Episode 50: Building a Chicago Empire with Andrew Holmes


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 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!


Guest Introduction 7:20

When you were a young agent, what separated you from the crowd? 8:40

How did you pivot from real estate agent to real estate investing? 13:10

How did you scale during 2008? 15:30

How are you doing this today with your students? 22:50

What are some strategies you teach students? 27:30

How are you suggesting students to underwrite for the soft costs? 31:50

How are you teaching students to buy properties in this competitive environment? 40:00

Why do you prefer single family over multifamily? 42:45

How are you accounting for some of the issues around the Chicagoland area? 45:20

How did you start and grow Chicago REIA? 47:20

Wrap Up

What is your competitive advantage? 50:00

What is one piece of advice you’d give to a new investor? 50:40

What do you do for fun? 51:35

What is a good self development activity you’d recommend? 52:20

Who is one person you’d recommend from your local network? 54:40

How can we learn more about you? 55:50

Thanks so much for listening. Please check out our website, we’ve got plenty of free resources available for you.


Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest Name: Andrew Holmes

Guest Company: Andrew Holmes Real Estate

Guest Link: https://andrewholmesrealestate.com/

The Intelligent Investor

National RE Invest


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