Episode 432: Strategic Chicago House Hacking with Zach Posey

Feb 12, 2026

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Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career!

Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required!

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Email the Show: StraightUpChicagoInvestor@gmail.com

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Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

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Guest: Zach Posey, Chicago Multifamily Club

Link: Chicago Multifamily Club Meetup

Link: Wisdom Takes Work (Book Recommendation)

Link: SUCI Ep 52 - Aaron Zimmerman

Link: SUCI Ep 326 - RJ de Leon

Guest Questions:

01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals!

03:57 Intro to our guest, Zach Posey!

07:38 Starting off with a 4-unit house hack.

17:25 Acquiring a second house hack in Roscoe Village.

26:28 Property Management tips for house hackers!

28:44 Leveraging assumable loans to make the numbers pencil.

34:41 The value of networking events.

37:40 Zach's REI goals and outlook on Chicago!

42:42 What is your competitive advantage?

43:13 One piece of advice for new investors.

43:35 What do you do for fun?

43:50 Good book, podcast, or self development activity that you would recommend?

44:40 Local Network Recommendation?

45:39 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media