Shows
The Wisdom, Lifestyle, Money, ShowUnlock 100% Financing for Owner-Occupied Commercial Properties in CanadaIn this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham from LendCity reveals a powerful yet underutilized financing program that allows business owners and real estate investors to purchase owner-occupied commercial properties—like offices, industrial, or manufacturing buildings—with up to 100% financing. Ideal for self-employed professionals transitioning from renting to owning, this program leverages your business's net operating income (NOI) to maximize leverage, often far beyond standard commercial loans. Scott shares real-world examples, including clients achieving 90-100% loan-to-value (LTV) ratios, freeing up capital for business growth while building equity in real estate.Scott breaks down how...
2025-12-0109 min
The Wisdom, Lifestyle, Money, ShowHow A Tinder-Like App Helps Investors Find, Analyze, And Close Better PropertiesIn this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Saqib Dareshani, founder of RealSwipe, a platform revolutionizing real estate investing. Saqib shares his journey from computer engineering to real estate, starting in 2009 when he sold his stocks to invest in a fourplex multifamily property. He discusses renovating the building, increasing NOI by 50%, and growing its value from $375,000 to over $1 million today. Drawing on skills from teaching app development at Carleton University and contributing to over 500 apps downloaded millions of times, Saqib explains how he merged tech and real estate to create RealSwipe—Tinder for real es...
2025-11-2419 min
The Wisdom, Lifestyle, Money, ShowFrom Immigration Enforcement to Real Estate Law: Shawn Quigg's JourneyIn this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Shawn Quigg, a real estate investing-focused lawyer and partner at Cardinal Law in Ontario. Shawn shares his unexpected entry into real estate investing while transitioning from a career in immigration enforcement to law school in 2014-2015. Starting with a $133,000 five-bedroom house in Windsor, he rented rooms to fellow students, achieving positive cash flow and even "beer money" to ease through school. Inspired by finance classes revealing cash's vulnerability to inflation, he expanded to a second property for $236,000, converting it into a six-bedroom rental. This hands-on...
2025-11-1722 min
The Wisdom, Lifestyle, Money, ShowEp 74 - Harnessing Energy Flow for Peak Performance and Mental Wellness with host Scott Dillingham and guest Kimberly KingsleyHere are the best ways I can help you as an Investor:Investor Network AccessRun the numbers like a pro of any property.Access Insider Events, ONLY for members.Network with other investors.Create joint venture partnerships.Get direct access to a team of experts.Get preferred interest rates on mortgages & lending products.Ask questions and get answers to any investing challenges you have.Book A FREE Strategy Call With My TeamDiscover the financing options available to you.Create the proper financing structure for success.Get your portfolio reviewed and identify...
2024-03-0823 min
Playing InjuredObtaining Financial Freedom: Grit, Mentorship & Impact w/ Mason Eddy (EP 118)When the weight of financial hardship from Mason's family loomed over him, a pivotal shift occurred as he cracked open the book "Rich Dad, Poor Dad." That moment sparked the entrepreneurial fire that would eventually lead him to where he is today. Grateful for this transformative journey, Mason Eddy and Josh Dillingham invite you to explore the multifaceted roles of mentorship, personal grit, and the unwavering pursuit of financial independence on this episode of our podcast. Reflect with us on the not-so-talked-about aspects of character development and how they're intrinsically linked to overcoming adversity and achieving success.T...
2024-02-1541 min
The Wisdom, Lifestyle, Money, ShowPros and Cons of Buying Real Estate in a Corporation vs PersonallyIn 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 investors to qualify for more loans without impacting their personal debt ratios. He highlights how some residential lenders ignore corporate holdings entirely, enabling repeated "resets" for further acquisitions. Additionally, corporations provide enhanced liability protection, shielding personal assets from potential lawsuits related to...
2023-07-2009 min
The Wisdom, Lifestyle, Money, ShowOvercoming Negative Cash Flow: 3 Strategies for Rental InvestorsIn 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 exit penalties, higher prepayment options, and lower overall rates—but notes how recent hikes have flipped this dynamic. Drawing from frequent client inquiries, he outlines practical solutions to restore profitability without selling properties, emphasizing the importance of consulting experts like the team...
2023-07-0107 min
The Wisdom, Lifestyle, Money, ShowMortgage Admin Insights: Documents, Processes & Tips from LendCityIn 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 Dillingham's guidance. They emphasize that getting a mortgage is simpler than expected for many, but success hinges on proper documentation, budgeting wisely, and avoiding impulse buys like expensive cars that depreciate and impact financing power. The discussion highlights...
2023-05-2517 min
The Wisdom, Lifestyle, Money, ShowEp 37: Should I Buy in This Market and Other Frequently Asked QuestionsHere are the best ways I can help you as an Investor:Investor Network AccessRun the numbers like a pro of any property.Access Insider Events, ONLY for members.Network with other investors.Create joint venture partnerships.Get direct access to a team of experts.Get preferred interest rates on mortgages & lending products.Ask questions and get answers to any investing challenges you have.Book A FREE Strategy Call With My TeamDiscover the financing options available to you.Create the proper financing structure for success.Get your portfolio reviewed and identify...
2022-08-0309 min
The Wisdom, Lifestyle, Money, ShowMortgage Stress Test: Protecting Power in Rising RatesIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham explains the mortgage stress test—qualifying at 5.25% or contract rate +2% (higher of)—and its erosion of purchasing power amid rising rates.Scott discusses using variable rates (lower payments) to maximize approvals, then locking to fixed post-closing (no fees/penalties)—a strategy for aggressive buyers, but warns of risks if rates rise further.He covers post-COVID rate hikes (variable up 0.25% already, targeting pre-COVID levels ~2.75%), housing supply shortages, and Ontario's foreign buyer tax increase to 20% province-wide to ease demand.Advice: Get preapprovals now (spring...
2022-07-1718 min
The Wisdom, Lifestyle, Money, ShowAnalyzing Rental Properties: Cash Flow and Due Diligence TipsIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham explains how to analyze rental properties to avoid mistakes, emphasizing accurate numbers over "analysis paralysis" for beginners and experienced investors.Scott stresses targeting monthly cash flow per door (e.g., $100-200 for smaller units), using a free rental worksheet factoring legal units, rents, vacancies (4-8%), additional income (e.g., parking, laundry), and expenses like management, repairs, taxes, insurance, utilities, and fees.He warns against relying on MLS listings—request sellers' utility history, T1 generals, bank statements to verify income/expenses; check for legal un...
2022-03-0818 min
The Wisdom, Lifestyle, Money, ShowManaging Real Estate Investments When BusyIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham addresses the challenge of managing real estate investments amid busy lives, sharing tips he wishes he knew earlier.Scott emphasizes building a strong team: Property managers handle tenant issues/vacancies, investor-focused lenders optimize financing/structure for growth, specialized realtors avoid high-turnover areas, knowledgeable bankers accelerate down payments, inspectors/lawyers versed in LTB matters prevent pitfalls—even contractors tested on small jobs first.He advises automating finances: Direct deposit rents into one account, auto-withdraw mortgages/utilities/taxes (waives setup fees, saves time); set reserves (3 mo...
2022-03-0421 min
The Wisdom, Lifestyle, Money, ShowLendCity Hosts Interns And Gets the Behind The Scenes Info on Business FinanceIn this episode, host Scott Dillingham discusses the differences between single-family property investing and multi-family investing. He highlights the benefits of single-family investing, such as easier entry into the market, the ability to sell the property quickly, and the potential for appreciation. He also explains the advantages of multi-family investing, including higher cash flow, potential cost savings on repairs and renovations, and the ability to leverage CMHC financing. Dillingham recommends starting with single-family properties and then transitioning to multi-family properties as your portfolio grows.(00:00) - Introduction
(01:30) - Should You Get Into Investing?
(10:15) - The Advantages of Multi-Family...
2022-03-0419 min
The Wisdom, Lifestyle, Money, ShowSingle Family vs Multifamily: Investing StrategiesIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham compares single family vs multifamily real estate investing, offering guidance for beginners and experienced investors in Windsor and Southwestern Ontario.Scott explains single family benefits: Easier entry (5% down if occupying), quick sales to all buyers (investors/owners), tenant-paid debt reduction, and strong appreciation amid housing shortages—ideal for testing investing without high commitment.He notes challenges like lower cash flow and initial vacancies (hardest on first property), recommending variable rates for low penalties/exit flexibility, and property managers to minimize headaches.Fo...
2022-02-1118 min
The Wisdom, Lifestyle, Money, ShowBehind the Scenes at LendCity: Career and CultureIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham shares insights into working at LendCity Mortgages, highlighting opportunities amid job losses from layoffs, closures, and mandates.Scott emphasizes a fun, politics-free culture with dedicated departments: Sales for client options, admin for fast processing, social media/marketing for education, commercial for specialized lending, and head office for compliance.He discusses unique perks like profit-sharing for salaried staff, community events (e.g., golf tournaments, snow shoveling, gift baskets), and team outings (e.g., limo bus light tours)—fostering collaboration and rewards.For sa...
2022-01-3118 min
The Wisdom, Lifestyle, Money, ShowHow Exercise Won a $3M Client and Changed My LifeIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham shares how answering "because I exercise" won a $3M mortgage client, transforming his mindset, health, and business.Scott recounts a client shopping lenders who asked why choose him; his response highlighted exercise's benefits—more energy, sharper mind, better service—leading to the deal and inspiring his fitness focus.He details starting with organic multivitamins for health, then light jogging (building habits over 60 days), progressing to 10-30 minute routines combining leg presses and curls—emphasizing small starts to avoid burnout.Benefits include weight...
2022-01-2418 min
The Wisdom, Lifestyle, Money, ShowStarting a Business: Overcoming Fear and Mindset TipsIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham shares his journey starting LendCity Mortgages, inspired by job losses from layoffs, closures, and mandates amid economic challenges.Scott discusses embracing risk from real estate investing, viewing setbacks as learning opportunities—like potholes to navigate—and urges listeners to "just do it" to overcome fear.He emphasizes mindset: Write down goals affirmatively, visualize success as already achieved, break big goals into small steps for accomplishment, and focus on strengths over weaknesses via feedback from others.Maintain positivity by reframing negative thoughts, surr...
2022-01-2120 min
The Wisdom, Lifestyle, Money, ShowFixed vs Variable Mortgages: Pros, Cons, and ChoicesIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham debates fixed vs variable mortgages, explaining differences: Fixed locks rates (1-10 years) for stability; variable fluctuates with prime (historically lower, adjusts quarterly by 0.25%).He covers pros/cons: Fixed offers payment certainty but higher penalties (IRD/3 months interest); variable provides lower payments, more prepayments (15-20% annually), easier exits (3 months interest), and convertibility to fixed—no fees.Scott recommends variable for investors/uncertainty/flexibility (his choice for all properties), fixed for strict budgets/fear of changes; history (1995-2025) shows variable averaging ~4.5% vs fixed ~5.75%, cheaper long-term....
2022-01-1117 min
The Wisdom, Lifestyle, Money, ShowFunding Multiple Rentals: Refinance and Renovate StrategiesIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham shares strategies for funding multiple rental properties, addressing the common challenge of sourcing capital for investors.Scott details his approach: Start with a live-in property (e.g., duplex) at 5% down, renovate and rent one unit for max income and minimal issues—up to 3 such properties possible via insurers.After appreciation builds equity (overall market trends upward long-term), refinance to 80% value to extract funds for 20% down on full rentals—repeat by renovating via mortgage plus improvements (lump sum post-completion) or progress draws (staged funds).
2021-12-2818 min
The Wisdom, Lifestyle, Money, ShowTop Mortgage Questions Answered: Rates, Down Payments, and MoreIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham addresses the most common mortgage questions from buyers and sellers in Windsor, Ontario.Scott explains why accurate rate quotes require a preapproval: Factors like credit score, down payment, and debt-to-income ratio affect rates, as some lenders have minimums or adjustments—avoid phone quotes to prevent surprises.He covers down payments: Starting at 5% on the first $500K (then 10% up to $1M for owner-occupied); 10% for 3-4 unit properties if occupying one; 20% for full rentals, often avoiding CMHC fees.CMHC and insurers (Sagen, Canada Gu...
2021-12-2818 min
The Wisdom, Lifestyle, Money, ShowThe 3 Types of Mortgage Preapprovals: Which One Protects You Best?In this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham explains the three types of mortgage preapprovals and their implications for buyers in Windsor's hot market.Scott breaks down verbal preapprovals: Quick phone estimates based on self-reported info, inaccurate due to unverified income, debts, and credit—only useful as rough guidelines, not for firm offers.He discusses calculator-based or rate-hold preapprovals: Often just locking rates (90-120 days) without full review, commonly mistaken for approvals but stating "no approval implied"—better with documents but still risky without underwriting.The ideal is fully unde...
2021-12-1518 min
The Wisdom, Lifestyle, Money, ShowBanks vs Mortgage Brokers: Choosing the Best Lender for YouIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham draws from his extensive experience in both banking and mortgage brokerage to compare banks versus brokers for home and investment property financing.Scott discusses service differences: Banks offer superior customer service training but can lack flexibility in hours and speed, while brokers provide quicker approvals and extended availability due to commission-driven motivation and lender options.He covers rates: Brokers often secure lower rates through monoline lenders and credit unions with less overhead, though banks may offer exceptions for loyal clients with all products...
2021-12-0919 min
The Wisdom, Lifestyle, Money, ShowAchieve Any Goal: Mindset & Visualization TipsIn 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 availability), Scott hit #2 nationally but felt depressed post-goal—realizing he loved helping clients, not the structure. Taking a 6-month reflection "break" (exercising to release endorphins/reduce stress, analyzing likes/dislikes), he visualized success (e.g., a Google-like office in Windsor) per Think and Gr...
2021-11-1518 min
The Wisdom, Lifestyle, Money, ShowImprove Credit Score: Tips for Investors & HomeownersIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham shares practical strategies to build or boost your credit score, essential for mortgages, investing, or loans amid 2025's evolving market (BoC cuts to 2.25% easing affordability, per forecasts). Drawing from his denial story (erroneous Best Buy card lowered score; disputed/removed via Equifax), he emphasizes reviewing reports annually (free at equifax.ca) to spot/correct errors like mismatched debts or typos. Key tips include maintaining 680) unlock better rates/more borrowing (e.g., higher ratios), aiding jobs/approvals. In 2025's recovery (CMHC notes tightening vacancies ~2-3%, rents up 4-6...
2021-11-1016 min
The Wisdom, Lifestyle, Money, ShowHow To Buy Unlimited Rental Properties: Lender StrategiesIn this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham reveals strategies for investor clients to finance unlimited rental properties in Canada, emphasizing calculated leverage where returns exceed costs. He categorizes lenders: A-lenders (major banks/credit unions/trusts, using 50% rent income, capping at 5-12 properties with 44% debt ratios); B-lenders (higher 3-4% rates, 1-1.5% fees, for maxed ratios/credit issues); commercial (property-cash-flow focused, 95% asset/5% borrower, low-2% rates post-2025 BoC cuts to 2.25%, no stress test, 1-1.5% fees); and MICs/privates (5-8%/10-12% rates, prefer MICs over individuals for stability, 1.5-3% fees).Scott stresses lender order: Start with...
2021-10-3117 min
The Wisdom, Lifestyle, Money, ShowKids Take Over: Isaiah & Aubrey on Pokémon & BusinessIn this fun, family-focused episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham interviews his children, Isaiah (age 6) and Aubrey (age 9), sharing laughs about hobbies, summer adventures, and future dreams. Isaiah obsesses over Pokémon cards (recently scoring a rare Charizard), reveals his bike-riding trick (remove pedals/training wheels for balance), and plans to transform LendCity into a Pokémon store with card challenges. He dislikes online school for missing friends and recounts Niagara Falls highlights like arcades and buffets. Aubrey loves karate (learning self-defense), Harry Potter (redecorating her room with 9¾ wallpaper/brick theme), and aspires to acting—findi...
2021-10-1015 minPlaying InjuredEP 64: Adventure of Venture Capital w/ Steve Hoffman & MasonJoin us for Ep. 57, where Mason chats with entrepreneur, investor and venture capitalist, Steve Hoffman!Contact UsSupport the showWant to be a guest on Playing Injured? Send Joshua Dillingham a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/playinginjured
2021-09-2327 min