Advertise on podcast: A Canadian Investing in the U.S. with Glen Sutherland

A client once told Glen that ChatGPT named him the top coach for Canadians investing in the US, and Glen had no idea how it happened. This week he brings in Patrick Yepez to find out. Patrick has been a real estate investor for over 30 years, a former broker, and runs Dream Big Marketing Agency. He explains Generative Engine Optimization (GEO): how to get AI engines like ChatGPT and Google's AI Overview to cite, mention and recommend your business. He covers why one AI prompt sets off many background searches, and why an AI recommendation is worth far more than a ranking on Google. The key difference from SEO: SEO tells the world what you do, while GEO has to prove you actually do it. Patrick goes through what AI engines look for: citations, regular reviews, schema markup, an LLM text file, service pages, unique location pages, process pages, FAQ "content capsules", YouTube video, and a consistent name, address and phone number everywhere. He explains the four layers (indexability, clarity, evidence, corroboration) and Google's updated E-E-A-T standard. He also shares a client whose 100 copy-paste location pages got only one page indexed, and another who got a ChatGPT-referred seller lead within about 27 days. If you're a real estate investor, agent, lender or coach and you don't want your competitors to become the businesses AI recommends, this episode is for you.

Stewart Heath is a CPA turned commercial real estate sponsor and founder of Harvard Grace Capital, where he buys "boring," already-stabilized properties instead of chasing ground-up development or heavy value-add deals. After years of doing both, Stewart explains why predictable, recurring cash flow beats the higher-risk upside promised by construction and renovation plays. He walks through his favorite scenario: buying mismanaged, doctor-owned medical office buildings where the physical asset is well kept but the leases are stuck far below market, then raising rents gradually over two to three years without losing tenants. Stewart and Glen dig into the math behind his model: locking in fixed-rate debt to eliminate interest rate risk, focusing on the spread between the cap rate and the interest rate rather than the rate itself, and using cost segregation studies to generate roughly 30 percent of the purchase price in bonus depreciation, which shelters cash flow from tax for several years. They also cover how the recent run-up in interest rates actually created buying opportunities from sellers stuck in expiring bridge loans, and why sticking to the numbers, not the asset class, is what keeps his model asset-class agnostic. Stewart closes by sharing his book, "My 10 Rules for Investing in Commercial Real Estate: Don't Do What I Did," free at harvardgrace.com.

Marc Younger is back on the show after six years (he was previously on episodes 76, 77, and 116). He grew up in Edmonton, moved to Orlando, and built Home Theme Orlando, a company that has themed roughly 200 short-term rental homes for investors near Walt Disney World. Marc also runs a property management arm that now handles 40 to 50 vacation homes for owners. In this episode, Glen and Marc dig into what buying and running a themed short-term rental in the Orlando area actually looks like today, from price cycles to the strict zoning line that decides where you can even legally rent nightly. Marc breaks down real numbers: a plain, non-themed 7 to 8 bedroom home might bring in $40,000 a year, while the same house themed around a Disney-style concept can pull $140,000 to $160,000. He explains why Highway 192 splits Orange County (no short-term rentals allowed) from Osceola and Polk counties (rentals allowed), why buying inside a large amenity-rich community beats a standalone house, and how cost segregation lets investors get back a big chunk of their down payment through accelerated depreciation. If you're a Canadian or American investor weighing a themed vacation rental near Orlando, this episode gives you current price ranges, the zoning rules, and the real revenue math.

In this episode of Canadian Investing in the US, Glen reconnects with Bryce Kaminsky to compare the realities of real estate investing in Canada versus the United States. Bryce shares his experience investing in Cleveland and explains why many Canadian investors are struggling to make buy-and-hold rentals work due to higher purchase prices, rising renovation costs, mortgage renewals at higher rates, and increasingly thin cash flow. He contrasts that with lower-cost U.S. markets where investors may still be able to find stronger rental yields, especially by targeting off-market opportunities and properties that can be improved through renovations. The conversation also explores where opportunities may still exist for investors who want to stay in Canada. Bryce suggests buying aggressively below market value, focusing on solid working-class neighborhoods, using forced appreciation, and being careful not to over-leverage during refinances. Glen and Bryce also discuss property management for remote U.S. investing, including why scenario-based interview questions can reveal far more than simply comparing management fees. The broader message is that investors should focus less on geography alone and more on finding properties that truly produce cash flow, fit their risk tolerance, and support their long-term goals.

In this episode of Canadian Investing in the US, Glen speaks with security-awareness expert Robert Siciliano about the growing threat of scams, identity theft, wire fraud, and social engineering—especially for Canadians investing remotely in U.S. real estate. Robert explains that modern scammers operate like sophisticated businesses and often rely less on hacking technology than on manipulating human behaviour. He introduces the concept of becoming a “strategic human firewall” and shares his AAA protocol: Analyze, Authenticate, Act. Investors should recognize manufactured urgency, independently verify who they are communicating with, and never rely on phone numbers, email addresses, links, or wiring instructions contained in an unexpected message. The conversation becomes especially relevant to real estate investors when Robert explains why criminals target email accounts and how compromised or spoofed communications can be used to impersonate title companies, attorneys, lenders, buyers, and sellers. He shares a sophisticated scam in which criminals impersonated Google Security, triggered legitimate Google emails and text messages, and nearly convinced him to authorize access to his own account. Robert recommends using unique passwords for every account, a password manager, and two-factor authentication on all critical financial and email accounts. The takeaway for investors is simple: when money, account access, or wiring instructions are involved, slow the process down and independently verify everything before acting.

In this episode of Canadian Investing in the US, Glen speaks with repeat guest Tim Miron, founder of Pursuit CPA, about when a Canadian real estate investor should add a Canadian corporation to their U.S. investment structure. Tim explains that the answer depends on the investor’s long-term goals, where the original investment capital comes from, and what they eventually plan to do with U.S. profits. One major reason to use a Canadian corporation is when the investor already has retained earnings inside an operating company or holding company; instead of withdrawing those funds personally and triggering another layer of tax, the corporation may be able to deploy more of that capital into U.S. investments. They also discuss moving money between Canadian and U.S. entities through properly documented management fees and intercompany loans. The conversation also covers the additional compliance that comes with adding a Canadian corporation, including setup costs, annual corporate tax filings, foreign reporting requirements, legal minute-book maintenance, and HST considerations. Tim explains that services provided by a Canadian company to a U.S. customer may generally be zero-rated for HST, while the Canadian corporation can potentially recover HST paid on eligible business expenses. They also discuss a second major reason to add a Canadian holding company later: once a U.S. real estate portfolio becomes profitable, investors may want to move profits back to Canada without taking the money personally, allowing the corporation to reinvest in stocks, bonds, Canadian real estate, or other opportunities

In this episode of Canadian Investing in the US, Glen speaks with Fernando Angelucci, CEO of SSSE, a private equity firm focused on self-storage acquisitions and development across the United States. Fernando explains why he moved away from single-family and small multifamily investing after years of dealing with high management demands, contractor issues, tenant problems, and relatively lower profits. He shares how self-storage allowed him to operate fewer, larger transactions while increasing profitability and working with more sophisticated lenders, operators, and professionals. The conversation dives into Fernando’s self-storage strategy, including sourcing more than 90% of acquisitions off-market, building long-term relationships with owners, targeting larger facilities, expanding properties, increasing NOI, and eventually selling to institutional buyers. He also discusses financing options such as SBA loans and seller financing, the legal advantages of self-storage compared with residential rentals, auction procedures for delinquent units, stabilized occupancy levels, and dynamic pricing strategies similar to airlines. For investors looking for a scalable commercial real estate niche with fewer traditional landlord headaches, Fernando makes a strong case for self-storage as a business as much as a real estate investment.

In this episode of Canadian Investing in the US, Glen reconnects with experienced real estate investor Tim Tsai to discuss one of the most overlooked decisions in real estate: when it makes sense to sell a rental property instead of continuing to hold it. Tim explains that he evaluates properties based on cash flow, NOI, cash-on-cash return, maintenance costs, and opportunity cost rather than simply focusing on how many doors he owns. After more than two decades of investing across Canada, the U.S., and the UK, Tim is now exiting the UK market because the numbers no longer justify keeping the properties. He emphasizes that aging properties often require increasing amounts of capital and attention, and investors should regularly ask whether their equity could be producing stronger returns somewhere else. Glen and Tim also challenge the popular real estate mindset of accumulating as many rental units as possible, arguing that portfolio performance matters more than door count. They discuss lease options as a strategy that can generate upfront option money, monthly cash flow, and a future sale while potentially reducing traditional landlord-management headaches. The conversation also explores the hidden emotional cost of owning troublesome properties, the importance of redeploying trapped equity, and why inherited or underperforming rental portfolios can eventually become liabilities rather than assets. Tim closes by emphasizing that investors make much of their money—and protect themselves from future problems—by buying correctly from the very beginning.

In this episode of Canadian Investing in the U.S., Glen reconnects with repeat guest Matthew Scott, a Canadian real estate investor who has flipped approximately 40 properties in Southwestern Ontario and raised more than $10 million in capital. After travelling to Mexico and deciding to spend more time there, Matthew shifted his attention toward Mexican real estate, land development and the process of preparing land for future development. He discusses his work with local developers, plans to create a real estate agency and his involvement in a large land-entitlement project that could eventually be sold to a developer. Matthew explains how he evaluates potential areas by studying tourism, government development plans, infrastructure expansion and the activity of other developers. The conversation also examines the risks of purchasing land in Mexico, including unclear ownership records, restrictions on certain types of land, unreliable representatives and the importance of working with experienced lawyers and notaries. Matthew discusses cash purchases, financing and residency considerations before sharing how living in Mexico has changed his lifestyle and perspective. He describes his personal experiences with the culture and safety while emphasizing the importance of knowing the area, avoiding flashy displays of wealth and building relationships with trustworthy local professionals.

In this episode of Canadian Investing in the U.S., Glen speaks with Steve Harmer, president of FrontLobby, about how rent reporting and tenant screening can help landlords reduce risk while helping responsible tenants build their credit history. Steve explains how rental payments can be reported to major credit bureaus in both Canada and the United States, including Equifax, TransUnion and Experian depending on the country. Because rent is often a tenant’s largest monthly financial obligation, reporting on-time payments can help establish or strengthen a tenant’s credit profile. Steve also discusses a study conducted with Equifax Canada that found some participants experienced credit-score increases in the range of 40–80 points during their first six months, although the impact varies significantly depending on each tenant's existing credit history. The conversation also explores how landlords can use rent reporting as part of their tenant-screening and rent-collection strategy. Steve explains how landlords can screen applicants using credit reports, background checks and identity verification, while rental-payment history can provide additional insight into how applicants have handled previous leases. They also discuss reporting late or unpaid rent, obtaining tenant consent for positive reporting, reporting former tenant debt, and how small landlords can implement the system with only a few rental properties. Ultimately, the episode shows how rent reporting can create accountability for tenants while rewarding those who consistently pay on time, potentially creating a more balanced relationship between landlords and renters.

In this episode of Canadian Investing in the U.S., Glen speaks with Jeff, an experienced real estate investor, hard money lender and coach who operates Best REI Funding, Alpha Lending and Best Capital Management. Jeff explains how his career evolved from actively flipping houses and managing rentals to focusing primarily on real estate lending and education. He emphasizes that successful investors should avoid becoming locked into a single strategy and instead develop the skills to evaluate whether each property is best suited for wholesaling, flipping, refinancing, holding as a rental or selling on the retail market. Jeff also discusses how higher interest rates have caused a major shift from fix-and-flip projects toward the BRRRR strategy. His lending companies previously financed approximately 80% flips and 20% BRRRR projects, but that ratio has now reversed. The conversation also explores the increasing challenges surrounding DSCR loans, including changing underwriting requirements, reduced loan-to-value ratios, higher reserve requirements and unexpected closing delays. Jeff explains that investors can reduce their risk by underwriting properties with multiple exit strategies and matching the property, financing and investment plan rather than forcing every deal into a predetermined strategy.

Interest rates, lending guidelines, and real estate investing strategies are changing faster than ever. In this episode, Glen sits down with experienced lender and investor Jeff Cichocki to discuss why today's investors need to stop forcing every property into a single strategy and instead focus on finding the highest and best use for every deal. They dive into the shift from flipping toward BRRRR investing, why wholesalers often have the greatest flexibility, and how having multiple exit strategies can dramatically improve your odds of success. Jeff also shares what he's seeing from the lending side of the business, including why DSCR loans have become more difficult to close, how underwriting requirements are changing almost daily, and why investors need to understand financing just as well as they understand real estate. Whether you're flipping houses, building a rental portfolio, wholesaling, or simply trying to navigate today's financing landscape, this episode is packed with practical insights to help you make better investment decisions.

In this episode of Canadian Investing in the US, Glen Sutherland sits down with Paul Hopkins, VP of Investments at CPI Capital, to break down why Dallas–Fort Worth has become one of the most attractive apartment investment markets in the United States. Paul shares his journey from construction and engineering into large-scale multifamily investing before explaining the key economic drivers behind Dallas' continued growth, including population migration, Fortune 500 employers, job creation, infrastructure investment, and why major investors continue to target Texas. The conversation also tackles one of the biggest questions investors are asking today: Is now actually the right time to invest in Dallas? Glen and Paul discuss the recent apartment oversupply, the challenges many syndicators faced with bridge financing and rising interest rates, and why those same market conditions have created opportunities to purchase quality apartment communities at significant discounts. They also explain why Class B multifamily properties remain attractive, how supply and demand are shifting back in investors' favor, and what makes the Louisville, Texas submarket stand out for long-term growth. Whether you're an active investor or simply want to understand where the U.S. multifamily market is heading, this episode provides valuable insights into today's investment landscape.

Finding great real estate deals starts with finding motivated sellers—and that's exactly what we dive into in this episode. I sit down with digital marketing expert and real estate investor Brian Driscoll to discuss how investors can generate high-quality direct-to-seller leads using Google Ads and other inbound marketing strategies. We compare inbound marketing with traditional methods like cold calling, driving for dollars, and purchased lists, and explain when each approach makes the most sense as your investing business grows. Brian also shares the systems successful investors use to convert more leads into deals, including why speed to lead is one of the biggest factors in closing profitable opportunities. We discuss CRMs, automation, lead management, negotiation, and why approaching sellers with a problem-solving mindset consistently outperforms high-pressure sales tactics. Whether you're wholesaling, flipping, buying rentals, or using creative financing strategies like lease options and seller financing, this episode is packed with practical advice to help you find more off-market opportunities and scale your real estate business.

Canadians investing in U.S. real estate often assume the financing process works just like it does at home—but that assumption can lead to costly mistakes. In this episode, Glen Sutherland sits down with cross-border mortgage expert Chris Micucci to break down the biggest lending misconceptions Canadian investors make and explain how U.S. investment financing really works. From DSCR loans and reserve requirements to closing costs, corporate structures, wire transfers, and choosing the right lender, you'll learn the practical lessons that can save you thousands of dollars and prevent deals from falling apart. Whether you're buying your first U.S. rental or expanding your portfolio, this episode will help you avoid the mistakes that catch many Canadian investors off guard. glensutherland.com/lenders The 13 Lending Mistakes Canadians Make: 1. Thinking you qualify based on your personal income Many Canadians assume U.S. lenders care about salary, T4s, tax returns, or employment. For DSCR loans, the property qualifies—not you. 2. Assuming you need perfect personal finances to buy Canadians often believe they need extensive financial documentation. In reality, many U.S. investment loans primarily focus on the property's cash flow and your down payment funds. 3. Believing Canadian mortgage rules apply in the U.S. Many investors expect pre-approvals, qualification rules, and lending policies to work the same way they do in Canada. They don't. 4. Getting pre-approved before finding the property In Canada, you're approved for a dollar amount. In the U.S., you're generally approved for a specific property that cash flows. Many Canadians misunderstand this difference. 5. Buying properties that are too inexpensive Ironically, smaller loan amounts are often harder to finance because many lenders prefer larger loans and higher-value properties. 6. Being surprised by U.S. closing costs Many Canadians experience sticker shock because title fees, lender fees, appraisals, escrow deposits, and other costs are itemized instead of hidden in the mortgage. 7. Waiting until the last minute to transfer money International wire transfers can be delayed by compliance reviews or audits. Waiting until the week of closing can jeopardize the deal—and potentially your earnest money deposit. 8. Waiting too long to set up your U.S. entity and EIN Many investors don't realize that obtaining an EIN can take weeks, especially during busy IRS periods. Waiting can delay financing and closing. 9. Setting up the wrong ownership structure Some Canadian tax structures work well legally but are difficult—or impossible—for many U.S. lenders to finance. Structuring without considering lending requirements can create expensive delays. 10. Not having enough reserve funds Many first-time investors budget only for their down payment. Most lenders also expect to see several months of mortgage reserves in a U.S. bank account. 11. Shopping only by interest rate A lower rate isn't always the better loan. Points, lender fees, closing costs, and how long you plan to hold the property all matter. 12. Comparing different loan products as if they're identical Many investors compare refinance quotes, construction loans, fix-and-flip loans, and purchase loans without realizing they're completely different products. 13. Using lenders who don't understand Canadian investors One of the biggest mistakes is working with lenders who primarily serve Americans. They may quote attractive terms initially, only for underwriting to discover you're Canadian and change the loan shortly before closing