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Straight Up Chicago Investor Podcast Episode 229: From Roofing To Real Estate: Ivan Hernandez And Jacquelina Jablonski's Journey To Success In Chicago's Southwest Side

Straight Up Chicago Investor Podcast Episode 229: From Roofing To Real Estate: Ivan Hernandez And Jacquelina Jablonski's Journey To Success In Chicago's Southwest Side

Ivan Hernandez and Jacquelina Jablonski's appearance on the Straight Up Chicago Investor Podcast offers a fascinating insight into their journey from running a successful roofing business to building a real estate portfolio on Chicago's Southwest side. In this episode, they share their experiences, strategies, and lessons learned along the way.

The podcast kicks off with Ivan and Jacquelina discussing their entrepreneurial beginnings and how they ventured into the roofing business. They provide valuable insights into the challenges they faced and the steps they took to establish a thriving enterprise.

Moving on to their real estate investing journey, Ivan and Jacquelina delve into their decision to start investing in Englewood and gradually expand their portfolio to encompass neighborhoods like Gage Park, Brighton Park, and Marquette Park on Chicago's Southwest side. They offer a deep dive into their approach to screening tenants, scaling their investments, and the valuable lessons they acquired throughout their journey.

One highlight of the episode is Ivan and Jackie's discussion of the Southwest Housing Provider's Group. They passionately share their thoughts on the group's mission to serve as a resource for investors in the area. Their words underscore the significance of community support and collaboration within the real estate industry.

Overall, the Straight Up Chicago Investor Podcast episode featuring Ivan Hernandez and Jacquelina Jablonski is a must-listen for aspiring entrepreneurs and real estate investors. Their transition from a thriving roofing business to a successful real estate portfolio showcases the power of determination, adaptability, and community engagement.

Watch Straight Up Chicago Investor Podcast Episode 229 in Full Here

Questions We Answer In this Show:

Q. Master the Real Estate Game with These Must-Read Books

  1. Video

Q. The Real Estate Wealth Game: Unveiling the Secret of Diversification!

  1. Video

Q. Exploring the World of Entrepreneurship: Testing Out Various Business Ventures!

  1. Video

Show Notes:

  • 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?

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)

Chicago Investor Resources Shared

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