explains why the 5% Rule Cash Flow Test is one of his first considerations when evaluating an investment property. The framework compares annual cash flow against a benchmark investment amount based on a 20% down payment. Wayne's general benchmarks are: 5% to 6%: Sufficient cash flow 7% to 9%: Strong cash flow 10% or higher: Excellent cash flow The objective is to identify properties with enough cash flow to help withstand changes in operating costs, mortgage expenses, and rental income. The test is a screening tool, not a guarantee against investment losses. 3. Research the Entire Market, Not Just Property Prices Wayne explains that researching another province requires much more than finding affordable houses. Investors need to understand the city, its economy, individual neighbourhoods, and the types of rental properties that attract suitable tenants. An inexpensive property isn't necessarily a good investment. The neighbourhood may have weak rental demand or limited employment opportunities. A property may look affordable but require substantial repairs. Or the local rental market may not support the expected rental income. Wayne recommends researching: Local employment and major industries Economic stability and diversification Confirmed infrastructure and development projects Population growth and migration Rental supply and demand Market rents for specific property types Neighbourhood characteristics and rental demand Long-term housing demand Property values and potential for appreciation He also encourages investors to distinguish temporary economic activity from sustainable growth. For example, a major construction project may attract workers for several years. But what happens when that project is completed? Will those workers remain in the community, or will they leave when their employment ends? Wayne prefers markets with stable, diversified employment opportunities that can continue supporting population growth and housing demand. Why Wayne Prefers Larger Cities Wayne explains that he generally prefers investing in larger cities rather than smaller communities. Larger markets often have more diversified economies, broader employment opportunities, and deeper rental demand. Smaller markets may offer attractive prices or strong returns, but they can be more vulnerable to changes in a particular industry or employer. That doesn't mean smaller markets cannot produce successful investments. It means investors need to understand the additional risks and determine whether the potential returns justify them. 4. Understand Provincial Laws, Financing, and Taxes One of the biggest differences between investing locally and investing out of province is the legal and regulatory environment. Wayne discusses why landlord-tenant legislation is a major consideration in his investment strategy. Different provinces have different rules governing tenancy agreements, rent increases, evictions, and dispute resolution. Those differences can influence an investor's financial exposure and ability to resolve problems. Wayne encourages investors to research the applicable residential tenancy legislation rather than assuming the rules are the same across Canada. Investors should also examine financing options, closing costs, provincial taxes, and other expenses that may affect the investment. A property with an attractive purchase price may become less appealing after accounting for all ownership and operating costs. 5. Build a Reliable Local Real Estate Team The listener also asks how important it is to have a good local realtor and property manager when investing across the country. Wayne's answer is that having the right local team is essential. When you cannot easily visit a property yourself, you need reliable professionals who understand the local market and can respond when problems occur. Wayne recommends developing relationships with: An investor-focused local real estate agent A knowledgeable mortgage broker Reliable plumbers, electricians, and other contractors A trustworthy handyman Professional cleaning services A qualified property manager, if you choose not to self-manage These professionals can help investors evaluate opportunities, coordinate repairs, manage property maintenance, and deal with issues without travelling across the country. Gabby adds that online investor communities have made finding reliable local professionals easier than ever. The key is to obtain recommendations, verify credentials, and build relationships before they're urgently needed. Should You Hire a Property Manager or Self-Manage? Wayne and Gabby explain that they have managed their own rental property portfolio remotely for many years. Some of their properties are located hours away from where they live. Their approach relies on established systems, reliable local contractors, and clearly defined management processes. Wayne explains that professional property management can be an excellent option for investors who don't have the time or confidence to handle operations themselves. However, property management fees and additional charges need to be incorporated into the investment analysis. He also discusses Gab

    5 Things to Consider Before Investing Out of Province in Canada

  2. 1d ago

    Secrets To Finding Great Tenants - Gabby Hillier

    Secrets To Finding Great Tenants - Gabby Hillier Are you actually reading your prospective tenants' credit reports, or are you just checking their credit scores? For many landlords, tenant screening consists of reviewing an application, verifying income, checking references, and looking for a satisfactory credit score. But according to experienced landlord and property manager Gabby Hillier, there's much more valuable information hiding inside those credit reports. On today's Canadian Real Estate Investing Morning Show, Wayne and Gabby Hillier discuss some of the tenant screening strategies Gabby has developed over more than 15 years of managing rental properties. Following Gabby's appearance as a guest speaker at a FrontLobby tenant screening webinar, the conversation focuses specifically on how to interpret credit reports, assess an applicant's financial obligations, recognize recent borrowing activity, and look beyond the credit score when selecting tenants. If you own rental properties in Canada, this episode offers practical insight into how experienced landlords evaluate applications and manage tenant selection risks. Why Credit Scores Don't Tell the Whole Story Most landlords understand that reviewing a prospective tenant's credit history is an important part of the application process. But Wayne and Gabby explain that many investors don't fully understand what they're reviewing. They obtain the credit report, look at the credit score, and decide whether the applicant has passed or failed. Gabby believes this approach overlooks some of the most important information available. A credit score provides a general indication of creditworthiness, but it doesn't necessarily tell a landlord everything about the applicant's current financial situation. A person might have a strong credit score while carrying substantial debt. Another applicant may have a lower score because of past circumstances that are no longer affecting their finances. Gabby explains why landlords need to understand the information behind the number. Using Credit Reports to Verify an Application Before even examining an applicant's financial history, Gabby reviews the personal information contained in the credit report. She compares the applicant's legal name and address history with the information provided on the rental application. This helps identify inconsistencies that may need clarification. Gabby emphasizes that credit reports are only one component of the process. She also verifies identification and requests supporting documentation to confirm that the applicant's circumstances match what they've disclosed. The objective is to make an informed decision using multiple reliable sources of information rather than relying on a single report. Understanding Credit Utilization One of the most important sections Gabby reviews involves an applicant's credit accounts and outstanding balances. Credit utilization refers to how much available revolving credit an individual is currently using. For example, someone might have access to $20,000 in credit and carry a balance of $19,000. That tells a different story from someone who has the same credit limit but only owes $1,000. Gabby examines available credit, outstanding balances, and reported loan obligations to better understand the applicant's financial commitments. She also considers installment loans, including vehicle financing and other personal loans. The goal is to determine whether an applicant has sufficient financial flexibility to manage their rent alongside their existing obligations. A Real Tenant Application With Significant Debt Wayne and Gabby discuss a recent rental application that initially looked excellent. The applicant had strong income, good communication, and appeared to be a suitable match for the property. The rent was approximately $1,500 per month, and the applicant reportedly earned around $120,000 annually. Based on income alone, affordability appeared promising. However, the credit report revealed additional financial obligations. The applicant had a vehicle loan of approximately $70,000 and roughly $65,000 in additional credit accounts and loans, much of which was already utilized. Those obligations could translate into substantial monthly debt payments. Wayne explains why someone who earns $120,000 annually may still experience financial pressure if a significant portion of their income is committed to servicing existing debts. The lesson is that landlords should not evaluate affordability using income and rent alone. They should also consider the applicant's broader financial commitments. Available Credit vs Outstanding Debt Gabby makes another important distinction. Having access to a large amount of credit is not the same as actually owing that amount. For example, an applicant with $100,000 in unused available credit may have much more financial flexibility than someone who has borrowed nearly all of it. Gabby explains that she would not automatically reject an otherwise strong applicant simply because they have access to substantial credit. However, she considers whether the applicant's financial situation could change if that credit were heavily utilized. Tenant screening is about evaluating the overall picture rather than treating any single number as an automatic approval or rejection. One of Gabby's Favourite Sections: Credit Inquiries Gabby explains why one of her favourite sections of the credit report is the section showing recent credit inquiries. This information can reveal when an applicant has applied for certain credit products. The dates and types of inquiries can help landlords understand whether the individual has recently been seeking additional financing. Gabby particularly looks for clusters of recent inquiries involving high-interest lenders, payday loan providers, and other sources of short-term borrowing. These may warrant additional questions about the applicant's current financial situation. She also explains why context matters. Multiple inquiries related to shopping for a vehicle loan may have a reasonable explanation. An older period of financial difficulty may be less relevant if the applicant's recent payment history and finances demonstrate improvement. The goal is not to make assumptions about someone based on a single credit inquiry. It's to recognize patterns, investigate relevant concerns, and understand whether the applicant appears financially stable today. Hard Credit Checks vs Soft Credit Checks Wayne and Gabby also discuss the difference between hard and soft credit inquiries. Hard inquiries commonly occur when someone applies for certain forms of credit and may affect their credit score. Soft inquiries generally don't affect a person's credit score. This distinction is important because prospective tenants sometimes express concern that a landlord's credit check could lower their score. Landlords should understand the type of inquiry performed by their screening provider and explain it accurately to applicants. Looking at Someone's Financial History and Current Situation Throughout the conversation, Wayne and Gabby emphasize two important considerations. The first is an applicant's history. Have they generally met their financial obligations? Do their reported accounts show a consistent pattern of responsible payments? The second is their current circumstances. Are they carrying unusually high balances? Have they recently applied for multiple loans? Are there indications that their financial obligations may be difficult to manage? By considering both, landlords can develop a more complete picture of the applicant's finances. Why Past Financial Problems Don't Always Mean Future Problems Wayne and Gabby also explain that not every applicant with a difficult financial history should automatically be rejected. People go through challenging circumstances. Sometimes someone experiences financial difficulties because of a change in employment, an unexpected expense, or another life event. Gabby explains that she considers the context, how long ago the problem occurred, and what the applicant's financial situation looks like today. Wayne adds that they have occasionally accepted applicants while recognizing that certain aspects of their history presented additional risk. The key is making deliberate, informed decisions rather than ignoring concerns or assuming that past events will necessarily repeat. Why Good Systems Matter More Than Fancy Software Gabby reflects on being invited to speak at FrontLobby's tenant screening webinar despite not personally using the platform in her property management business. She explains that she and Wayne have established their own screening and management systems over the years. Wayne emphasizes that screening platforms and software can be useful, but their effectiveness depends on how people use them. A tool cannot replace judgment, proper verification, or a thorough understanding of tenant selection. The objective is to build an effective, consistent screening process using the tools and systems that make sense for your business. What Is FrontLobby? FrontLobby provides tenant screening, rent reporting, and debt recovery services for landlords. Gabby participated in a FrontLobby webinar about common tenant screening mistakes and shared her experience as a landlord. The discussion highlights why credit reports and screening tools can be useful resources, but landlords still need to know how to interpret the information they receive. The Goal of Tenant Screening Wayne closes the discussion by returning to the most important objective. Landlords want tenants who can afford the rent, communicate responsibly, and fulfill their obligations under the lease. No screening process can predict the future or eliminate every possible risk. However, reviewing financial information thoroughly, verifying documentation,

    Secrets To Finding Great Tenants - Gabby Hillier

  3. 2d ago

    Should I Buy a Rental Property Right Now With This Crappy Rental Market?

    Should I Buy a Rental Property Right Now With This Crappy Rental Market? Is now a bad time to buy a rental property in Edmonton? With rental vacancies becoming more challenging, additional rental supply entering the market, and winter approaching, many Canadian real estate investors are questioning whether they should continue purchasing properties or wait until conditions improve. On today's Canadian Real Estate Investing Morning Show, Wayne and Gabby Hillier answer an excellent listener question about buying a second investment property during a slower rental market. The listener already owns a suited property and is considering purchasing a townhouse but is concerned about finding tenants during the winter months. Should they buy now, potentially face a longer vacancy, or wait until spring? Wayne and Gabby explain why there are advantages and disadvantages to both approaches, how they manage seasonal vacancies in their own portfolio, and why waiting for the perfect time to buy could mean missing an excellent investment opportunity. The episode also covers condominium document reviews, utility billing strategies for suited properties, and an update on the REI Masters Costa Rica Retreat. Is It a Bad Time to Buy a Rental Property? The main question comes from a listener who has been following the Morning Show for almost a year. They currently own a property with a secondary suite and are considering adding a townhouse to their portfolio. Their biggest concern is timing. With fewer tenants looking for rental properties during the fall and winter, should they purchase a property in October or wait until December or January and arrange possession for April or May? Wayne and Gabby agree that the concern is legitimate. Rental activity is seasonal, and fewer people typically want to move during the coldest months of the year. However, they explain that the rental market is only one part of the equation. Investors also need to consider the conditions in the real estate sales market. Why Winter Can Be a Great Time to Buy Wayne explains that the same seasonal factors that make finding tenants more challenging can also create opportunities for property buyers. During the spring and summer, the real estate market often experiences stronger buyer demand. More buyers compete for available properties, which can make negotiations more difficult. During the colder months, fewer people are actively purchasing homes. Properties may sit on the market longer, sellers may become more motivated, and investors can sometimes negotiate more favourable terms. That can mean paying less for a property or avoiding multiple-offer situations. Wayne explains that a strong investment opportunity doesn't always appear when it's convenient. You need to be actively looking so that you're prepared to act when the right property becomes available. The Trade-Off Between Purchase Price and Vacancy Gabby acknowledges that purchasing a vacant rental property in December or January may create additional holding costs. It could take longer to find a suitable tenant. That means carrying the mortgage, condominium fees, utilities, insurance, and other expenses without rental income. However, investors should compare those potential costs against the savings they might achieve when purchasing the property. If an investor can negotiate a significantly better purchase price during the slower season, the long-term financial benefit may outweigh the temporary cost of vacancy. The important thing is to account for those potential costs before purchasing. A lower price is only valuable if the property still makes sense financially. Why You Should Always Be Looking for Deals Wayne emphasizes that investors shouldn't restrict their property searches to certain months of the year. A great investment opportunity may appear in October, January, May, or August. Waiting until spring doesn't guarantee that a suitable property will be available. It could also mean competing against more buyers. His recommendation is to analyze opportunities throughout the year and make decisions based on the quality of the investment rather than simply the season. Investors should have their financing, criteria, and analysis systems ready so they can act when a property meets their requirements. How to Avoid Winter Rental Vacancies One of the most practical lessons from today's episode concerns structuring lease terms. Wayne and Gabby explain that they prefer having their rental property leases expire during the spring and summer months. Those months typically offer a larger pool of prospective tenants and more favourable moving conditions. But what happens if you purchase a property in December and secure a tenant for January? A standard 12-month lease would expire the following January, potentially creating another vacancy during the slowest time of year. Gabby shares a strategy they use in their own rental portfolio. Instead of signing a standard 12-month lease, they may offer a longer initial term, such as 16, 17, or 18 months. This allows the lease to expire during a more favourable rental season. If the tenant renews, the landlord can then return to a standard 12-month lease cycle. It's a simple strategy that can improve the timing of future rental turnovers. Why Shorter Leases Aren't Always the Answer Some landlords consider signing six- or seven-month leases when filling winter vacancies. The idea is to bring the lease expiration date into the spring or summer. However, Wayne and Gabby generally prefer longer initial leases. A short lease can create another vacancy only a few months after the property was first rented. That may lead to additional advertising, cleaning, turnover expenses, and periods without rental income. Gabby also discusses Alberta's rent increase rules. Landlords cannot simply sign a six-month lease and automatically increase the rent when it expires. Applicable notice requirements, the length of time since the last increase, and the type of tenancy must all be considered. The takeaway is to understand the legal and financial consequences before choosing a lease term. Good Tenants Are Still Looking Despite discussing the challenges of the rental market, Wayne and Gabby share positive news from their own portfolio. They have filled several vacancies recently and received applications from strong prospective tenants. Their first garden suite tenant also moved in earlier than expected. This is particularly encouraging because they are operating during a slower seasonal rental period. Wayne explains that a smaller tenant pool doesn't mean there are no suitable tenants. People still relocate for employment, family circumstances, and other reasons throughout the year. The challenge is making sure your property stands out and your advertising reaches the right applicants. Why Rental Marketing and Tenant Selection Matter Wayne discusses the importance of marketing rental properties effectively, particularly when prospective tenants have many options. It's not enough to simply publish a listing and hope someone applies. Landlords need to understand what tenants are looking for and how to communicate the advantages of their properties. They also need effective systems for reviewing applications, communicating with prospective tenants, and completing leases. Wayne shares an example involving an applicant who was interested in a rental property but delayed signing the lease. Until the agreement is completed, there is still uncertainty. Landlords should maintain clear expectations and avoid assuming that verbal interest guarantees a completed tenancy. Should You Install Separate Utility Meters in a Suited Property? Another listener asks about installing individual utility meters in legally suited rental properties. Wayne and Gabby explain that they generally prefer charging tenants a flat monthly utility amount rather than installing separate meters. Under their system, the utility accounts remain in the landlord's name. They review historical consumption, calculate the average expenses, and establish a flat utility charge with a reasonable buffer. This can produce additional income when the amounts collected exceed actual utility costs. Installing separate meters may make billing more convenient, but the installation costs need to be considered. Wayne and Gabby explain that they use a similar approach in their multi-unit garden suite developments. The key is understanding the property's actual utility consumption and ensuring the billing arrangement complies with applicable rules and lease terms. Can You Review Condo Documents Before Making an Offer? The original listener also asks an important question about purchasing a condominium townhouse. Can you review the condominium corporation's documents before submitting an offer? Wayne explains that buyers can sometimes obtain existing documents from sellers, owners, or other residents before making an offer. However, those documents may not be current. He prefers submitting an offer that includes an appropriate condition allowing time for condominium document review. Once the offer is accepted, the buyer can obtain and review the necessary documents before deciding whether to remove the condition. Important documents include: Current condominium bylaws Financial statements Reserve fund information and studies Annual general meeting minutes Board meeting minutes Condominium fees and budgets Information about special assessments and outstanding issues Wayne emphasizes that buyers should complete proper due diligence rather than relying exclusively on older documents or informal conversations. A properly drafted conditional offer can allow investors to secure an opportunity while completing necessary investigations. The ability to terminate an agreement and recover a deposit depends on the contract's specific conditio

    Should I Buy a Rental Property Right Now With This Crappy Rental Market?

  4. 3d ago

    The Best Real Estate Investing Advice If You're Struggling

    How to Overcome Your Fear of Real Estate Investing What's stopping you from buying your first rental property? For many aspiring real estate investors, it isn't necessarily money, financing, or finding the right opportunity. It's fear. Fear of making a mistake. Fear of losing money. Fear of bad tenants. Fear of buying the wrong property. And sometimes, simply the fear of not knowing what could go wrong. On today's episode of the Canadian Real Estate Investing Morning Show, Wayne and Gabby Hillier tackle one of the most common challenges facing new and experienced investors: overcoming the fears that prevent them from taking action. Drawing on more than 15 years of investing experience and countless coaching conversations, Wayne shares the concerns he hears most frequently and explains how education, careful planning, cash flow, and strong business systems can help investors manage those risks. Gabby also reflects on the fears she experienced when they began their own real estate investing journey and how knowledge and experience gradually changed her perspective. This episode isn't about pretending real estate investing is risk-free. It's about understanding what can go wrong, preparing for those situations, and developing the confidence to move forward. Why So Many Investors Never Buy Their First Property Wayne opens the episode by sharing a recent coaching conversation with an aspiring investor. The individual had spent considerable time learning about real estate investing, watching others purchase rental properties, and developing an understanding of the business. Yet despite feeling knowledgeable and prepared, he still couldn't bring himself to purchase his first investment property. Wayne explains that this is an incredibly common situation. Many aspiring investors spend years researching markets, analyzing opportunities, attending seminars, and learning strategies without ever taking meaningful action. Sometimes they know exactly what they're afraid of. Other times, they simply have an overwhelming feeling that something could go wrong. Wayne's approach is to identify those fears individually, determine whether the risks are realistic, and develop a plan for managing them. Gabby Shares Her Own Experience With Fear Gabby explains that she was extremely anxious when she and Wayne first started investing in real estate. While Wayne appeared confident about moving forward, she struggled with uncertainty about what they were getting into. There were so many unknowns. She didn't fully understand how everything worked or what would happen if something went wrong. Looking back, Gabby recognizes how much of that fear came from a lack of experience and information. Today, after years of managing rental properties, purchasing investments, and handling challenging situations, she approaches those same concerns very differently. Her experience reinforces an important point. Confidence often develops through education, preparation, and experience rather than appearing overnight. Confidence vs Ignorance Wayne makes an important distinction between confidence and recklessness. He explains that his confidence never came from believing he knew everything about real estate investing. Instead, he believed in his ability to find answers. When he encountered something unfamiliar, he would research it, ask questions, seek professional guidance, and develop a solution. That willingness to be resourceful allowed him to move forward without pretending that risks didn't exist. For aspiring investors, this means developing the ability to recognize what they don't know and finding reliable sources of information before making important decisions. What If I Buy the Wrong Property? One of the biggest fears among new investors is purchasing a property that turns out to be a poor investment. A listener shares concerns about eventually converting her current residence into a rental property. Wayne explains that a home purchased primarily as a personal residence may not necessarily perform well as an investment property. The financing, purchase price, amortization, operating expenses, and achievable market rent may not produce the cash flow needed to make it a strong rental. Rather than assuming the property will work, investors should run the numbers. Wayne discusses why understanding rental demand, cash flow, and the 5% Rule Cash Flow Test is essential before purchasing an investment property. He also emphasizes that making a less-than-ideal decision in the past doesn't mean someone cannot improve their investment strategy moving forward. What If My Tenant Doesn't Pay Rent? This is one of the most common concerns for prospective landlords. Wayne explains that no screening process can guarantee a tenant will always pay rent. Even an applicant with good credit, stable employment, strong references, and a history of making payments could eventually stop paying. The goal is not to eliminate every possible risk. It's to reduce the likelihood of problems and understand the appropriate response if they occur. That includes: Thorough tenant screening Verifying employment, income, and references Understanding applicable landlord-tenant legislation Maintaining accurate documentation Following proper procedures when rent is unpaid Having financial reserves available to cover temporary shortfalls Knowing how to respond can make unexpected situations far less intimidating. What If the Tenant Trashes My Property? Property damage is another concern that prevents some people from becoming landlords. Although the episode does not go into a detailed damage-recovery process, Wayne identifies this as one of the fears investors need to plan for. Proper screening, inspections, documentation, adequate insurance, and maintenance reserves are all important parts of protecting a rental property business. Landlords should also understand their legal rights and responsibilities before renting a property. What If Interest Rates Go Up? Wayne discusses why rental properties should be purchased with sufficient cash flow to withstand changing financing costs. For example, an investment property generating $500 per month in cash flow may have some room to absorb a $200 monthly increase in mortgage expenses. The remaining cash flow would be approximately $300 per month, assuming everything else stayed the same. This doesn't make rising interest rates harmless. It demonstrates why purchasing properties with a reasonable financial cushion can help protect investors from being forced to sell when financing costs increase. What If Rental Prices Go Down? Rental markets are constantly changing. New construction, increased supply, shifting demand, and broader economic conditions can all influence market rents. Wayne explains that investors should be prepared for rents to soften. If a property generates strong cash flow when purchased, the investor may have more flexibility to lower the rent when necessary. A property operating with little or no cash flow has much less room to absorb unexpected changes. This is one reason Wayne places so much importance on buying properties that pass his 5% Rule Cash Flow Test. What If the Roof Needs Replacing? Wayne gives a straightforward answer to this common fear. Eventually, it probably will. Roofs, furnaces, hot water tanks, appliances, and other property components have finite useful lives. Replacing them is a normal part of owning rental real estate. Rather than worrying about whether major repairs will eventually happen, landlords should prepare financially for them. Wayne recommends directing rental cash flow into reserve funds so money is available when significant repairs are necessary. He emphasizes that having sufficient reserves can make the difference between an inconvenience and a financial emergency. What If My Property Doesn't Appreciate? Another common concern is purchasing a property that doesn't increase in value. Wayne explains that one of his core investing fundamentals is to avoid relying on appreciation to make an investment successful. Instead, he prefers purchasing properties that generate cash flow from the beginning. Although property values can increase over time, appreciation is uncertain. By prioritizing cash flow, investors can build an investment strategy that isn't entirely dependent on selling a property for more than they paid. What If I Can't Find a Tenant? Vacancy is another important risk. Wayne explains that investors need to purchase properties people actually want to rent. That means choosing appropriate markets, neighbourhoods, property types, and tenant profiles. A low purchase price does not automatically make a property a good investment. The property also needs to attract suitable tenants at a rent that supports the investment's financial performance. Understanding rental demand before purchasing can reduce vacancy risk, although no property is guaranteed to remain occupied. The 5% Rule and Five Fundamentals Throughout the episode, Wayne repeatedly returns to the principles he teaches through REI Masters. His Five Fundamentals help investors evaluate cash flow, market quality, tenant demand, landlord-tenant legislation, and long-term growth potential. The 5% Rule Cash Flow Test helps investors assess whether a property provides an appropriate return relative to the capital invested. These frameworks are designed to help investors make more consistent decisions and manage risk. Wayne emphasizes that strong cash flow and adequate reserves provide investors with more options when unexpected situations occur. Stop Worrying About What You've Already Done Wayne also addresses investors who regret previous decisions. Some people purchase properties before fully understanding the numbers. Others follow advice that turns out to be unsuitable for their particular circumstances. Wayne encourages tho

    The Best Real Estate Investing Advice If You're Struggling

  5. 4d ago

    How I'd Grow a Canadian Real Estate Portfolio With $0 in 2026

    How I'd Grow a Canadian Real Estate Portfolio With $0 in 2026 How to Build a $1 Million Real Estate Portfolio Starting With $0 Can you really build a million-dollar real estate portfolio without using your own money? According to Wayne Hillier, absolutely. And he's spent more than 15 years proving that it's possible. On today's episode of the Canadian Real Estate Investing Morning Show, Wayne and Gabby break down how they would approach building a Canadian real estate portfolio from scratch in 2026 and 2027. Wayne shares two strategies he has personally used to acquire properties with little to none of his own money, explains why some popular investing strategies aren't realistic for beginners without capital, and identifies three Canadian markets he believes offer opportunities in the current economic environment. Plus, Wayne and Gabby officially announce their upcoming REI Masters Costa Rica Retreat. Can You Really Invest in Real Estate With $0? One of the biggest obstacles preventing Canadians from getting started in real estate investing is the belief that they need substantial savings. Between down payments, closing costs, financing requirements, and unexpected expenses, purchasing investment properties can feel out of reach. And even investors who have enough money to purchase their first rental often discover they don't have enough capital to purchase their second or third. Wayne explains that creative financing becomes increasingly important as investors try to scale. He shares that, throughout their investing journey, he and Gabby have used approximately $15,000 of their own money to build their multimillion-dollar real estate portfolio. The remainder of their acquisitions have been funded using strategies that involve partners and alternative financing arrangements. These strategies require education, experience, planning, and an understanding of their risks, but they can offer alternatives to funding every property purchase personally. Why the BRRRR Strategy Isn't the Best Starting Point With $0 The BRRRR strategy is one of the most widely discussed methods of building a real estate portfolio. It involves purchasing a property, renovating it, renting it, refinancing based on its new value, and potentially repeating the process. When executed successfully, investors may be able to recover some or all of their initial capital through refinancing. But Wayne highlights one major problem for someone starting with no money. You still need money to begin. The down payment, renovations, carrying costs, and other acquisition expenses must generally be funded before a refinance can occur. For that reason, Wayne doesn't consider BRRRR the ideal starting strategy for someone who genuinely has no capital. Instead, he focuses on two alternatives. Strategy #1: Joint Venture Partnerships The first strategy Wayne recommends learning is joint venture investing. A joint venture involves two or more people contributing different resources toward the purchase and operation of an investment property. In the structure Wayne describes, one partner provides the money and financing, while the other contributes the opportunity, real estate investing expertise, and ongoing management. The partners then share the profits according to their agreement. This can be an attractive arrangement because many Canadians are interested in investing in real estate but don't necessarily have the time, experience, or confidence to acquire and manage properties themselves. An educated investor can help bridge that gap. Wayne explains that a successful joint venture should create value for both partners. One person has capital but may lack the knowledge or time to invest directly. The other has the knowledge and ability to operate the investment but lacks the required capital. Together, they may be able to acquire a property that neither would have purchased independently. The key is building expertise, identifying strong opportunities, and structuring partnerships that are financially sustainable and mutually beneficial. Strategy #2: Agreements for Sale and Seller Financing Wayne's second strategy is one of his personal favourites. Agreements for Sale. He explains that this strategy played an enormous role in accelerating his real estate investing journey. At one point, Wayne was struggling to find new joint venture partners willing to finance additional acquisitions. Despite already owning several investment properties, potential partners wanted him to demonstrate more experience. Rather than waiting for someone else to fund his growth, Wayne learned how to acquire properties using Agreements for Sale. An Agreement for Sale is a seller financing arrangement in which the seller agrees to finance the purchase under negotiated contractual terms. Depending on the agreement, the buyer may acquire beneficial ownership and take responsibility for operating the property while the seller retains legal title until the agreed completion date. In certain circumstances, investors may be able to acquire properties with little or no money down. Wayne explains that sellers may consider these arrangements for a variety of reasons. Some homeowners are struggling with mortgage payments. Others are dealing with properties they no longer want to manage. Some need an alternative when a conventional sale is not meeting their needs. Seller financing can sometimes provide a solution. However, Wayne emphasizes that the objective is not to pressure sellers or take advantage of difficult circumstances. It's to identify situations where a properly structured agreement can benefit everyone involved. Why Seller Financing Could Become More Relevant Wayne believes changing market conditions are creating renewed opportunities for creative financing strategies. When housing markets become more competitive, properties take longer to sell, or homeowners experience financial difficulties, some sellers may become more open to alternative arrangements. Investors who understand seller financing may be better equipped to recognize those opportunities. Wayne explains that the most important skill is learning how to solve problems. By understanding Agreements for Sale, investors can determine whether the strategy provides an appropriate solution for a particular homeowner. Not every property or seller will be suitable. And investors need to understand the contractual, financing, legal, and operational risks involved before proceeding. Why Education and Integrity Matter Wayne also discusses the importance of learning Agreements for Sale properly. He credits Barry and Donna Maguire with teaching him the importance of structuring transactions that create positive outcomes for both buyers and sellers. Creative financing contracts can become complicated, particularly when there is an existing mortgage, the seller retains legal title, or the agreement includes future financing and exit obligations. Wayne encourages investors to take the time to understand how the contracts work and ensure the arrangement is appropriate for everyone. If a seller has a better alternative, investors should be willing to recommend it. Building a successful investing business requires trust, integrity, and strong relationships. Three Canadian Real Estate Markets Wayne Is Watching Wayne also shares three markets he believes investors should pay attention to in 2026 and 2027. 1. Edmonton, Alberta Edmonton remains Wayne's preferred real estate investing market. He believes the city continues to provide opportunities for investors who understand the rental market and can identify properties with strong long-term fundamentals. However, he cautions that markets operate in cycles. Edmonton will not necessarily remain the strongest opportunity forever. Investors need to understand changing rental conditions, supply, demand, property values, and cash flow before making decisions. 2. Red Deer, Alberta Red Deer is Wayne's second market to watch. Although he generally prefers larger markets, he believes Red Deer offers interesting opportunities. He highlights the city's growth, comparatively limited rental supply, and potential for continued rental demand. Wayne also discusses how development restrictions can sometimes produce unexpected effects on the existing rental market. He believes investors should research Red Deer as a potential alternative to larger Alberta cities. 3. Saskatoon, Saskatchewan Wayne's third market is Saskatoon. He identifies relative affordability, rental demand, economic activity, and its more measured construction environment as reasons the city deserves attention. He also discusses how investor interest can shift between cities as market cycles change. Just as some investment capital moved from Calgary toward Edmonton, Wayne believes Saskatoon could attract additional attention in future years. These are Wayne's market opinions, and individual property performance still depends on local conditions and deal analysis. The New Agreement for Sale Course Wayne and Gabby are preparing an Alberta-focused Agreement for Sale course through REI Masters. The course will cover how the strategy works, how to identify appropriate opportunities, how to approach sellers, how transactions can be structured, and how investors should plan their exits. The goal is to help investors understand how seller financing may allow them to acquire properties without relying entirely on their own savings or conventional mortgage financing. More information about the course will be announced soon. REI Masters Costa Rica Retreat Officially Announced Wayne and Gabby also announce that the REI Masters Costa Rica Retreat has been booked for January 16 to 20, 2027. The retreat will take place at a private lodge near Playa Negra in Costa Rica. The lodge has only nine guest rooms, creating an intimate, adults-only experience for participants. The s

    How I'd Grow a Canadian Real Estate Portfolio With $0 in 2026

  6. Oct 23

    Real Estate Tax Talk w/ Steve Tsonev

    Real Estate Tax Talk: What Canadian Investors Need to Know With Steve Tsonev Are you paying more tax than you need to on your rental properties? Many Canadian real estate investors spend years learning how to buy properties, negotiate deals, finance acquisitions, and generate cash flow. But understanding the tax implications of those investments is just as important. In today's episode of the Canadian Real Estate Investing Morning Show, Wayne and Gabby Hillier welcome Steve Tsonev, managing partner at Finngo Bookkeeping & Tax, for a conversation about Canadian real estate investing taxes. Steve has more than 14 years of experience in accounting and taxation and specializes in working with real estate investors and business owners. Together, they answer questions from listeners about converting principal residences into rental properties, seller financing, Agreements for Sale, beneficial ownership, trust reporting, family income splitting, travel expenses, and business deductions. They also discuss why working with professionals who understand real estate investing can make an enormous difference in your financial results. Why Real Estate Investors Need Specialized Accountants Wayne begins the episode by explaining why having the right professionals on your team is so important. Real estate investing involves tax situations that are often more complicated than those of a typical salaried employee. Investors may own multiple properties, work with joint venture partners, use creative financing arrangements, refinance investments, operate corporations, or change how properties are used. An accountant who regularly works with real estate investors is more likely to recognize these situations and identify issues before they become costly mistakes. Steve explains that part of his job is recognizing what clients don't know they need to ask. Sometimes the most valuable tax planning opportunities come from a detail that an investor mentions casually during a conversation. Turning Your Principal Residence Into a Rental Property One of the first major topics is what happens when someone moves out of their personal residence and converts it into a rental property. This is a common strategy for Canadians building rental portfolios. An investor might purchase their first home with a relatively small down payment, live in it for several years, and eventually move into another property while retaining the first as a rental. However, Steve explains that changing the property's use can trigger important tax consequences and reporting requirements. Under Canadian tax rules, converting a principal residence into an income-producing property can result in a deemed disposition, subject to applicable elections and exceptions. That means the Canada Revenue Agency may treat the change similarly to a sale for certain tax purposes, even though the property has not actually been sold. Steve explains why investors should speak with their accountant before making the change. Important considerations include: Establishing the property's fair market value when its use changes Understanding the principal residence exemption Reviewing the applicable CRA reporting requirements Determining whether any available tax elections may be appropriate Maintaining documentation for future capital gains calculations Planning for the eventual sale or refinancing of the property Wayne explains that many investors fail to recognize these requirements until years after converting their homes into rentals. Failing to plan appropriately can create complications and potentially increase taxes when the property is eventually sold. Steve's advice is simple: whenever the use of a property changes, speak with your accountant. Seller Financing and Agreements for Sale The next major discussion involves a listener question about seller financing. In an Agreement for Sale transaction, the seller may retain legal title while the buyer acquires beneficial ownership under the terms of the agreement. The seller might also have an existing mortgage that remains in their name. Wayne explains an important distinction. The buyer is not necessarily making payments directly on the seller's existing mortgage. Instead, the buyer makes the agreed seller financing payments, and the seller remains responsible for their underlying mortgage obligations. The listener asks whether the buyer can deduct interest associated with the financing. Steve explains that beneficial ownership is an important consideration in determining who reports the property's income and expenses. Where the buyer is the beneficial owner, the transaction can generally involve the buyer reporting rental income and claiming eligible property expenses, including qualifying financing costs. The exact tax treatment depends on the agreement, the use of borrowed funds, and the facts of the transaction. This leads to a much bigger topic. Beneficial Ownership and Trust Reporting Steve introduces an important tax reporting issue that Canadian real estate investors need to understand. When one person holds legal title to an asset while another person has beneficial ownership, the arrangement may create trust-related reporting considerations. These types of arrangements can appear in Agreements for Sale, bare trust structures, and other real estate ownership situations. Steve discusses the potential application of T3 trust reporting requirements. He explains that Canadian trust reporting rules have undergone changes and that investors need to determine whether their particular ownership arrangements create filing obligations. Not every arrangement is automatically reportable, and the rules and available exemptions must be reviewed. Wayne emphasizes that this topic is significant enough to deserve an entire future episode. He and Steve plan to return for a more detailed discussion about beneficial ownership, bare trusts, and the potential consequences for Canadian real estate investors. Can You Write Off a Real Estate Investing Retreat? Another listener asks whether family travel can be deducted as a business expense when some of the time is spent on financial education. Steve explains that ordinary personal vacation expenses do not become deductible simply because someone spends time learning about money. There must be a legitimate connection to earning business or property income. Potentially relevant activities could include attending a qualifying business conference, participating in investment-related education, or conducting legitimate business activities. Where a trip combines business and personal activities, expenses may need to be reasonably allocated based on their purpose and the applicable tax rules. Wayne and Gabby also ask how this might apply to their proposed REI Masters Costa Rica retreat. Steve explains that they would need to examine the educational program, trip structure, and specific expenses before determining what could qualify. There is no automatic deduction simply because a trip includes a retreat. This is an important consideration for investors attending conferences, educational events, and business-related travel. Can You Split Rental Income With Your Children? Another listener asks whether rental property income could be allocated to children who have little or no other taxable income. The idea is that children may have lower marginal tax rates, potentially reducing the family's overall tax burden. Steve explains that Canadian income attribution and ownership rules place significant restrictions on these types of arrangements. Parents generally cannot simply choose to report their rental income on their children's tax returns. The actual ownership, contributions, relationships, and applicable tax rules matter. Steve also discusses why filing a tax return for a young person who has started working can still be worthwhile even if they do not owe income tax. Potential benefits can include establishing a tax filing history and generating RRSP contribution room through eligible earned income. The discussion also introduces the possibility of a future episode about employing children in a family business and teaching them about income, taxes, savings, and financial responsibility. Home Office Deductions for Real Estate Investors A listener asks whether claiming business-use-of-home expenses is worth the administrative effort when only a small percentage of expenses qualify. Steve explains that the answer depends on the situation. For many business owners, calculating an eligible home office deduction can be relatively straightforward. Relevant expenses may include eligible portions of: Mortgage interest Utilities Property taxes Home insurance Other qualifying home operating expenses The appropriate calculation depends on the type of business, how the space is used, and the applicable rules. Steve explains that if the records are already available, the calculation may take relatively little time. Even a modest deduction can be worth claiming when it is legitimate and properly supported. Vehicle Expenses and Mileage Tracking Steve also discusses why real estate investors should consider tracking vehicle expenses and business-related mileage. For someone with only one rental property and very little business driving, the administrative effort may sometimes outweigh the benefit. However, investors who frequently travel for property-related activities may have larger eligible expenses. Steve shares his own example of reviewing missed mileage records. Although the potential tax benefit for a short period seemed relatively small, the annual total was more meaningful. This reinforces one of the biggest lessons from the episode. Small expenses can add up. And without good bookkeeping systems, investors may overlook deductions they are legally entitled to claim. Why Every Dollar Matters Wayne and Gab

    Real Estate Tax Talk w/ Steve Tsonev

  7. Oct 22

    Real Estate Investing Wins, Garden Suite Success & Exciting New Opportunities

    Real Estate Investing Wins, Garden Suite Success & Exciting New Opportunities After an incredibly challenging week, Wayne and Gabby Hillier are changing the conversation. Today's Canadian Real Estate Investing Morning Show is all about the good things happening in real estate investing, entrepreneurship, and life. While investors often spend most of their time dealing with problems, unexpected expenses, difficult tenants, and changing market conditions, it's easy to forget just how much is actually going right. In today's episode, Wayne and Gabby celebrate recent successes, share inspiring stories from the REI Masters community, discuss the early leasing success of their first completed fourplex garden suite, and explore the possibility of hosting an international real estate investing retreat in Costa Rica. They also talk about why experience makes entrepreneurs more resilient, how investors can identify opportunities in a changing real estate market, and why taking action is so important. Why We Need to Celebrate the Wins After discussing one of their most difficult business days in yesterday's episode, Wayne and Gabby explain why they wanted to shift their focus toward something more positive. Real estate investing comes with challenges. Sometimes things break. Sometimes plans change. Sometimes unexpected expenses or circumstances create additional work. But those problems don't necessarily mean the overall investment is unsuccessful. Wayne points out that investors often spend much more time thinking about the things that go wrong than celebrating everything that goes according to plan. When a tenant pays rent on time, a renovation finishes successfully, or an investment property performs as expected, investors often simply move on to the next task. But those are successes worth recognizing. Instead of waiting for something extraordinary to happen, Wayne encourages investors to appreciate when their planning, research, and hard work produce the results they intended. Gabby Reflects on How Much She's Grown Gabby shares a personal reflection about the difficult year they have experienced. She compares 2026 to 2022, a year she remembers as being particularly challenging and stressful. Despite facing more responsibilities and difficult circumstances today, Gabby feels that she is handling the pressure much better. That leads to an important conversation about personal growth. Wayne explains that the business has become larger and more complex over the last several years. With more properties, more businesses, and more responsibilities, there are naturally more opportunities for unexpected problems. But their ability to manage those challenges has improved dramatically. Experience has helped them develop better systems, stronger coping mechanisms, and greater confidence in their ability to solve problems. The lesson is that becoming more resilient doesn't necessarily mean life becomes easier. Sometimes it means you become better equipped to handle increasingly difficult situations. REI Masters Members Share Their Success Stories One of the highlights of today's episode is hearing about recent accomplishments from members of the REI Masters community. Wayne and Gabby invite listeners to share their wins, regardless of how big or small those accomplishments may seem. The responses include successful refinances, investment property acquisitions, new business ventures, completed real estate transactions, and personal growth. The conversation reinforces the importance of surrounding yourself with people who support your goals and celebrate your accomplishments. Kyla and Fabian's Recent Successes Kyla shares several exciting developments. She and Fabian were recognized by their fellow REI Masters members during the annual retreat for being action takers. Fabian also shared his personal story with the community, creating an important moment of connection. On the investing side, they are refinancing a property with the goal of recovering invested capital while retaining significant equity. They also successfully closed a wholesale transaction on October 15. Wayne and Gabby congratulate them on their progress and discuss why recognition from other investors who are actively pursuing their own goals can be particularly meaningful. Stephanie Takes a Chance on Entrepreneurship Stephanie shares that she made the decision to start a new side hustle this year. Rather than allowing fear to prevent her from taking action, she decided to move forward and try something new. Wayne and Gabby discuss why starting a business can be such a rewarding experience. Wayne explains that one of his favourite parts of entrepreneurship is the startup phase. He enjoys developing an idea, researching the opportunity, figuring out how the business will work, and creating the systems needed to bring it to life. They also discuss how artificial intelligence and modern technology have made researching and developing new business ideas more accessible than ever. Amanda Finds Two Excellent Edmonton Investment Opportunities Another major success story comes from REI Masters member Amanda Dick. After deciding to explore Edmonton as a potential real estate investing market, Amanda quickly identified two promising investment properties. During the previous evening's REI Masters coaching session, Wayne helped her analyze both opportunities. The properties offered different advantages. One was in better overall condition and required less work. The other needed some cosmetic improvements but had features that could make it more attractive to prospective tenants. One of the key differences was the number of bathrooms. One property had one bathroom, while the other had one and a half. Wayne explains why even a small difference in a property's layout can influence rental demand, especially when tenants have plenty of options. The discussion also highlights how investors can use market knowledge, rental demand, property condition, and cash flow analysis to compare opportunities. Amanda was considering making an offer, and Wayne encouraged her to explore whether both opportunities could fit into her investment strategy. Nori Discovers an Off-Market Investment Opportunity Wayne and Gabby also share another success story from their mentorship community. Nori, who had recently travelled to Edmonton for the REI Masters Retreat, was actively looking for investment opportunities through his wholesaling business. While the group was participating in their weekly coaching session, Nori was speaking directly with a property owner about a potential off-market transaction. He contacted Wayne to ask whether they could review the opportunity. After examining the information, they identified the potential to create additional value through relatively modest renovations. The property also appeared to have potential to generate cash flow. Nori was working toward negotiating terms that would make sense for both the buyer and seller. Wayne explains why identifying off-market opportunities and understanding the numbers before making an offer are valuable skills for real estate investors. Our First Fourplex Garden Suite Is Leasing! One of the biggest personal wins Wayne and Gabby share is the early success of their first completed fourplex garden suite in Edmonton. After spending considerable time designing, developing, and constructing the property, the units have finally entered the rental market. And the initial response has been extremely encouraging. Wayne and Gabby explain that every prospective tenant who had attended a viewing at the time of recording had submitted an application. The feedback has been overwhelmingly positive. Pros

    Real Estate Investing Wins, Garden Suite Success & Exciting New Opportunities

  8. Oct 21

    Real Estate Investing Is HARD! Why You Should Still Bet on Yourself

    Real Estate Investing Is HARD! Why You Should Still Bet on Yourself Real estate investing is not always easy. There will be difficult days, difficult weeks, and sometimes even difficult years. And even after more than 15 years of investing experience, Wayne and Gabby Hillier are not immune to those challenges. In today's episode of the Canadian Real Estate Investing Morning Show, Wayne and Gabby have an unusually personal and unscripted conversation about resilience, entrepreneurship, financial freedom, and what happens when everything seems to go wrong at once. After experiencing one of the most difficult business days they've had in years, Wayne shares how unexpected setbacks affected their investment portfolio, why even experienced investors can be overwhelmed, and what allows them to continue moving forward. But this episode isn't about complaining or feeling sorry for yourself. It's about understanding that difficult times are part of building something worthwhile. And more importantly, it's about why Wayne believes you should always bet on yourself. When Everything Goes Wrong at Once Wayne opens the episode by explaining that he and Gabby recently experienced an unusually difficult day across their businesses. Several unrelated problems appeared at nearly the same time. Each issue was manageable on its own, but the combination created a level of pressure they hadn't experienced in quite some time. Wayne admits that the day affected him emotionally. He even missed his daughter's soccer practice, something that was particularly difficult because one of the reasons he became an entrepreneur was to have more flexibility and time with his family. Gabby explains that 2026 has been a challenging year overall. At times, the only way to move forward has been to focus on the immediate task rather than becoming overwhelmed by everything happening around them. Their experience is a reminder that successful entrepreneurs and investors still have bad days. Experience doesn't prevent problems. It changes how you respond to them. Resilience Is One of the Most Important Skills in Real Estate Investing Wayne explains that resilience is not simply about being mentally tough. It's about preparing your business so that unexpected problems don't destroy everything you've built. Real estate investors cannot control every external factor. They cannot control interest rates, market conditions, contractors, unexpected expenses, or every decision made by other people. What they can control is how they structure their business. That means developing systems, maintaining financial reserves, planning for unexpected situations, and creating backup options. Wayne and Gabby have spent years developing their investment businesses to withstand difficult circumstances. Those preparations are what allow them to experience setbacks without being forced to sell properties or abandon their long-term plans. Why Cash Reserves Are So Important One of the biggest lessons from today's episode is the importance of having money available when things go wrong. Wayne explains that cash reserves provide investors with options. Imagine owning a rental property where rents suddenly fall by 30%. An investor without sufficient cash flow or savings may be forced to sell, potentially at a substantial loss. An investor with adequate reserves may have the ability to continue operating the property until conditions improve. That doesn't mean the setback disappears or that holding the property guarantees a recovery. It means the investor has more flexibility and time to make decisions. Wayne reinforces a principle he regularly teaches through the REI Masters Mentorship Program. Cash flow protects your investments, and reserves help protect you from being forced to sell. This is one of the reasons Wayne places so much importance on the 5% Rule™ Cash Flow Test. Even the Worst Investment Can Still Be Profitable Wayne also shares a difficult conversation he recently had with one of his joint venture partners. An unexpected development had affected an investment property. Although Wayne does not disclose the specific details publicly, he explains that the situation changed how the investment was expected to perform. It was not a conversation he was looking forward to having. However, his partner understood the circumstances and recognized that finding out about the issue early provided them with more options. Wayne explains that the investment may now be one of the least successful deals he has ever completed. Yet he still expects it to be profitable over the long term. The lesson is not that every real estate investment will succeed. It's that strong fundamentals, careful planning, appropriate reserves, and a long-term investment horizon can help investors withstand unexpected challenges. Choosing the Right Joint Venture Partners Another important lesson from the experience is the value of choosing compatible investment partners. Wayne explains that the conversation could have gone very differently with someone who had unrealistic expectations or could not accept that unexpected problems are part of investing. Instead, his partner understood the circumstances and focused on identifying solutions. For anyone considering joint venture real estate investing, Wayne emphasizes the importance of working with people who understand the business, appreciate the risks, and share a long-term perspective. The right partnership is not simply about finding someone with money. It is about finding someone you can work with when things don't go according to plan. Why Time Can Be an Investor's Greatest Advantage Wayne discusses why he approaches real estate investing with a long-term perspective. When a property has strong fundamentals and the financial ability to withstand difficult periods, time can provide opportunities for mortgage paydown, rental income, and potential appreciation. Not every investment will perform according to its original projections. Some properties will require more time, money, or effort than expected. But a temporary setback does not necessarily mean the entire investment has failed. Investors who understand their financial position and have the ability to hold an asset may have more choices than those who are forced to sell at the first sign of trouble. This is why Wayne encourages investors to plan for difficult market conditions before they arrive. What's the Alternative to Entrepreneurship? One of the biggest questions Wayne raises during the episode is simple. What's the alternative? He acknowledges that entrepreneurship is difficult. Business owners assume responsibility for their decisions, finances, employees, clients, and the problems that arise. But traditional employment comes with its own compromises. Employees may have greater income predictability, but they often have less control over their schedules, working conditions, and earning potential. Wayne and Gabby discuss the trade-offs between employment and business ownership, including the flexibility they have created by becoming full-time entrepreneurs. Even after a terrible business day, Wayne says he would still choose the life they have built over returning to a traditional job. Why Wayne Left His Career to Become an Entrepreneur Wayne shares a story about the day he decided to leave his previous career. After an unpleasant interaction with someone at a job site, he began questioning why he was continuing to work for someone else. By that point, he had already developed a profitable business outside his employment. He was staying in his job primarily for the security of a regular paycheque. That experience helped him realize that he no longer needed to continue working in an environment where he felt he had little control over his time. He had already proven to himself that he could create income independently. So he made the decision to leave. Wayne explains that becoming an entrepreneur meant taking responsibility for his own financial future. His ideas, decisions, effort, and results would now directly affect his own businesses. The Airport Story That Changed Wayne's Perspective Wayne also revisits a story he shared years ago on the podcast. While travelling through an airport, he witnessed a manager unexpectedly tell an employee that she would need to work additional hours. The employee appeared visibly upset but seemed unable to challenge the decision. Wayne remembers how strongly that interaction affected him. It reinforced his belief that having control over your time is one of the most valuable forms of freedom. He reflects on how many people remain in jobs or circumstances they dislike because they feel they have no alternative. For Wayne, the experience strengthened his commitment to entrepreneurship and building a life where he could make more of his own decisions. Your Story Doesn't End at 18 One of Wayne's most important messages is that the direction of your life is not permanently determined by your education, early career choices, or circumstances at 18 years old. He reflects on his own struggles with school and how he initially entered the workforce without the direction or opportunities he would eventually create for himself. At one point, he was working at a gas station. He did not have the real estate portfolio, businesses, financial freedom, or lifestyle that he enjoys today. Those things came later. Through education, experience, hard work, and a willingness to take responsibility for his choices, Wayne was able to change the direction of his life. His message is that people can continue learning, improving, and pursuing new opportunities at any age. Whether you're 19, 35, 47, or 64, your past does not have to determine your future. Sometimes You Have to Take a Step Back to Move Forward Wayne discusses why making a meaningful change sometimes requires accepting temporary di

    Real Estate Investing Is HARD! Why You Should Still Bet on Yourself
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About

"Real Estate Investing Morning Show" with Canadian investor power couple, Wayne and Gabby Hillier. We talk everything real estate. Joint Ventures, Landlording, Buying/Selling, Financing, Flipping, BRRRR, Multi-Family, Secondary Suites, Condominiums, Agreement For Sales, Rent to Own, Wholesaling. Not to mention, sharing routines and strategies that we've implemented into our lives that have helped us 10X our performance, our drive and our efficiency.

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