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.

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Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: James Williams, Mainstreet Real Estate Services

Link: Boss (Book Recommendation)

Link: American Pharaoh (Book Recommendation)

Link: Henry Cardenas (Network Referral)

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Guest Questions

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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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2023.

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

Straight Up Chicago Investor

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