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Straight Up Chicago Investor

Mar 25, 2021

Many fear what they don’t understand. That’s exactly why we put together this round table discussion with two other great CHA section 8 property managers. Listen in as we address the entire workflow from screening the applicants, to the move in, and everything that happens in between. Section 8 can be a great...


Mar 18, 2021

It’s March and taxes are top of mind! However, by only reactively focusing on taxes during this one part of the year, you are potentially leaving money on the table. Aaron Zimmerman, a Chicago investor and CPA, provides great insights into how to best work with a CPA, the importance of maintaining good records,...


Mar 11, 2021

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...


Mar 4, 2021

For our 50th episode we thought we’d give everyone a special treat... Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few investment deals. Andrew dives into specifics on...