In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Carmen Da Silva, a cross-border CPA and co-founder of SHARE, who specializes in helping Canadians invest in U.S. real estate. Carmen shares her journey from articling at PricewaterhouseCoopers (now PwC) in tax programs to building a family wealth management business, before relocating to Florida in 2003. She discusses her pivot to real estate investing during the 2008 financial crisis, starting with single-family rentals to replace income after selling her business. Emphasizing opportunity and preparedness, Carmen explains how she expanded her portfolio through bulk purchases in Florida and Texas, leveraging strategies like refinancing to acquire more properties without additional personal capital. She highlights the challenges of early investments, such as mortgage issues with condos and navigating hedge fund influences, leading her to focus on single-family homes.
As CFO and co-founder of SHARE (established in 2021), Carmen describes how the platform simplifies U.S. real estate investing for Canadians, offering end-to-end services from entity creation to asset management. She stresses the importance of cross-border tax planning, including foreign tax credits, state-specific filings, and entity structures like Wyoming holding companies for privacy and asset protection. Carmen warns against using U.S.-centric structures like LLCs without considering Canadian tax mismatches, which can lead to double taxation. The conversation touches on potential impacts from U.S. tax reforms under the One Big Beautiful Bill signed in July 2025, which extended 2017 tax cuts, kept corporate rates at 21%, and introduced higher tariffs—potentially affecting cross-border flows but favoring personal holdings for capital gains benefits. She advises consulting cross-border experts to avoid pitfalls in taxation, estate planning, and probate.
Carmen also shares her passion for educating the next generation, teaching her children to invest early for cash flow and tax advantages, using affordable U.S. entry points compared to Canadian markets. Drawing from Robert Kiyosaki's Cashflow 101 game, she illustrates behavioral lessons in investing, such as seizing opportunities and maintaining a cash flow mindset over scarcity. For 2025, U.S. real estate remains attractive for Canadians amid stable markets, with tools like SHARE's portal providing real-time tracking, discounted insurance, and property tax reassessments. This episode offers practical insights for building wealth across borders, blending personal stories with updated strategies amid evolving tax landscapes.
Key Takeaways
- Cross-Border Tax Essentials: Consider residency and property location for taxation; file U.S. federal (and state where applicable) returns, then claim foreign tax credits in Canada to avoid double taxation, with no state income tax in places like Texas.
- Entity Structures for Protection: Use a Wyoming parent holding company for privacy, registering subsidiaries in each state; avoid U.S. LLCs without Canadian alignment to prevent timing mismatches and higher effective taxes.
- Investing Strategies: Leverage refinancing (e.g., using equity from six properties to buy more) for portfolio growth; focus on single-family rentals over condos due to mortgage and resale challenges, especially post-2008 and amid 2025 tariff impacts.
- Accountant Selection: Choose professionals with knowledge of both Canadian and U.S. systems; hybrid entities can cause issues, so integrate estate planning like local wills to streamline probate and avoid administrative delays.
- Family Wealth Building: Start young investors with affordable U.S. properties for cash flow (e.g., $100,000 homes yielding $1,000 monthly); teach a cash flow mindset to enable financial freedom, using tools like SHARE for seamless management.
- SHARE's End-to-End Support: Benefit from acquisition teams, institutional-grade property managers, monthly financials, and cost reductions (e.g., 40% insurance discounts, property tax reassessments); ideal for hands-off investing in 2025's stable U.S. markets.
- 2025 Tax Updates: Under the One Big Beautiful Bill, extended tax cuts favor personal holdings for capital gains; corporate rates remain at 21%, but Canadian passive investment rules may still impose high rates—prioritize flow-through structures.
Links to Show References
- (00:03) - Welcome and Introduction
- (01:30) - The Journey into Real Estate
- (02:56) - Starting Share: A New Venture
- (04:07) - Tax Considerations for Canadians
- (09:15) - Choosing the Right Accountant
- (12:10) - How to Work with Carmen
- (17:22) - Teaching the Next Generation
- (21:15) - The Importance of Cash Flow
- (23:48) - Lessons from the Cash Flow Game
- (25:33) - Wrap-Up and Resources
