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The Wisdom, Lifestyle, Money, Show
Scott Dillingham
79 episodes
2 days ago
Host Scott Dillingham discusses opportunities for real estate investors in Canada, the US, and Mexico, focusing on LendCity’s approach to finding cash-flowing deals. He highlights challenges in Canada’s residential market and shares strategies for leveraging new construction and commercial-style financing, particularly in Alberta. Key Points Market Challenges in Canada: Residential cash flow is tough in many Canadian markets (e.g., Ontario) due to rent control (e.g., 2.5% rent increase caps d...
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All content for The Wisdom, Lifestyle, Money, Show is the property of Scott Dillingham and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Host Scott Dillingham discusses opportunities for real estate investors in Canada, the US, and Mexico, focusing on LendCity’s approach to finding cash-flowing deals. He highlights challenges in Canada’s residential market and shares strategies for leveraging new construction and commercial-style financing, particularly in Alberta. Key Points Market Challenges in Canada: Residential cash flow is tough in many Canadian markets (e.g., Ontario) due to rent control (e.g., 2.5% rent increase caps d...
Show more...
Investing
Education,
Business,
How To,
Courses
Episodes (20/79)
The Wisdom, Lifestyle, Money, Show
How To Find Good Real Estate Opportunities in Canadian Markets
Send us a text Host Scott Dillingham discusses opportunities for real estate investors in Canada, the US, and Mexico, focusing on LendCity’s approach to finding cash-flowing deals. He highlights challenges in Canada’s residential market and shares strategies for leveraging new construction and commercial-style financing, particularly in Alberta. Key Points Market Challenges in Canada: Residential cash flow is tough in many Canadian markets (e.g., Ontario) due to rent control (e.g., 2.5% rent ...
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4 weeks ago
12 minutes

The Wisdom, Lifestyle, Money, Show
Beyond Buy and Sell: Expert Strategies for Toronto's Property Market
Send us a text Host Scott Dillingham interviews Ming, President of Volition Properties, a Toronto real estate team specializing in investor-focused deals. Ming shares his journey from Kiyosaki-inspired investing to building a scalable portfolio, plus strategies for cash-flowing Toronto properties through risk management and tenant-targeted buys. Key Points Ming's Journey: Inspired by Rich Dad Poor Dad at 21; built 21 doors in Waterloo but found it non-passive. Networked via meetups, partnered...
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1 month ago
20 minutes

The Wisdom, Lifestyle, Money, Show
Investing in the Midwest: Insights from Carlos Rodrigues
Send us a text Host Scott Dillingham interviews Carlos Rodrigues, a Canadian investor who transitioned his portfolio to the US Midwest (focusing on Cleveland, Ohio). Carlos shares his story of overcoming Canadian financing challenges, discovering cash-flowing Section 8 properties, and now mentoring other Canadians through joint ventures, mentorship, and E2 visa support. Key Points Carlos's Origin Story: Struggled with Canadian financing despite strong income; a denied refinance pushed him to ...
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1 month ago
19 minutes

The Wisdom, Lifestyle, Money, Show
David From Cash Flow Rentals Interview Scott About DSCR Loans In The U.S.A.
Send us a text Financing US Real Estate for Canadians & Foreign InvestorsEpisode Summary David interviews Scott Dillingham of LendCity, a dual-licensed mortgage broker in Canada and the US, to discuss DSCR loans for Canadians and foreign investors buying US properties. They cover loan terms, refinancing strategies, and key tips for non-US residents. Key Points DSCR Loans Explained: Debt Service Coverage Ratio loans focus on a property’s rental income, not borrower’s income or credit. Idea...
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1 month ago
38 minutes

The Wisdom, Lifestyle, Money, Show
The Advantage of Expert Brokers & Developers in Multi-Family Financing
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 commonly occur when going direct to banks or working with inexperienced brokers. Key Insights & Takeaways Scott shares a compelling example of how bro...
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4 months ago
8 minutes

The Wisdom, Lifestyle, Money, Show
Always Work With Investor Focused Experts Who Also Invest With Rhys Trenhaile
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 practice what they preach. Key Insights & Takeaways The Power of Early Real Estate Education Reese's story demonstrates how early exposure to real e...
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4 months ago
21 minutes

The Wisdom, Lifestyle, Money, Show
Value Add CMHC MLI-Select Apartment Building Financing Strategy
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 Value-Add Multi-Family Investing Focus on forcing appreciation vs. just cashflowWhy controlling income and expenses matters in multifamilyPredicta...
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5 months ago
5 minutes

The Wisdom, Lifestyle, Money, Show
Building Wealth Through Commercial Mortgages
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 Trainor, the experts behind the commercial mortgage arm, specializing in financing across Canada and expanding into the US. Learn about their individual backgrounds, areas of focus, and how their unique perspectives can benefit your...
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5 months ago
11 minutes

The Wisdom, Lifestyle, Money, Show
From Windsor to Wealth: Tom McCormick's Real Estate Adventure into the United States
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 Guest Background - Tom's journey into real estate during COVID-19 - From automotive engineering to property investing - How his brother inspired his f...
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8 months ago
21 minutes

The Wisdom, Lifestyle, Money, Show
Tax Strategies and Real Estate Investment with Carmen Da Silva In Canada & U.S.A.
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 comprehensive insights on tax strategies, investment structures, and wealth building approaches for Canadians investing in U.S. real estate. Her unique per...
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9 months ago
27 minutes

The Wisdom, Lifestyle, Money, Show
Profiting in U.S. Real Estate from Canada With Derek Wormsbecker
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 advantages of U.S. real estate investment. Key Timestamps: [0:00] Investment Journey - Starting in Canadian real estate - Transition to U.S. markets ...
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9 months ago
24 minutes

The Wisdom, Lifestyle, Money, Show
How To Save Thousands When Buying U.S. Properties With FX - Foreign Exchange
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 compared to traditional banking options. Key Timestamps: [0:00] Market Overview - Political impacts - Economic indicators - Currency forecasts [4:...
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9 months ago
28 minutes

The Wisdom, Lifestyle, Money, Show
From Canada to the U.S.: Strategic Real Estate Investing with Dmitri
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, Dmitri explains Share's comprehensive approach to property acquisition and management. Key Timestamps: [0:00] Professional Background - In...
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10 months ago
18 minutes

The Wisdom, Lifestyle, Money, Show
Don't Overpay For Real Estate Investing Courses - Do This Instead
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 quality education without paying thousands for questionable coaching programs. Key Timestamps: [0:00] Course Overview - Marketing vs exper...
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10 months ago
7 minutes

The Wisdom, Lifestyle, Money, Show
How To Get Your EIN In 2 Hours To Purchase U.S.A. Real Estate
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 - Importance of proper structure - Common investor roadblocks [4:30] Entity Benefits - Tax implications - Liability protection - Lender access [...
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10 months ago
9 minutes

The Wisdom, Lifestyle, Money, Show
Setting Up The Right Entity For Protection & Tax Benefits
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 Structure Basics - Shareholder agreements - Entity selection - Investor protection strategies [4:30] Multiple Structure Options - GPLP advan...
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10 months ago
38 minutes

The Wisdom, Lifestyle, Money, Show
Easily Qualify For Any Purchase
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] Traditional Qualification - Income requirements - Property limits - Equity lending issues [4:30] DCR/DSCR Programs - Cash flow qualification - Str...
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11 months ago
12 minutes

The Wisdom, Lifestyle, Money, Show
Empowering Investors With the Right Team
Send us a text In this episode, Scott Dillingham shares insights from his presentation at a Wealth Genius event about the importance of building the right team for real estate investing success. Drawing from his experience managing a team of expert investor-focused mortgage agents, Scott explains why investors often make critical mistakes in choosing their professional partners and provides actionable strategies for building an effective investment team. Key Timestamps: [0:00] Team Bu...
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11 months ago
13 minutes

The Wisdom, Lifestyle, Money, Show
Discover Challenges Canadians Face Investing In The U.S.A. & How To Get Over Them
Send us a text In this episode, Scott Dillingham interviews Andrew Kim from Share, discussing how his tech company helps Canadians invest in U.S. real estate through comprehensive asset management services. Andrew shares insights from his journey from Canadian real estate investor to U.S. tech entrepreneur, explaining how the challenges he faced led him to create a solution for other investors looking to build their portfolios across the border. Key Timestamps: [0:00] Introduction &am...
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11 months ago
25 minutes

The Wisdom, Lifestyle, Money, Show
Why Canadians Need To Invest In The U.S.A.
Send us a text In this episode, Scott Dillingham discusses why Canadians should consider investing in U.S. real estate, backed by statistical data and market trends. Key Timestamps: [0:00] Investment Trends - Canadian capital outflow - U.S. market attraction - Statistics Canada data [4:30] Investment Challenges in Canada - Landlord tribunal issues - Rent control limitations - Property sale restrictions [8:45] U.S. Market Advantages - Property affordability - Landlord-friendly regulati...
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11 months ago
36 minutes

The Wisdom, Lifestyle, Money, Show
Host Scott Dillingham discusses opportunities for real estate investors in Canada, the US, and Mexico, focusing on LendCity’s approach to finding cash-flowing deals. He highlights challenges in Canada’s residential market and shares strategies for leveraging new construction and commercial-style financing, particularly in Alberta. Key Points Market Challenges in Canada: Residential cash flow is tough in many Canadian markets (e.g., Ontario) due to rent control (e.g., 2.5% rent increase caps d...