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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

There’s no shortage of real estate hustle stories in Chicago, but few are as practical — and repeatable — as what Micah White is doing. He didn’t start with millions, institutional investors, or shiny new construction. He started like most Chicago landlords: with an old three-flat, below-market rents, and an inspection report thicker than a phone book.

Through transparent conversations with residents, calculated renovations, and a disciplined underwriting process, Micah has scaled from house hacking in Logan Square to building out a broader portfolio in neighborhoods like North Lawndale — while also structuring deals to bring in investor capital.

If you’re a Chicago property manager, landlord, or aspiring investor, this episode is packed with lessons you can apply immediately.

Questions We Answer in This Episode

Q: How can landlords raise rents fairly without burning bridges?
A: Be transparent. Micah sat down with residents, explained his purchase price and rising property taxes, and showed market comparables. By inviting residents into the conversation, increases felt like a shared decision — not a surprise. In one case, a resident moved out and the unit was renovated from $545/month to $1,325. Another long-term resident agreed to move from $1,495 to $1,900 — still under market but fair to all parties.

Q: What should landlords focus on in a 120-year-old Chicago inspection report?
A: Don’t panic over slanted stairs or uneven floors. Focus on roof life, foundation integrity, masonry (parapets, lintels), and major mechanicals. These are the items that will sink your budget if ignored.

Q: What’s a common seasonal mistake Chicago landlords make?
A: Leaving window A/Cs in over winter in boiler buildings. That’s like heating the street all season. Either require residents to remove them or send maintenance to pull them each fall.

Q: How should landlords compare Logan Square to North Lawndale?
A: Both work, but for different reasons. Logan offers higher acquisition costs and long-term residents. Lawndale provides better basis per unit and more upside, but requires strong screening and management systems. Good tenants exist everywhere — your screening process determines your outcome.

Q: What are the pitfalls of DIY maintenance?
A: A $50 wax ring “fix” turned into a $1,500 drywall and plumbing job when the toilet leaked into the unit below. Lesson: know when to call professionals.

Q: How should partners structure ownership?
A: Avoid both partners going on the same mortgage if possible. Each carries the full debt on their personal balance sheet. Better strategy: alternate ownership or hold personally until refinancing, then transfer to an LLC.

Q: How can young investors start raising capital?
A: Build a track record with your own money first. Then start with friends and family. Micah uses two approaches: (1) short-term preferred returns (8–12%) with a refinance exit, or (2) a 70/30 split where investors capture depreciation benefits and exit multiples after 3–5 years.

Q: What’s Micah’s biggest competitive advantage?
A: His institutional background at LaSalle Investment Management gave him experience in underwriting large deals, understanding investor sentiment, and applying that rigor to Chicago’s smaller, non-institutional market.

Show Notes

00:00 Transparent rent increases and how to handle resident conversations
02:30 Housing provider tip: removing window A/C units in winter
04:00 Micah’s background: from Indiana University to Chicago real estate
05:45 Lessons from institutional investing at LaSalle Investment Management
08:00 Institutional vs. mom-and-pop underwriting differences
11:00 Predicting rent growth and the risks of being wrong
14:00 Buying the first three-flat in Logan Square and house hacking
16:30 Understanding the hidden value of oversized Chicago lots
18:00 How to analyze deals quickly and move fast in competitive markets
20:00 Negotiating with sellers using 1031 timelines to your advantage
22:00 What to focus on in inspection reports of 120-year-old buildings
26:00 Masonry, parapets, and why they matter more than cosmetic issues
27:00 Resetting rents with transparency and renovations
31:00 The wax ring disaster: when DIY repairs cost $1,500+
36:00 Scaling to a four-unit in North Lawndale with a side lot
39:00 Structuring partnerships, mortgages, and LLCs
41:00 Comparing Logan Square to North Lawndale tenant pools
43:00 Why basis matters more than location in early scaling
44:00 Raising money: preferred returns vs. equity splits
52:00 How to find investors (hint: start with your own network)
56:00 The accountability of taking friends’ and family’s money
57:00 Micah’s competitive advantage: experience + team
61:00 Book and podcast recommendations
62:00 Final advice: “If you’re going to miss the bus, miss the bus running.”

Takeaways for Chicago Property Managers and Landlords

Transparent rent resets work. Residents accept increases when shown purchase price, tax impact, and local comps.
Inspections: prioritize roof, foundation, and masonry. Don’t waste budget on cosmetic quirks.
Systems prevent seasonal waste. Pull window A/C units to save on heating bills.
Neighborhood choice = strategy. Logan offers stability; Lawndale offers better basis and upside.
DIY repairs can backfire. Know when to hire licensed professionals.
Partnerships require planning. Don’t double-stack debt obligations; alternate ownership or hold personally until refi.
Raising capital requires proof. Start with your own money, then leverage friends and family with clear structures.
Competitive edge = experience + team. Institutional underwriting discipline combined with trusted local contractors, lenders, and agents makes scaling possible.

Guest Info

Guest Name: Micah White
Company: Real Estate with Micah
Instagram: @realestatewithmicah

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,