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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
It is also about knowing the right people, staying involved, understanding legislation, supporting housing provider advocacy, and learning from the investors, brokers, lenders, and organizations that are actively shaping the market.
In this episode, Mark Ainley and Tom Shallcross take the Straight Up Chicago Investor Podcast on the road to the NBOA Summer Soiree. Instead of one long-form guest interview, this episode features short conversations with several Chicago real estate leaders, including Nathan Andis, Mike Glasser, Brie Schmidt, Cory Oliver, Erica Miles, Noah Birk, Gabe Horstick, and Eric Workman.
The conversations cover why housing providers need to get involved with NBOA, how Chicago policies can affect small landlords, where investors are still finding opportunities, why South Side investing requires stronger underwriting, how CIC supports housing providers through training, and why Chicago real estate remains a relationship-driven business.
For Chicago landlords and investors, this episode is a reminder that your network is not optional. It is part of your risk management, your deal flow, your advocacy strategy, and your long-term growth.
Questions We Answer in This Episode
Q: Why does NBOA matter for Chicago housing providers?
A: NBOA gives landlords, investors, and housing providers a way to stay informed, advocate, and push back on policies that could make it harder or more expensive to provide housing.
Q: What was the main takeaway from the Summer Soiree?
A: The event showed how many serious Chicago real estate operators are willing to come together, network, fundraise, and support the industry beyond their own portfolios.
Q: What did Nathan Andis share about investing in his backyard?
A: Nathan talked about buying 24 units in the Proviso corridor, including multiple six-unit buildings. His biggest point was that knowing your market lets you move quickly when the right opportunity appears.
Q: How did Nathan find one of his recent deals?
A: One six-unit building hit the MLS and was clearly underpriced. Nathan already knew the area, moved quickly, called his broker, and had the property under contract within hours.
Q: What did Mike Glasser say about NBOA’s role right now?
A: Mike explained that NBOA has grown through major challenges, including COVID, city-level policy fights, and state-level advocacy. He emphasized that housing providers need to stay organized and involved.
Q: Why did Brie Schmidt get more involved in advocacy?
A: Brie said she had long supported the RLTO when owners understood and followed the rules. But proposed ordinances like the Northwest Side Preservation Ordinance and the new pro-tenant proposals pushed her to get more involved.
Q: What was Brie’s concern about just cause rules?
A: Brie warned that if landlords cannot non-renew without major relocation payments, owners may become much stricter in screening and buyers may want buildings delivered vacant, which could create more displacement.
Q: What did Cory Oliver say about investing on the South Side?
A: Cory said investors often fail because they do not run realistic numbers. He recommends higher vacancy and collection loss assumptions and understanding the real cost of operating in the area.
Q: What does CIC offer Chicago housing providers?
A: Erica Miles explained that CIC provides property management training, in-person classes, certificates, and education for independent landlords and housing providers.
Q: What did Eric Workman say about why events like this matter?
A: Eric said Chicago is a large market but a small industry. The right room can connect investors with brokers, lenders, attorneys, title companies, elected officials, and people who can help solve problems.
Show Notes
00:25 Mark and Tom recap the NBOA Summer Soiree and why new faces matter in real estate networking
03:36 Nathan Andis shares why WSBOA supports NBOA and why Chicago policy can move into Cook County
04:32 Nathan breaks down buying 24 units in the Proviso corridor
07:34 Mike Glasser discusses NBOA growth, advocacy, and the state of Chicago housing provider issues
11:48 Brie Schmidt explains why she became more involved in landlord advocacy
14:02 Brie breaks down concerns around Mayor Brandon Johnson’s proposed ordinance and just cause rules
18:29 Cory Oliver talks South Side investor groups, tenant relationships, and operating realities
22:19 Cory explains why South Side investors fail when they underestimate vacancy, collections, taxes, and insurance
23:52 Erica Miles shares how CIC supports independent landlords through property management training
45:16 Eric Workman explains Renovo’s July lending volume, larger loans, and why certainty of closing matters
Takeaways for Chicago Property Managers and Landlords
Housing provider advocacy is becoming more important in Chicago.
Policies passed in Chicago can influence the rest of Cook County and nearby suburbs.
NBOA is a key resource for landlords who want to stay informed and involved.
Good deals still exist on the MLS when investors know their market and move quickly.
South Side investing requires realistic vacancy, collection loss, taxes, insurance, and operating assumptions.
Tenant relationships matter, especially in communities where owners are part of the neighborhood fabric.
CIC remains an important training resource for independent housing providers.
Brokers who also own buildings often develop more empathy for investor clients.
Chicago still has strong demand for well-located, quality rental housing.
Networking events are not just social events. They are where investors build trust, solve problems, and find future opportunities.
Guest Names:
Nathan Fernandez, Mike Glasser, Brie Schmidt, Corey Oliver, Jessica Miles, Noah Birk, Gabe Horstick, and Eric Workman
Guest Organizations Mentioned: NBOA, WSBOA, CIC, Renovo Financial, Essex Realty Group, and local Chicago investor groups
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
