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Scott Dillingham Podcasts

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Send us a text In this episode, Scott is joined by Jennifer Champion and Christine Traynor to discuss the critical advantages of working with experienced brokers who specialize in multi-family financing. The conversation highlights real-world examples of how the right expertise can save investors millions while avoiding costly mistakes that commonl…
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Send us a text In this episode, Scott interviews Rhys Trenhaille, a commercial real estate specialist who focuses on working with investors in Windsor Essex County. Reese shares his unique journey from university track athlete to successful commercial real estate investor and agent, emphasizing the importance of working with professionals who pract…
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Send us a text In this episode, Scott is joined by Jennifer Champion and Christine Traynor to discuss value-add strategies for multi-family apartment buildings. The hosts share their active investing experience and explain how to force appreciation through strategic property improvements and rent optimization. Key Timestamps: [0:00] Introduction to…
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Send us a text Welcome back to the Wisdom Lifestyle Money Show! In this episode, host Scott Dillingham introduces you to the core team dedicated to helping you achieve your commercial real estate investment goals. Meet Mike Peters, Jennifer Champion, and Christine Traynor, the experts behind the commercial mortgage arm, specializing in financing ac…
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Send us a text In this episode, Scott interviews Tom McCormick, a Canadian investor who successfully transitioned from investing in Windsor to flipping properties in Detroit. Tom shares his engineering background, initial property ventures, and how he navigated the challenges of cross-border investments. Key Timestamps: [0:00] Introduction and Gues…
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Send us a text In this episode, Scott Dillingham interviews Carmen Da Silva, a CPA and cofounder of Share, who brings over two decades of cross-border tax and investment expertise to the discussion. Drawing from her journey from PricewaterhouseCoopers to managing a significant U.S. real estate portfolio and co-founding Share, Carmen shares comprehe…
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Send us a text In this episode, Scott Dillingham interviews Derek Wormsbecker, a mortgage agent and investor who shares his experience transitioning from Canadian to U.S. real estate investing. Having sold his Canadian property, Derek describes his journey finding and purchasing a new construction home in Arkansas through Share, highlighting the ad…
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Send us a text In this episode, Scott Dillingham interviews Mark Racette from Pulse FX about saving money when conducting foreign exchange transactions for U.S. real estate investments. Drawing from over a decade of experience in international finance, Mark explains how investors can secure better exchange rates and reduce transaction costs compare…
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Send us a text In this episode, Scott Dillingham interviews Dmitri Bourchtein from Share, discussing his journey from institutional real estate lending to managing over $1 billion in transactions and helping retail investors access U.S. real estate opportunities. Drawing from his extensive experience at one of Canada's largest private equity firms,…
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Send us a text In this episode, Scott Dillingham addresses the issue of expensive real estate investing courses and coaching programs, introducing a free alternative called "Fire Your Boss" that covers comprehensive real estate investing education. Drawing from his team's expertise and industry professionals, Scott explains how investors can access…
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Send us a text In this episode, Scott Dillingham reveals an innovative solution for foreign investors to obtain U.S. Employer Identification Numbers (EINs) in just two hours, dramatically reducing the typical 4-8 week waiting period for entity setup when purchasing U.S. real estate. Key Timestamps: [0:00] Background - Entity setup challenges - Impo…
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Send us a text In this episode, Scott Dillingham interviews real estate lawyer Milena Cardinal to discuss maximizing shareholder value through proper corporate structuring for real estate investments. Milena shares expertise on balancing legal, tax, and financing considerations when setting up investment entities. Key Timestamps: [0:00] Corporate S…
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Send us a text In this episode, Scott Dillingham explains how investors can qualify for mortgages based on property cash flow rather than personal income through Debt Coverage Ratio (DCR) and Debt Service Coverage Ratio (DSCR) programs in Canada and the USA, providing alternatives to traditional qualification methods. Key Timestamps: [0:00] Traditi…
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