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Showing episodes and shows of
The Dillingham Group
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The Wisdom, Lifestyle, Money, Show
LendCity Investor Resources: Tools, Calculators & Education for Real Estate Investing Success
In this episode of the Wisdom, Lifestyle, Money Show, host Scott Dillingham walks viewers through the comprehensive suite of investor resources available through LendCity Mortgages. Many investors are unaware of the extensive tools and educational content available to help them succeed in Canadian real estate investing. From specialized podcasts to AI-powered calculators, Scott reveals the resources designed to empower investors at every stage of their journey.Scott begins by introducing the Close More Deals Podcast, a companion show that focuses on special lending programs across residential and commercial real estate. While primarily targeting realtors, the content benefits...
2026-02-02
15 min
The Wisdom, Lifestyle, Money, Show
Canadian Real Estate Market Update 2026: Interest Rates, Investment Strategies & Financing Options
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers a comprehensive Canadian real estate market update for 2026, providing investors with actionable insights on interest rates, financing strategies, and investment opportunities. Scott, who recently appeared on Erwin Szeto's The Truth About Real Estate Investing podcast, shares his expert perspective on where the market is headed and why now may be the optimal time to invest.With the Bank of Canada holding rates at 2.25% following aggressive cuts in 2024-2025, Scott explains why we've likely reached the bottom of the interest rate cycle. Most major banks...
2026-01-26
22 min
The Wisdom, Lifestyle, Money, Show
Canadian Real Estate Market Update 2026: Interest Rates, Investment Strategies & Financing Options
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers a comprehensive Canadian real estate market update for 2026, providing investors with actionable insights on interest rates, financing strategies, and investment opportunities. Scott, who recently appeared on Erwin Szeto's The Truth About Real Estate Investing podcast, shares his expert perspective on where the market is headed and why now may be the optimal time to invest.With the Bank of Canada holding rates at 2.25% following aggressive cuts in 2024-2025, Scott explains why we've likely reached the bottom of the interest rate cycle. Most major banks...
2026-01-26
22 min
The Wisdom, Lifestyle, Money, Show
Canadian Real Estate Market Update 2026: Interest Rates, Investment Strategies & Financing Options
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers a comprehensive Canadian real estate market update for 2026, providing investors with actionable insights on interest rates, financing strategies, and investment opportunities. Scott, who recently appeared on Erwin Szeto's The Truth About Real Estate Investing podcast, shares his expert perspective on where the market is headed and why now may be the optimal time to invest.With the Bank of Canada holding rates at 2.25% following aggressive cuts in 2024-2025, Scott explains why we've likely reached the bottom of the interest rate cycle. Most major banks...
2026-01-26
22 min
The Wisdom, Lifestyle, Money, Show
Canadian Real Estate Market Update 2026: Interest Rates, Investment Strategies & Financing Options
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers a comprehensive Canadian real estate market update for 2026, providing investors with actionable insights on interest rates, financing strategies, and investment opportunities. Scott, who recently appeared on Erwin Szeto's The Truth About Real Estate Investing podcast, shares his expert perspective on where the market is headed and why now may be the optimal time to invest.With the Bank of Canada holding rates at 2.25% following aggressive cuts in 2024-2025, Scott explains why we've likely reached the bottom of the interest rate cycle. Most major banks...
2026-01-26
22 min
The Wisdom, Lifestyle, Money, Show
Canadian Real Estate Market Update 2026: Interest Rates, Investment Strategies & Financing Options
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers a comprehensive Canadian real estate market update for 2026, providing investors with actionable insights on interest rates, financing strategies, and investment opportunities. Scott, who recently appeared on Erwin Szeto's The Truth About Real Estate Investing podcast, shares his expert perspective on where the market is headed and why now may be the optimal time to invest.With the Bank of Canada holding rates at 2.25% following aggressive cuts in 2024-2025, Scott explains why we've likely reached the bottom of the interest rate cycle. Most major banks...
2026-01-26
22 min
The Wisdom, Lifestyle, Money, Show
Canadian Real Estate Market Update 2026: Interest Rates, Investment Strategies & Financing Options
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers a comprehensive Canadian real estate market update for 2026, providing investors with actionable insights on interest rates, financing strategies, and investment opportunities. Scott, who recently appeared on Erwin Szeto's The Truth About Real Estate Investing podcast, shares his expert perspective on where the market is headed and why now may be the optimal time to invest.With the Bank of Canada holding rates at 2.25% following aggressive cuts in 2024-2025, Scott explains why we've likely reached the bottom of the interest rate cycle. Most major banks...
2026-01-26
22 min
The Wisdom, Lifestyle, Money, Show
From Engineer to Real Estate Syndicator: Lucas Jensen's Multifamily & Condo Conversion Strategies
In this episode of The Wisdom Lifestyle Money Show, host Scott Dillingham speaks with Lucas Jensen, founder of Winter Capital, about his transition from a corporate engineering career at Microsoft to becoming a multifamily real estate investor and syndicator. Lucas shares how being laid off during the 2022 tech downturn exposed a critical weakness in his financial strategy—relying solely on employment income—which ultimately led him to pursue real estate investing as a path to financial independence and passive income generation.Lucas explains the economics behind scaling real estate investments, noting that single-family rentals carry significant vacancy risk...
2026-01-19
24 min
The Wisdom, Lifestyle, Money, Show
How to Control $100K in Stocks with Only $25K Down With Erwin Szeto
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Erwin Szeto, a seasoned real estate investor, licensed realtor, and insurance professional who has built an eight-figure portfolio through strategic investing. Erwin shares his remarkable journey from immigrant child to successful investor, revealing how the book Rich Dad Poor Dad transformed his understanding of wealth-building and led him from stock market losses during the dot-com bubble into decades of profitable real estate investing across more than 40 properties.The conversation takes a fascinating turn when Erwin introduces a game-changing investment strategy that allows...
2026-01-12
24 min
The Wisdom, Lifestyle, Money, Show
Document Secrets Every Real Estate Investor Needs Before Getting Financing
In this joint episode of the Wisdom Lifestyle Money Show, host Scott Dillingham of LendCity teams up with real estate investing coach Teresa Beneteau to deliver critical year-end financial preparation advice for investors heading into the new year. Recorded in mid-December, this timely conversation addresses one of the most overlooked yet essential aspects of building a real estate portfolio: having your documentation and tax filings in order before seeking financing.Scott opens by sharing a powerful cautionary tale about a commercial client with a multimillion-dollar trucking facility loan who faced serious consequences from disorganized paperwork. Despite having...
2026-01-05
35 min
The Wisdom, Lifestyle, Money, Show
How the Wealthy Build Multimillion-Dollar Real Estate Portfolios with 95% Financing
In this episode of the Close More Deals Podcast, host Scott Dillingham sits down with Rhys Trenhaille from the Vanguard Team at Manor Realty to reveal how everyday investors can own multimillion-dollar real estate properties using surprisingly little of their own capital. The conversation dismantles the myth that large-scale multifamily investing is only for the ultra-wealthy, showcasing government-backed financing programs that are revolutionizing apartment building acquisition across Canada.Scott and Rhys dive deep into the mechanics of construction financing that covers up to 95% of project costs, combined with amortization periods extending to 50 years. This powerful combination dramatically...
2025-12-29
28 min
The Wisdom, Lifestyle, Money, Show
From House Hacking to US Multifamily Investing: Mike Nikolica's Real Estate Journey
In this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham sits down with serial real estate investor Mike Nikolica to explore his evolution from first-time house hacker to US multifamily property investor. Mike shares his two-decade journey that began at age 22 with a duplex purchase near the university, progressing through live-in flips across various cities, and ultimately discovering the cash flow potential of US markets like Cleveland and Detroit. The conversation covers practical investment strategies including house hacking to reduce housing costs, the benefits of owner-occupied financing with as little as 5% down, and the significant advantages of...
2025-12-22
19 min
The Wisdom, Lifestyle, Money, Show
Unlock 90% CMHC Financing for Secondary Suites & ADU's
In this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham dives into the transformative CMHC refinance program for adding secondary suites across Canada, empowering homeowners to tap into up to 90% of their property's completed value. Designed to combat the housing shortage, this investor-focused initiative allows refinancing on primary residences to fund Accessory Dwelling Units (ADUs), garden suites, or basement apartments—without needing cash out for other purposes. Scott breaks down how this aligns with provincial policies like Ontario's three-unit rule, enabling seamless additions for multifamily investing and cash flow generation. Whether you're exploring laneway homes or underpinning ba...
2025-12-15
11 min
The Wisdom, Lifestyle, Money, Show
Unlocking Multi-Family Wealth: CMHC MLI Select Financing & Alberta Opportunities
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham teams up with mortgage agents and commercial developers Christine Traynor and Jennifer Champion to break down CMHC multifamily financing and reveal why Alberta has become the hotspot for multifamily property investment. This comprehensive discussion provides investors with everything they need to know about accessing government-backed financing for multifamily real estate while building long-term wealth through strategic property development.Scott begins by providing a detailed overview of the MLI Select program, explaining how investors can access up to 95% loan to value financing with amortizations extending up...
2025-12-08
29 min
The Wisdom, Lifestyle, Money, Show
Unlock 100% Financing for Owner-Occupied Commercial Properties in Canada
In 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...
2025-12-01
09 min
The Wisdom, Lifestyle, Money, Show
How A Tinder-Like App Helps Investors Find, Analyze, And Close Better Properties
In 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...
2025-11-24
19 min
The Wisdom, Lifestyle, Money, Show
From Immigration Enforcement to Real Estate Law: Shawn Quigg's Journey
In 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...
2025-11-17
22 min
The Wisdom, Lifestyle, Money, Show
Maximizing Profits in Canadian Real Estate: Alberta vs. Ontario Insights
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham discusses strategies for profiting in today's real estate market, with a focus on Canadian investors. He highlights challenges in Canada, such as difficulties in cash flowing residential properties in many areas, though opportunities persist in markets like Windsor, Sarnia, Sudbury, and Thunder Bay. Scott explains how external factors, including companies shifting operations due to U.S. tariffs, are impacting Canada's appeal for investment. For instance, as of October 15, 2025, Stellantis announced it would move production of one model to the U.S., redirecting 5,000 jobs that could have gone...
2025-10-15
12 min
The Wisdom, Lifestyle, Money, Show
From Tech to Toronto Real Estate: Ming Lim's Investing Journey & Strategies
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Ming Lim, President of Volition Properties, a Toronto-based real estate team specializing in investor-focused strategies. Ming shares his origin story, starting at age 21 after watching Robert Kiyosaki on Oprah and reading Rich Dad Poor Dad. Fresh out of university and working at Research in Motion (BlackBerry's former name), he dove into real estate investing in Waterloo, Ontario, scaling up to 21 doors. However, the hands-on hassle of managing student rentals—painting rooms, fixing doors, and dealing with tenants—proved far from the passive income dream, leading him to s...
2025-10-13
20 min
The Wisdom, Lifestyle, Money, Show
Canadian to US Real Estate Shift: Carlos Rodrigues' Journey & Tips
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Carlos Rodrigues, a Canadian real estate investor who transitioned his portfolio from Ontario to the US Midwest, focusing on Cleveland, Ohio. Carlos shares his frustrations with Canadian financing limitations, including being denied a standard refinance despite strong income, leading him to explore US opportunities. He highlights discovering affordable properties in Cleveland, where he started with a $35,000 duplex that required $60,000 in renovations but appraised at $150,000 post-rehab. Emphasizing subsidized housing through the Section 8 program, where the government covers part of tenants' rent, Carlos explains how this strategy...
2025-10-06
19 min
The Wisdom, Lifestyle, Money, Show
Financing US Real Estate for Canadians: DSCR Loans & Expert Tips
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews David Garner, founder of Garnaco Group, a real estate investment firm specializing in passive US property investments for international clients. David shares insights on helping Canadians and UK investors navigate US real estate financing, drawing from his 10+ years of experience in acquisitions, asset management, and private lending. The discussion focuses on Debt Service Coverage Ratio (DSCR) loans, a product tailored for rental properties where qualification is based on the property's income potential rather than the borrower's personal finances. They bust myths about credit requirements, loan terms...
2025-09-30
38 min
The Wisdom, Lifestyle, Money, Show
Benefits of Experienced Brokers for Multifamily Financing in Canada
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Jennifer Champion and Christine Trainor from LendCity Mortgages to discuss the advantages of working with seasoned mortgage brokers for multifamily and commercial investments. Drawing from real-world examples, they highlight common pitfalls when investors go directly to banks, such as limited options, higher rates, and outright denials. Scott shares a case where a client with a 57-unit property leased to a single corporate tenant was initially offered $13 million by their bank but faced rejection upon deeper review. Through LendCity's broker network, the client secured approximately $16 million at...
2025-07-09
08 min
The Wisdom, Lifestyle, Money, Show
From Track Star to Real Estate Investor: Rhys Trenhaile's Journey & Tips
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Rhys Wyn Trenhaile, broker and team leader of The Vanguard Team at Manor Windsor Realty Ltd. in Windsor, Ontario. Rhys shares his unique path from being a national championship-winning track and field athlete at the University of Windsor to becoming a seasoned real estate investor and broker. Starting in university, he and his teammates dove into student rentals during long training runs, sparking a passion for landlording that led to owning multiple properties early on. After earning a law degree but opting out of...
2025-06-19
21 min
The Wisdom, Lifestyle, Money, Show
Value-Add Strategies for Multi-Family Investing: Forcing Appreciation
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Jennifer Champion and Christine Traynor from LendCity's commercial mortgage team to explore value-add strategies for multi-family apartment buildings. They emphasize shifting focus from pure cashflow to forcing appreciation through rent increases to market levels and expense reductions, which are more controllable than in single-family investments. Drawing from their own active investing experiences, the guests explain how renovations and stabilization can dramatically boost property values, leading to tax-efficient wealth building without relying on market comparables.Using a practical example, they illustrate purchasing a $1.5 million building...
2025-06-05
05 min
The Wisdom, Lifestyle, Money, Show
Commercial Mortgages & Multifamily Investing: Jennifer Champion & Christine Traynor's Insights
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Jennifer Champion and Christine Traynor from the LendCity Mortgages team to discuss commercial financing options for Canadian investors. Jennifer shares her journey starting as a value-add investor in New Brunswick during the uncertain times of March 2020, focusing on duplexes and fourplexes before shifting to commercial projects and now concentrating on Alberta's opportunities. She emphasizes strategies like targeting landlord-friendly provinces and leveraging the CMHC MLI Select program for 6-10 unit buildings, highlighting the importance of building to fit financing models from the outset. Christine, with her 20-year...
2025-05-22
09 min