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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
If you’ve been around Chicago real estate long enough, you’ve probably seen some property management companies pop up fast, make noise, and disappear just as quickly. The ones that last, the ones that build a real business, understand one thing: success isn’t just about doors. It’s about systems, people, and reputation.
That’s what I talked about when I joined the Unfilter podcast from propertymanagement.com. We covered the early days of GC Realty, why scaling a management company gets tougher the bigger you get, and how I see the industry evolving over the next decade.
Here’s a breakdown of what I shared, and how it ties back to the reality of managing properties in Chicago.
Building a Reputation that Outlasts Competitors
“I’ve always tried to have enough Google reviews online that I was out far enough ahead that the other people in the market would think it’s too tiresome to actually try to chase me.”
That’s been one of my strategies since day one. Long before everyone was fighting for online credibility, I made reviews a priority. When new companies start out, they have zero, and in this business, social proof is everything.
Reputation is your moat. When landlords search “Chicago property manager,” the companies that show up first, with hundreds of positive reviews, automatically earn trust. That didn’t happen overnight for us. It took years of consistency and actually delivering the service behind those reviews.
If you’re a landlord or investor, look for a manager with that kind of credibility. It’s proof they’ve been through the ups and downs and are still standing strong.
My First Tenant Was an Eviction
The first tenant I ever placed, on my own property, ended in an eviction. That experience taught me more about property management than any seminar or book ever could.
Back in 2005 to 2007, the market was booming. Everyone could get a loan, anyone could buy a property, and as long as you could “fog a mirror,” you were an investor. I was selling houses left and right, but investors kept asking if I could manage their rentals.
At first, I said no. I didn’t want the headache. But one client turned into two, two turned into five, and before I knew it, property management started paying the bills. One property covered our electric bill, another paid for the office water cooler.
By 2012, we stopped calling ourselves a brokerage that “did some management” and became a property management company that happened to have a brokerage. That shift changed everything.
The Growth Ceilings No One Warns You About
Every property management company hits walls, usually around 300, 700, and 1,200 doors.
At 250 doors, we were managing half a million square feet of space and didn’t even have written processes. We had chaos disguised as success.
Each time you hit a ceiling, you’re forced to mature. You can either stay where you’re comfortable or push through and rebuild from the inside out. New systems. New hires. New leadership habits.
Some owners chase growth and burn out. Others build a lifestyle business and stay happy managing 400–500 doors, making great income, and staying lean. There’s no right answer, just know what kind of business you want before chasing a bigger number.
Culture Changes as You Grow
When GC Realty was small, we only hired people we’d hang out with. Everyone knew each other. We grabbed beers on Fridays and shared inside jokes.
But when you get to 30 or 50 employees, that dynamic changes. You now have multiple generations, career paths, and personalities under one roof. Culture takes work. You can’t just expect it to stay aligned on its own.
It’s one of the biggest growing pains no one talks about. You stop managing properties and start managing people.
The Regulation Game: Blessing and Curse
Regulation has two sides. On one hand, it’s great for our business. Every time managing rentals gets harder for small landlords, more of them call us.
But when new laws start cutting into your revenue model, that’s when things get tricky.
For example, Illinois recently discussed capping application fees at $20. Ours are $65, which helps cover screening costs and staff time. That kind of cap would mean a $160,000 hit to our top line. And if that money disappears, you have to make it up somewhere, through volume, efficiency, or restructuring.
The same goes for Resident Benefit Packages (RBPs). If they become optional, and residents start opting out, that’s another major change to how property managers nationwide make money.
Still, the upside is that tighter rules discourage self-management. Landlords realize it’s easier to hire a professional than risk making a costly mistake under the RLTO or RTLO.
If you’re not sure what rules apply to you, check out GC Realty’s Legal Resource Center. We keep it updated with new laws, amendments, and best practices for Cook County and Chicago landlords.
The Opportunity Ahead for Property Managers
Twenty years ago, if you were a property manager, people assumed you couldn’t make it as a realtor. Today, property management is a legitimate profession and a growing industry.
Vendors, software, and training options have exploded. When I first went to conferences, there were maybe a handful of vendors. Now, there are 70-plus. The industry is evolving fast.
And at its core, property management is a subscription business, recurring revenue, predictable cash flow, long-term relationships. The more value you deliver, the longer clients stay.
That recurring model allows us to reinvest in technology, training, and better systems to serve both landlords and residents.
The AI Question
Everyone’s talking about artificial intelligence replacing jobs. I don’t buy it, at least not in our world.
Sure, AI might automate some front-line tasks like scheduling or data entry. But it can’t replace relationships, judgment, or accountability.
Landlords still need someone they can call when a tenant stops paying rent, or when an inspection fails. Chicago’s housing laws are too detailed for an algorithm to handle without context.
AI will make us faster, not replace us. The future of property management is hybrid: technology behind the scenes, humans in front of the clients.
Content Built the Brand
I didn’t always have confidence on camera. The first time I recorded myself, I thought, “Wow, I sound boring.” You have to turn it up a little, bring energy, and talk like you care.
Consistent content has been one of the best long-term investments we ever made. LinkedIn, YouTube, podcasts, all of it helps landlords see who we are before they ever call us.
Every post is either solving a problem or showing that we’ve already solved it. That’s what builds trust, and trust is what drives new business.
Chicago Landlord Q&A
1. Why is property management in Chicago so complicated?
Between the RLTO, RTLO, Fair Housing, and the Just Housing Amendment, Chicago landlords operate under some of the strictest regulations in the country. Missing a disclosure or charging a fee the wrong way can land you in legal trouble. That’s why professional management isn’t optional, it’s protection.
Read: Cook County RTLO Explained
2. What’s the biggest mistake new landlords make?
Trying to do everything themselves. From listing to screening to maintenance, it’s easy to get overwhelmed or scammed by bad tenants. GC Realty’s Tenant Placement Service helps landlords find qualified residents fast.
3. How do I know if my rent price is right?
If your property sits vacant for more than 21 days, you’re likely overpriced. Use our Free Rent Analysis to compare your property to current listings and stay competitive.
4. How large is GC Realty today?
We manage over 1,400 residential units and 1 million square feet of commercial and industrial space throughout the Chicago area. That scale gives us strong vendor relationships and operational leverage that benefit our clients directly.
5. Is property management still a good investment?
Absolutely. As laws tighten and landlords seek passive income, demand for professional property management continues to grow. As I like to say, we’re still in the early chapters of a maturing industry, and the best is yet to come.
The Takeaway
Whether you are a first-time landlord or an experienced investor, the lesson is clear.
Growth in real estate does not come from shortcuts. It comes from systems, reputation, and adapting before the market forces you to.
Mark Ainley did not build GC Realty overnight. It took mistakes, evolution, and a refusal to stay comfortable.
And that is exactly what Chicago landlords need today:
to think long term, stay compliant, and partner with experts who have already been where they are headed.
Looking to grow your rental portfolio the smart way?
🔍 Get your Free Rent Analysis
🏠 Or learn more about our Tenant Placement Services
About GC Realty & Development
GC Realty & Development LLC is a full-service Chicago property management company that has been managing residential, multifamily, and commercial properties since 2003. With over 1,400 units and 1 million square feet of commercial and industrial space under management, GC Realty has built a reputation as Chicago’s Responsive Property Manager.
Our team is known for clear communication, transparency, and quick action. Whether you need help with tenant placement, full-service property management, or understanding Chicago landlord laws like the RLTO or RTLO, GC Realty provides the expertise, systems, and local insight to protect your investment and increase profitability.
Visit www.gcrealtyinc.com to learn more or request your Free Rent Analysis today.
Don’t Want To Go At This Alone?
We’ve shared a lot of information here on investing in real estate locally in Chicagoland. If you live outside the area, it may seem overwhelming for those wanting to invest in the Chicago market. But we really just look at it as a team sport.
Who’s on your investing team? Do you even have a team? GC Realty & Development, LLC has a dedicated team of professionals willing to share decades of experience in all facets of real estate investment. We handle everything from brokerage, leasing, and property management. Whether you hire us or not, we’re happy to provide our resources and expertise.
What gets me up in the morning and keeps me going 12 hours a day is the ability to add value to local area investors in Chicago and beyond! Those who connect with me often hear me say that our goal is to bring value to everyone we come in contact with.
We hope that in return, they will one day hire us for our tenant placement or property management services, refer us to someone they know, or leave a review about our services. We would clearly love all three; however, we’re happy whenever we get the opportunity to help!
Reach out today!
Partner / Co-Host of Straight Up Chicago Investor Podcast
