Straight Up Chicago Investor Podcast

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.

06/03/2026

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!

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

04/07/2026

02/27/2026

Stop guessing rent. Know the range.

If you are pricing rentals in Chicago or the suburbs right now, be honest.

Are you using last year’s comp?
A Zillow estimate
Or what just feels right

Here is the problem.

Underprice it, and you lose thousands.
Overprice it, and you lose weeks.

Both cost you money.

We built a Free Rent Analysis tool that shows you the realistic rent range based on current demand, not guesswork.

It takes about 60 seconds.

If you are a landlord, investor, or realtor working in Chicago and the suburbs, this is a simple way to price with confidence.

Get your Free Rent Analysis here https://www.gcrealtyinc.com/free-rental-analysis

12/28/2025

A client of ours needs a furnished rental as close to Hinsdale as possible for three months! They need it ASAP. Anyone got anything?

You can text me 630-781-6744.

Thanks.

12/26/2025

NEW EPISODE 🎙️
From corporate real estate to a 6-unit gut rehab on day one, Alec Greenberg didn’t ease into Chicago multifamily, he dove in headfirst.
In this week’s episode, the Principal of Base 3 Development breaks down how he’s scaling large residential projects in Chicago, including the real talk on zoning, underwriting, and leasing that most investors skip over.
Plus: his playbook for leveraging VAs and offshore staffing to run lean—and why he’s still bullish on Chicago.
🔗 Link in bio