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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Breaking into Chicago real estate isn’t about flashy deals or perfect timing — it’s about learning the market from the ground up, understanding buildings, and taking action before you feel “ready.” On this episode of the Straight Up Chicago Investor Podcast, Reed Meyer joins Mark Ainley and Tom Shallcross to walk through his rapid growth from a first Logan Square three-flat to flipping small neighborhood warehouses and scaling into multifamily ownership across Chicago.
Reed’s story is a reminder that progress comes from doing the work: leasing units, walking neighborhoods, underwriting deals, and learning Chicago’s block-by-block dynamics. This episode is packed with real lessons for housing providers, property managers, and investors looking to grow intelligently in one of the most competitive markets in the country.
How Leasing Became the Fastest Way to Learn Chicago Real Estate
Before Reed ever scaled into larger multifamily deals, he focused on leasing. That hands-on exposure gave him daily insight into what actually drives demand — not just what spreadsheets say should work.
Leasing taught him:
- Where pricing breaks down by neighborhood
- How unit layouts outperform bedroom counts
- What amenities tenants actually pay for
- How fast the market reacts to bad listings
That experience eventually led to the creation of Lease 312, a leasing operation handling hundreds of Chicago apartments each year while Reed continued growing his own portfolio.
Reed’s First Deal: Buying a Logan Square Three-Flat at 22
Reed bought his first property shortly after graduating college — a Logan Square three-flat using owner-occupied financing. He didn’t have deep reserves or years of experience, but he did have:
- A stable income
- A strong location
- A solid brick Chicago building
The deal wasn’t perfect, but it worked — and more importantly, it created momentum. That first building became the foundation for everything that followed.
Flipping a Tiny Lakeview Warehouse into a Capital Stack Breakthrough
One of the most unique deals Reed discusses is a small, triangular warehouse tucked into a Lakeview alley. It was:
- Poorly marketed
- Too small for institutional buyers
- Perfect for a niche local user
Reed purchased the building, marketed it directly to neighbors and hobbyists, and sold it roughly 45 days later for nearly double. without rehabbing it. That capital rolled directly into his next multifamily acquisition.
Q&A: Chicago Real Estate Lessons from the Ground Up
Q: Why did Reed focus on leasing before scaling acquisitions?
A: Leasing provides real-time feedback from the market. It sharpens pricing instincts, exposes demand trends, and builds relationships with owners and developers — all without overleveraging early.
Q: What’s the biggest mistake landlords make when listing rentals?
A: Inaccurate listings and poor photos. If a properly marketed unit isn’t generating at least 7 inquiries per week, it’s usually overpriced or misrepresented.
Q: What amenities matter most for North Side rentals?
A: In-unit laundry is no longer optional. Layout, light, and functional living space outperform extra bedrooms. Central HVAC and outdoor space are major differentiators.
Q: Why are leases such a major risk in Chicago?
A: Chicago lease requirements change constantly. Missing disclosures or outdated language can expose landlords to lawsuits and class-action risk, especially for larger portfolios.
Q: What rent growth is Reed seeing going into 2026?
A: New leases around 5–6%, renewals closer to 3–4%, with prime neighborhoods seeing higher jumps on turnover due to limited inventory.
Q: What advice does Reed have for newer investors?
A: Start where you can add value immediately. Leasing, management, or small value-add deals build experience faster than waiting for the “perfect” acquisition.
Show Notes & Timestamps
00:00 – Reed’s background and early investing mindset
03:40 – Buying a Logan Square three-flat at 22
09:55 – Learning Chicago block-by-block
14:30 – Flipping a Lakeview warehouse
20:18 – Why leasing accelerates market knowledge
26:40 – Pricing rentals based on inquiry volume
32:15 – Designing units tenants actually want
38:50 – Lease risk and compliance in Chicago
44:10 – Rent growth outlook for 2026
Takeaways for Chicago Property Managers & Landlords
Leasing is one of the fastest ways to understand real market rent
Brick buildings in strong neighborhoods forgive early mistakes
In-unit laundry is a baseline expectation on the North Side
Accurate listings drive speed and pricing power
Outdated leases create serious legal risk in Chicago
Market knowledge beats perfect timing
Momentum comes from action, not waiting
Guest Name: Reed Meyer
Guest Company: Lease 312
Guest Company Website: https://lease312.com
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
