The Wisdom, Lifestyle & Money Show

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham addresses a listener's request to explore the advantages and disadvantages of purchasing investment properties through a corporation versus in one's personal name. Drawing from his experience as a mortgage expert at LendCity, Scott explains key benefits like keeping corporate mortgages off personal credit reports, allowing i...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham addresses a common challenge facing rental property investors in Canada amid high interest rates. With many investors holding variable rate mortgages, rising rates have eroded positive cash flow, often leading to negative scenarios. Scott explains why variable rates have historically been ideal for investors—offering low exi...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares insights on navigating mortgage interest rates amid economic uncertainty. Recorded in June 2023 during a period of rising rates, Scott discusses common investor dilemmas: whether to lock into shorter 2- or 3-year fixed terms anticipating future drops or opt for a 5-year fixed for immediate stability. He cautions again...

In this special admin edition of the Wisdom Lifestyle Money Show, host Kristen Dillingham sits down with LendCity Mortgages admins Kayla Miller and Jillian Barnes to demystify the mortgage application process. Drawing from their backgrounds in healthcare and medical care before joining the team in 2018, the trio shares how they've learned the ins and outs of mortgages from scratch under Scott Dill...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Paul D'Abruzzo, an investor-focused realtor and developer in the GTA. Paul shares his background as a former Toronto firefighter for 10 years, retiring to focus on real estate after juggling multiple roles as a husband, father, investor, and realtor. He started investing in 2009 with his first property in Hamilton...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Gillian Irving, a mortgage agent at LendCity specializing in investment properties and student rentals. Gillian shares her journey as an "accidental investor," starting in 2008 after reading Rich Dad Poor Dad. She bought her first property in Toronto's Leslieville neighborhood on a whim, refinancing it multiple ti...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Ryan Giles, owner of RFG Plumbing and Electrical in Essex, Ontario. Ryan shares his journey growing up in a family of plumbers, starting from childhood helping his dad and uncle on jobsites. As a fourth-generation plumber, he discusses how early exposure to the trade built his work ethic and problem-solving skills...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Amy Eliza Wong, a transformational leadership coach and author. Amy shares her upbringing in Sacramento, California, surrounded by unconditional love from her parents who overcame poverty and hardship to build a life filled with joy and hard work. She opens up about the chaos of growing up with a home daycare,...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Paul Lue Pann, a financial planner and owner at PLP Financial Services Inc. with The Co-operators in Windsor, Ontario. Paul shares his unique background as a Chinese Jamaican who grew up in Toronto and spent 18 years climbing the corporate ladder at Sun Life, moving between cities before settling in Windsor. A...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Scott Thompson, a realtor with at RE/MAX in Windsor, Ontario. Scott shares his background growing up in Windsor, from playing sports in Roseville Gardens to caring for his grandfather with dementia, which inspired his entry into social work. He discusses his time at a rehab facility helping young men overcome addi...

Canadas mortgage stress test has blocked more buyers than almost any other policy change in recent history — but most people do not fully understand how it works or how to plan around it. In this episode, Scott Dillingham explains it clearly and shares strategies to protect your buying power. Scott discusses using variable rates (lower payments) to maximize approvals, then locking to fixed post-cl...

Buying a rental property without running the numbers is one of the most expensive mistakes an investor can make. In this episode, Scott Dillingham walks through the complete property analysis process — from cash flow calculations and cap rates to due diligence checklists. Scott stresses targeting monthly cash flow per door (e.g., $100-200 for smaller units), using a free rental worksheet factoring...

Most real estate investors do not quit their jobs before building their portfolio — they build it while working. In this episode, Scott Dillingham shares the systems and delegation strategies that let busy professionals manage a growing real estate portfolio without sacrificing their career. Scott emphasizes building a strong team: Property managers handle tenant issues/vacancies, investor-focused...

Single family or multifamily — which investment strategy actually builds more wealth in Canada over time? In this episode, Scott Dillingham compares the two approaches head to head across cash flow, financing, management complexity, and long-term appreciation. Scott explains single family benefits: Easier entry (5% down if occupying), quick sales to all buyers (investors/owners), tenant-paid debt...

What actually makes LendCity different? In this episode, Scott Dillingham goes behind the scenes to share the culture, career paths, values, and team philosophy that drive the business — and what he looks for when building a team that truly serves clients. Scott emphasizes a fun, politics-free culture with dedicated departments: Sales for client options, admin for fast processing, social media/mar...

Scott Dillingham did not expect that getting in shape would change his business — but it did, in a way that directly led to a $3M client. In this episode, he shares the story of how physical discipline rewired his professional approach and the unexpected ways lifestyle changes translate into business results. Scott recounts a client shopping lenders who asked why choose him; his response highlight...

The fear of starting a business is real — but it does not have to be a permanent barrier. In this episode, Scott Dillingham shares the exact mindset shifts and practical first steps that helped him push through fear, build momentum, and create a business that has helped thousands of Canadians. Scott discusses embracing risk from real estate investing, viewing setbacks as learning opportunities—lik...

Fixed or variable — it is one of the most consequential mortgage decisions a Canadian can make, and most people make it based on gut feel rather than strategy. In this episode, Scott Dillingham cuts through the noise with a clear breakdown of when each option wins. He covers pros/cons: Fixed offers payment certainty but higher penalties (IRD/3 months interest); variable provides lower payments, mo...

The refinance-and-renovate strategy is one of the most powerful tools available to Canadian rental investors — and most people are not using it to its full potential. In this episode, Scott Dillingham explains how to recycle equity to fund additional properties and grow a rental portfolio without constantly needing new cash. Scott details his approach: Start with a live-in property (e.g., duplex)...

Rates, down payments, amortization, penalties — your buyers and investors have questions and you need the right answers. In this episode, Scott Dillingham tackles the mortgage questions that come up most often from Canadians, including things the banks quietly leave out. Scott explains why accurate rate quotes require a preapproval: Factors like credit score, down payment, and debt-to-income ratio...

Not all mortgage pre-approvals are created equal — and the wrong one can cost you a deal when it matters most. In this episode, Scott Dillingham breaks down the 3 types of pre-approvals and explains which one actually protects buyers in a competitive Canadian market. Scott breaks down verbal preapprovals: Quick phone estimates based on self-reported info, inaccurate due to unverified income, debts...

Most Canadians assume their bank is the best place to get a mortgage. They are wrong — and it costs them thousands. In this episode, Scott Dillingham explains the real difference between banks and mortgage brokers, which option actually gives you access to better rates, and how to choose the right one. Scott discusses service differences: Banks offer superior customer service training but can lack...

In this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham interviews Manny Cabral, a seasoned real estate investor specializing in flipping and wholesaling over 30 properties in Simcoe County and Hamilton, Ontario. Manny shares his dynamic career path starting as a carpenter's apprentice after George Brown College, co-founding a construction firm (SCI) focused on commercial compu...

In this motivational episode of The Wisdom, Lifestyle, Money Show , host Scott Dillingham shares his personal journey from unfulfilling banking roles to founding LendCity Mortgages, revealing how mindset, visualization, and determination can help anyone achieve dreams. Starting with his "golden handcuffs" at a bank (top mortgage rep but unhappy with policies like face-to-face mandates amid tech av...

Your credit score is not just a number — it is the key to lower rates, higher approvals, and better investing power. In this episode, Scott Dillingham shares the exact strategies that Canadian investors and homebuyers use to rapidly improve their scores and qualify for the financing they need. He advises debt consolidation loans (7-12% rates vs. 20% cards, 1-7 year payoffs) for savings/principal r...