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Straight Up Chicago Investor

Mar 10, 2022

Think it’s possible to scale to 80 rental units while working a W2 job? We know it sounds tough, but our guest David Pezzola explains how he did that and then continued on to build a massive portfolio!

David shares insights on how was able to grow and manage his large portfolio while having his W2 job. He then talks about his post W2 investment journey including his acquisition strategy and lessons learned. David closes out with why Chicago is the “mutual fund” of cities and why he continues to be bullish on investing here!

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Guest: David Pezzola, from Icarus Investment Group

Link: Rich Dad Poor Dad (Book Recommendation)

Link: Chris Puleo (Lender)

Sponsors: GC Reality and Kiser Group


Guest Questions

02:42 House Provider Tip: Seal holes/gaps inside and outside your property to prevent animals from getting in!

04:54 Intro to our guest, David Pezzola!

05:40 How did David get to 80-units and how did he balance owning that many units while working a W2?

07:56 How was David financing his deals while scaling?

09:38 Does David see similarities between the West Loop prior to its emergence and any neighborhoods currently? Why did David hold on to his W2 for as long as he did?

12:12 After establishing a credit line to allow for acquisition/scale, what was the next step?

14:48 What was the extent of the rehab when beginning to scale?

19:13 What goes into making a condo warrantable?

21:02 What are some of the lessons learned while David was scaling?

25:09 What were some of the management challenges in the south side of Chicago? 

28:36 How has David’s group improved management efficiencies?

30:50 How did David purchase 300 units near Midway Airport?

34:45 What advice would David give to new investors on Section 8 rentals?

37:10 Why is David still bullish on the south side and on Chicago in general?

Wrap Up Questions

45:56 What is David’s competitive advantage? 

48:16 One piece of advice for new investors.

50:26 What do you do for fun?

52:25 Good book, podcast, or self-development activity that you would recommend? 

53:45 Local Network Recommendation?

56:15 How can the listeners learn more about you and provide value to you?

That’s our show! Thanks for listening!


Production House: Flint Stone Media

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