In this episode of The Housing Provider Show, hosts Tim Harstead and David Bovyn break down The Monopoly Strategy, the method Chicago landlords use to scale from one rental to fifty doors. Learn how real investors grow their portfolios in today’s market, even with high interest rates and tough competition. You’ll learn:
- Why waiting for the “perfect” deal kills your progress
- How to use the 1031 exchange to build wealth tax-free
- The truth about cash flow and long-term returns
- Real stories from Chicago landlords who made it happen
This episode is packed with actionable insights, local landlord stories, and proven strategies for building long-term wealth through real estate.
Timestamps (Chapters)
00:00 – Welcome to The Housing Provider Show
00:25 – Copper theft & the realities of C/D class properties
02:00 – Creative ways to secure vacant homes (and a wild dog idea)
05:00 – Networking with Chicago real estate groups (MBA Event Recap)
06:40 – Introducing The Monopoly Strategy
07:15 – Lesson 1: Start small - scale with equity
09:10 – Why big multifamily means more stability and efficiency
10:30 – Understanding cap rates and how raising rent builds equity fast
13:20 – Lesson 2: Buy what you can, not what you dream of
15:00 – Using 1031 exchanges to grow tax-free
18:15 – Why location efficiency matters
19:40 – How out-of-state investors can succeed
21:10 – Cash flow reality check: patience pays off
23:00 – Building reserves and avoiding overleveraging
26:40 – The danger of refinancing too often
28:00 – Diversifying income streams in real estate
29:30 – Cash reserves and the importance of emergency funds
31:10 – Common real estate myths busted
33:40 – The truth about “luck” in real estate success
35:00 – The Monopoly Challenge (real estate game idea!)
36:20 – Is My Landlord an Asshole? - Chicago Case Study
40:00 – Avoiding tenant lawsuits & documentation tips
41:10 – Landlord Tip of the Day: Tenant payment options
43:30 – New Illinois law for payment acceptance
44:00 – Episode wrap-up
