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Michael Kaplan joins us to share his inspiring journey from a young broker struggling to make ends meet to scaling his real estate business and building a rental portfolio in the Chicago area. His story reflects grit, persistence, and strategic decision-making that any aspiring investor or broker can learn from.
Michael opens up about his decision to leave college during the pandemic and dive into real estate full-time. He breaks down the early challenges he faced, including months without income and the tough realities of building a client base. Eventually, Michael found his footing in leasing, leveraging relationships and hustling across Chicago neighborhoods. This early hustle paved the way for long-term success, as his leasing clients later became buyers and investors.
Watch Straight Up Chicago Investor Podcast Episode 372 in Full Here
Throughout the episode, Michael emphasizes the importance of mentorship, staying disciplined during turnovers, focusing on long-term wealth over short-term gains, and maintaining authenticity as a young professional in a competitive market.
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Questions We Answer in This Show
Q: How can new Chicago real estate agents succeed with limited capital?
A: Success with limited capital demands a relentless work ethic and relationship-building. Michael built his business by committing fully to leasing work, connecting with clients, and building a long-term reputation instead of expecting instant sales success.
Q: What challenges do new Chicago landlords face and how can they overcome them?
A: New landlords often underestimate the workload involved in turnovers and leasing. Michael advises new landlords to be patient, take tenant screening seriously, and avoid desperate decisions when units are vacant.
Q: Why is leasing critical to successful property management in Chicago?
A: Proper leasing sets the tone for the entire landlord-tenant relationship. Mistakes at the leasing stage can cause ongoing management headaches, legal issues, and financial losses.
Q: What are the best tenant screening strategies for Chicago landlords?
A: Michael stresses verifying all applicant information, contacting employers directly, reviewing paystubs carefully, and trusting your instincts. Using professional screening services can also help prevent costly mistakes.
Q: Why should landlords avoid telling tenants they own the building?
A: Disclosing ownership can blur boundaries and open the door to emotional appeals, late-night calls, and additional stress. Presenting as a property manager maintains professionalism and shields the owner from unnecessary drama.
Q: How can young real estate investors in Chicago build lasting wealth?
A: Living below your means, reinvesting profits, focusing on cash flow, and staying disciplined over time are key. Michael sees real estate brokerage as a way to fund long-term investment success.
Q: What’s the benefit of investing in Chicago suburbs like McHenry instead of Cook County?
A: Michael Kaplan chose McHenry for his first investment due to its more landlord-friendly environment compared to Cook County. He emphasizes the importance of not only running the numbers, but also physically exploring the neighborhood—checking foot traffic, businesses, and local energy—to validate an area’s potential.
Q: How should new investors in Chicago balance leasing responsibilities with a full-time job?
A: Michael warns that leasing and tenant management can easily demand 50+ hours per turnover, especially for inexperienced landlords. For those working another job, hiring a Chicago property management company allows you to protect your time and reduce risk without sacrificing the quality of tenant placement.
Q: Why do so many Chicago brokers fail to build wealth through investing?
A: Michael notes that while many brokers focus on closing deals, few take the extra step of becoming property owners. He believes real estate brokerage should be a stepping stone toward long-term wealth through investing in Chicago’s housing market—and that living below your means and reinvesting early is key to scaling.
Michael's Journey: From Uncertainty to Scaling Big
When Michael Kaplan left DePaul University during the COVID-19 pandemic, he committed fully to pursuing a real estate career. Online classes felt disconnected and wasteful, and he knew he needed to take bold action if he wanted to make a real impact. Despite facing skepticism from peers and a heavy burden of uncertainty, Michael relied on the support of his entrepreneurial family to navigate this major decision.
Starting with no network, no experience, and no significant capital, Michael found early opportunities by focusing on leasing. Leasing offered a faster path to transactions, allowed him to build rapport with clients, and helped him learn neighborhood dynamics throughout Chicago.
His first year brought minimal income. His second year brought some improvement. It wasn’t until his third and fourth years that Michael saw compounding returns—clients he leased apartments to were now calling him to help with home purchases and investments.
Michael's story shows that consistency, building authentic relationships, and providing real value over time is what creates true long-term success in real estate.
Why Leasing Matters (And Why Many Ignore It)
Leasing often gets overshadowed by flashier sales activities, but Michael is adamant that leasing is the backbone of property management and real estate investing.
A bad tenant placed during the leasing process can lead to months of headaches: unpaid rent, legal disputes, damage to units, costly turnovers, and even eviction. Leasing isn't just about filling a vacancy—it's about setting up the investment for long-term success.
Key Leasing Tips from Michael:
Always meet applicants in person when possible to get a sense of their reliability.
Use detailed and professional applications.
Verify employment and income directly with employers.
Cross-reference applicant information.
Never rush the leasing process because of fear of vacancy.
Michael's experience highlights that a careful leasing process saves thousands of dollars and months of stress.
The McHenry Investment: A Calculated First Step
When it came time for Michael to invest himself, he took a strategic approach. Rather than purchasing in the heart of Chicago, he opted for McHenry—a growing, landlord-friendly area.
Michael focused on several factors when selecting his first property:
Avoiding Cook County's increasingly restrictive landlord-tenant rules.
Selecting a property in an area with a strong rental demand.
Choosing a multi-unit building to reduce vacancy risk.
Buying at a price point that allowed positive cash flow from day one.
He put down a strong down payment, thanks to years of savings and living frugally at home. His approach reflects a mindset every investor should emulate:
Patience + Discipline = Opportunity.
By saving carefully, studying the market, and selecting a solid asset, Michael positioned himself for success without overleveraging.
Building Wealth While Young: Michael's Mindset
Michael's long-term vision is rooted in discipline and strategic action. He doesn't chase overnight success or social validation. Instead, he reinvests earnings, builds meaningful client relationships, and focuses on education.
Key elements of his mindset:
Live below your means. Lifestyle creep is the enemy of investing.
Think long-term. Real estate wealth compounds over decades.
Focus on relationships. Trust builds referrals and opportunity.
Embrace hard work. Hustle in your twenties to enjoy freedom later.
Michael encourages young professionals to see real estate not just as a career, but as a tool for creating freedom, stability, and generational wealth.
Show Notes
02:32 Housing Provider Tip: Clean dryer vents regularly to prevent fire hazards.
05:35 Michael Kaplan introduction and real estate background.
08:50 Leaving college during COVID to pursue real estate full-time.
12:16 Financial struggles and learning curve early in his career.
19:20 Joining a leasing team for mentorship and experience.
24:12 Tenant fraud stories and screening tips.
31:10 Time and effort involved in turnovers and leasing.
36:25 Choosing McHenry for his first investment property.
42:18 Living below means and investing for long-term wealth.
49:10 Staying authentic with clients as a competitive advantage.
52:22 Avoiding disclosure of ownership to tenants.
55:35 Building networks and evolving friendships through business.
59:00 Future vision: growing sales while staying connected to leasing.
Guest Info
Guest Name: Michael Kaplan
Guest Company: The REKAP Group
Guest Link: https://www.rekapgroup.com/michael-kaplan
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 give me a call.
Best Investing,
Mark Ainley
Founder, Partner, Podcast Co-Host, and Investor
