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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
Sometimes it starts with one building, one partner, one refinance, one off-market call, and the willingness to move faster than most people are comfortable moving.
In this episode, Tom Shallcross and Mark Ainley sit down with Arthur Barkan to talk about how he went from working as a chemist to building an 80-unit portfolio in roughly two years. Arthur shares how he bought his first building in Rogers Park with his brother, moved into Evanston, found opportunity in North Chicago, used cash-out refinances to recycle capital, and eventually left his W2 job to focus on real estate full time.
The conversation covers North Chicago investing, Section 8, Lake County evictions, off-market deals, cash flow, water chargebacks, self-management systems, maintenance staffing, inspections, and why concentrating units in one area can make operations easier.
For Chicago and suburban investors, Arthur’s story is a reminder that the deal matters, but operations matter just as much. If you can buy at the right basis, raise rents responsibly, manage expenses, and keep your team close to the properties, you can scale faster than most people think.
Questions We Answer in This Episode
Q: What’s the housing provider tip of the week?
A: Cost segregation can be a powerful tool, but Mark reminds investors that it usually makes more sense for properties they plan to hold long term. If you plan to sell in a couple of years, the strategy may not fit.
Q: Who is Arthur Barkan?
A: Arthur is a Chicagoland investor and realtor who built an 80-unit portfolio in about two years, with a heavy focus on North Chicago and nearby suburban markets.
Q: How did Arthur get into real estate?
A: Arthur studied chemistry and worked in pharmaceutical and lab jobs. After getting laid off, he wanted to do something different and bought his first building in Rogers Park with his brother.
Q: What was Arthur’s first real estate deal?
A: His first deal was a building in Rogers Park that he bought with his brother. His brother lived upstairs while they rented out the downstairs unit, giving them an early version of a house hack.
Q: Why did Arthur start buying in North Chicago?
A: Arthur saw strong rent-to-price ratios in North Chicago. He liked that units could be bought for under $100,000 per door while still producing rents that made the numbers work.
Q: What are the risks of investing in North Chicago?
A: Arthur is direct that crime and tenant issues can be real. He also says investors need to understand the municipality, inspections, landlord licensing, Section 8, and operational challenges before buying there.
Q: How did Arthur grow so quickly?
A: He used cash-out refinances to recycle capital. After buying and stabilizing properties, he refinanced, pulled out capital, and moved that money into the next deal.
Q: What happened with Arthur’s 25-unit deal?
A: Arthur bought a 25-unit property for $1.9 million, dealt with seven evictions and five vacancies, turned over units, improved rents, refinanced at a higher valuation, and pulled out roughly half a million dollars.
Q: How does Arthur manage 80 units?
A: He uses property management software, RingCentral, a secretary to handle calls and bills, and a maintenance person who handles repairs, showings, and day-to-day property needs.
Q: What is Arthur’s biggest advice for new investors?
A: Do not be afraid. Arthur believes investors need to take action, understand the numbers, build a team, and learn how to make deals work instead of waiting for perfect conditions.
Show Notes
01:37 Housing provider tip: when cost segregation makes sense for long-term holds
02:50 Arthur Barkan joins the podcast and shares how he got started in real estate
03:22 From chemistry and lab work to buying a first building in Rogers Park
05:14 Buying in Evanston and using early momentum to keep moving
07:56 Why Arthur focuses on North Chicago and sees it as a hidden opportunity
11:19 How a neighbor call led to buying 12 units and 25 units off market
14:48 Using cash-out refinances to recycle capital into the next building
15:37 Buying a 25-unit building for $1.9 million and dealing with evictions and vacancies
23:58 Leaving a W2 job after building enough cash flow and real estate income
36:34 Self-managing 80 units with software, RingCentral, a secretary, and a maintenance person
Takeaways for Chicago Property Managers and Landlords
- Cost segregation is usually a long-term hold strategy, not a short-term flip strategy.
- The first deal does not need to be perfect, but it needs to teach you how the business works.
- North Chicago can offer strong rent-to-price ratios, but the operational risk is real.
- Investors should understand crime, tenant quality, inspections, licensing, and local rules before entering a market.
- Cash-out refinancing can help investors recycle capital and scale faster.
- One strong deal can create the capital for the next deal.
- Concentrating units in one area can make maintenance and management more efficient.
- Water chargebacks can make a meaningful difference when utility costs are high.
- Self-management requires systems, not just effort.
- A good maintenance person, call system, and property management software can help an owner scale beyond a few units.
Guest info
Guest Name: Arthur Barkan
Guest Company: Barkan Realty
Guest Link:https://www.barkanrealty.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
