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Episode 39: Scaling a Multi-Million Dollar Real Estate Business in Chicago

In today’s episode, Sean Connolly talks about his not so usual journey of scaling to a multi- million dollar portfolio and the lessons and tools he’s acquired over the past 8 years. Sean provides his advice on investing in certain southside markets as a new investor and if you’re not doing volume, why it’s so important to control your material cost. Sean also provides his thoughts on the imminent future of the Chicago real estate market. Lastly, he explains the role and significance of virtual assistants and how they can help you scale. 

If you want to see how we can improve your property performance, check us out at GC Realty & Development, LLC.: Chicago Property Management, Chicago Homes for Rent.


Guest Introduction 6:25

Where have you been investing over the past 8 years? 7:50

Why move from Austin to the southside? 10:00

Are you mostly flipping or holding? 10:25

How did you do your first 50 units in Austin? 11:18

What is your outlook on the Chicago housing market?19:10

How did you start using virtual assistants to scale? 27:18

At what point can an early investor get involved with a virtual assistant? 33:30

Tell us about your bad cash for keys experience? 39:55

Wrap Up

What is your competitive advantage? 43:04

What is one piece of advice you would give a new investor? 44:00

What do you do for fun? 44:55

What is a good self development activity you would recommend? 45:25

Can you name someone who you’d recommend as a resource? 46:00

How can we learn more about you? 47:10

That’s our show! Thanks for taking the time to listen and please leave us a 5 star review. Also consider joining our facebook group at


Guest Name: Sean Connolly

Guest Company: Scale Virtually

Guest Link: Scale Virtually: Home

The Experience Transformer

Emerging Real Estate Markets: How to Find and Profit from Up-and-Coming Areas

Scale Virtually: Home

Virtual Freedom: How to Work with Virtual Staff to Buy More Time, Become More Productive, and Build Your Dream Business

Traction: Get a Grip on Your Business: Wickman, Gino: 0783324916904

Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork

Sean’s number - (773) 295- 7345

Straight Up Chicago Investor Club | FB Group