A Canadian Investing in the U.S. with Glen Sutherland

Glen Sutherland

Helping anyone invest in the U.S. real estate market from anywhere!

  1. 3h ago

    EP 443 - Why a $1,650 Rental Can Suddenly Earn $4,000 a Month With Sarah Larbi

    Sarah Larbi has been investing in real estate since 2013 and runs Midterm Rental Properties. She joins Glen to explain how midterm rentals sit between short term and long term: furnished, all inclusive stays of 30 days or more, often three to six months. She shares how one of her Brantford, Ontario properties went from about $1,650 a month as a long term rental to about $4,000 a month as a midterm rental, who the typical guests are (homeowners in transition, insurance claim and renovation stays, healthcare workers and companies housing staff), and which property features matter most, like a functional kitchen, laundry, parking and a fenced yard for pets. Glen and Sarah also dig into the mistake that sank Glen's own midterm rental: letting short Airbnb bookings break up the calendar. Sarah walks through her approach of setting a 30 plus day minimum with a monthly discount and filling gaps with shorter stays. They cover insurance, contracts, guest screening, inspections and damage deposits, plus a real story of a guest who left drug paraphernalia behind. Sarah's comments on bylaws, tenancy rules and tax reflect her own experience, mostly in Ontario. Rules vary by city, province and state, so check with a local lawyer, paralegal, accountant and insurer before you change your rental strategy.

    EP 443 - Why a $1,650 Rental Can Suddenly Earn $4,000 a Month With Sarah Larbi

  2. Oct 22

    EP 442 - How to Get Ai or ChatGPT to Recommend your company With Patrick Yepez

    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.

    EP 442 - How to Get Ai or ChatGPT to Recommend your company With Patrick Yepez

  3. Oct 19

    EP 441 - Why Boring Commercial Real Estate Beats Risky Value-Add Deals With Stewart Heath

    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.

    EP 441 - Why Boring Commercial Real Estate Beats Risky Value-Add Deals With Stewart Heath

  4. Oct 8

    EP 440 - Why a $40K Airbnb Near Disney Can Suddenly Earn $160K a Year With Marc Younger

    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.

    EP 440 - Why a $40K Airbnb Near Disney Can Suddenly Earn $160K a Year With Marc Younger

  5. Oct 1

    EP439 Canada vs. USA Real Estate Where Can Investors Still Find Cash Flow with Bryce Kaminsky

    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.

    EP439 Canada vs. USA Real Estate Where Can Investors Still Find Cash Flow with Bryce Kaminsky

  6. Sep 24

    EP438 Real Estate Wire Fraud How Investors Can Avoid Losing Their Money with Robert Siciliano

    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.

    EP438 Real Estate Wire Fraud How Investors Can Avoid Losing Their Money with Robert Siciliano

  7. Sep 17

    EP437 When To Add a Canadian Corp to your USA Structure with Tim Miron

    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

    EP437 When To Add a Canadian Corp to your USA Structure with Tim Miron

  8. Sep 9

    EP436 Why Self Storage Beats Rental Properties with Fernando Angelucci

    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.

    EP436 Why Self Storage Beats Rental Properties with Fernando Angelucci
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