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Episode 229: From Roofing to Real Estate: Ivan Hernandez and Jacquelina Jablonski's Journey to Success in Chicago's Southwest Side

Ivan and Jacquelina discuss their journey from a thriving roofing business to a real estate portfolio on Chicago’s Southwest side!

Ivan and Jacquelina lead off with their start in the entrepreneurial realm and how they started their roofing business. They discuss starting their real estate investing in Englewood and expanding further west into Gage Park, Brighton Park, and Marquette Park. They dive deep into screening tenants, scaling, and lessons learned during their investing journey. Ivan and Jackie with powerful words on the Southwest Housing Provider’s Group and their mission to be a resource to investors in the area!

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03:30 Housing Provider Tip: Ensure sewer lines and drains are clear!

04:34 Intro to our guests, Ivan and Jackie!

09:21 Starting a roofing business and other entrepreneurial ideas!

13:30 Early struggles in the roofing business.

17:09 Discussing the first rehab in Englewood!

23:12 Choosing the neighborhood(s) to invest in.

27:47 Lessons learned the hard way in C/D class neighborhoods!

31:02 Automating and creating systems.

32:54 Tenant screening in C/D class neighborhoods!

37:37 Discussing the Southwest Housing Provider’s Group.

49:54 What is Ivan’s and Jackie’s competitive advantage?

50:09 One piece of advice for new investors.

51:16 What do you do for fun?

51:48 Good book, podcast, or self development activity that you would recommend? 

52:36 Local Network Recommendation?

53:33 How can the listeners learn more about you and provide value to you?

Connect with Mark and Tom:

Email the Show:

Guest Name: Ivan Hernandez and Jacquelina Jablonski 

Guest Company: Roofing by Hernandez & Southwest Housing Provider’s Group

Guest Link:

Other Links for show notes:

SUCI Ep 171 - Sonia Del Real

Everything Is Figureoutable (Book Recommendation)

Crushing It in Apartments and Commercial Real Estate (Book Recommendation)

Joe Kroc with FNBC Bank (Network Referral)

Roofing By Hernandez (Facebook Page)