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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Feedspot just updated its list of the best Chicago real estate podcasts and Straight Up Chicago Investor came in at number one. You can see the full list right here: Best Chicago Real Estate Podcasts on Feedspot.
Tom and I have been doing this show for six years now and it has never been about rankings. What actually matters is what happened on the other side of the microphone. We have watched listeners go from zero properties to their first one. We have watched a lot of them go from one to four. And we have watched people who owned nothing when they started listening build a real portfolio in the six years since.
Key Takeaways
Straight Up Chicago Investor ranks number one on Feedspot's list of the best Chicago real estate podcasts.
We also hold the top spot in the real estate category of Feedspot's broader Best Chicago Podcasts list, and we come in at number 12 out of 100 on their Best Midwest Real Estate Podcasts list.
Feedspot weighs relevance, authority, engagement, ratings and reviews, listener counts, and publishing consistency.
We just crossed episode 470, with a 5 out of 5 Apple rating across 278 reviews.
Episode 500 lands in December 2026.
How the Ranking Works
Feedspot scores shows on relevance to the category, authority in the space, audience engagement, ratings and reviews, listener counts, and how consistently a show publishes. It is a blended score rather than one metric, and it gets refreshed periodically, so the order can shift.
Two other placements worth mentioning. On Feedspot's larger Best Chicago Podcasts list, which puts us up against news, sports, food, and true crime shows across the city, we hold the top spot in the real estate category. And on their Best Midwest Real Estate Podcasts list, a field of 100 shows across the entire region, we land at number 12. Given some of the names on that one, I will take it.
Feedspot is an RSS Reader that lets you follow your favorite podcasts alongside blogs and news in one place.
Where We Are at 470
We are at episode 470. Here is what the schedule looks like:
Thursdays. The full episode. Roughly an hour with a guest who owns, builds, lends, litigates, or manages in this market.
Every other Tuesday. Straight Up Tuesday Tip. Fifteen minutes, one idea, no fluff. Built for the drive to a showing or a walkthrough.
That adds up to thousands of minutes of neighborhood breakdowns, ordinance explanations, deal autopsies, and hard earned lessons. No paywall, no course at the end of it.
And here is the milestone we are fired up about: episode 500 hits in December 2026. Do the math on our cadence and it lines up almost perfectly. Thirty more episodes gets us there right before the calendar flips.
When we started this in 2020 I would have laughed at anyone who told me we would get to 500. Now it is a few months out.
Thank You
The people who earned this are not Tom and me.
It was the guest who drove in from every corner of the city and the suburbs to "The Underground" in Roselle, where we have the best studio around. It was the listener who left a review. It was the investor who emailed to say one episode changed how they underwrote a three flat. It was everyone who sent a link to a friend who was about to buy their first rental in Chicago and had no idea what the RLTO was.
If you have never left the show a review, that is the most helpful thing you can do as we push toward 500. It takes 30 seconds and it is a big part of why lists like this one notice us at all. Leave a review on Apple Podcasts here.
Know Someone Who Would Make a Great Guest?
We are always thinking about how this show keeps getting better, and the answer has never been Tom and me talking louder. It is bringing more of the right voices into the room.
So here is the ask. If you know someone in this market who would make a great guest, an operator who has actually done the reps and can break down what they know without turning it into a pitch, let us know. Tell us who they are and why you think they belong behind a microphone. We read every one of these.
Every good thing that has happened to this show started with somebody in this community making an introduction. Episode 500 is coming. Help us make what comes after it even better.
Listen or Watch
Listen on Apple Podcasts, Spotify, or wherever you get your podcasts. If you would rather see the conversation than just hear it, every single episode is also up on our YouTube channel.
The full archive, sorted by neighborhood, strategy, and topic, lives at straightupchicagoinvestor.com/podcast.
