Straight Up Chicago Investor Podcast

Straight Up Chicago Investor Podcast Podcast - Join us as we share our winning strategies, success stories, obstacles we've encountered, If so, this podcast is for you!

Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.

One of the best things about running a podcast is all the value that our guests provide to our listeners each and every ...
09/18/2026

One of the best things about running a podcast is all the value that our guests provide to our listeners each and every episode. Here are some of our favorites!

09/17/2026

Join two Chicagoland Property Managers Tim Harstead(Chicago Style Management) and Mark Ainley(GC Realty & Development) as we explore what is going on in the world of managing real estate in the Chicago market!

We appreciate news outlets like Hoodline featuring Straight Up Chicago Investor in one of their most recent articles! ...
09/17/2026

We appreciate news outlets like Hoodline featuring Straight Up Chicago Investor in one of their most recent articles!

06/04/2026

Mark your calendar for June 13th.

We’re getting together for an investment summit built around one thing: what’s actually working in the local market right now. No pitches. No products being shoved at you. Just real education from people doing this every day.

I’ll be breaking down the real story of being a landlord and property manager, including what it actually takes to go from your very first building to your second, third, and beyond. After managing around 1,500 units across Chicagoland, I’ve seen what separates the investors who grow from the ones who stall out.

You’ll also get the chance to meet other investors, tap into a room full of resources, and yeah, the food is on us.

Whether you’re still thinking about buying your first property or you’ve got a portfolio already running, this room is for you.

Spots are limited. Sign up using the link or visit the events page at gcrealtyinc.com.

Episode 450 drops tomorrow.That’s 450 conversations, 450 lessons, and 450 looks at what’s actually happening in Chicago ...
05/06/2026

Episode 450 drops tomorrow.

That’s 450 conversations, 450 lessons, and 450 looks at what’s actually happening in Chicago real estate.

And for this milestone, we’re bringing in Alderman Bennett Lawson from the 44th Ward, talking about city decisions, what’s coming, and how it directly impacts you as an investor.

This isn’t surface-level stuff. This is the kind of insight most investors don’t get access to.

If you own property in Chicago or plan to… don’t miss this one.

Watch on YouTube:
https://youtu.be/bJTZtVKgmxQ

Or listen on iTunes and Spotify: https://podcasts.apple.com/us/podcast/straight-up-chicago-investor/id1513012457

More here:
www.straightupchicagoinvestor.com

Address

Roselle, IL
60172

Website

Alerts

Be the first to know and let us send you an email when Straight Up Chicago Investor Podcast posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Straight Up Chicago Investor Podcast:

Shortcuts

Share

Category