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
- (00:03) - Welcome to the Wisdom Lifestyle Money Show
- (02:12) - Andrew's Journey in U.S. Real Estate
- (05:14) - Overcoming Investment Fears for Canadians
- (08:33) - Asset Management vs. Property Management
- (10:32) - Setting Up for Success
- (12:38) - Popular U.S. States for Canadian Investors
- (14:48) - Political Landscape and Real Estate Impact
- (20:31) - The Case for U.S. Single Family Rentals
- (24:04) - Final Thoughts and Resources
