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Episode 262: From FBI Agent to Hundreds of Doors In Chicago with James Williams

By Mark Ainley

James Williams is a real estate investor, attorney, and former FBI agent who embarked on his real estate journey in the early 90s!

James starts by discussing how he chose a career path which includes a period of working in the FBI, all while having real estate investing on the back of his mind. He discusses his first real estate purchase, a graystone on Chicago’s Northside purchased in the 90s! James shares insights raising capital, acquiring hundreds of units, and extremely rough times in his investing career that resulted in him selling off most of his portfolio. He shares the impact of losing a valued business partner and friend. The silver lining of the rough times is that James still holds a nice portfolio and has the team in place to continue scaling! Throughout the show, James emphasizes the importance of patience, due diligence, and building a great team. Most importantly, after 262 episodes, we finally get to drop a Point Break reference. 

If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

02:31 Clean leaves to prevent clogging of gutters and drains!

03:39 Intro to our guest, James Williams! 

09:30 James’ quest to buy his first piece of real estate!

18:53 Working in the FBI!

25:33 Raising capital for RE Investing.

37:32 Lessons learned from 4 years in a tough market.

47:55 Selling off most of the portfolio.

53:36 Costs of Selling.

56:35 What’s next for James?

59:43 What is James’ competitive advantage?

61:13 One piece of advice for new investors.

62:50 What do you do for fun?

63:45 Good book, podcast, or self development activity that you would recommend?

64:28 Local Network Recommendation?

65:04 How can the listeners learn more about you and provide value to you?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest Name: James Williams

Guest Company: Mainstreet Real Estate Services 

Guest Link: https://www.mainstreetrealestateservices.com/

Other Links for show notes:

Boss (Book Recommendation)

American Pharaoh (Book Recommendation)

Henry Cardenas (Network Referral)

Show Sponsors:

Build Your Team
Cost Segregation Services, Inc. - Kevin Cawley

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Author

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Mark Ainley
Investor, Managing Broker, and Property Manager
Price is what you pay, Value is what you get! I want to provide value to others and make some money along the way. I have a solid foundation in Chicago real estate because I am a Real Estate investor in both Residential and Commercial/Industrial markets while being a founding partner at GC Realty & Development LLC and co-host of Straight Up Chicago Investor Podcast. In the last 20 years we renovated 500+ properties, invested in commercial properties, managed over 7000 units/tenants, leased...
Price is what you pay, Value is what you get! I want to provide value to others and make some money along the way. I have a solid foundation in Chicago real estate because I am a Real Estate investor in both Residential and Commercial/Industrial markets while being a founding partner at GC Realty & Development LLC and co-host of Straight Up Chicago Investor Podcast. In the last 20 years we renovated 500+ properties, invested in commercial properties, managed over 7000 units/tenants, leased over 4,000 properties, featured on CNBC’s TV show The Deed, co-host on Chicago's AM560 Real Estate Revealed Radio Show, and invited to speak & sit on panels at numerous investment summits across the country. I have also been blessed with the opportunity to be a guest on over 30 top podcast platforms. GC Realty & Development, LLC, currently manages over 1,200 investment properties throughout the Chicagoland area. In 2019, 2020, 2020 and 2022, GCR&D was featured on the Inc. Magazine list of top 5,000 fastest growing companies in the United States. I take great pride in providing valued feedback to beginners and less experienced entrepreneurs on what steps not to take or what steps to take sooner in growing a younger business.
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