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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast
There’s no shortcut to success in real estate, only discipline, consistency, and a belief in the market you serve. Chicago multifamily broker Joe Smazal has proven that formula works. Over 15 years, Joe has built a career that surpassed $1 billion in closed real estate sales, all while helping investors navigate one of the most dynamic urban markets in the country.
In this episode of the Straight Up Chicago Investor Podcast, Joe shares what it takes to build a career rooted in long-term focus and authenticity. From his early brokerage grind to launching the Real Estate Chicago Style podcast, Joe has made it his mission to create pro-Chicago conversations, showing how belief in this city can fuel both personal and professional success.
He dives deep into what’s driving the North Side multifamily market, how interest rate stability is affecting deal flow, and why patience, adaptability, and consistent effort remain the defining traits of top-performing investors. Whether you’re just starting out or managing a growing portfolio, this episode is a roadmap for navigating Chicago real estate with purpose and resilience.
Questions We Answer in This Episode
Q: What inspired Joe to launch his podcast, Real Estate Chicago Style?
A: Joe was tired of hearing negativity about Chicago. He wanted a platform focused on pro-Chicago stories, featuring people creating value, investing, and growing their businesses here. His only rule for guests? No city-bashing.
Q: What are the biggest mistakes landlords are making right now with security deposits?
A: Many are violating Cook County and Chicago regulations by collecting too much or failing to disclose proper bank details. In Cook County, landlords can’t collect more than 1.5 months’ rent, and even that half-month must be payable in installments if tenants request it. Joe recommends considering non-refundable move-in fees instead, which can simplify compliance.
Q: How did Joe grow from a new broker to surpassing $1 billion in closed transactions?
A: Through consistency and discipline. Joe explained that the early years were all grind, no vacations, no balance, just relentless focus. He built his success deal by deal, keeping the same energy and integrity through every cycle.
Q: What’s the biggest challenge for Chicago multifamily sales in 2025?
A: Buyer and seller psychology. Even when deals make sense, hesitation caused by rate expectations or shifting market sentiment can derail transactions. Joe says brokers must act as steady navigators, setting clear expectations, staying proactive, and adding value throughout the process.
Q: What was unique about the 94-unit West Rogers Park deal Joe recently closed?
A: It involved a CMBS loan assumption, notoriously difficult in mid-market multifamily. Joe credits the buyer’s simplicity, preparedness, and teamwork for closing in just 75 days, a near record for this type of transaction.
Q: How does Joe’s experience as an investor shape his brokerage approach?
A: Joe and his wife now own and manage multiple Chicago buildings. He says operating property firsthand makes him a better advisor, understanding the late-night maintenance calls, financing stress, and renovation realities that owners face.
Q: What did Joe learn from selling one of his own Lincoln Park buildings?
A: He hired another brokerage team to handle it, because representation matters. “I believe in the value of having a buffer and exposure,” he says. “Just because I can sell it doesn’t mean I should.”
Q: What areas is Joe buying in now, and what’s his investment criteria?
A: Joe focuses on North Side neighborhoods like Lincoln Park, Roscoe Village, North Center, and Logan Square. He avoids heavy rehabs, preferring stabilized or lightly improved assets in A+ locations that can perform for decades.
Q: What’s Joe’s long-term vision for the next five years?
A: Grow his personal portfolio to about 50 units and continue acquiring one to two buildings per year, balancing brokerage work with hands-on investing. He’s also focused on having more fun and celebrating wins along the way.
Q: What’s Joe’s outlook for Chicago’s real estate market?
A: Joe remains bullish on Chicago. Crime is down, the neighborhoods are vibrant, and rental demand remains strong. He expects rent growth to continue, moderate politics to return, and new development to help balance supply and affordability.
Show Notes
00:00 Hiring opportunities at GC Realty & Development and other Chicago real estate companies
01:23 Housing Provider Tip of the Week – Security deposit mistakes in Cook County and Chicago
03:16 Guest intro: Chicago multifamily broker and podcaster Joe Smazal
05:25 Why Joe started Real Estate Chicago Style
07:35 The mission behind promoting pro-Chicago stories
10:10 Advice for creating engaging real estate content
13:17 How Joe built a billion-dollar brokerage career
16:10 Early challenges and lessons from lost deals
20:21 2025 North Side Chicago market update
23:00 How interest rate expectations impact deal flow
25:07 Case study: 94-unit CMBS loan assumption in West Rogers Park
28:05 How operating rental properties improved Joe’s brokerage perspective
33:22 Selling his own building and navigating the 1031 exchange process
36:07 Lessons learned from the Northwest Side Preservation Ordinance
40:32 Why Joe hires professional brokers even when he could sell himself
41:28 His first 1031 exchange experience
42:58 What Joe’s buying next and why he prefers stabilized assets
44:02 The next five years: expanding his portfolio to 50 units
47:06 Mindset shifts: enjoying success and celebrating milestones
48:42 Joe’s five-year outlook for Chicago real estate
50:12 How discipline and consistency built his billion-dollar career
52:15 Advice for first-time Chicago investors
53:06 Lifestyle, family balance, and staying grounded
54:21 Recommended resources and local professionals
55:40 Where to connect with Joe and learn more
Takeaways for Chicago Property Managers and Landlords
- Discipline and consistency are the foundation of long-term success, whether you’re brokering deals or managing rentals.
- Chicago’s security deposit laws remain a major pitfall; landlords should understand Cook County’s 1.5-month rule and consider non-refundable move-in fees.
- Strong North Side rental demand continues to drive value, especially for quality, well-located buildings.
- Buyer and seller psychology are as critical as financing, manage expectations early to keep deals on track.
- Owning property personally gives brokers and property managers deeper credibility and insight.
- Chicago’s rental market remains fundamentally strong with limited new supply.
- Real estate success is a long game, focus on steady improvement and celebrate small wins along the way.
Guest Name: Joe Smazal
Guest Company: Interra Realty
Guest Link: https://interrarealty.com/team/jsmazal/
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
