Jeffrey Ma may have started out in his family’s restaurant business, but his mindset, discipline, and grit have transformed him into a rising force in Chicago real estate. In this episode, Jeffrey shares how the lessons learned in his family’s restaurant helped shape his real estate investing career, from building systems and automating processes to managing guilt, culture, and family obligations along the way.

This one’s a must-listen for any Chicago Property Manager or aspiring investor who thinks their daily job (or family business) is keeping them from launching their real estate career.

Questions We Answer in This Show

Q: What can landlords and property managers learn from the restaurant industry?
A: Discipline, customer service, and process-driven operations. Jeffrey explains how the restaurant industry taught him to work under pressure, serve consistently, and build the systems that real estate investing requires.

Q: How do you handle guilt and family obligations while growing a real estate business?
A: For Jeffrey, it was about learning to systematize both businesses. He didn’t want to abandon his family’s restaurant, but also knew he had to grow. He shares how automating and streamlining his roles helped him support both dreams.

Q: What role does culture play in Jeffrey's real estate journey?
A: Jeffrey’s family obligation is tightly woven into Jeffrey's identity. He shares how balancing that cultural responsibility with personal growth is difficult, but possible with the right systems in place.

Q: What’s Jeffrey’s advice to new Chicago investors?
A: Believe in yourself. Don’t wait for everything to be perfect. You’ll make mistakes, but that’s part of the process. Just get started, and focus on making daily progress.

Q: What do successful property managers and investors have in common?
A: A love for systems, process, and continual self-improvement. Jeffrey stresses the importance of mental flow states, batching tasks, and being present—critical lessons for every Chicago Property Manager looking to scale.

Q: What mindset shift helped Jeffrey scale his investing?
A: Moving from survival mode to strategic growth. He stopped reacting to every issue and started designing systems that would allow him to build wealth and stay connected to his roots.

Q: What’s the most overlooked skill a Chicago Property Manager needs to develop?
A: Emotional intelligence. Whether dealing with tenants, vendors, or owners, staying calm under pressure, and listening well, helps resolve issues faster and build stronger relationships.

Q: How does martial arts influence Jeffrey’s approach to property management?
A: It taught him to stay calm in chaos, trust the process, and remain patient during long-term investments. Jiu-jitsu especially mirrors real estate: leverage, positioning, and mindset matter more than brute force.

Q: How do you know when it’s time to scale or automate in your business?
A: When recurring issues start eating up your time. Jeffrey believes property managers should look for patterns and implement solutions once they’ve handled the same fire twice.

From Restaurants to Real Estate: The Grit Behind the Growth

Jeffrey Ma didn’t just stumble into real estate. He grew up watching his parents hustle in the restaurant industry, working long hours without the luxury of delegation. The challenge? His mother’s work ethic was so hands-on, she couldn’t be replaced. And for Jeffrey, stepping away wasn’t as simple as hiring a manager.

The cultural pull of family loyalty is real. And instead of walking away, Jeffrey built his real estate business around his family. He developed systems that allowed him to stay involved at the restaurant while also investing, wholesaling, and creating passive income streams.

This is what makes Jeffrey’s story resonate with so many Chicago landlords: He didn’t make excuses. He built solutions.

Even with a newly growing family and the dream of building a future that includes children, Jeffrey remains committed to balancing it all. That balancing act mirrors what many property managers and landlords in Chicago go through—managing personal responsibilities while scaling rental portfolios.

He’s not just working in real estate. He’s building a life with real estate.

Mental Models That Matter for Chicago Property Managers

Jeffrey talks openly about "mind management over time management," a strategy from David Kadavy’s book that changed how he structures his work. Instead of juggling outreach, admin, cold calls, and marketing all day long, he batches tasks based on his mental energy. That focus helped him scale faster, with less burnout.

Every property manager in Chicago juggling leasing, renewals, maintenance, and owner updates can learn from this. Understanding when to do deep work, creative work, or simple administrative work is key to long-term success.

And don’t overlook flow: Jeffrey’s black belt in Brazilian Jiu-Jitsu and Taekwondo didn’t just give him discipline—it gave him perspective on how to stay calm and focused even when things go sideways.

He explains how martial arts taught him to stay centered, respond instead of react, and build stamina through discomfort—lessons every Chicago landlord could use when navigating evictions, turnovers, and late-night maintenance emergencies.

His productivity habits—built on flow, energy cycles, and focus—mirror what high-performing Chicago Property Managers need to thrive.

Real Estate Takeaways for Landlords in Chicago

Balance isn’t either/or — You can support your family and build wealth, but only with the right systems.
Use mental states to your advantage — Deep work during focused hours, light admin during slower moments.
Mistakes are the price of admission — Don’t wait until everything’s perfect. The best Chicago property managers learn by doing.
Automate and delegate — Whether it’s maintenance requests or lease renewals, systematize where you can.
Cultural values matter — Your "why" can be rooted in your family. It doesn’t have to be separate from your business.
Build flow into your process — Learn to recognize when you’re most focused, and protect those windows of time.
Start where you are — You don’t need everything figured out. Just begin.
Find local mentors — Jeffrey gives credit to people like RJ De Leon, who supported him through tough deals.
Respect the grind — Whether it’s washing dishes or patching drywall, every job has lessons if you’re willing to learn.
Stay calm and systematize — Don’t build your rental business on adrenaline. Build it on process.
Don't ignore your day job skills — Customer service, inventory control, and operations from your current work might be your secret landlord advantage.
Consistency beats intensity — Jeffrey's growth came from steady effort, not overnight success. Focus on what you can do every day.

Show Notes

00:00 – Jeffrey's internal struggle: family restaurant vs. real estate dreams
01:06 – Seeking clarity at Clever Summit in Las Vegas
02:35 – Why cultural identity plays a big role in business decisions
04:25 – How Jeffrey balances support for his parents while building his own career
06:14 – Automating systems in the restaurant to stay involved
07:40 – Thinking about the future: kids, legacy, and lifestyle design
08:40 – The truth about growing up in the restaurant industry
09:45 – Thoughts on The Bear: How close is it to real life?
11:00 – Competitive advantage: falling in love with self-improvement
12:03 – Advice to new investors: believe in yourself and start
13:17 – How Brazilian Jiu-Jitsu impacts mindset and business
14:46 – Book recommendation: Mind Management, Not Time Management by David Kadavy
16:16 – Strategic batching vs. inefficient multitasking
18:00 – Community shoutout: RJ De Leon and real estate support
19:00 – Connect with Jeffrey Ma for JV opportunities and support
20:00 – Final thoughts, gratitude, and wrap-up

Guest Name: Jeffrey Ma

Guest Company: Keller Williams Preferred Realty

Guest Link: https://www.linkedin.com/in/jeffmarealestate

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,