My Story & Why You Should Listen to This Show
- Author
- Scott Dillingham
- Published
- Sun 11 Jul 2021
- Episode Link
- None
In this inaugural episode, host Scott Dillingham shares his personal journey from early challenges to becoming a successful entrepreneur and real estate investor. His story demonstrates how setbacks and "mistakes" can become stepping stones to success.
Key Timestamps:
[0:00] 🏡 Early Life and Family Background
- Born in Lewiston, Maine
- Family separation and move to Canada
[3:15] 📚 Childhood Challenges
- Struggles with school and authority
- Experiences with babysitters
- Early signs of entrepreneurial spirit
[7:30] 🏫 Academic Struggles and Personal Growth
- Failing Grade 6
- High school challenges
- Expulsion and turning point
[12:45] 💼 First Steps in Professional Life
- Entering sales
- Initial success at Sears
- Transition to Future Shop
[16:30] 🏠 Accidental Real Estate Investment
- Unexpected property purchase
- Turning a potential setback into an opportunity
- First steps in real estate investing
[20:15] 📈 Building Investment Portfolio
- Growing to 8 residential properties
- Transition to mortgage banking
- Starting Lend City mortgage brokerage
Key Points from Scott's Journey:
- Early challenges included family separation, frequent moves, and struggling in school
- Was expelled from high school but used this setback as motivation to succeed
- Found early success in sales positions at Sears and Future Shop, consistently becoming a top performer
- An accidental real estate investment (due to a failed wholesale deal) became the catalyst for his investment career
- Built a portfolio of 8 residential properties with 12 combined units
- Leveraged banking industry experience to start Lend City, expanding into commercial lending
- Currently working toward building Canada's largest online mortgage brokerage
Key Insights for Listeners:
- Success Despite Adversity: Academic struggles or early setbacks don't determine your future success
- Sales Experience: Can provide valuable foundational skills for entrepreneurship
- Learning from "Mistakes": Sometimes our biggest "mistakes" can lead to our greatest opportunities
- Multiple Income Streams: Scott discusses diversifying through:
- Real estate investments
- Sales careers
- Business ownership
[25:45] 🎯 Future Goals and Vision
- Becoming the largest online mortgage brokerage in Canada
- Commitment to helping others grow financially
About the Host:
Scott Dillingham is a mortgage broker, real estate investor, and entrepreneur based in Windsor, Canada. Despite early academic challenges, he has built successful businesses and investment portfolios through persistence, self-education, and strategic risk-taking.
Resources Mentioned:
- Rich Dad Poor Dad (Book)
- Think and Grow Rich (Book)
- Dare to Lead (Book)
Note: While financial topics are discussed, Scott emphasizes he is not a financial advisor and will bring in qualified experts for detailed financial guidance.
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