Episode 51: Becoming "Brick Rich" on the Northside; Owning 74 Doors by Age 29


Would you trade salary for knowledge? John Westbrook spent time straight out of college working for one of Chicago’s largest property managers to build-up his foundational knowledge of the industry. John has since transformed this knowledge into a substantial portfolio of multifamily buildings on the Northside. John explains how he plans for the long-term with his rehabs, appreciates previously gutted buildings, and focuses on the end users experience to differentiate his investments (it’s much more than numbers on a spreadsheet). John also shares the importance of finding mentors and how his partnerships have catapulted him to success. If you enjoy today’s episode, please leave us a review and share us with someone who may also find value in this content.


Intro. 9:30

What are some key things you learned while working for such a large landlord? 13:20

Did you ever consider buying smaller buildings rather than larger buildings? 14:30

What are some neighborhoods you’re active in? 16:00

What are you looking for on a deal in Humboldt Park? 17:45

When you got artwork commissioned, did you need to get permissioned for it? 25:30

What would you tell someone who owns a 3 unit in terms of financing? 32:10

Walk us through this large multi family. 33:50

How do you estimate how long it will take to rehab a large building? 38:20

What can you tell us about west humboldt park? 42:30

What is your competitive advantage? 45:33

What is one piece of advice you’d give to a new investor? 46:23

What do you do for fun? 47:30

What is a good self development activity you would recommend? 49:20

Quality resource 50:10

How can we reach you? 50:50

That’s our show, see you next week!


Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest Name: John Westbrook 

Guest Company: @properties

Guest Link: John Westbrook | Logan Square Real Estate Broker | @properties

Other Links for show notes:

Luke Blahnik - Chicago Real Estate Broker | @properties

Muros | A Global Art Activation Agency

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