Skip to main content


Straight Up Chicago Investor Podcast Episode 233: Navigating Chicago's North Side: Insights From Commercial Real Estate Expert Alan Goldberg

Straight Up Chicago Investor Podcast Episode 233: Navigating Chicago's North Side: Insights From Commercial Real Estate Expert Alan Goldberg

In the world of real estate, few stories are as captivating and enlightening as that of Alan Goldberg. A titan in the Chicago real estate scene, Alan's illustrious career spans several decades, offering a treasure trove of experiences and insights for both aspiring and seasoned investors. In a recent episode of the Straight Up Chicago Investor Podcast, Alan takes us on a journey through his remarkable career, shedding light on his early days, the importance of prospecting, surviving market cycles, and the ever-evolving Chicago neighborhoods. This episode is a masterclass in real estate investing, with Alan emphasizing the potency of real estate as an investment vehicle and the importance of strategic decision-making.

Alan Goldberg's journey into the world of real estate began in the late 1970s. His very first deal marked the genesis of a career that would become the stuff of legends. He shares with us the challenges and excitement of his early days, showcasing how perseverance and a proactive approach to seeking out potential clients and opportunities were instrumental in building a successful real estate career.

One of the key takeaways from Alan's discussion is the importance of prospecting. Alan underscores that in real estate, proactivity is everything. To drive business growth, one must constantly search for potential clients and opportunities. His early experiences exemplify how taking the initiative can open doors to long-lasting success.

Alan Goldberg has seen it all when it comes to market cycles. Over the years, he has navigated through various market ups and downs, and in this episode, he shares his invaluable insights on some of the toughest markets in the last five decades. His ability to adapt and make strategic decisions during challenging times is truly inspiring.

We extend our heartfelt thanks to Alan Goldberg for sharing his invaluable experiences and insights with us in this episode of the "Straight Up Chicago Investor Podcast." Alan's journey from humble beginnings to becoming a prominent figure in the Chicago real estate scene is an inspiration to all. His expertise, optimism, and wisdom provide a roadmap for success in the world of real estate investing. Whether you're a novice investor or a seasoned pro, this episode is a must-listen-to gain a deeper understanding of the Chicago real estate landscape and how to thrive in it. Alan Goldberg is a true testament to the enduring power of real estate and the opportunities it can offer to those who are willing to embark on the journey.

Watch Straight Up Chicago Investor Podcast Episode 233 in Full Here

Questions We Answer In this Show:

Q. Unveiling the Mesmerizing Evolution of Real Estate and Investments

  1. Video

Q. The Devastating Market Crash of the 80s

  1. Video

Q. The Evolution of Flipping and Renovations: Unlocking the Secrets of Investment Properties

  1. Video

Show Notes:

  • 02:30 Housing Provider Tip: Ensure you’re getting a warranty and all issues fixed when buying new construction.

  • 04:33 Intro to our guest, Alan Goldberg!

  • 06:26 Alan’s start in real estate!

  • 10:09 Alan talks about his first deal!

  • 21:03 How did Alan establish his area of focus?

  • 25:01 Areas that have drastically improved since the 70s.

  • 27:12 What were rehabs like in the 70s?

  • 33:30 Toughest stretch in real estate since the 70s!

  • 36:37 Adjusting in a tough market.

  • 48:27 Did Alan ever question being a real estate agent?

  • 50:55 Outlook on Rogers Park, Uptown, and surrounding Neighborhoods.

  • 52:56 What is Alan’s competitive advantage?

  • 54:02 One piece of advice for new investors.

  • 54:20 What do you do for fun?

  • 56:25 Good book, podcast, or self-development activity that you would recommend?

  • 57:24 Local Network Recommendation?

  • 57:47 How can the listeners learn more about you and provide value to you?

Connect with Mark and Tom:

Email the Show:

Guest Name: Alan Goldberg

Guest Company: Alan Goldberg Real Estate LLC

Guest Link:

Other Links for show notes:

NBOA / Mike Glasser (Network Referral)

Glenwood Ave Arts Fest

Rogers Park Builders Group

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