In this inaugural episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham opens up about his personal story, from a challenging childhood in Lewiston, Maine, to becoming a successful mortgage broker and real estate investor in Windsor, Ontario. Scott recounts his early family upheavals, including his parents' separation and move to Canada sponsored by Windsor Raceway, leading to a latchkey kid life filled with mischief, babysitter woes, and a budding entrepreneurial spirit. He shares school struggles—failing grade 6, high school suspensions for pranks like air horns and paper snowstorms—and ultimate expulsion in grade 12, which taught him valuable lessons about trust and self-reliance.
Turning setbacks into fuel, Scott dove into sales roles at Sears, a call center, and Future Shop, where he excelled as a top performer and won awards. Inspired by Rich Dad, Poor Dad, he ventured into real estate wholesaling, accidentally acquiring his first investment property in Sarnia after a partner backed out—leading to a full renovation and portfolio growth to 8 properties with 12 units. While rising to #2 in Canada for mortgages at a major bank, he founded LendCity Mortgages to offer flexible financing options for investors across Canada. Scott emphasizes personal development through books like Think and Grow Rich and Dare to Lead, and teases future episodes on calculated leverage for risk-minimized wealth building.
This episode is a must-listen for aspiring entrepreneurs, real estate investors in Canada, and anyone seeking motivation to overcome adversity, build financial independence, and scale a business like a mortgage brokerage in Ontario.
Host Bio
Scott Dillingham is the founder and CEO of LendCity Mortgages, a premier online mortgage brokerage specializing in financing for real estate investors across Canada and the USA. As host of The Wisdom, Lifestyle, Money Show, Scott draws from his own journey—from sales excellence at Future Shop to building a multi-property investment portfolio—to educate listeners on mortgages, investing, and personal growth. Based in Windsor, Ontario, he has achieved top national rankings in mortgage sales and now leads a team helping Canadians secure creative financing solutions. Connect with Scott on Facebook at facebook.com/scott.dillingham or visit lendcity.ca for mortgage advice and resources.
Scott Dillingham is the founder and CEO of LendCity Mortgages, a premier online mortgage brokerage specializing in financing for real estate investors across Canada and the USA. As host of The Wisdom, Lifestyle, Money Show, Scott draws from his own journey—from sales excellence at Future Shop to building a multi-property investment portfolio—to educate listeners on mortgages, investing, and personal growth. Based in Windsor, Ontario, he has achieved top national rankings in mortgage sales and now leads a team helping Canadians secure creative financing solutions. Connect with Scott on Facebook at facebook.com/scott.dillingham or visit lendcity.ca for mortgage advice and resources.
Key Takeaways
- Early independence from a tough childhood fostered an entrepreneurial mindset, teaching Scott to explore and innovate without strict authority.
- School failures and expulsion highlighted the value of self-directed learning over forced education, turning negatives into lifelong motivation.
- Sales careers provided financial control, allowing Scott to "write his own paycheck" through effort and quickly rise to top performer status.
- An accidental real estate investment—buying a fixer-upper in Sarnia after a wholesaling deal fell through—sparked a portfolio of 8 properties and 12 units.
- Banking experience revealed investor strategies, like direct stock purchases with discounts, which Scott applied to grow his net worth efficiently.
- Founding LendCity Mortgages addressed bank limitations, offering diverse lenders for better client approvals and creative financing in Canada.
- Personal development via books like Rich Dad, Poor Dad and Think and Grow Rich was crucial for productivity, mindset, and achieving goals.
- Future focus: Becoming Canada's largest online mortgage brokerage while teaching "calculated leverage" to minimize investing risks.
- (00:10) - Introduction to My Journey
- (08:03) - Trust and Lessons Learned
- (12:21) - Discovering Real Estate Investing
- (13:40) - Starting LendCity
- (15:18) - Personal Development and Growth
- (16:41) - Upcoming Topics on Wealth and Leverage
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