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Glen Sutherland Podcasts

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These are the stories that shape us. The Brave and The Wild is about honest conversations with everyday people. Some have faced heavy stuff. Some have done amazing things. Others are just figuring it out as they go. It’s a space for stories that don’t always get told… stories of resilience, growth, and the unpredictable nature of being human. It’s a mix raw storytelling with expert insight to help make mental health feel more normal, and easier to talk about. But it’s not all struggle. This ...
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In this episode, Glen Sutherland talks with Marian Welch, a Canadian investor and creative dealmaker who turned adversity into opportunity. Marian shares how she uses strategies like rent-to-own and vendor take-back to solve problems for buyers and sellers, and how her investing journey has expanded from Canada into the U.S. and Mexico.…
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In this episode, Glen welcomes back Canadian CPA Kris McEvoy to unpack the hidden tax challenges Canadian investors face with U.S. real estate. They break down common pitfalls—like FIRPTA withholding, state taxes, and timing issues—and share proactive strategies to avoid surprise tax bills. From choosing the right entity setup to tracking expenses …
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In this episode of Canadian Investing in the U.S., Glen Sutherland chats with Donalta Hall about her journey from an IT career in Toronto to U.S. residency through the E2 visa program. Donalta shares how short-term rentals helped her qualify, what it was like relocating her family to Alabama, and why the state is attracting more Canadian investors.…
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What if you could earn steady real estate income without tenants, repairs, or property management headaches? In this episode, Glen Sutherland talks with Eddie Speed, a 45-year veteran and founder of Note School, about the power of note investing—becoming the bank instead of the landlord.Eddie shares why mortgage notes can deliver:💸 Higher monthly c…
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In this episode, Bronson Hill shares a simple framework to help passive investors vet real estate sponsors before committing capital. From assessing the market and sponsor to asking the right questions—like “What’s the biggest risk in this project?”—you’ll learn how to spot integrity, experience, and conservative underwriting. If you want to protec…
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In this episode of Canadian Investing in the US, Glen Sutherland interviews Nathan Turner, also known as “The Canadian Note Guy.” Nathan shares how he transitioned from traditional real estate to buying non-performing mortgage notes in the U.S. He explains how he works with borrowers, modifies loans, and creates returns through creative strategies.…
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In this episode of Canadian Investing in the US, Glen Sutherland welcomes back CPA Kristopher McEvoy for another installment of their monthly accounting Q&A series. Kristopher, a Canadian accountant based in Fonthill, Ontario, specializes in cross-border taxation and real estate investing. He tackles a key question from investors: when should you s…
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In this episode of Canadian Investing in the US, Glen Sutherland speaks with Torrin Brauch, an American expat who relocated to Ecuador in search of a better food supply and overall quality of life. Torrin shares his journey from growing organic food on a farm in Florida to building a 17-unit eco-lodge in the Andes Mountains of Ecuador. He discusses…
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In this episode, Glen Sutherland reconnects with Aurelien Bonin to explore how AI and automation are transforming real estate investing. Aurelien shares how he uses tools like ChatGPT, Zapier, and N8N to streamline operations across his Canadian and U.S. portfolio, while Glen adds how he leverages AI for contract analysis and VA systems. They also …
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In this episode of Canadian Investing in the US, Glen Sutherland welcomes back immigration attorney Mena Maimone of Maimone Legal to clarify recent misinformation circulating online about a so-called "$250 visa fee" for Canadians entering the United States. Mena explains that this is actually the Visa Integrity Fee, which applies only to new U.S. v…
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In this episode, Glen Sutherland chats with Linda Holtz about her inspiring path from managing other people’s properties to co-founding M2RE (Married to Real Estate) with her husband.Linda shares how she started with single-family homes, moved into passive syndications, and then took the leap into active ownership — all while staying true to her va…
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In this episode, Glen Sutherland is joined by his personal accountant, Kristopher McEvoy, a Canadian CPA specializing in cross-border taxation. Kristopher works with clients investing in U.S. real estate, as well as those relocating or expanding businesses between Canada and the U.S.The discussion centers around a frequently asked question: what’s …
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What if your fatigue, anxiety, brain fog… even your skin issues, are rooted in what you’re eating? In this episode, I sit down with Abby Soares, a registered nurse, qualified nutritionist, and founder of Nourish Health & Nutrition. Abby shares how food, gut health, and mental wellbeing are deeply connected, and why functional medicine looks beyond …
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In this episode, Glen Sutherland talks with financial advisor and author John De Goey about how common behavioral biases—like confirmation bias, loss aversion, and overconfidence—can quietly influence our money choices. John shares real-life examples and practical tips to help investors become more self-aware and make smarter financial decisions.Le…
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In this episode, Glen Sutherland chats with Lindsey Davis, CEO of Spartan Invest, about why Alabama is becoming a prime rental market for out-of-state and international investors. Lindsey explains how Alabama’s low property taxes, landlord-friendly laws, and affordable turnkey properties create an ideal environment for real estate investors.They al…
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Glen Sutherland welcomes back Marcin Drozdz to share how his U.S. real estate journey has grown since his earlier appearances. Marcin talks about his shift from single-family homes to larger commercial deals, including industrial and multifamily properties. He shares valuable lessons on partnerships, deal structures, lender challenges, and the impo…
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Glen Thurston is a builder, father, husband, and hunter from Wānaka, New Zealand - and the founder of the charity Mental Hunts. In this episode, Glen shares his journey from hitting rock bottom to losing his firearms license after seeking mental health support, and how that experience sparked a campaign to climb a mountain 53 times for suicide awar…
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In this episode, Glen Sutherland and Kristopher McEvoy dive into the potential impact of proposed U.S. tax legislation on Canadian investors with U.S. assets. They discuss why proper investment structuring is more important than ever, the risks of increased withholding taxes, and how treaty changes could affect future returns. Kristopher shares why…
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In this insightful podcast interview, Glen speaks with experts about the E2 visa process, offering invaluable advice for Canadians interested in launching or expanding their businesses in the U.S. They delve into key topics such as the essential elements of a successful business plan, the importance of creating jobs, and the flexibility of the E2 v…
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In this new episode I dive deep into the world of ADHD with Selena Thomson, a late-diagnosed mum, and lawyer… who shares her unfiltered journey from anxiety and depression to unshakable self-acceptance. Selena shares her experiences, from the "fuzzy vision" before medication to the crucial realisation that pills alone couldn't erase a lifetime of s…
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In this conversation, Brady shares the powerful mindset shift that helped him level up: you're either learning or earning, but rarely both at once. He explains that growth often comes through discomfort, whether it’s financial loss, stress, or failure. The key is to not quit during the learning phase, as that’s what ultimately leads to the big wins…
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In this episode of "Canadian Investing in the US," host Glen Sutherland interviews Brett Henry, a real estate broker in the Dominican Republic. Originally from Saskatchewan, Canada, Brett transitioned from a 20-year career as a police officer to becoming a successful entrepreneur in real estate. He shares his journey of moving to the Dominican Repu…
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Mathieu Bourgouin, a Canadian real estate investor and agent from Mont-Tremblant, Quebec, started investing in the U.S. in 2014. His journey began in Florida and then expanded to Pittsburgh, including ventures in wholesaling and mobile home parks. He has now transitioned primarily to short-term rental properties in Florida.• Initial Investments: Ma…
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In this episode of "A Canadian Investing in the U.S.," host Glen Sutherland interviews Jonathan Nichols, co-founder of Apogee Capital, a multifamily real estate investment company based in the Dallas-Fort Worth area. Jonathan shares his journey into real estate investing, which began about seven or eight years ago with single-family rentals. Along …
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⚠️ Content warning: This episode contains open discussions of suicide, which may be distressing for some listeners, please take care or skip this one if you need to. In this episode I’m joined by Gareth Hughes, owner of Victory Knives. We have an honest and candid conversation about moving through life after losing a number of close friends to suic…
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In this episode, Glen Sutherland interviews Amresh Singh, who runs Home Abroad, a firm that assists international investors in purchasing U.S. real estate. Amresh shares insights into the challenges foreign investors face and how his company provides a comprehensive solution.Key Points Discussed:Introduction to Home Abroad:Home Abroad is a one-stop…
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Burnout isn’t just stress or laziness… it’s often a full mindbody shutdown that creeps in quietly, then takes over everything. In this episode, I’m joined by Clinical Psychologist Charlotte Gibson to unpack what burnout really is, why it happens, and how to recover. This conversation blends clinical insight with lived experience, including my own s…
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In this episode, Glen interviews Taha Khan, a Canadian CPA with a U.S. license, who specializes in helping Canadians navigate the complex world of cross-border taxation. The conversation is centered around real estate investors, snowbirds, and business owners who spend time or have assets in the United States.Key Topics Covered:Substantial Presence…
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In this deeply personal episode, writer and creative Monica Shepherd shares the emotional journey of losing her father to cancer. We explore anticipatory grief, hospice care, the healing power of storytelling, and how grief affects creativity and life itself. Listeners will walk away with heartfelt insights on how to live with loss - and support ot…
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Trisha Lehane – Realtor based in Scottsdale, Arizona with RE/MAX, specializing in working with Canadian buyers and sellers.Background:Originally from Canada, Trisha has lived in Arizona for 20 years.She has deep roots in Canadian provinces like Manitoba, Saskatchewan, Alberta, BC, and Yukon.Her real estate career pivoted to working with Canadians a…
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In this episode, Glen sits down with Ian, founder of Avoca Property, for a candid and action-packed conversation about the real behind-the-scenes journey of closing a multifamily deal. From early missteps in digital marketing and investor engagement, to legal battles, PE fund bait-and-switches, and $200,000 in legal fees — Ian doesn’t hold back on …
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In this episode, I sit down with Laura Kuggeleijn - a teacher, passionate diver, and someone who brings a lot of thoughtfulness to the way she moves through life. We talk about her experience living with chronic fatigue syndrome and fibromyalgia, being diagnosed with ADHD at 27, and how the ocean became a space for calm, challenge, and healing. Lau…
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In this episode of "A Canadian Investing in the US," host Glen Sutherland interviews Chris Micucci, a college professor and real estate investor who began investing just over three years ago. After taking Glen's class, Chris quickly seized an opportunity presented in an email and bought his first property. Since then, he has engaged in various inve…
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In this episode, we dive into how FrontLobby helps landlords report rent payments to credit bureaus, screen tenants, and improve rental management. Our guest explains how incorporating FrontLobby into lease agreements and rental ads can attract high-quality tenants and ensure timely rent payments.By Glen Sutherland
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In this episode, Glen Sutherland sits down with David Chris from Action to Call to explore how AI-powered virtual agents are transforming business communication. They discuss how AI can handle customer interactions, schedule appointments, and improve response times—ensuring businesses never miss a call. David shares real-world applications, includi…
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In this episode of The Brave and The Wild, Craig Sutherland opens up about grief, anxiety, anger, and the pressure to always appear strong. From losing his father and falling into deep anxiety, to finding healing through the gym, the beach, music and brutal self-reflection - this is a raw, honest conversation about mental health, identity, and rebu…
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This podcast features a conversation with a real estate investor who specializes in the "rent-by-the-room" strategy, particularly targeting college students near major universities. The guest shares their expertise on identifying suitable properties, adapting spaces to maximize rental income, and navigating financing challenges in this niche.Key To…
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Kayla Andrade emphasizes the importance of landlords staying informed and advocating for policy changes to better support the housing industry in Ontario.She encourages collaboration with elected officials and industry experts to address issues like tenant accountability and affordable housing.Tenant Screening and Rent Reporting:Tenant screening is…
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The podcast episode is a deep dive into creative financing for land deals, focusing on strategies like land contracts, due diligence, and automation in the land investing business. Here’s a summary of the key points:Selling Land with Creative FinancingThe guest discusses selling land using a land contract rather than a lease option or contract for …
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This podcast episode of Canadian Investing in the USA features Rich Monroe, an experienced real estate investor based in Atlanta, Georgia, who focuses on short-term rentals, Airbnbs, and boutique hotels. Over his 20-year career, Rich has worked with single-family homes, multi-family properties, and hotels. His main focus has shifted toward distress…
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This episode explores the world of manufactured housing as a unique investment opportunity in the US. Glen is joined by Alden and Sean, who specialize in originating notes and investing in manufactured housing communities, providing insights into this niche market.Key Highlights1. Defining Manufactured HousingOften confused with RVs or trailers, ma…
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Hey, I’m Tim Kavermann, and after a long break, The Brave and The Wild is back - with a refined direction. In this episode, I’m taking a moment to share where this podcast came from, why it exists, and what I hope it can offer you. This is the story behind The Brave And The Wild, how my own mental health journey, a lifelong obsession with understan…
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In this episode, I sit down with Ian Horowitz from Equity Warehouse to discuss the journey of scaling a real estate portfolio, managing risk, and knowing when to sell. Ian shares his experience transitioning from high-risk investments in Baltimore to more stable and profitable deals in primary markets like Philadelphia.…
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In this engaging episode, we sit down with Scott Kidd, a seasoned yacht manager and real estate investor, to explore the fascinating parallels between managing luxury yachts and navigating the world of real estate syndication. Scott shares valuable insights from his unique career journey, emphasizing leadership, problem-solving, and building strong…
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Glen Sutherland hosts Canadian Investing in the US with guest Dave Mastronardi.Dave runs a real estate investment firm in Canada focused on the southern US, particularly Florida. He is also a partner at Midfield Investments, focusing on multifamily properties in Texas.Dave's Real Estate JourneyPreviously the CEO of a large manufacturing company; tr…
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This podcast episode of "A Canadian Investing in the USA" talks about real estate investors moving into the U.S. market. The conversation touches on a variety of themes, including:Key Points:Affordability and Opportunities in U.S. Markets:Canadian investors are drawn to U.S. markets for more affordable housing, better weather, and lending products …
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In this episode of A Canadian Investing in the US, we discuss Brooke's transition from investing in Ontario to focusing on other regions and passive investing in the US.Leaving Ontario for Other MarketsBrooke moved out of Ontario's real estate market due to challenges, including:Landlord-Tenant Board (LTB): Ongoing disputes and difficulties with en…
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