Vendor Portal
Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Let me be real with you from the start: I didn’t grow up thinking I was going to own a property management company. I wasn’t the kid dreaming of big buildings or flipping properties. I was the kid patching up his shoes to make 'em last another year, hustling side to side between divorced parents, and watching people around me struggle to get by. I didn’t grow up with much, but I grew up hungry.
And that hunger taught me something: if you want options in life, you’ve got to create them yourself.
That’s how I ended up here—23 years later, co-founder of GC Realty & Development, managing over 1,400 residential units and millions of square feet of industrial space across the Chicago area. But it didn’t happen overnight, and it definitely didn’t happen without some scars along the way.
This blog isn’t a how-to. It’s a story. My story. One with some wins, plenty of bruises, and more learning moments than I can count. Because success in real estate isn’t a straight line—and I’m living proof of that.
The $1,000.00 Mortgage That Taught Me Cash Flow Before I Knew the Term
I was 21 when I bought my first property. No fancy spreadsheet. No investing seminar. Just gut instinct and a nudge from the idea that owning real estate was... responsible. That first mortgage—along with taxes and insurance—came out to about a thousand bucks a month. I didn’t have a plan for rental income, I just wanted to own something.
But then something happened. Friends needed a place to crash. So I did what any resourceful 21-year-old would do: I charged rent. One guy paid $500 for the spare bedroom. Another one snagged the couch for $300.
I was covering my entire mortgage while sleeping on the couch in my own place.
That was the first time I tasted financial leverage. I didn’t know it then, but I had stumbled into house hacking. And that one moment shaped everything that came after.
The Tenant That Nearly Made Me Quit Real Estate
Fresh off that first success, I figured I’d do it again. I bought another property, listed it in the paper—yeah, the physical paper—with a simple rental ad.
First person that responded? It seemed nice. I had a story. I got soft. I took a partial deposit and gave them the keys.
Big mistake. Lesson learned.
What followed was a long series of missed payments, broken promises, and me driving all over town to collect $60 at a time. Eventually I had to do what we now call “cash for keys.” Paid them to leave. I lost money, time, and sleep.
I told myself I was done being a landlord.
But I also realized: this happened because I didn’t have a system. I didn’t screen properly. I let emotion override the process. It was then that I learned, I wasn’t alone—this is how most new landlords learn. The hard way.
From "I’ll Never Manage Again" to Accidentally Building a PM Company
I was in full-time brokerage mode after that. Helping investors buy and sell. That’s it. I was making good money. Making clients and some good money too. So naturally, they started asking:
"Hey Mark, can you manage this for me?"
"Nope."
"Come on, just this one."
"Nah, it's not really my thing."
But then my real estate attorney cornered me. He had just bought a rental and said, “I want you to manage this.” I laughed. He didn’t.
He wrote up the contract himself and offered to pay me $50 a month. I thought it was a big joke.
And that, my friends, is how GC Property Management started, no joke.
Next thing I know, a friend of his calls. Then another.And another! Within a few months, I had a small portfolio—and no clue what I was doing. But I learned fast, really fast.
2008: The Crash That Turned Chaos Into Opportunity
When the market tanked, everyone became an accidental landlord. Properties that wouldn’t sell had to be rented. And guess what? They needed a property manager.
We went from managing dozens of units to hundreds in a short time. Our phones were ringing off the hook, and we said yes to everything. There was nothing we weren’t able to accomplish.
There was just one problem: we didn’t have any processes. This was huge.
Every decision flowed through me or Bryan, my long time partner. We were at the center of it all, in the core of it. Everything spoke to us. That’s not scalable. It’s not even sustainable. It’s amazing.
It wasn’t until I conducted an online search for “property management in Bartlett” that I realized we had zero online presence. I couldn’t find us anywhere, and this was despite all of the recent growth we had. No systems. No org chart. Just pure chaos. All the time.
That was our wake-up call.
Systemizing the Hustle: How We Turned Chaos into a Company
I picked up a book called Work the System. It changed everything.
I started documenting every process—from tenant screening to maintenance calls. We stopped hiring friends who “needed something to do” and started hiring the right people for clearly defined roles. They helped Bryan and us grow to what we are today.
Shadowing became SOPs. Guesswork became a workflow. And little by little, we built something real. Something documented, something for all to review and abide by.
Today we employ over sixty extremely talented team members. They are genuine. They are modern day “superheros”. We also have processes, and those get reviewed quarterly. Every new hire goes through an official onboarding process. That’s the difference between being busy and building a business. You just put processes into place, and let your team follow them.
Re-Discovering Investing: The South Side Auction That Opened My Eyes
In 2009, I tagged along with a client to a South Side auction. He bought three units for $70K. One of them looked like it had been through a major world war—busted doors, copper missing, wires stripped.
I was ready to run. He was excited. I had no idea what I was in for.
He explained: “We’re all in for $25K. We’ll rent it for $1,000/month. That’s cash flow.”
That moment flipped a switch in my head. It went from on, to off, so quickly.
I went home, ran the numbers, and realized this wasn’t about appreciation. This was about income. Predictable, monthly income.
We scaled hard. Over the next few years, we did hundreds of BRRRRs, sold turn-key packages, and even had someone buy 27 units! This was accomplished with just one digital post - unreal!
Biggest Regrets and Lessons That Still Hit Me Hard Today
As an Investor - I didn’t keep enough properties. The ones I have today are the BESt of the BEST … and the $30,000 or $40,000 I made along the way selling off this property or flipping that property … I have no clue where that money went. And that is sad.
As a business owner - We hired too slow, then sometimes wrong. Culture fit matters. But so does competence. We have hired some amazing people and some of our employees have been here for decades!
As a business owner - I waited too long to document and delegate. The earlier you create systems, the easier scaling becomes. Don’t wait, put the process in writing and then watch it work for you.
The Podcast That Became the Ultimate Sales Tool
When we leaned into property management full-time in 2018, I knew we needed a way to scale trust. I couldn’t be on the phone with every investor in Chicago. It would be impossible! There are millions of them!
Enter: Straight Up Chicago Investor. YAY!
My co-host Tom pitched it. I loved it. We recorded 10 episodes right away just to get past the “podcast death zone” that 98% of podcast producers never make it to episode 10.
Five years later, we’ve got a full studio, we record six episodes a month, and we boast a referral network that’s built on sharing knowledge. It’s the ultimate "I’ve got someone for that" machine. Someone asks me a question? Boom. I send them a podcast episode that references it, and a personalized video.
It’s relationship-building at scale. An arrangement, some may say.
Business Is Built on People: The "I Know Someone" Rule Still Wins
Real estate is a people game.
You need a lender? I’ve got a network of them! You need a plumber at 2AM? I’ve got some contacts! You need a property manager who won’t ghost you? I know a few.
Give value first. Give without expecting. That’s how relationships work. Always.
The universe pays you back eventually—just maybe not how or when you expect. Trust in this.
From Jordans to Legacy: What Really Matters Now
Back in the day, I saved up for months to buy one Champion basketball or football jersey. I used to chase all that. Now? I chase different things.
Peace of mind. Stability. Building a team that gets better every quarter.
I drove a Civic for almost a decade—not because I couldn’t afford something else, but because it got the job done. It’s not about flash. It’s about staying grounded.
That’s what property management gave me. That’s what real estate—done right—can give anyone. The ability to create options. When you have options, you have the ability to achieve great things.
This Ain’t Easy, But It’s Worth It
If you’re building something in Chicago real estate—don’t expect it to be smooth. Expect to make mistakes. Expect people to let you down. Expect to doubt yourself. Expect to fail. Be scared.
Do it anyway.
Learn fast. Hire smart. Give more than you take. Document everything. And never forget that the long game always beats the short hustle.
And if you ever need help navigating the mess? I’ve been there.
Let’s talk. Again.
Need Help Managing Your Chicago Property?
👉 Schedule a call with our team and learn how GC Realty & Development helps landlords win long-term
Or tune into the Straight Up Chicago Investor podcast and learn from the city’s best (and worst) investor stories. Because success is never a straight line. And we’re proof of that.
There is a lot of information contained here if you plan on investing in real estate locally. It may seem overwhelming for those wanting to invest in the Chicago market, but it is really just a team sport. Who is on your investing team? Do you even have a team? GC Realty & Development, LLC. has a dedicated team of professionals that are willing to share their decades of experience in all facets of real estate. We handle everything from Brokerage, Leasing and Property Management. Whether you hire us or not, we are happy to provide you with our resources and expertise.
What gets me up in the morning and keeps me going twelve 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 us a review about our services. We would clearly love all three, however, we are happy whenever we get the opportunity to help!
Reach out today!
Partner / Co Host of Straight Up Chicago Investor Podcast
