Best Glen Sutherland Podcasts (2025)

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EP374 The Big Beautiful Bill What U.S. Tax Changes Mean for Canadian Investors Kristopher McEvoy 18:26

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5d ago18:26

18:26

In this episode, Glen Sutherland and Kristopher McEvoy dive into the potential impact of proposed U.S. tax legislation on Canadian investors with U.S. assets. They discuss why proper investment structuring is more important than ever, the risks of increased withholding taxes, and how treaty changes could affect future returns. Kristopher shares why…

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The Hidden ROI of Getting Punched in the Face with Daniel Deville 34:10

5d ago34:10

34:10

In this episode, Matt shares what it really takes to build a business that lasts. From losing $500K to building better income streams, training his team, and staying mentally strong through it all—this is a behind-the-scenes look at the wins, the mistakes, and the mindset that drives long-term success. If you're a founder, investor, or operator, yo…

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EP373 E2 Visa Secrets How Canadians Can Build a Thriving U.S. Business Filomena Maimone 25:06

12d ago25:06

25:06

In this insightful podcast interview, Glen speaks with experts about the E2 visa process, offering invaluable advice for Canadians interested in launching or expanding their businesses in the U.S. They delve into key topics such as the essential elements of a successful business plan, the importance of creating jobs, and the flexibility of the E2 v…

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You Don’t Deserve Passive Income Until You’ve Done This First with Johnny Walker 32:15

12d ago32:15

32:15

Most people want passive income. But few understand what it really takes to earn it consistently. In this episode, Matt shares why owning hard assets yourself, even just a few, builds the knowledge base you need to invest wisely with others. From the hidden costs of poor due diligence to the power of strategic diversification, we break down the har…

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EP372 You're Either Learning or Earning The Hard Truth About Building Wealth w Brady McDonald 26:44

19d ago26:44

26:44

In this conversation, Brady shares the powerful mindset shift that helped him level up: you're either learning or earning, but rarely both at once. He explains that growth often comes through discomfort, whether it’s financial loss, stress, or failure. The key is to not quit during the learning phase, as that’s what ultimately leads to the big wins…

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Why Most Capital Raisers Fail (And What Actually Works) with Adam Carswell 31:30

19d ago31:30

31:30

Most people rely too much on cold outreach or digital funnels to raise capital, and it's slowing them down. In this episode, we break down why in-person events, better vetting, and smarter systems are the real drivers of long-term success in capital raising. What you’ll learn: Why online-only capital strategies usually fail How live events speed up…

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Most Investors Are Ignoring the Best Opportunity in SoCal with Anthony Walker 33:30

25d ago33:30

33:30

By Mathew Owens

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EP345 Short Term Rentals In FL With Mathieu Bourgouin 27:17

26d ago27:17

27:17

Mathieu Bourgouin, a Canadian real estate investor and agent from Mont-Tremblant, Quebec, started investing in the U.S. in 2014. His journey began in Florida and then expanded to Pittsburgh, including ventures in wholesaling and mobile home parks. He has now transitioned primarily to short-term rental properties in Florida.• Initial Investments: Ma…

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EP371 Investing in the Dominican Republic- Insights from Real Estate Broker Brett Henry 36:06

26d ago36:06

36:06

In this episode of "Canadian Investing in the US," host Glen Sutherland interviews Brett Henry, a real estate broker in the Dominican Republic. Originally from Saskatchewan, Canada, Brett transitioned from a 20-year career as a police officer to becoming a successful entrepreneur in real estate. He shares his journey of moving to the Dominican Repu…

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EP370 Navigating from Single-Family Homes to Multifamily with Jonathan Nichols 22:02

1M ago22:02

22:02

In this episode of "A Canadian Investing in the U.S.," host Glen Sutherland interviews Jonathan Nichols, co-founder of Apogee Capital, a multifamily real estate investment company based in the Dallas-Fort Worth area. Jonathan shares his journey into real estate investing, which began about seven or eight years ago with single-family rentals. Along …

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EP369 Navigating U.S. Real Estate Strategies for International Investors with Amresh Singh 16:42

1M ago16:42

16:42

In this episode, Glen Sutherland interviews Amresh Singh, who runs Home Abroad, a firm that assists international investors in purchasing U.S. real estate. Amresh shares insights into the challenges foreign investors face and how his company provides a comprehensive solution.Key Points Discussed:Introduction to Home Abroad:Home Abroad is a one-stop…

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The Capital Raising Process 99% of Operators Screw Up on the Raise Masters Podcast 20:55

1M ago20:55

20:55

How do you go from hating your CPA job… to flipping 1,000+ houses, raising $150M, and buying back your time? In this episode of Masters of Real Estate, we break down the real systems behind the capital raising machine, and how we set it up to run without us while traveling across Vietnam. Whether you’re stuck doing everything yourself or just strug…

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EP368 Snowbirds Beware- How to Stay Out of IRS Trouble with Taha Khan 16:07

2M ago16:07

16:07

In this episode, Glen interviews Taha Khan, a Canadian CPA with a U.S. license, who specializes in helping Canadians navigate the complex world of cross-border taxation. The conversation is centered around real estate investors, snowbirds, and business owners who spend time or have assets in the United States.Key Topics Covered:Substantial Presence…

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How to Restart In Real Estate After Losing it All with Glen Sutherland 24:22

2M ago24:22

24:22

In this episode of Canadian Investing in the US, Glenn Sutherland sits down with CPA-turned-real estate investor Matthew Owens. After losing everything in the 2008 crash, Matthew didn’t go back to his safe job—he rebuilt from scratch. Now with over 1,000 flips and $150M+ raised, he shares the strategies, lessons, and mindset that helped him come ba…

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EP367 The Hidden Costs (and Benefits) of Selling U.S. Real Estate as a Canadian with Tricia Lehane 23:19

2M ago23:19

23:19

Trisha Lehane – Realtor based in Scottsdale, Arizona with RE/MAX, specializing in working with Canadian buyers and sellers.Background:Originally from Canada, Trisha has lived in Arizona for 20 years.She has deep roots in Canadian provinces like Manitoba, Saskatchewan, Alberta, BC, and Yukon.Her real estate career pivoted to working with Canadians a…

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EP366 How We Almost Lost It All — And Closed Anyway with Ian Drewe 22:34

2M ago22:34

22:34

In this episode, Glen sits down with Ian, founder of Avoca Property, for a candid and action-packed conversation about the real behind-the-scenes journey of closing a multifamily deal. From early missteps in digital marketing and investor engagement, to legal battles, PE fund bait-and-switches, and $200,000 in legal fees — Ian doesn’t hold back on …

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EP365 From Flips to Financing: Hidden Strategies f/ Canadians Investing in the US with Chris Micucci 23:59

2M ago23:59

23:59

In this episode of "A Canadian Investing in the US," host Glen Sutherland interviews Chris Micucci, a college professor and real estate investor who began investing just over three years ago. After taking Glen's class, Chris quickly seized an opportunity presented in an email and bought his first property. Since then, he has engaged in various inve…

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EP364 How Landlords Can Build Tenant Credit & Ensure On-Time Rent with Grant Burwash 21:36

2M ago21:36

21:36

In this episode, we dive into how FrontLobby helps landlords report rent payments to credit bureaus, screen tenants, and improve rental management. Our guest explains how incorporating FrontLobby into lease agreements and rental ads can attract high-quality tenants and ensure timely rent payments.By Glen Sutherland

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EP363 How AI is Revolutionizing Business/ Real Estate Communication with David Criss 29:59

3M ago29:59

29:59

In this episode, Glen Sutherland sits down with David Chris from Action to Call to explore how AI-powered virtual agents are transforming business communication. They discuss how AI can handle customer interactions, schedule appointments, and improve response times—ensuring businesses never miss a call. David shares real-world applications, includi…

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EP362 Rent-by-the-Room Real Estate Strategy with Ryan Chaw 25:44

3M ago25:44

25:44

This podcast features a conversation with a real estate investor who specializes in the "rent-by-the-room" strategy, particularly targeting college students near major universities. The guest shares their expertise on identifying suitable properties, adapting spaces to maximize rental income, and navigating financing challenges in this niche.Key To…

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EP361 Building USA Fico Credit Scores on ITINs for Canadians with Jane Mepham 21:51

3M ago21:51

21:51

In this week’s episode, I sat down with Jane from Elgon Financial Advisors, who specializes in helping foreign-born individuals navigate US finances. We covered everything you need to know about building US credit as a Canadian investor!By Glen Sutherland

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Self-Directed IRAs: The Secret Wealth Tool Nobody Talks About with Kaaren Hall 38:30

3M ago38:30

38:30

In this episode of Masters of Real Estate, host Matthew Owens sits down with longtime friend and powerhouse entrepreneur Kaaren Hall, founder of uDirect IRA Services. From being a single mom who got laid off during the Great Recession to building a company that now manages over $1 billion in assets, Kaaren shares the raw, unfiltered story of grit, …

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EP356 Mastering Tenant Screening and Landlord Advocacy with Kayla Andrade 24:16

3M ago24:16

24:16

Kayla Andrade emphasizes the importance of landlords staying informed and advocating for policy changes to better support the housing industry in Ontario.She encourages collaboration with elected officials and industry experts to address issues like tenant accountability and affordable housing.Tenant Screening and Rent Reporting:Tenant screening is…

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EP360 How to Restart Real Estate After Losing it All with Mathew Owens 24:12

3M ago24:12

24:12

EP360 How to Restart Real Estate After Losing it All with Mathew Owens by Glen SutherlandBy Glen Sutherland

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EP359 The Land Investor’s Playbook Buy Low, Sell High, Get Paid Monthly w Mark Podolsky (1) 25:15

4M ago25:15

25:15

The podcast episode is a deep dive into creative financing for land deals, focusing on strategies like land contracts, due diligence, and automation in the land investing business. Here’s a summary of the key points:Selling Land with Creative FinancingThe guest discusses selling land using a land contract rather than a lease option or contract for …

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EP355 From Airbnb to Boutique Hotels Scaling Your Real Estate Investments with Rich Monroe 22:39

4M ago22:39

22:39

This podcast episode of Canadian Investing in the USA features Rich Monroe, an experienced real estate investor based in Atlanta, Georgia, who focuses on short-term rentals, Airbnbs, and boutique hotels. Over his 20-year career, Rich has worked with single-family homes, multi-family properties, and hotels. His main focus has shifted toward distress…

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EP358 Manufactured Housing Using the Fund Model with Sean Gibson and Alden Guajardo 23:34

4M ago23:34

23:34

This episode explores the world of manufactured housing as a unique investment opportunity in the US. Glen is joined by Alden and Sean, who specialize in originating notes and investing in manufactured housing communities, providing insights into this niche market.Key Highlights1. Defining Manufactured HousingOften confused with RVs or trailers, ma…

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Unlocking Profits in Land Investing with Pete Reese 36:23

4M ago36:23

36:23

In this episode of Masters of Real Estate, host Matthew Owens welcomes Pete Reese, a seasoned land investor and entrepreneur, to discuss his journey from house flipping to building a thriving business in land development. Pete shares valuable insights into the unique strategies and systems he’s developed to capitalize on land investments, even in t…

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EP357 Scaling Your Real Estate Portfolio & Knowing When to Sell with Ian Horowitz 22:29

4M ago22:29

22:29

In this episode, I sit down with Ian Horowitz from Equity Warehouse to discuss the journey of scaling a real estate portfolio, managing risk, and knowing when to sell. Ian shares his experience transitioning from high-risk investments in Baltimore to more stable and profitable deals in primary markets like Philadelphia.…

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How to Invest in Real Estate Without Letting Market Crashes Derail Your Goals | Re-Air From the Success In Motion Podcast 25:22

4M ago25:22

25:22

CONNECT WITH US: Facebook: https://www.facebook.com/mathew.owens2 Instagram: https://www.instagram.com/mathew_owens1/ LinkedIn: https://www.linkedin.com/in/mathewowens/ Free 200-Point Due Diligence Checklist: https://mathewowens.com/due-diligence-checklist/ Free Deal Analysis Masterclass: https://mathewowens.com/masterclass-form/…

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How to Scale Your Real Estate Business Without Breaking the Bank | Re-Air From the Extra Rvrb Podcast 1:04:21

4M ago1:04:21

1:04:21

CONNECT WITH US: Facebook: https://www.facebook.com/mathew.owens2 Instagram: https://www.instagram.com/mathew_owens1/ LinkedIn: https://www.linkedin.com/in/mathewowens/ Free 200-Point Due Diligence Checklist: https://mathewowens.com/due-diligence-checklist/ Free Deal Analysis Masterclass: https://mathewowens.com/masterclass-form/…

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How to Master Real Estate Investing Without Taking on Excessive Risk | Re-Air From the Freedom Founders Podcast 42:20

5M ago42:20

42:20

CONNECT WITH US: Facebook: https://www.facebook.com/mathew.owens2 Instagram: https://www.instagram.com/mathew_owens1/ LinkedIn: https://www.linkedin.com/in/mathewowens/ Free 200-Point Due Diligence Checklist: https://mathewowens.com/due-diligence-checklist/ Free Deal Analysis Masterclass: https://mathewowens.com/masterclass-form/…

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EP354 From Luxury Yachts to Lucrative Properties- Teamwork and Real Estate Triumphs with Scott Kidd 26:01

5M ago26:01

26:01

In this engaging episode, we sit down with Scott Kidd, a seasoned yacht manager and real estate investor, to explore the fascinating parallels between managing luxury yachts and navigating the world of real estate syndication. Scott shares valuable insights from his unique career journey, emphasizing leadership, problem-solving, and building strong…

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How to Build a Real Estate Empire Without Losing Control of Operations | Re-Air From the Global Investors Podcast 38:29

5M ago38:29

38:29

CONNECT WITH US: Facebook: https://www.facebook.com/mathew.owens2 Instagram: https://www.instagram.com/mathew_owens1/ LinkedIn: https://www.linkedin.com/in/mathewowens/ Free 200-Point Due Diligence Checklist: https://mathewowens.com/due-diligence-checklist/ Free Deal Analysis Masterclass: https://mathewowens.com/masterclass-form/…

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EP353 Creative Financing and Cash Flow Opportunities in US Multifamily Real Estate Dave Mastronardi 17:32

5M ago17:32

17:32

Glen Sutherland hosts Canadian Investing in the US with guest Dave Mastronardi.Dave runs a real estate investment firm in Canada focused on the southern US, particularly Florida. He is also a partner at Midfield Investments, focusing on multifamily properties in Texas.Dave's Real Estate JourneyPreviously the CEO of a large manufacturing company; tr…

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EP352 Trump, the Economy, and the Future with Bryce Kaminsky 38:31

5M ago38:31

38:31

This podcast episode of "A Canadian Investing in the USA" talks about real estate investors moving into the U.S. market. The conversation touches on a variety of themes, including:Key Points:Affordability and Opportunities in U.S. Markets:Canadian investors are drawn to U.S. markets for more affordable housing, better weather, and lending products …

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EP351 The Evolution of an Investor Brooke Shang's Story of Growth and Diversification 26:51

6M ago26:51

26:51

In this episode of A Canadian Investing in the US, we discuss Brooke's transition from investing in Ontario to focusing on other regions and passive investing in the US.Leaving Ontario for Other MarketsBrooke moved out of Ontario's real estate market due to challenges, including:Landlord-Tenant Board (LTB): Ongoing disputes and difficulties with en…

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EP350 Navigating the 2025 Currency Exchange CAD vs USD with Rahim Madhavji 23:49

6M ago23:49

23:49

Guest: Raheem Madjavi, President of Knightsbridge Foreign ExchangeTopic: Currency Exchange, Interest Rates, and Economic TrendsKey Points Discussed:1. Knightsbridge FX Overviewo Knightsbridge FX specializes in currency exchange services, offering better rates than banks for buying/selling US dollars.o It's often cheaper than using traditional banks…

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EP349 The Consistency Code Joe Fairless on Scaling Your Real Estate Business 25:04

6M ago25:04

25:04

This podcast interview between Glen Sutherland and Joe Fairless touches on several key insights for those looking to get into real estate investing, particularly through podcasts and attracting investors.Starting a Podcast: Joe reflects on the importance of starting a podcast to build a brand, even if the beginning is slow. He mentions how a podcas…

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EP348 Navigating Real Estate Opportunities: A Journey from Ontario to Alberta with Alex Pal 26:35

6M ago26:35

26:35

This podcast highlights a variety of key aspects of real estate investing, particularly the strategic considerations in Alberta compared to Ontario. Here's a summary and analysis:Why Alberta?Tenant Laws: Alberta's landlord-tenant regulations are much more favorable compared to Ontario's, where eviction processes can be long and cumbersome.Market Dy…

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EP347 Real Estate Investing with Partnerships and Raising Capital with Michael Ponte 24:22

6M ago24:22

24:22

In this weeks episode we discuss working with partners and scaling through joint ventures or syndications. When you're managing other people's money, you’re not just managing dollars and cents; you’re managing trust, expectations, and relationships. Mismanagement of these can lead to more than just financial losses—it can harm your reputation, whic…

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How to Keep More of Your Money: Tax Strategies for Real Estate Investors with James Bohan 36:04

6M ago36:04

36:04

On this episode of Masters of Real Estate, host Mathew Owens, CPA, welcomes fellow CPA and real estate investor James Bohan to discuss tax planning and investment strategies that help real estate professionals keep more of what they earn. With tax season approaching, James shares actionable advice on how to optimize your finances through smart plan…

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EP346 Exploring Savannah: U.S. Real Estate Insights with Wendy Russell & Mike Moroz 23:30

7M ago23:30

23:30

This podcast episode discusses Wendy Russell and Mike Moroz's experience with Canadian investing in U.S. real estate. Here’s a breakdown of key points:Investment Background: Wendy and Mike started investing in Canada over 25 years ago and expanded into the U.S. in 2010. They’ve invested in various properties, including multifamily homes, single-fam…

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Navigating Volatile Markets: Real Estate Strategies for Today’s Economy with David Phelps 36:39

7M ago36:39

36:39

In this episode of Masters of Real Estate, host Mathew Owens, CPA, sits down with David Phelps, founder of Freedom Founders, to discuss building financial freedom through real estate investing. David shares how he transitioned from dentistry to real estate and breaks down the lessons he learned along the way—both the wins and the hard knocks. Toget…

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Unlocking Capital: Marketing Strategies for Real Estate Success with Julia Anderson 35:18

7M ago35:18

35:18

In this episode of Masters of Real Estate, host Mathew Owens, CPA, discusses the often-overlooked aspect of real estate investing: marketing for capital raising. Joined by Julia Anderson, a seasoned fractional CMO with extensive experience in real estate marketing, they explore the strategies needed to create a successful capital investment stream.…

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EP344 Wholesaling Without Boarders With Nathan Payne 23:36

7M ago23:36

23:36

Nathan Payne, shares his experience with virtual wholesaling, emphasizing that it can be done from anywhere, including internationally. He explains the process, noting that the key is solving the seller's problem—whether it's a distressed property or a situation like foreclosure or troublesome tenants.Here are some key insights from the conversatio…

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From Commercial Sales to Multifamily Success with Haley John 33:47

7M ago33:47

33:47

Join our host, Mathew Owens, CPA, as he interviews Haley John, a seasoned expert in the multifamily real estate market. In this episode, Haley shares her journey from commercial brokerage sales to becoming a formidable force in multifamily investments. Discover the unique challenges and opportunities in the current real estate market landscape and …

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EP343 Turning Challenges Into Cash Flow Real Estate Success with Ben Humble 21:17

7M ago21:17

21:17

This week on "A Canadian Investing in the USA Ben Humble shares his journey from being a refugee from Romania to building a successful career in real estate. Key points include:Background:Born in Romania, his family fled communism in 1989, eventually settling in Canada.Initially pursued a music career but shifted to real estate after recognizing th…

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EP342 The Dos and Donts of Flipping with Danielle Chaisson 34:20

8M ago34:20

34:20

EP342 The Dos and Donts of Flipping with Danielle Chaisson by Glen SutherlandBy Glen Sutherland

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EP340 Real Estate Horror Stories With Darcy White 27:04

8M ago27:04

27:04

Darcy discusses Halloween horror stories in the context of real estate, particularly focusing on property management challenges. They emphasize the heightened alert around events like Halloween and long weekends due to potential property damage caused by rowdy behavior.The speaker shares personal experiences, admitting to making poor decisions in m…