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

In this episode of Canadian Investing in the US, Glen Sutherland sits down with returning guest Tim Miron, founder and president of Pursuit CPA, to discuss what investors should do when they receive an unexpected tax bill. Tim explains that the most important step is to file your taxes on time, even if you cannot immediately pay the balance. Filing late can trigger significant penalties—such as Canada’s 5% late filing penalty plus additional monthly interest—which can quickly increase the amount owed. Instead of avoiding the issue, Tim encourages investors to determine the exact amount owed as early as possible so they can create a plan to deal with it. The conversation also explores practical strategies for managing a surprise tax bill, including using lower-interest financing (such as a line of credit or refinancing), negotiating payment arrangements with tax authorities, and exploring taxpayer relief programs if extraordinary circumstances caused the issue. Tim emphasizes the importance of proactive tax planning, recommending that investors review their tax strategy in mid-year so there’s still time to make adjustments before year-end. Glen and Tim also highlight the value of communicating with your accountant before making major financial decisions—like buying vehicles or structuring business expenses—so that investors can deploy their money in the most tax-efficient way possible.

Glen Sutherland interviews Bobby Casey, an American international tax lawyer and “slowmad” who splits his time between North Carolina, Mexico, and Latvia. Bobby explains how his residency lifestyle works in practice, and why Americans are “unicorns” globally: the U.S. taxes citizens on a citizenship basis, meaning Americans still file (and may owe) U.S. taxes even when living abroad—though tools like the Foreign Earned Income Exclusion and foreign tax credits can reduce the hit. The conversation then shifts to Canadians and cross-border tax/residency strategy. Bobby outlines how Canadians can more easily exit Canadian tax residency by minimizing key residential ties (e.g., primary home, spouse, dependent children) and properly filing their departure return—while noting there can be exit-tax considerations and changed tax treatment of property kept behind. He also shares practical notes on living abroad (including why he disliked Belize) and digs into real estate rules for foreigners (e.g., Mexico’s restricted zones and use of a fideicomiso). Finally, Bobby explains why a U.S. LLC can be a powerful structure for non-U.S. digital nomads/remote entrepreneurs (depending on “effectively connected income” and where work is performed), and closes by describing his company formation/compliance platform, BusinessAnywhere.io.

Brandon Cobb returns to the show to break down how he went from medical device sales to building a real estate business focused on land development and land entitlements. After getting fired unexpectedly, Brandon learned a hard truth: nobody is going to protect your financial future but you. That turning point led him through a few failed ventures before he discovered real estate—starting with flipping and building homes, then scaling into larger land deals after national builders began offering to buy his parcels. In this episode, Brandon explains a simplified, lower-risk approach to land development investing: identify the right parcels, put land under contract with a 90–120 day due diligence period, hire a civil engineer for a concept plan, get early buy-in from the city, and secure an end buyer (often national home builders) before moving through approvals. He also shares where deals can break down—traffic studies, municipal requirements, unexpected costs—and how they mitigate risk with non-refundable buyer deposits to cover entitlement expenses. If you’re an experienced investor looking to level up from single deals into bigger land opportunities, this is a step-by-step look at how the entitlement and development game really works.

Glen brings back Joe Evangelliti to share his “5 Bottlenecks” framework—a universal set of constraints that keep entrepreneurs (especially real estate investors) stuck. The 5 bottlenecks framework 1) Mindset / limiting beliefs You don’t get what you “conceive”—you get what you believe you can achieve. “Rational lies” = the stories we tell ourselves to avoid action (not smart enough, not ready, what will people think, etc.). Fastest unlock question: “What do I want?” (not what spouse/parents/friends want). 2) Clarity + reverse engineering (Point B → Point A) People plan vacations with precision but plan their lives in vague “wish” language. Define Point B clearly, assess Point A honestly, then close the gap. 3) Toolkit audit (simplify your tools/systems) Too much tech can create complexity and distraction. Quote-worthy idea: if you can’t do it with notepad + pen + phone, software won’t save you. Build consistent deal flow first; avoid shiny-object “easy button” chasing. 4) Rule of 168 (time control) Everyone has 168 hours/week—top performers just allocate it differently. Focus on: High-income activities (directly produce revenue now) High-gain activities (life/relationships/health that matter long-term) Track what moves the needle (e.g., offers made). Many people feel busy but do zero needle-moving actions. Calendar discipline = presence. “Show me your calendar and I can almost tell you your net worth.” 5) The trifecta (the “bow”) Execution (do the work, ship the offer, take the shot) Course correction (pivot around obstacles instead of quitting or forcing a broken plan) Radical accountability (someone outside your inner circle who won’t let you off the hook)

In this episode, Glen Sutherland sits down with Ontario landlord advocate Kayla Andre to unpack what Bill 60 really means for landlords navigating the challenges of the Ontario Landlord and Tenant Board. Kayla explains how the bill shortens the timeline for filing non-payment applications, limits last-minute maintenance complaints used to delay hearings, and aims to standardize what qualifies as persistently late rent. She also highlights efforts to improve enforcement through additional sheriffs, clearer rules around set-aside orders, and better visibility of LTB decisions to help landlords identify repeat offenders. Beyond the legal changes, the conversation explores the bigger picture: landlords leaving the Ontario market, municipal renoviction bylaws conflicting with provincial authority, and how policy missteps may be driving rental prices higher and discouraging investment. Kayla shares real examples of serial non-payment cases that escalated to fraud charges and emphasizes why both landlords and taxpayers should be paying attention. For many listeners, this episode explains why Ontario investors have increasingly looked to U.S. real estate—and whether reforms like Bill 60 could begin to restore confidence at home.

In this episode of A Canadian Investing in the U.S., Glen sits down with Ali Rostamee to discuss his journey from immigrating to Canada in 2010 to ultimately becoming financially free through real estate. Ali shares how reading Rich Dad Poor Dad shaped his mindset early on, leading him to pursue cash-flowing duplexes in Edmonton before hitting lending limits. That forced him to expand his education through BiggerPockets and explore new strategies like BRRRR, multifamily, and flipping. After realizing Alberta’s long recession wasn’t supporting appreciation, Ali relocated to Toronto, caught the COVID appreciation wave with successful flips, and reinvested the profits into Hamilton triplexes and fourplexes—ultimately reaching financial independence. Ali then explains why he moved from Canada to the U.S.: access to DSCR asset-based loans, dramatically lower prices, superior data transparency, and a more efficient permitting system. He highlights Cleveland, Charlotte, and Phoenix as his top markets for Canadians—Cleveland for cash flow and Charlotte/Phoenix for appreciation. Glen and Ali dive into the importance of diversification across markets (and countries), different strategies working better in different cities, and how balancing multiple markets helped Ali smooth out downturns. Ali also shares challenges of moving to the U.S. as an Iranian-Canadian—border issues, difficulty getting a phone number or bank account without an SSN, and long-distance property management. He now lives in Washington, D.C., placing him within a day’s drive of his key U.S. markets. Ali can be reached on Instagram at @AliRostamee (with two E’s).

Raheem Madjavi from Knightsbridge FX joins Glen Sutherland to unpack what’s driving the Canadian dollar vs. U.S. dollar and what Canadians should watch in 2026. They discuss key macro factors that move currency markets—interest rate differentials, jobs/GDP, oil and commodities, and trade-policy uncertainty—plus why the USD/CAD rate can stay volatile when policy shifts and headlines change fast. Raheem shares practical scenarios for how the loonie could strengthen modestly if U.S. rates come down, and why Canada’s outlook also depends on broader economic resilience and trade outcomes. They also get tactical for Canadians investing in U.S. real estate: why bank FX spreads and wire mistakes can quietly cost hundreds (or thousands), and how to avoid getting “hosed” on exchange rates when moving large sums. Raheem explains how Knightsbridge works and walks through the common ways to move money cross-border—bill payment (CAD only), wire transfers (fast, often same/next day), and debit/credit between accounts (slower but convenient)—including when each method makes sense. The big takeaway: don’t obsess over perfectly timing the currency market; focus on the underlying investment, reduce friction and fees, and execute a clean transfer strategy when you’re ready.

In this episode, Glen Sutherland reflects on eight years of releasing a podcast episode every single week and breaks down how long-term consistency has played a major role in his success. He explains that his results didn’t come from viral moments or overnight wins, but from showing up week after week—even when it was boring, unsexy, and felt like nothing was happening. Glen highlights why most people quit too early, often confusing activity with progress or expecting momentum before they’ve earned it, and emphasizes that consistency compounds in business, real estate, and life. However, Glen makes a critical distinction: consistency alone is not enough. Success comes from consistent, correct actions, not just staying busy. Using real estate as an example, he explains why education without execution keeps investors stuck in a “comfort zone trap” and outlines the actions that actually move the needle—deal analysis, building teams, making offers, tracking KPIs, and creating systems that outperform motivation. He closes by reminding listeners that results take time, lag is normal, and real growth comes from doing the right things long enough for them to compound, while challenging listeners to reflect on where they may be consistent but not effective.

Lancelot Lennard is a Florida realtor, investor, contractor, and non-profit founder who focuses on the Daytona / Volusia County area. He explains why he left Miami for Daytona: Miami’s become a “billionaire playground” with weak ROI for small investors, while Daytona still has mom-and-pop landlords, realistic prices, and solid opportunities for both buy-and-hold and flips. He breaks down where he sees opportunity in Florida right now, noting that the market is still somewhat buyer-leaning, allowing strong negotiation on both price and repairs. He also walks through the short-term rental landscape around Daytona Beach, Daytona Beach Shores, Port Orange, and parts of Ponce Inlet—stressing the importance of zoning, municipal rules, and HOA bylaws to ensure Airbnb/STR is actually permitted. A big part of the discussion is around the recent changes to realtor commissions in the U.S. After the NAR settlement, buyer-agent commissions are no longer automatically offered in the MLS, and agents must now have buyers sign an exclusive agreement before showings. Lancelot explains how this impacts first-time buyers, lower-income buyers, and Canadian investors who are used to the old “seller pays both sides” model. He also touches on Florida’s proposed elimination of property tax on primary residences, current homestead rules, and what that could mean for dual citizens or retirees relocating from high-tax states. The episode closes with practical tips on how Canadians should vet investor-friendly agents (ask about zoning maps, NOI and cap rates) and how to clearly define scope in buyer-broker agreements so you don’t accidentally commit yourself to multiple agents at once.

In this episode of A Canadian Investing in the U.S., Glen Sutherland sits down with Dave Seymour to unpack his incredible journey from blue-collar firefighter to nationally recognized real estate investor and educator. Dave shares how financial illiteracy, predatory lending, and the 2008 financial crisis nearly cost him everything—and how a pivotal decision to invest in education and take massive action changed the trajectory of his life. From learning real estate fundamentals during the crash to completing his first deal and eventually leaving the fire department, Dave’s story is a raw and honest look at what’s possible when preparation meets opportunity. The conversation dives deep into the importance of execution, relationships, and coaching in real estate investing. Dave explains why real estate is fundamentally “5th-grade math,” why mentorship is worth every dollar, and how buying access to other people’s mistakes can save investors hundreds of thousands—or more. He also breaks down his current focus on larger multifamily opportunities (25+ units), market selection, underwriting discipline, and capital alignment, offering valuable insight for investors ready to move beyond single-family deals.

In this episode of Canadian Investing in the U.S., Glen sits down with Tim Miron, CPA, founder of Pursuit CPA, to walk Canadian investors through how to properly prepare for tax season, especially when dealing with cross-border real estate and business income. Tim explains why January–March is the ideal time to get organized instead of waiting until April, and highlights common bottlenecks that slow down tax filings. The discussion covers ITIN requirements, what documents accountants actually need (and what they don’t), how to properly summarize rental income and expenses, and when large repairs should be reviewed more closely. The conversation also dives into cross-border reporting, including T1134 and T1135 filings, HST considerations for short-term rentals, Airbnb reporting rules, and why tracking exchange rates on major capital expenses matters. This episode is a must-listen for Canadian investors who want to reduce stress, avoid penalties, and make tax season smoother on both sides of the border.

In this special 400th episode, Glen shares the full story of how he bought his very first U.S. investment property and all the mistakes that came with it. After struggling to scale his Canadian portfolio due to rising prices, lender limitations, and tenant issues, he turned to U.S. podcasts for answers and eventually bought a turnkey property in Huntsville, Alabama using a HELOC from his Ontario home. Glen admits he didn’t understand lending, valuations, property management, wire transfers, or the major differences between Canadian and American real estate. He trusted every number from the turnkey provider, bought the property sight unseen, and quickly learned the challenges of using a large national property manager, handling accounting disputes, and navigating cross-border money transfers. Despite all the mistakes, Glen stresses that taking action mattered more than having everything figured out. That first imperfect deal became the catalyst for every U.S. property he bought afterward in Kansas City, Indianapolis, and Ohio. Looking back, he says hiring an experienced coach would have saved him money, stress, and years of slow growth—but he still credits that first deal for creating momentum and opening doors. Today, Glen encourages Canadians to leverage the abundance of U.S. real estate opportunities, do proper due diligence, and get guidance so they can scale faster, avoid expensive errors, and build a real business. If listeners are ready to take the next step, he invites them to book a free consult call and get personalized help. glensutherland.com/consult

In this episode of A Canadian Investing in the U.S., Glen Sutherland welcomes renowned data-driven real-estate investor Neil Bawa. Neil shares his journey from tech entrepreneur to full-time real-estate operator after selling his company in 2013 and facing a huge tax bill that pushed him into multifamily investing. He now manages a $660 million portfolio across multifamily, self-storage, industrial, and student-housing projects, backed by 1,300 accredited investors. Neil explains why he diversifies across asset classes—citing supply-cycle shifts, learning opportunities, and partnerships—as well as the value of publishing commercial-real-estate data to attract like-minded, analytical investors. Later, the conversation turns to market cycles and practical indicators of when new opportunities emerge. Neil predicts that within 18 months, most U.S. metros will transition from oversupply to shortage, starting a new bullish phase. He outlines how professionals can track this shift using CoStar, Yardi, RealPage, or Hello Data, and even simple rent-growth trends above 2 percent as a signal of recovery.

In this episode of Canadian Investing in the U.S., host Glen Sutherland interviews Priscilla (Pre) Cosentino, a U.S.-based financial advisor, author, and mentor who specializes in helping clients build a true wealth mindset. Priscilla explains that financial planning is about much more than simply accumulating money—it’s about aligning one’s financial goals with personal values and life purpose. She shares examples of clients with vastly different goals, from relocating overseas to buying a first home or going back to school, emphasizing that understanding what matters most to each person drives the right financial and investment strategies. The conversation then dives into tax planning—a subject many people only think about when faced with a large bill. Priscilla stresses that effective tax planning must be proactive, not reactive, and should begin now, regardless of the time of year. She encourages investors to build an “A-Team” of professionals—financial planner, CPA, and attorney—who collaborate to design forward-looking strategies that balance current actions with future goals. She also offers practical advice on how to prepare for planning meetings, such as bringing an overview of assets, account types, and investment values. The episode closes with a thought-provoking reminder: financial planning should start with your end goal in mind—how you want to be remembered and what legacy you want to leave behind—and then reverse-engineer your path toward that vision.

In this episode of Canadian Investing in the U.S., Glen Sutherland welcomes two guests — cross-border CPA Chris McAvoy of LEAP ACT and Tim Myron, founder of Pursuit CPA in Burlington, Ontario. The discussion centers on the merger between LEAP ACT and Pursuit CPA, which will combine their teams into a single 20-person firm with offices in both Burlington and Niagara. The merger allows clients from the GTA and Niagara regions to access the same cross-border tax expertise more conveniently, while maintaining continuity of service. Tim highlights that his firm already handles numerous U.S.-related corporate structures and cross-border clients, ensuring that the expertise LEAP ACT clients rely on will remain in place. Chris also announces his departure from LEAP ACT to join a technology company as an executive officer, a longtime client that recently achieved significant scientific breakthroughs and funding. He expresses confidence in Tim’s leadership and notes that key relationships with partners like Global Tax Services (Ali Ajami) and cross-border legal collaborators will remain intact. The group discusses how the transition will strengthen service delivery and maintain collaboration between Canadian and U.S. advisors. Chris thanks Glen and the investing community for their support and shares plans to become more active personally in real-estate investing, coming full circle from accountant to investor. Glen closes by expressing excitement for the transition and the continued partnership with the expanded Pursuit-LEAP team.

Patrick Grimes joins Glen Sutherland to share his evolution from a corporate engineer to a full-time investor focused on building recession-resilient wealth. After losing big during the 2008 financial crisis, Patrick rebuilt his strategy by shifting away from speculative deals toward stabilized, cash-flowing assets in diversified markets like Houston. He emphasizes the importance of learning from failure, studying how the wealthy allocate capital, and building portfolios that can withstand economic downturns through diversification across asset classes and industries. Today, Patrick leads Passive Investing Mastery, a platform educating investors on more than 50 types of alternative investments beyond the stock market—from private credit and legal funds to industrial and healthcare opportunities. He advocates blending non-correlated assets such as real estate, energy, and precious metals to protect and grow wealth regardless of market cycles. As Patrick notes, “The best time to diversify was two years ago. The second best time is today.”

In this episode, Glen sits down with Joel Friedland to explore the power of buying real estate entirely in cash—no mortgages, no financing contingencies. Joel shares how this strategy gives investors a competitive edge by reducing risk, speeding up deals, and building stronger trust with sellers. They also discuss how all-cash acquisitions can strengthen long-term portfolio stability and investor confidence. In uncertain markets, this episode reveals why sometimes the safest move is the smartest one.

In this episode, Glen sits down with Mike Zlotnik to break down where we are in the current real estate cycle—and what it means for investors. Mike shares insights on how interest rates, inflation, and capital flows shape market trends and timing. They discuss how to recognize the signals of expansion, peak, contraction, and recovery, plus practical strategies to stay profitable in uncertain times—like diversifying assets, stress-testing deals, and focusing on cash flow. Whether you’re a seasoned investor or just getting started, this episode will help you think strategically, stay flexible, and make smarter moves through every market phase.

In this episode, Glen sits down again with cross-border CPA Kris McEvoy to unpack a critical topic for Canadian investors with U.S. properties — how to properly move money into your U.S. entity. They break down the key differences between funding as debt vs. equity, why that distinction matters for tax and structure, and what can go wrong if it’s not documented correctly. Kris shares practical examples, planning tips, and best practices for keeping your contributions clean, compliant, and strategically sound. Whether you’re wiring funds for your first deal or restructuring an existing portfolio, this conversation will help you avoid costly mistakes and stay on the right side of both tax and legal requirements.

In this episode, Glen Sutherland talks with Chris Prefontaine about how realtors can become key partners in sourcing seller-financed deals. Chris shares how creative financing helps sellers close faster, bypass banks, and create win-win solutions—while giving investors steady opportunities and long-term cash flow.