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Always Work With Investor Focused Experts Who Also Invest With Rhys Trenhaile
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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 estate investing can create lasting wealth. While training for track and field at university, he and his teammates purchased seven student rental properties and even two race horses by the time they won a national championship in 1998. This early start led to one teammate retiring at 48 years old, showcasing the long-term wealth-building potential of strategic real estate investment.
Why Experience Matters in Real Estate Teams
Scott emphasizes a crucial point for listeners: always work with real estate professionals who are actively investing themselves. Reese and his team don't just sell properties—they own substantial portfolios, including major development projects worth over $100 million in downtown Windsor. This hands-on experience means they understand the challenges investors face and can provide guidance based on real-world results, not just theory.
Overcoming the First Investment Hurdle
The biggest barrier for new investors isn't financial—it's mental. Reese explains that people who have been employees their entire adult lives struggle most with learning to take calculated risks with their money. The fear and endless questions that plague first-time investors prevent them from moving quickly on good deals, which experienced investors can capitalize on immediately.
Investment Timeline Reality Check:
- First Property: Usually not a "steal" due to inexperience and hesitation
- Second Property: Still learning, asking many questions
- Third-Fourth Property: Finally ready to recognize and act on great deals quickly
This progression is normal and expected. New investors shouldn't expect to hit home runs immediately—building expertise takes time and experience.
Strategic Property Selection for Portfolio Growth
Rather than traditional duplexes that can create financing roadblocks, Reese recommends the BRRRR strategy (Buy, Renovate, Rent, Refinance, Repeat) using properties with additional dwelling unit (ADU) potential:
By adding a basement suite, investors can achieve $1,000+ monthly cash flow, increase property value, and refinance to recover most or all of their initial investment for the next purchase.
Working with the Right Team
Successful real estate investing requires partnerships between experienced agents and financial experts who specialize in investment properties. The team approach helps investors avoid common roadblocks and structure deals for maximum growth potential, including mortgage-plus-improvement financing to fund renovations without using personal capital.
Resources Mentioned
- The Vanguard Team Website: thevanguardteam.com
- Team YouTube Channel: Features recent market analysis videos and investment strategies
Book A Strategy Call With An Expert On The Team
Support the show
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By Scott DillinghamSend 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 estate investing can create lasting wealth. While training for track and field at university, he and his teammates purchased seven student rental properties and even two race horses by the time they won a national championship in 1998. This early start led to one teammate retiring at 48 years old, showcasing the long-term wealth-building potential of strategic real estate investment.
Why Experience Matters in Real Estate Teams
Scott emphasizes a crucial point for listeners: always work with real estate professionals who are actively investing themselves. Reese and his team don't just sell properties—they own substantial portfolios, including major development projects worth over $100 million in downtown Windsor. This hands-on experience means they understand the challenges investors face and can provide guidance based on real-world results, not just theory.
Overcoming the First Investment Hurdle
The biggest barrier for new investors isn't financial—it's mental. Reese explains that people who have been employees their entire adult lives struggle most with learning to take calculated risks with their money. The fear and endless questions that plague first-time investors prevent them from moving quickly on good deals, which experienced investors can capitalize on immediately.
Investment Timeline Reality Check:
- First Property: Usually not a "steal" due to inexperience and hesitation
- Second Property: Still learning, asking many questions
- Third-Fourth Property: Finally ready to recognize and act on great deals quickly
This progression is normal and expected. New investors shouldn't expect to hit home runs immediately—building expertise takes time and experience.
Strategic Property Selection for Portfolio Growth
Rather than traditional duplexes that can create financing roadblocks, Reese recommends the BRRRR strategy (Buy, Renovate, Rent, Refinance, Repeat) using properties with additional dwelling unit (ADU) potential:
By adding a basement suite, investors can achieve $1,000+ monthly cash flow, increase property value, and refinance to recover most or all of their initial investment for the next purchase.
Working with the Right Team
Successful real estate investing requires partnerships between experienced agents and financial experts who specialize in investment properties. The team approach helps investors avoid common roadblocks and structure deals for maximum growth potential, including mortgage-plus-improvement financing to fund renovations without using personal capital.
Resources Mentioned
- The Vanguard Team Website: thevanguardteam.com
- Team YouTube Channel: Features recent market analysis videos and investment strategies
Book A Strategy Call With An Expert On The Team
Support the show