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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Between my role at GC Realty & Development & connections with investors around Straight Up Chicago Investor podcast the conversation around scaling comes up daily. In the end everyone has 24 hours in a day but how do some investors grow faster than others?
Buying the First Property Is Easy. What Comes After? That’s Where the Game Changes.
Everyone remembers their first unit. Maybe it was a condo you lived in and decided to keep when you moved up. Maybe it was a two-flat in Avondale you house hacked. That first lease signed? That first rent payment received? Nothing beats it. It’s the moment you realize this might actually work.
Then it seems to slow down or I see investors pull back and focus more on their 9-5. There is no 100% right way to scale but here are a couple of ways to try to stay on track with your focused discipline.
#1 Stabilize & Systematize Property Management
A lot of first time investors don't realize that the day you close on a property you now become a Landlord. This means you have to learn everything from maintenance, leasing, rental laws, rental license codes, and simple communication to not mess things up with your new tenant.
There's a lot to learn and we build out many resources you can also check out on our website that are specific for Chicago and Chicagoland landlords.
Even if I give you all the information for free and it is out there beyond what we provide you still have to take the time to absorb it all and put it into practice.
This is where I see a lot of first time investors hit a pause button on their next purchase. The time previously spent finding, saving, and learning about the first purchase is now being used to manage the day to day.
For investors that purchase a 3 flat or larger this only becomes an exponentially larger learning curve and if there is any level of rehab that has to be done it can be years before you open up Zillow or Redfin again.
I called this section “Stabilize” not for stabilizing the property but stabilizing your emotions around learning everything you need to know and systemizing it all.
Know When to Stop Wearing Every Hat
Most people don’t scale because they do everything themselves. They swing the hammer, they show 40 prospects the unit they have for rent, they take the 10pm and weekend maintenance calls and texts.
I often reference the book “Who Not How” by Dan Sulivan & Benjamin Hardy, which if you are reading this article you need to buy today. In the book it talks about not having to learn every single step of “How” to do something when you just need to know “Who” to call to do it for you.
The biggest unlock for me—and I’ve seen this over and over again with our clients—is realizing that you should only do the things that multiply your time and capital. Everything else? You outsource, systematize, or eliminate. Find your “whos”
You don’t need to take every leasing photo. You don’t need to handle every application. That’s what Tenant Placement services are for. A good placement partner in Chicago doesn’t just find you a warm body—they prevent future evictions, minimize vacancy, and protect your time. That time? That’s what you use to underwrite the next deal.
#2 Be Aggressive With Your Time
We all have 24 hours in a day but yet some of us grow our business and portfolios faster than others? What is the secret…it isn't even a secret. Some people just spend their 24 hours more aggressively than others.
Often it can be as simple as allowing as much time to focus on finding your next property as you did with your first property.
I get it, now that you are years beyond when you first started your search and you have a wife, new kid, and more job responsibilities! So do other investors which means you just have to be much more aggressive with your time.
How Can You Get Your Time Back
When I talk to people that struggle with getting things done or managing their productivity I tell them to start with tracking their time for 2 weeks. When I say track I mean every single minute.
From that time study you will see where your time is going. Here are common areas I see people spending time on that they don't even realize how much opportunity they are losing out on.
Watching Football - If you are watching 6 hours of Football on Sunday then that is 4.5 days you can get back in a season. If you are a college football fan that can be even more on Saturdays.
Grocery Shopping - Pay the fee to have groceries to be delivered and get 10 hours back a month.
Commute To Work - Take an UBER to work 2x per week and use that time to read, look at properties, or some growth activity and get over 200 hours back if you have a 2 hour a day commute.
Cooking Food - I understand some people like the process of cooking but most dont and most don't like even more so the process of cleaning up. Hire a shelf or order preplanned/cooked meals and get 60-80 hours back per year. You cant outsource eating but I would try too if there was options.
Cleaning Your House - Get 26-52 hours back per year by hiring a cleaning company.
Property Management - Hire a company to help you with placing your tenants or doing everyday management and get 20 hours back in a non turnover year and up to 80 hours back during a turnover year.
There are many examples more of what you will find if you do a time study but any amount of savings that allows you to allocate 1.5 hours per day to financing and locating your next property will get you that next property months or years faster.
If you still have a real estate investing team to build, make sure you check out “Build Your Team” on our website.
Chicago Is Still a Great City to Scale—If You Know the Rules
The Chicago market has complexity as its advantage. The RTLO, the Just Housing Amendment, zoning overlays—it all makes this market tough for out-of-towners and inexperienced landlords. That’s your edge. Just don't take forever to be comfortable with your edge that it slows you down.
Because if you do know how to operate here, how to lease strategically, screen legally, manage seasonality, and comply without slowing down, then you’re already ahead.
Our clients who’ve scaled to 10+ doors didn’t do it overnight. They did it by focusing on practicing the two items above. By taking control over their property management and their time vs the two controlling them they are able to pay attention to what is next and not what is in front of me right now that I am going to deal with.
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
