How To Build A Chicagoland Empire

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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 how he finds deals, what attributes he looks for in an investment property, how he underwrites properties, and how he teaches others to scale. There is so much to break down here it’s an episode you’ll need to listen twice!

Podcast key points:

  • How to pivot from real estate agent to real estate investing
  • Single Family vs. Multi Family properties in Chicago
  • Andrew Holmes’ philosophy for cash flow
  • Best cash flow strategy for long term holding
  • How to handle lending when scaling in Chicago
  • Chicago REIA


As a property management company in Chicago, we at GC Realty & Development, LLC, are investors ourselves. Each employee of GC R&D are Chicago property managers and landlords themselves, and understand how to manage properties from the owner’s perspective. Get in touch with one of our experts to answer any questions and maximize your rental property profits. 

Make sure to check out the FREE resources that Straight Up Chicago Investor Podcast offers:

House Hacking Calculator

Top 10 Lending Mistakes

Investor Stories

SUCI Blog

Download your FREE copy of: What They Don't Tell You About Real Estate Investing

See our available Turnkey Cash-Flow Rental Properties
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