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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
If you’ve ever looked at Chicago real estate and thought, “Man… I just want to buy one small building and not screw it up,” this episode is for you.
Because Niko Apostal isn’t out here selling a fantasy. He’s telling the real story, the one most people skip over. The long version. The messy version. The version where you start in residential, ride a hot market, get punched in the face by the crash, pivot into property management, scale to 800+ doors, sell at the right time, take a breath, then come back and build again, this time with a laser focus on the 2 to 4 unit game in Chicago.
And that’s the thread I want you to hear, whether you’re a first-time house hacker, a seasoned investor, or a Chicago property manager trying to understand what your owner clients are thinking right now.
Niko’s biggest message is simple, real estate works when you keep it simple. Buy a small building, live below your means, build your reserves, learn the physical building systems, and stack wins. Brick by brick.
Questions We Answer in This Episode
Q: What’s the simplest way to prevent eviction and rent collection problems before they start?
A: Stop taking people at their word and get serious about the front end. Most applicants are good people, but it only takes a few bad apples to wreck your year. The whole theme of this conversation is that the best “fix” is better screening and better decision-making before you sign the lease.
Q: What did Niko learn scaling from 0 to 800+ doors?
A: Scaling is people and systems. Hire for attitude, hustle, and resilience. Give people resources and clear goals, then let them run. If you try to scale by micromanaging, you hit the ceiling fast. If you scale with systems and operators, you can grow with only incremental fixed cost increases.
Q: Why did Owl Management stop managing condo associations?
A: Reporting burden. One owner with 12 units is one report with 12x the revenue potential. A 12-unit condo association is 12 owners, 12x the work, for one fee. They realized the time cost and complexity were not worth it, so they focused on rentals.
Q: What did buyers actually want when they tried to acquire the property management company?
A: Not just the door count. They wanted the staff and the systems. Hiring and training is hard, so an acquisition that comes with trained people on the same software and processes can be more valuable than the book of business alone.
Q: What’s the “house hacking” math that most people miss?
A: You’re buying a building with leveraged appreciation. If you put 10 percent down on a $525,000 two-flat, appreciation hits the full asset value, not your down payment. You still have responsibility and a mortgage, but if you buy responsibly, the leverage works in your favor.
Q: What are the biggest “gotchas” when buying a 2 to 4 unit in Chicago?
A: The unsexy stuff that becomes expensive fast.
- Galvanized plumbing vs copper, galvanized means more calls, more leaks, more cost.
- Fuse panels vs circuit breakers, fuses can mean safety risk, higher insurance, and costly upgrades.
- Hot water delivery time to the farthest fixture, it hints at system layout and potential future headaches.
- Tiny bedrooms, like 7x9 layouts, limit rent growth more than people realize.
- Signs of water intrusion, stains on walls, basement issues, rear masonry problems.
- Non-conforming garden or attic units, insurance and compliance can change the deal economics quickly.
Q: How does Essex 312 differ from Essex Realty Group?
A: Essex Realty Group is known for selling larger multifamily and portfolios, often 20 to 400 units. Essex 312 is built for smaller buildings, generally 3 to 12 units, and they structure the information differently because the debt and buyer mindset is different, especially for 4 units and under where buyers can finance like a single-family and put as little as 5 percent down, sometimes less depending on the program.
Q: What’s the outlook for Chicago over the next 5 to 10 years?
A: Niko is bullish. Chicago has massive unrealized potential. The housing stock supports small investing. The affordability relative to coastal cities is still a shock to people moving in. The city needs more coordination and will, but he believes a few changes can unlock a lot of upside.
Timestamped Show Notes
00:00 The episode vibe, languages on the pod, and why this one is pure simple value
01:42 Housing provider tip, Cook County tax timing and reassessment reminders
02:50 Niko’s background, growing up in real estate, and entering the business in 2001
06:03 The early 2000s market, volume, fast transactions, and how little you learn in frothy times
07:46 2006 team growth, condo conversions, and the north side multifamily pipeline
10:52 The crash, the phone stops ringing, and the slow realization that things changed
13:11 Starting Owl Management, why responsiveness alone won business, and referral-first growth
14:50 Scaling doors, the milestones from 200 to 500 to 800, and what breaks at each stage
15:50 The pivot away from condo associations and why unit economics matter
17:30 Starting Keller Williams Chicago and the hidden overhead nobody expects
23:48 Frothy acquisition interest, selling the management company, and the timing into 2020
26:21 The reset, cutting obligations, family time, and rebuilding with intention
31:26 Hiring Elise, hiring for attitude, and setting real goals that build buy-in
33:17 Niko’s Logan Square two-flat, renovation, equity, and why house hacking changed everything
36:36 Rebranding to Nico Collaborative and leaning into 2 to 4 unit investing
38:01 Elise’s 3-flat story, life transformation, and why this model creates options
40:54 Essex 312 gets created, referrals dry up, and why the division exists
43:50 Financing differences for 4 units vs 5+, and simplifying the buyer experience
48:17 “Gotchas” checklist, plumbing, electric, hot water, bedroom sizes, and insurance swings
52:18 A West Town deal example near the United Center, rent growth, and why the pocket matters
58:42 ADU upside, adding units, and why some areas are more pro-development than others
60:08 Chicago macro outlook, affordability, housing stock, and unrealized potential
61:59 Competitive advantage, win-win mindset and abundance approach
62:39 First-time buyer advice, live below your means and save capital
63:07 Resources, Cityscape, the book Hold, and simple evaluation tools
64:20 How to connect with Niko and the value he’s looking to create
65:00 Chicago fact, Pilsen name origin trivia, and wrap-up
Takeaways for Chicago Property Managers and Landlords
If you manage property in Chicago, or you’re self-managing and trying to keep your sanity, this episode has a few reminders worth taking seriously.
Hire and scale the same way you screen tenants.
Hire on attitude and resilience. Thick skin matters in property management because the feedback loop is mostly complaints. Great operators can handle criticism, adapt, and keep moving.
Economies of scale are real, but only if your service model matches them.
Managing condo associations and rental units at the same time can crush your team. The work to fee ratio can be brutal. Know what you are actually being paid to do, and what it costs in time.
The 2 to 4 unit “owner occupant” buyer thinks differently than an investor.
They care about monthly out-of-pocket cost, safety, and livability, not just NOI. If you’re leasing or managing for these owners, educate them on building systems, insurance, compliance, and long-term planning.
Physical building basics will save you thousands.
Galvanized pipes, fuse panels, water stains, undersized bedrooms, slow hot water delivery, these aren’t “inspector trivia.” These are rent ceiling and maintenance call multipliers.
Chicago’s small multifamily stock is still one of the best training grounds on the planet.
That’s not hype. It’s density. It’s access. It’s the ability to buy a building and have the rents reduce your monthly cost in a city where single-family inventory can be limited and expensive.
Guest Name: Niko Apostal
Guest Company: Niko Collaborative - Essex 312
Guest Link: https://nikocollab.com/agent/niko-Apostalal
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC, we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique, and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Founder, Partner, Podcast Co-Host, and Investor
