Skip to main content


Straight Up Chicago Investor Podcast Episode 262: From FBI Agent To Hundreds Of Doors In Chicago With James Williams

Straight Up Chicago Investor Podcast Episode 262: From FBI Agent To Hundreds Of Doors In Chicago With James Williams

In a captivating episode of the Straight Up Chicago Investor Podcast, listeners were treated to an insightful conversation with James Williams—a multifaceted real estate investor, attorney, and former FBI agent whose journey in the industry spans over three decades.

James's story is as intriguing as it is inspiring. He provides a glimpse into his unique career trajectory, which includes a stint with the FBI while nurturing his passion for real estate investing in the background. From his early days navigating the Chicago real estate landscape to acquiring his first property—a graystone on the Northside in the 90s—James's journey is a testament to perseverance and strategic foresight.

One of the most compelling aspects of the episode is James's candid discussion about the highs and lows of his investing career. He shares insights into raising capital, acquiring hundreds of units, and weathering the storms of adversity that inevitably accompany the real estate journey. James doesn't shy away from discussing the challenges he faced, including the heartbreaking loss of a valued business partner and friend, which forced him to reassess and restructure his portfolio.

Despite encountering rough patches along the way, James's resilience shines through. He underscores the importance of patience, due diligence, and surrounding oneself with a competent and trustworthy team. His emphasis on building strong foundations and fostering meaningful relationships underscores the timeless principles that underpin successful real estate investing.

A highlight of the episode comes with the long-awaited dropping of a Point Break reference—a playful nod to the camaraderie and lighthearted moments that punctuate the serious business of real estate.

As the episode draws to a close, listeners are left with a profound appreciation for James's journey—a journey marked by determination, growth, and an unwavering commitment to excellence. His story serves as a beacon of inspiration for aspiring investors and seasoned professionals alike, reminding us that success in real estate is not merely measured by financial gains but by the resilience of the human spirit and the depth of one's character.

Watch Straight Up Chicago Investor Podcast Episode 262 in Full Here

Questions We Answer In this Show:

Q. The Devastating Impact of the 2008 Financial Crash on Tenants

A. Video

Q. Renovating a Dilapidated Property while Living Upstairs

A. Video

Q. Unforeseen Bidding War for Dream Investment Property

A. Video

Show Notes:

  • 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?

Connect with Mark and Tom:

Email the Show:

Guest Name: James Williams

Guest Company: Mainstreet Real Estate Services 

Guest Link:

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

Looking for a property manager?

Chicago Investor Resources Shared

Want extra Hacks & Tricks? Follow us on Facebook & Youtube!

Looking for a breakthrough in your career? Join Our Team!

SUBSCRIBE on to our podcast on iTunes | Spotify | Stitcher | TuneIn Radio 

Need More Info?

Should I Rent or Sell

ROI Calculator

Rental Analysis

Speak To A GCR&D Team Member