Passive Real Estate Investment | Casmon Capital Group | United States

Investing in Chicago’s South Side with Mark Ainley, Episode 85

Passive Multifamily Investing

Mark Ainley has rehabbed and stabilized over 450 properties and currently manages over 900 investment properties throughout the Chicagoland area. Mark is the co-founder of GCR&D, a full-service Real Estate Brokerage, Property Management, and real estate investment firm in the Chicago Market that consults with both local and out of state investors on the acquisition, stabilization, and management of their rental property portfolio. GCRI has become one of the premier turnkey companies in Chicago, working with both US and International investors.

Key Market Insights

  • Started investing back in 2003

  • Helps out of town investors looking on the South Side of Chicago

  • Porches in Chicago can be a challenge if not up to code

  • Preferred access to south side and cash flow opportunities

  • Implemented the BRRRR model starting out

  • Started by looking at the University of Chicago and their long-term expansion plans

  • Focus in Woodlawn and the 60617 zip code

  • Looked for a standard house to renovate and replicated the model

  • Started selling turnkey to international investors

  • Turnkey = renovated property with no capital improvements, market rate tenants in place

  • Turnkey has received a negative reputation

  • Ask about property management

  • GC Realty has taken over projects from other turnkey providers

  • Tips for turnkey deals – find property manager first, then find a turnkey provider, and ensure you get a home inspection

  • Every South side property right now is “near” the Obama library

Bull’s Eye Tips:

Winning Your Market (as a property manager): Knowing the investor’s perspective

Tracking Market Changes: Network

Daily Habit: Get up early between 4am – 4:30am


Best Business Books:

Ninja Selling by Larry Kendell

Dichotomy of Leadership by Jocko Willink

Digital Resources


Tweet This:

“Every [south side] property right now is near the Obama Library”

“Property managers have a stigma that they are just failed real estate agents”

Places to Grab a Bite:

Russell’s Barbecue in Elmwood Park

Connect with Mark:


Phone: 630-781-6744

Leave us a review and rating on iTunes or Stitcher. Be sure to check out more info at

Recent Posts

Leave a Comment


Whether you’re a savvy investor or just starting out, our Mastermind Membership provides you with the platform to connect with potential investors and raise capital for your deals.