Podcast 140: Agent, Property Manager, Investor Sean Morrissey in Chicago

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15 flips currently in progress. 146 flips completed. 19 rentals properties.
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On this episode of the InvestFourMore Real Estate Podcast, I speak with Sen Morrissey, who is a real estate investor, broker, and property manager in Chicago. Sean got into the real estate business in 2001 when he bought a rental property. He was then able to quit his corporate job by becoming a real estate agent. He has bought 23 rentals and managed over 200 properties at one time as a property manager. Sean has a very interesting story, and we hear all about it on this week’s show.

Click on the green button below to listen to the podcast

How did Sean get started in real estate?

Sean went to school to become a restaurant manager. He was able to get a job in his field but never enjoyed his career choice. During a discussion with his father about real estate, Sean knew he wanted to start buying rental properties. He was able to buy his first rental in 2001, but things went slowly after that. He bought a few more rentals over the next five years but still hated his job as a restaurant manager. Sean decided to get his real estate license. He started out as a part-time agent, but after two years as an agent was able to quit his job and get into real estate full time.

Can you be a successful part-time real estate agent?

What niche did Sean discover as a real estate agent?

Sean helped people buy and sell houses as an agent. It was his commissions that allowed him to make enough money to quit his job. As an agent, he worked in a down market in the Chicago area. He had people who needed help selling their homes or renting them out because they were too under water to sell. Sean began managing properties for investors and realized there was a huge need for good property managers. After a couple of years working with Keller Williams, Sean opened his own brokerage: Chicagoland Realty Group Partners. At one point, he was managing over 200 properties.

Why I am starting my own real estate brokerage.

What did Sean learn about property management?

Sean offered people many choices when managing their properties. He offered services that included just collecting rent, just taking care of maintenance, just doing checkups, or a combination of the three. Sean was able to grow his property management business very quickly and realized he could not offer an à la cart service anymore. He moved to a basic fee structure.

On the podcast, Sean also talks about the best way to manager properties. He discusses:

  • Credit scores.
  • Bankruptcy.
  • Eviction.
  • Income.
  • Criminal background.

How to find a great property manager.

What are Sean’s goals and plans in real estate?

Sean talks about what he wants to do in the future with real estate. He says he wants to focus on being a commercial real estate agent working with investors. He also talks about his goals for rental property income. Sean has 23 rentals but is under contract to buy a 16-unit multifamily property. He is hoping that in 2018, he will have enough income from his rentals to cover all his expenses.

What is financial freedom?

If you want to contact Sean, you can reach his real estate office at chicago-realty-group, or you can find his podcast on iTunes: Landlording for Life Podcast.


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  1. incester March 7, 2018
  2. Amelie February 23, 2018
    • Mark Ferguson February 26, 2018

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