Mortgage broker podcasts / For brokers and the industry

The Wisdom, Lifestyle & Money Show

Scott Dillingham

Host (mortgage expert with $1B+ in financing) covers real estate investing, private lending and financing strategy for Canadians.

Status: active · LendCity (Mortgage Architects LendCity)

YouTube channel: 434 subscribers · 140K views · 740 videosPublic YouTube figures as of 2026-10-29; subscriber counts are rounded by YouTube.

Episodes

Aug 13, 202617 min
Mortgage Investment Corporation Investing: Lending vs Equity with Keasy MIC & LendCity
Scott Dillingham is a mortgage expert who has helped clients finance over $1 billion in real estate across Canada. In this episode of The Wisdom Lifestyle Money Show, Scott sits down with Milan Djankovic of Keasy MIC to unpack how a mortgage investment corporation can give Canadian investors both private lending cash flow and real estate equity upside — through a LendCity partnership built for RRSP and TFSA capital. Investors keep asking how to put money to work in private lending real estate Canada without chasing handshake deals. Milan explains how Keasy MIC was structured with Castles couns
Jul 23, 202621 min
Value-Add Multifamily Investing in Canada: Scale to MLI Select with Millan Jankovich
Scott Dillingham is a mortgage expert who has helped clients finance over $1 billion in real estate across Canada. In this episode of The Wisdom Lifestyle Money Show, Scott sits down with Millan Jankovich for a practical look at value-add multifamily investing in Canada—from Toronto duplex and triplex conversions to apartment buildings in Kitchener, Cambridge, and a 107-unit Hamilton complex. Millan shares how operators earn the right to scale: build a track record on smaller deals, protect investor capital with governance and clean reporting, and keep control of construction, property managem
Jun 29, 202629 min
US Estate Tax for Canadian Real Estate Investors: Cross-Border Protection with Dave Peniuk
Scott Dillingham is a mortgage expert who has helped clients finance over $1 billion in real estate across Canada. In this episode of The Wisdom Lifestyle Money Show, Scott sits down with Dave Peniuk of Westpac Wealth Partners to tackle one of the biggest blind spots in cross-border real estate investing: U.S. estate tax exposure for Canadians who own rental property, vacation homes, or business assets in the United States. If you're a Canadian investing in U.S. real estate, you may already analyze cash flow and appreciation — but what happens to your heirs if you pass away with American a
Mar 23, 202619 min
How Canadians Can Invest in US Real Estate With Better Cash Flow and Simpler Financing
Scott Dillingham, a licensed mortgage broker who has helped clients finance over $1 billion in real estate, welcomes Chris Micucci — LendCity's US Division Lead and a hands-on real estate investor — to discuss why Canadian investors are increasingly looking south of the border for better cash flow and simpler financing. Chris shares how he got started just over a year ago with his first fix-and-flip in Ohio, quickly followed by BRRR deals in Michigan, and how that experience shaped the way he now helps Canadian clients navigate the US market. One of the most compelling reasons Canadians ar
Mar 16, 202614 min
Divorce-Proof Your Real Estate Portfolio: What Every Canadian Investor Needs to Know
Scott Dillingham is a licensed mortgage broker who has helped clients finance over $1 billion in real estate across Canada. In this episode of The Wisdom, Lifestyle & Money Show, Scott tackles one of the most overlooked risks in Canadian real estate investing: divorce. With Canada's divorce rate sitting at approximately 40%, the impact on real estate portfolios, mortgage qualification, and credit is something every investor needs to understand — whether they're currently married, partnered, or just beginning their investing journey. Scott walks through the equalization rules that apply in
Mar 9, 202615 min
Surviving the Mortgage Renewal Wave: Lower Your Payments and Protect Your Portfolio
Canada is in the middle of a massive mortgage renewal wave, and for millions of homeowners and investors, the timing couldn't be more challenging. Scott Dillingham, a licensed mortgage broker who has helped clients finance over $1 billion in real estate, breaks down exactly what this renewal wave is, why it happened, and — most importantly — what you can do about it right now. Whether you're a Canadian homeowner watching your payments climb or an investor looking for your next opportunity, this episode delivers practical, actionable strategies to protect your financial position. The renewal wa
Mar 2, 202623 min
Pros and Cons of Investing in US Real Estate as a Canadian: What Every Investor Needs to Know
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham delivers an unfiltered breakdown of the real pros and cons Canadian investors face when purchasing US investment properties. With more Canadians exploring cross-border real estate than ever before, Scott shares the behind-the-scenes conversations he and his team at LendCity have with investors every day — covering everything from politics and taxation to cash flow potential and landlord-friendly laws. Scott begins by addressing the elephant in the room — the political landscape. Whether investors support or oppose the cu
Feb 24, 202616 min
How to Recession-Proof Your Real Estate Portfolio | Mortgage & Cash Flow Strategies for Investors
In this solo episode of the Wisdom Lifestyle Money Show, host Scott Dillingham tackles one of the most pressing concerns facing Canadian real estate investors: how to protect and optimize your portfolio during times of economic uncertainty. With trade tensions between the U.S. and Canada, shifting interest rate forecasts, and growing vacancy rates across the country, Scott breaks down the proactive steps every investor should be taking right now rather than waiting for problems to arrive. Scott opens by reframing economic turbulence as opportunity. Rather than retreating from the market, he en
Feb 17, 202627 min
How Canadians Are Using DSCR Loans and Partnerships to Invest in U.S. Real Estate
In this episode of the Wisdom, Lifestyle, Money Show, host Scott Dillingham sits down with Araceli, a mechanical engineer turned full-time real estate investor and renovation contractor based in Cleveland, Ohio. Araceli shares her inspiring journey from working 17 years in the Canadian aerospace industry to building a thriving real estate investment and contracting business south of the border. Her story is one that many Canadians can relate to — a good job with a ceiling on time and income, and a life event that forced her to think differently about building wealth. After going through a divo
Feb 8, 202618 min
Private Lending, Bridge Loans & Real Estate Development: Investment Opportunities for Canadians
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham breaks down the investment opportunities available through his investor-focused mortgage brokerage, covering private lending, bridge financing, and real estate development partnerships. Scott explains why investor-backed private mortgage lending can be a compelling alternative to traditional fixed-income products like GICs, and how his brokerage structures these loans to protect lender capital through pre-arranged exit strategies and thorough underwriting. Scott begins by outlining how private lending works within his br
Feb 2, 202615 min
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
Jan 25, 202623 min
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
Jan 19, 202624 min
From Engineer to Real Estate Syndicator: Lucas Jensen's Multifamily & Condo Conversion Strategies
Syndication opens the door to multifamily real estate at a scale most investors cannot reach alone. In this episode, Scott Dillingham talks with Lucas Jensen, who transitioned from engineering to real estate syndication, about how he structures deals, raises capital, and executes condo conversions for outsized returns. Lucas explains the economics behind scaling real estate investments, noting that single-family rentals carry significant vacancy risk, while properties with 16 to 50 units offer better stability and cash flow protection. He discusses his current acquisition of a 50-unit multifam
Jan 12, 202625 min
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
Jan 5, 202635 min
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 w
Dec 29, 202528 min
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 projec
Dec 22, 202520 min
From House Hacking to US Multifamily Investing: Mike Nikolica's Real Estate Journey
House hacking is how many Canadian investors get their start — but what comes next? In this episode, Scott Dillingham sits down with Mike Nikolica, who went from house hacking in Canada to scaling a US multifamily portfolio, sharing the financing strategies and mindset shifts that made the transition possible. Mike explains his transition from flipping and Airbnb properties to focusing on multifamily acquisitions ranging from 8-24 units in cities like Cleveland, where properties can be purchased for under $700,000 while generating approximately $1,000 per unit in monthly rent. He discusses the
Dec 15, 202511 min
Unlock 90% CMHC Financing for Secondary Suites & ADU's
Secondary suites and ADUs are one of the fastest-growing real estate strategies in Canada — and CMHC has a program that lets you finance them with 90 percent leverage. In this episode, Scott Dillingham explains exactly how the program works, who qualifies, and how investors can use it to add rental income with minimal upfront capital. Scott emphasizes practical steps for success, including building in cost cushions for overruns, sourcing competitive contractor quotes, and evaluating lot sizes for compliance. He highlights variations by region—such as Alberta's flexible multi-unit allowances—an
Dec 8, 202528 min
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. Scott walks through MLI Select: up to 95% loan to value with amortizations up to 50 years, earned through a points system across affordability, energy efficiency and accessibility. Christine and Jennifer share their experience developing multifamily in Edmonton, including 20-unit and 8-unit new constructi
Dec 1, 20259 min
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 90-1
Nov 24, 202519 min
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 h
Nov 17, 202522 min
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
Oct 15, 202512 min
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 producti
Oct 13, 202520 min
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 t
Oct 6, 202519 min
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 subsidize
Sep 30, 202538 min
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 rathe
Jul 9, 20258 min
Why Your Multifamily Deal Needs a Specialized Mortgage Broker Not Just Any Bank
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Jennifer Champion and Christine Traynor 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 offered $13 million by their bank, then turned down on deeper review. Through L
Jun 19, 202521 min
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 opti
Jun 5, 20256 min
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-effic
May 22, 20259 min
Multifamily Financing & Commercial Mortgages in Canada: Jennifer Champion & Christine Traynor
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 path from value-add duplexes and fourplexes in New Brunswick in March 2020 to commercial projects, now focused on Alberta. Christine brings 20 years as a real estate appraiser on Vancouver Island before moving into mortgages in 2024, and helps investors build out-of-town portfolios, particularly in Edmonton. They explain how commercial mortgages are approved
Feb 18, 202521 min
From Engineering to US Real Estate: Tom McCormick's Cross-Border Investing Journey
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Tom McCormick, a mechanical aerospace engineer turned real estate investor from Windsor, Ontario. Tom shares his entry into real estate during the 2020 COVID era, motivated by job uncertainty and inspired by his brother's duplex purchase near the University of Windsor. Starting with a challenging single-family home converted into an additional dwelling unit (ADU), Tom discusses the sweat equity, city code navigation, and lessons from gutting the property to the studs. He highlights how his engineering backgrou
Feb 4, 202527 min
Cross-Border Real Estate: Carmen Da Silva's Tips for Canadians Investing in the US
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Carmen Da Silva, a cross-border CPA and co-founder of SHARE, who specializes in helping Canadians invest in U.S. real estate. Carmen shares her journey from articling at PricewaterhouseCoopers (now PwC) in tax programs to building a family wealth management business, before relocating to Florida in 2003. She discusses her pivot to real estate investing during the 2008 financial crisis, starting with single-family rentals to replace income after selling her business. Emphasizing opportunity and preparedness, Ca
Jan 28, 202525 min
Canadian's Guide to US Real Estate Investing: Derek Wormsbecker's Story
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Derek Wormsbecker, a mortgage agent at LendCity who specializes in helping Canadians invest in US properties. Derek shares his journey from starting as a real estate investor in Canada by renting out his first townhouse, to selling properties and redeploying capital into the US market. Motivated by rising costs and tenant issues in Ontario, he partnered with Share—a company founded by Andrew Kim that guides Canadians through US investments—to purchase a brand-new construction home in Arkansas for $176,000 USD.
Jan 21, 202528 min
Saving on FX for US Real Estate: Marc Racette's Tips for Canadians
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Marc Racette, CEO and co-founder of Pulse FX, a Toronto-based foreign exchange and global payments firm. Marc shares his journey starting in international business expansion in Asia, including time in Shanghai, before entering the FX industry over a decade ago. He discusses founding Pulse FX in 2024 to provide personalized FX services, emphasizing how Canadians can save significantly on currency exchanges when investing in US properties. Highlighting the convenience pitfalls of banks and online services, Marc
Jan 14, 202519 min
Canadian Investors' Path to US Real Estate: Dmitri Bourchtein's Insights
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Dmitri Bourchtein, CIO and Co-Founder of SHARE, a platform that simplifies US real estate investing for Canadians. Dmitri shares his journey from starting in the debt side of real estate after university to joining Starlight Investments, where he contributed to growing a portfolio from hundreds to nearly 20,000 units. He discusses overseeing over $7 billion in US residential real estate transactions through various funds and joint ventures, providing invaluable experience that shaped his approach to instit
Dec 31, 202410 min
Get Your EIN in 2 Hours: Canadian US Real Estate Investing Guide
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares a streamlined approach for Canadians and foreign investors to obtain an ITIN (Individual Taxpayer Identification Number) in as little as two hours to facilitate US real estate purchases. As the president of LendCity Mortgages, Scott explains how his company, which specializes in investor-focused financing across Canada, the US, and Mexico (with a recent soft launch there), addresses common hurdles for investors. Drawing from interactions with nearly 1,000 investors over the past year, he notes that 90-95% get stuc
Dec 24, 202438 min
Maximizing Shareholder Value in Real Estate: Milena Cardinal's Insights
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Milena Cardinal, founder of Cardinal Law in Ontario, about optimizing corporate structures for real estate investments. Milena explains how leveraging shareholder relationships in corporations can simplify multifamily and development projects, highlighting the benefits of a single corporation for holding investments where investors own shares. She discusses balancing simplicity with drawbacks like lender requirements for qualifications and personal guarantees, drawing from her experience in creating tailored s
Dec 17, 202412 min
Easy Mortgage Qualification for Canada & USA Real Estate Investors: DCR & DSCR Guide
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham, President of LendCity Mortgages, dives into strategies for qualifying for investment property mortgages in Canada and the USA without relying solely on personal income. He explains how investors can leverage the property's cash flow through Debt Coverage Ratio (DCR) programs in Canada and Debt Service Coverage Ratio (DSCR) loans in the USA. Drawing from his experience starting in banking and transitioning to specialized investor financing, Scott highlights how these options allow real estate investors to scale their por
Dec 15, 202413 min
How to Build a Real Estate Investing Team in Canada: Who You Need and Where to Find Them
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares insights from his recent presentation at the WealthGenius EXPAND Investor Conference in November 2025, where over 1,100 tickets were sold. Drawing from his experience speaking to a large audience of investors, Scott emphasizes the importance of assembling the right team for real estate success. Using the analogy of not going to a dentist for braces—instead seeking an orthodontist—Scott highlights why investors should partner with specialists rather than generalists. He warns against blindly following referrals fro
Dec 5, 202426 min
Canadian Guide to US Real Estate Investing: Andrew Kim's Story & Strategies
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Andrew Kim, CEO and co-founder of SHARE, a real estate technology company specializing in US single-family rental (SFR) investments. Andrew shares his entrepreneurial journey, starting with tech startups and transitioning into real estate after discovering the advantages of the US market in 2011 while living in California. He discusses his early investments in Ontario, which were costly and low-yield, compared to the US where properties offered lower prices, higher returns, and professional property manage
Nov 26, 202436 min
Why Canadians Should Invest in US Real Estate: Trends & Strategies
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham dives into the shifting investment landscape for Canadians, highlighting why many are turning to US real estate amid economic challenges at home. Drawing from charts shared on social media and Statistics Canada data, Scott explains how foreign direct investment has been flowing out of Canada since around 2015, with a significant uptick in outflows to the US by the end of 2023. He attributes this to factors like the recent capital gains tax inclusion rate increase effective June 25, 2024, which taxes two-thirds of gains o
Nov 24, 202436 min
Navigating GPLP Structures in Real Estate: Protection & Financing Tips
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Milena Cardinal, a real estate lawyer and founder of Cardinal Law Professional Corporation in Cornwall, Ontario. They dive into the essentials of bare trusts and GPLP (General Partner Limited Partner) structures, explaining how these tools help real estate investors navigate complex partnerships. Milena breaks down bare trusts as simple agreements that separate registered and beneficial ownership, often used in joint ventures or family setups to protect assets while allowing flexibility in financing. Scott sha
Nov 18, 202420 min
Canadian's Path to US Real Estate: Glen Sutherland's Journey & Tips
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Glen Sutherland, a seasoned Canadian real estate investor specializing in US properties. Glen shares his transition from investing solely in Canada to expanding into the United States, driven by limitations in Canadian lending and the desire for more scalable opportunities. Starting in 2016, he began with turnkey properties in Alabama but quickly learned the importance of strategic financing and value-add approaches. He discusses overcoming initial challenges like maxing out on Canadian bank loans and mana
Nov 10, 202420 min
Joint Ventures in Real Estate: Jonathan Faerman on Investium Platform
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Jonathan Faerman, founder of Investium, a platform designed to connect real estate investors for joint ventures. Jonathan shares his journey starting with a condo purchase in downtown Montreal, which he later rented out and sold for profit. Seeking to scale into multifamily properties, he faced challenges in finding partners, leading to the creation of Investium. Drawing from his experience meeting his wife online, Jonathan built the platform to facilitate long-term investment relationships, emphasizing pr
May 22, 202428 min
How Canadians Can Get a US Mortgage: Lending Options for Cross-Border Real Estate Investing
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham dives into LendCity's US lending options for Canadians and other foreign buyers interested in American investment properties. As a one-stop shop for residential and commercial lending in both Canada and the US, LendCity simplifies cross-border investing by offering competitive financing without requiring a US visa, partner, or income verification—focusing instead on the property's cash flow. Scott shares real-world examples, including a $4.65 million office purchase in Ohio financed at 7% over 25 years, an 8-unit propert
May 10, 202423 min
From Steel to Real Estate: Alex Ciotoli's Windsor Investing Journey
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Alex Ciotoli, an investment-focused realtor in Windsor, Ontario, now with RE/MAX Preferred Realty Ltd. Alex shares his unique background, born and raised in Windsor to immigrant parents who built a successful structural steel business. He discusses growing up in the family enterprise, learning project management, takeoffs, and quotes from a young age—skills that seamlessly translated to his real estate career after attending law school in Michigan and working abroad. Emphasizing his "Esquire Realtor" brand
Feb 12, 202433 min
From Guinness Records to Real Estate: Evan Ungar's Goal-Setting Journey & Investing Insights
In this episode of the Wisdom Lifestyle Money Show, host Gillian Irving interviews Evan Ungar, a real estate entrepreneur, Guinness World Record holder, and author of the Amazon bestselling book Make the Decision: From Goal Setting to Goal Getting . Evan shares his remarkable background, from breaking two Guinness World Records for the highest standing box jump (63.5 inches) and highest one-leg box jump, to transitioning into real estate development and consulting. He discusses how his athletic achievements inspired his goal-setting philosophy, emphasizing the importance of specific targets, d
Feb 8, 202443 min
From Canadian Markets to US Real Estate: Monika Jazyk's Investing Journey
In this episode of the Wisdom Lifestyle Money Show, host Gillian Irving interviews Monika Jazyk, a seasoned real estate investor and co-owner of RPI Education. Monika shares her background as a former teacher with a master's degree, mother of four, and how she transitioned into full-time investing over 14 years ago. Starting with buy-rent-hold properties in Northern Ontario, she and her husband built a portfolio that allowed her to stay home with her family while generating income. Monika discusses the challenges of distant markets like Timmins and Sudbury, including high vacancies, unreliable
Feb 7, 202433 min
US Real Estate for Canadians: Tax Setup & Investing Tips
In this episode of the Wisdom Lifestyle Money Show, host Gillian Irving, a mortgage agent with LendCity Mortgages, interviews Michael Matthew, a Chartered Professional Accountant with over 30 years of experience. Michael shares his expertise on helping Canadians navigate US real estate investments, drawing from his background in business consulting and his own experiences as a landlord. The discussion focuses on the essential steps for setting up corporate structures to avoid double taxation, ensure liability protection, and optimize financing options. Gillian highlights LendCity's new program
Nov 29, 202345 min
From Minnesota Winters to Florida Wealth: Ryan Poole's Real Estate Story
In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Ryan Poole, owner of RealTrade and a seasoned realtor specializing in South Florida properties. Ryan shares his journey from growing up in northern Minnesota, where harsh winters and personal loss prompted his move south over 25 years ago, to building a thriving real estate career. Influenced by a mentor's advice, he got his license early and focused on new construction and investments, eventually settling in West Palm Beach. He highlights the area's appeal for investors, including its elevation reducing flood

More active shows

Be The Better Broker

Active · 2026-09 · 197 episodes · Dustan Woodhouse & Jillian Pollard

Audio companion to the Be The Better Broker book series: conversational re-reads of the books plus weekly broker-development episodes.

Broker's Playbook - Real Estate Podcast

Active · 2026-05 · 109 episodes · Simeon Papailias & Laura Martin

Real-estate-and-mortgage industry show with leaders, coaches, economists and developers aimed at brokers; also a vodcast.

Canadian Private Lenders’ Podcast

Active · 2026-10 · 157 episodes · Neal Andreino & Ryan MacNeil

Show on private mortgage lending in Canada: MICs, private lenders, alternative lending, broker channel and regulation; hosts run private lending businesses.

Commercial Real Estate Podcast

Active · 2026-10 · 300 episodes · Aaron Cameron & Adam Powadiuk

Weekly Canadian commercial real estate show from lender First National employees, including lending/state-of-credit episodes.

Directory compiled 2026-10-28. Details come from public listings and the show’s own feed.