The Wisdom, Lifestyle & Money Show

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares a streamlined approach for Canadians and foreign investors to obtain an ITIN (Individual Taxpayer Identification Number) in as little as two hours to facilitate US real estate purchases. As the president of LendCity Mortgages, Scott explains how his company, which specializes in investor-focused financing across Canada, the US, and Mexico (with a recent soft launch there), addresses common hurdles for investors. Drawing from interactions with nearly 1,000 investors over the past year, he notes that 90-95% get stuck at the entity setup stage due to processing delays, complexity, or timing issues that could cause them to miss out on properties.

Scott highlights the advantages of using an entity like an LLC over personal name purchases, including access to more lenders, better mortgage terms, and liability protection amid the litigious US environment. He cautions that personal name holdings may risk double taxation between the IRS and CRA, though he emphasizes consulting a tax professional for personalized advice, as individual situations vary. To overcome delays, LendCity pre-sets up entities using Scott's US citizenship for quick EIN acquisition, then assigns them to clients within two business hours—no magic, just proactive innovation. This service is free for LendCity mortgage clients, with only the accountant's competitive fee required; non-mortgage users pay a small additional fee. As of November 2025, standard IRS ITIN processing times are approximately 7 weeks (9-11 weeks during tax season), while foreign EIN applications via mail or fax take 4-6 weeks or more, confirming the value of this expedited option.

The episode also covers building US credit, as most investor mortgages don't report to bureaus—Scott recommends US credit cards and banking products for better future rates. He stresses the importance of having the entity ready for pre-approvals and offers, with options to rename or transfer it based on the purchase state. For accuracy, note that while LLCs provide benefits, some tax experts warn they can lead to double taxation for Canadians due to CRA treating them as corporations, potentially limiting foreign tax credits; personal holdings often allow better flow-through with credits to avoid double tax. This practical guide empowers investors to act swiftly, blending LendCity's services with tips for long-term success in US real estate.

Key Takeaways

• Entity Setup Hurdles for Investors: 90-95% of Canadian investors stall at forming US entities due to 4-8 week delays, risking lost opportunities; LendCity's pre-setup inventory allows assignment in 2 business hours.
• ITIN vs. EIN Clarification: While the episode refers to quick ITIN assignment, the process likely involves instant EIN for pre-formed LLCs via a US resident, with ITIN needed later for personal tax filing—standard IRS times are 7-11 weeks for ITIN and 4-6 weeks for foreign EIN.
• Personal Name Risks: Buying in personal name may expose you to liabilities and potential double taxation (IRS and CRA), per professionals; always consult an accountant, as entertainment only.
• LLC Benefits: Entities like LLCs offer liability protection, access to more US lenders, and better mortgage terms; however, updated 2025 tax insights show LLCs might cause double taxation for Canadians due to CRA's corporate treatment—consider alternatives like LPs.
• No-Fee Service for Clients: Free for LendCity mortgage customers (just pay accountant); includes strategy sessions, renaming, and state transfers; non-clients pay a fair fee.
• Building US Credit: Investor mortgages typically don't report; use US credit cards and banking to establish a score for lower future rates.
• Broader LendCity Offerings: Specializes in US investment mortgages (fix-and-flips, rentals); expanding to Mexico; book a free strategy call to discuss goals.

Links to Show References

• LendCity Mortgages (for Mortgages, Entity Setup, and Pre-Approvals): lendcity.ca
• Wisdom Lifestyle Money Show on Spotify: open.spotify.com/show/6bzUXElshqVweiYSPkhqGZ
• Wisdom Lifestyle Money Show on Apple Podcasts: podcasts.apple.com/us/podcast/the-wisdom-lifestyle-money-show/id1580165534
• Official Podcast Site: podcast.lendcity.ca
• IRS ITIN Information: irs.gov/tin/itin
• IRS EIN Information: irs.gov/businesses/employer-identification-number

• (00:04) - Introduction to ITIN and Real Estate

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

[8:45] Rapid ITIN Process
- 2-hour setup
- Pre-registered entities
- Cost structure

[12:30] Implementation Details
- Entity naming/transfer
- State considerations
- Credit building options

Key Points:
1. Service Features
- Pre-registered entity inventory
- 2-hour ITIN assignment
- No fee for mortgage clients
- Flexible entity naming/transfer

2. Setup Benefits
- Avoid double taxation
- Enhanced liability protection
- Better lending options
- Faster property acquisition

3. Next Steps
- Entity selection
- Credit building strategy
- State-specific planning

Contact Information:
LendCity

Important Tips:
- Consult tax professionals
- Consider credit building
- Review state requirements
- Plan entity structure
- Act quickly on properties

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Milena Cardinal, founder of Cardinal Law in Ontario, about optimizing corporate structures for real estate investments. Milena explains how leveraging shareholder relationships in corporations can simplify multifamily and development projects, highlighting the benefits of a single corporation for holding investments where investors own shares. She discusses balancing simplicity with drawbacks like lender requirements for qualifications and personal guarantees, drawing from her experience in creating tailored structures that minimize complexity while maximizing value.

Scott and Milena dive into various structures, including general partner-limited partner (GP-LP) setups for larger deals requiring CMHC financing, joint ventures for collaborative projects, and transitions between structures during different project phases. They emphasize the importance of early consultations to align on financing options, as lenders vary in recourse levels—from full to none—and ownership thresholds for applications. As of November 2025, CMHC's MLI Select program continues to support multi-unit financing with updates to premiums and new low-interest loans for secondary suites, but structures must be chosen carefully to avoid disqualifying investors or limiting refinance opportunities.

The conversation covers Milena's six-pillar approach to decision-making: tax minimization, liability protection, financeability, investor attractiveness, life and legacy goals, and cost. They share practical tips, like using bare trusts for quick purchases before transferring to corporations, and warn against common pitfalls such as mismatched advice from accountants and lawyers. This episode provides actionable strategies for investors aiming to build portfolios efficiently while protecting assets and ensuring long-term growth in Canada's evolving real estate market.

Key Takeaways

• Simplest Structures for Investments: Use a single corporation with shareholders for straightforward projects like land banking or cash purchases, offering ease and low costs, but evaluate lender demands for qualifications.
• GP-LP Advantages: Ideal for multifamily deals with CMHC financing to avoid personal guarantees; limits investor liability to their contribution while allowing tax flow-through, though more complex and costly.
• Joint Venture Flexibility: Combine with corporations for projects without down payments or to mimic GP-LP benefits; pros include shared management, but cons involve potential joint liability and need for clear agreements.
• Six Pillars for Structure Decisions: Balance tax savings, liability shields, financing ease, investor protection, legacy planning, and costs; collaborate with accountants, lawyers, and brokers for holistic advice.
• Financing Considerations 2025: CMHC MLI Select offers up to 50-year amortizations with updated premiums; bare trusts aid quick buys but require corporate transfers for refis to show income.
• Early Consultation Key: Meet experts before raising capital to secure funds in trust, comply with anti-money laundering rules, and pivot structures as needed for optimal outcomes.
• Exit and Legacy Strategies: One property per corporation eases sales via share transfers (no land transfer tax) and assumes existing mortgages, supporting long-term wealth building.

Links to Show References

• Milena Cardinal's Contact: Email - [email protected]; Website - cardinallaw.ca; Instagram - @milena_cardinal; Office - 902 Second St. West, Cornwall, Ontario
• LendCity Mortgages (for Financing): lendcity.ca
• CMHC Multi-Unit Financing Info: cmhc-schl.gc.ca

• (00:03) - Introduction to Shareholder Value

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 advantages
- Joint venture possibilities
- Financing implications

[8:45] Setting Up Process
- Consultation importance
- Document requirements
- Capital raising considerations

[12:30] Evaluation Framework
- Six key pillars approach
- Tax minimization strategies
- Liability protection methods

[16:45] Team Collaboration
- Professional coordination
- Expert alignment
- Strategic planning

Key Points:
1. Core Considerations
- Liability protection
- Tax efficiency
- Financing qualification
- Investor attractiveness

2. Structure Selection
- Project-specific needs
- Financing requirements
- Growth objectives
- Cost considerations

3. Professional Integration
- Team collaboration
- Expert alignment
- Strategic planning

Contact Information:
Website: cardinallaw.ca
Email: [email protected]
Free consultations for LendCity members

Important Tips:
- Consider multiple factors
- Plan exit strategies
- Verify lender requirements
- Balance complexity costs
- Coordinate professional advice

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham, President of LendCity Mortgages, dives into strategies for qualifying for investment property mortgages in Canada and the USA without relying solely on personal income. He explains how investors can leverage the property's cash flow through Debt Coverage Ratio (DCR) programs in Canada and Debt Service Coverage Ratio (DSCR) loans in the USA. Drawing from his experience starting in banking and transitioning to specialized investor financing, Scott highlights how these options allow real estate investors to scale their portfolios beyond traditional lender caps, which often limit properties to 4-10. He emphasizes avoiding high-rate private equity loans by choosing lenders who focus on the asset's performance, enabling full-time investing without a 9-to-5 job.

Scott breaks down key differences: In Canada, DCR applies to residential and commercial properties, including single-family homes (though harder) and mixed-use, with up to 80% loan-to-value (LTV) on purchases or refinances. However, a mortgage stress test—qualifying at least 2% above the contract rate or 5.25% (whichever is higher)—makes it tougher, and lenders may scale back LTV if cash flow is insufficient. In the USA, DSCR loans are more lenient with no stress test, interest-only options, and even 40-year terms to boost qualification. LTVs are typically 75% on purchases and 65-75% on cash-out refinances for foreign nationals (like Canadians), with some lenders allowing up to 80% on stabilized properties. He warns against over-relying on BRRRR strategies in the USA due to conservative LTVs for non-residents and notes that mixed-use properties may not qualify under DSCR.

This episode is packed with practical advice for investors aiming to retire from traditional jobs and grow unlimited portfolios, as most DCR/DSCR lenders have minimal caps once debt is sold or switched. Scott stresses running upfront cash flow analyses—including rents, taxes, insurance, and HOA/condo fees—while factoring in Canadian expenses like vacancy and repairs (often using 50-75% of rents). For optimal rates, prioritize positive cash flow; otherwise, expect higher rates or reduced LTVs. Updated for 2025, with USA DSCR booming due to tech-driven closings and Canada maintaining strict stress tests amid stable markets, this guide helps avoid common pitfalls and build wealth through informed lending.

Key Takeaways

• Qualify on Property Cash Flow: Use DCR in Canada or DSCR in USA to approve mortgages based on rental income covering debt, bypassing personal debt-to-income ratios and property caps from traditional lenders.
• Canada DCR Specifics: Up to 80% LTV on rentals/mixed-use; stress test at 2% above rate or 5.25%; single-family possible but prefer 2+ units; scale back LTV if no cash flow, including vacancy/repair factors.
• USA DSCR Advantages: No stress test; interest-only and 40-year terms available; 75% LTV purchase, 65-75% refinance for foreign nationals; easier qualification excluding vacancy costs, but mixed-use often ineligible.
• Avoid Private Equity Traps: Steer clear of high-rate private loans; consult experts for upfront analysis on rents, taxes, insurance, and fees, which vary by loan size/complexity/rush.
• Unlimited Portfolio Growth: Most lenders allow ongoing funding after debt sales (USA cap example: 15 deals); switch institutions in Canada if market overexposure hits.
• Investor Strategy Tips: Schedule strategy calls for custom numbers; focus on long-term cash flow for best rates; BRRRR less effective in USA due to conservative foreign LTVs.

Links to Show References

• LendCity Mortgages (for Strategy Calls & Investor Financing): lendcity.ca
• Wisdom Lifestyle Money Show Host Contact: Email - [email protected]; Website - lendcity.ca
• For USA & Canada Investment Mortgages: Visit LendCity offices in Windsor, Ontario or book online consultations

• (00:05) - Introduction to the Wisdom Lifestyle Money Show

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
- Stress test differences
- Property eligibility

[8:45] Market Differences
- Canadian vs U.S. LTVs
- Mixed-use considerations
- Fee structures

[12:30] Program Benefits
- Interest-only options
- Extended amortization
- Portfolio expansion

[16:45] Qualification Process
- Required documentation
- Expense calculations
- Approval criteria

Key Points:
1. Program Features
- Property-based qualification
- No income requirements
- Unlimited portfolio potential
- Mixed-use property options

2. Market Differences
- Canadian 80% LTV maximum
- U.S. 75% purchase/65% refinance
- Different fee structures
- Interest-only availability

3. Cash Flow Requirements
- Rent calculation variations
- Expense considerations
- LTV adjustments
- Rate implications

Contact Information:
Book strategy call

Important Tips:
- Compare market options
- Consider amortization lengths
- Review fee structures
- Calculate cash flow accurately
- Plan refinance strategy

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares insights from his recent presentation at the WealthGenius EXPAND Investor Conference in November 2025, where over 1,100 tickets were sold. Drawing from his experience speaking to a large audience of investors, Scott emphasizes the importance of assembling the right team for real estate success. Using the analogy of not going to a dentist for braces—instead seeking an orthodontist—Scott highlights why investors should partner with specialists rather than generalists. He warns against blindly following referrals from friends or family, as they may not align with investment-specific needs like multifamily properties or international deals.

Scott discusses common pitfalls, such as trusting unverified online experts who sell courses but lack real-world experience. He provides practical tips for vetting team members, including slowing down to conduct due diligence, asking pointed questions about their personal investing history, and distinguishing true experts from marketers. Highlighting his team at LendCity Mortgages, Scott showcases their expertise as active investors with backgrounds in development (reviewing over $1.25 billion in deals), U.S. property ownership (over 20 properties), multifamily rentals (managing 1,800+ tenants), student housing (hundreds of units), and property flipping. This investor-first approach ensures clients receive value beyond basic financing, helping avoid costly mistakes.

As of November 2025, LendCity offers mortgage solutions across Canada, the USA (for investors), and Mexico (for both investors and homeowners), specializing in residential and commercial lending tailored to real estate strategies. Scott shares a real example of how his team's development expertise turned around a declined $10 million deal by better communicating project details to lenders. The episode encourages listeners to build portfolios wisely, book a strategy call with LendCity experts, and share the podcast to help others succeed in real estate investing.

Key Takeaways

• Specialists Over Generalists: Just as you'd see an orthodontist for braces, choose real estate team members like realtors or lenders who specialize in investments, not just home buying, to avoid mismatches.
• Vet Referrals Carefully: Don't blindly trust friend or family recommendations; ensure they apply to your goals, such as multifamily or international properties, rather than standard residential needs.
• Slow Down for Due Diligence: Take a day or two to research potential partners—it's not detrimental to deals and prevents long-term mistakes in your portfolio.
• Ask the Right Questions: Inquire about a provider's personal experience, like "How many rental properties have you owned?" or "Have you used this strategy yourself?" to gauge true expertise.
• Distinguish Experts from Marketers: Verify if team members are active investors; for example, LendCity's agents have reviewed $1.25 billion in developments and managed 1,800+ tenants across multifamily and student rentals.
• Leverage Niche Experience: For U.S. or Mexico investing, work with teams like LendCity that own properties abroad and offer North American-wide lending to minimize fees and pitfalls.
• Book Targeted Strategy Calls: Select the right service (e.g., U.S. lending, commercial, development) when scheduling with investor-focused lenders to get matched with the ideal expert.

Links to Show References

• LendCity Mortgages (for Strategy Calls and Pre-Approvals): lendcity.ca
• WealthGenius EXPAND Investor Conference: wealthgenius.ai/expand
• Wisdom Lifestyle Money Show Host Contact: Email - [email protected]; Website - lendcity.ca

• (00:05) - Introduction to the Wisdom Lifestyle Money Show

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 Building Fundamentals
- Expert vs generalist selection
- Common investor mistakes
- Due diligence importance

[4:30] Essential Tips
- Slow down decisions
- Ask critical questions
- Verify expertise

[8:45] Expert Validation
- Development experience
- Property management history
- Investment track record

[12:30] Team Capabilities
- Multi-market experience
- Cross-border lending
- Specialized knowledge

[16:45] Next Steps
- Strategy call booking
- Service selection
- Team connection

Key Points:
1. Expert Selection
- Verify investment experience
- Check specialization areas
- Confirm track record

2. Due Diligence
- Research thoroughly
- Ask detailed questions
- Verify claims

3. Service Matching
- Align expertise with needs
- Consider market focus
- Evaluate experience level

Contact Information:
Book strategy call

Important Tips:
- Take time with decisions
- Verify expertise claims
- Match services to needs
- Research thoroughly
- Choose specialists

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Andrew Kim, CEO and co-founder of SHARE, a real estate technology company specializing in US single-family rental (SFR) investments. Andrew shares his entrepreneurial journey, starting with tech startups and transitioning into real estate after discovering the advantages of the US market in 2011 while living in California. He discusses his early investments in Ontario, which were costly and low-yield, compared to the US where properties offered lower prices, higher returns, and professional property management. Motivated by the challenges of balancing family, business, and portfolio growth—especially during the 2020 pandemic—Andrew founded SHARE in 2021 to help busy investors, particularly Canadians, scale their US real estate holdings effortlessly through tech-driven asset management.

Andrew explains how SHARE acts as an "asset manager" for retail investors, going beyond traditional property management by handling entity setup, tax strategies, financing, renovations, leasing, and ongoing portfolio optimization. He highlights common barriers for Canadians, such as uncertainty in choosing locations and navigating cross-border setups, and emphasizes landlord-friendly Sun Belt states for their tax benefits and economic growth. The conversation touches on the appeal of US SFR as a stable, predictable asset class with modest but consistent appreciation and rents, contrasting it with Canada's more volatile markets. Scott shares his own experiences investing in Maine's Section 8 hubs, underscoring the mental roadblocks Canadians face and how guided services like SHARE can overcome them.

Recorded in December 2024, the episode also explores potential impacts of the incoming Trump administration, including proposed corporate tax cuts and pro-business policies. As of November 2025, the US federal corporate tax rate remains at 21%, with no implementation of the discussed 15% reduction. However, the administration's focus on deregulation and reshoring has boosted industrial real estate and investor confidence, though tariffs have slightly increased construction material costs. Overall, this episode provides actionable insights for Canadians eyeing US investments, blending personal stories with practical strategies for long-term wealth building in a resilient market.

Key Takeaways

• From Tech Entrepreneur to Real Estate Investor: Andrew Kim's background in tech startups led him to US SFR in 2011, where lower prices (one-third of Canadian equivalents) and double the returns after property management made it a no-brainer compared to Ontario BRRRR strategies.
• Why US Over Canada for Canadians: US markets offer cash flow after expenses, professional management, and stability; avoid choosing locations based solely on drive time—instead prioritize economic growth, job increases, and landlord-friendly states like those in the Sun Belt.
• Asset Manager vs. Property Manager: Property managers handle maintenance and rents, but asset managers like SHARE focus on portfolio growth, including tax alignment, entity setup, refinancing, and equity extraction to acquire more properties.
• Overcoming Common Hurdles: Key barriers include location uncertainty and entity/tax setup; SHARE provides education on risk-reward profiles (A-D class homes) and streamlined setups with cross-border CPAs for liability protection and lender compatibility.
• Impact of 2025 US Policies: Trump's pro-business stance has reduced regulations, benefiting investors, but the corporate tax rate stays at 21%; expect positive effects from reshoring, though tariffs may raise costs—US SFR remains resilient with steady appreciation.
• Tips for Stable Investing: View US SFR as the "most Canadian" asset—predictable, high-demand, and institution-backed; avoid expecting GTA-style rapid appreciation; focus on long-term hold for modest gains, conservative calculations, and autopilot growth.

Links to Show References

• Andrew Kim's Contact: LinkedIn - ca.linkedin.com/in/andrewkim83; Website - sharesfr.com; Instagram - @sharesfr
• LendCity Mortgages (for Pre-Approvals): lendcity.ca
• SHARE Office: Greater Toronto Area, Ontario for consultations

• (00:03) - Welcome to the Wisdom Lifestyle Money Show

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 & Background
- Tech entrepreneurship journey
- Early investment experiences
- Transition to U.S. markets

[4:30] Share Platform Overview
- Asset management services
- Property acquisition process
- Portfolio growth strategy

[8:45] Investment Challenges
- Location selection
- Entity setup
- Cross-border considerations

[12:30] Market Analysis
- State selection criteria
- Political implications
- Economic factors

[16:45] Investment Strategy
- Market stability
- Appreciation expectations
- Risk management

Key Points:
1. Asset Management Benefits
- Full-service portfolio growth
- Tax and entity structuring
- Property management oversight
- Investment strategy guidance

2. Market Selection
- Landlord-friendly states
- Economic indicators
- Population growth
- Job market strength

3. Investment Expectations
- Steady appreciation
- Stable cash flow
- Market resilience
- Portfolio diversification

Contact Information:
Website: sharesfr.com

Important Tips:
- Focus on market fundamentals
- Consider property management
- Understand appreciation rates
- Review tax implications
- Evaluate state regulations