Wonderful Togbey overcame tragedy, numerous immigration hurdles, and limited finances to build a 20-unit real estate portfolio in the Chicagoland area. In this inspiring episode, he breaks down the practical mindset shifts that took him from a W-2 job and paycheck-to-paycheck, to living financial freedom and multi-family ownership. Whether you're a new Chicago property manager or a seasoned landlord looking to grow, this is a masterclass in perseverance, automation, and building wealth with limited resources.

From house hacking his first 3-flat to leveraging local lender relationships, Wonderful lays out a blueprint that every aspiring Chicago landlord should follow. Learn how grit, community, and the right mindset helped him scale his portfolio while he worked full-time.

Questions We Answer in This Episode

Q: What strategies can new Chicago landlords use to buy their first multi-unit property?
A: Start with house hacking. Wonderful recommends buying a 2-4 unit property, living in one unit, and renting out the rest. This reduces personal living expenses and begins building cash flow and experience—making it one of the smartest ways to enter the market as a Chicago property manager.

Q: How can investors build a real estate portfolio while working a full-time job?
A: Wonderful grew his portfolio to 20 units while holding a W-2 job. He did this by building systems for property management, tenant communication, and rehab coordination—focusing on automation, strong relationships, and efficient time management.

Q: What’s the biggest mistake Chicago landlords make in the beginning?
A: Chasing immediate cash flow instead of long-term equity and system building. Wonderful emphasizes focusing on scalable models and building toward sustainable financial independence rather than flashy monthly returns.

Q: What financing options are available for foreign nationals investing in Chicago?
A: Local banks and credit unions may offer specific loan programs for foreign nationals. Wonderful navigated the process by working with flexible lenders, demonstrating strong income history, and saving diligently for larger down payments.

Q: How important is community in building a rental portfolio?
A: Extremely important. Wonderful built a support network through local meetups, BiggerPockets, and Chicago real estate groups. He credits shared knowledge and accountability with helping him scale faster.

Q: What mindset shift helped Wonderful go from survival mode to investor mode?
A: A focus on delayed gratification and long-term wealth. Wonderful chose to invest over spending on short-term luxuries. This decision fueled consistent portfolio growth and financial freedom.

Q: How can Chicago property managers create financial discipline to grow?
A: Automate savings and investing. Separate personal and business finances. Avoid lifestyle inflation. Set aside capital for reserves and reinvestment. These habits create sustainable, scalable success.

Q: How did Wonderful find deals in a hot Chicago market?
A: Networking with brokers, staying connected to wholesalers, and setting automated alerts on real estate platforms. Being ready to move quickly on deals made the difference.

Q: What should new landlords know about managing tenants in multi-family buildings?
A: Clear communication, strong leases, and professional boundaries are key. Wonderful treats his properties as a business and expects tenants to respect policies—especially in shared-living setups.

Q: What are the best Chicago neighborhoods for new investors in 2025?
A: South Shore, Chatham, and Auburn Gresham. These areas offer value-add opportunities, solid cap rates, and long-term upside for strategic Chicago property managers.

Q: Can I partner with someone to make up for my lack of credit or income?
A: Yes, but the partner must bring more than just a credit score. They need to contribute capital, experience, or both. Wonderful emphasizes that lenders want strong partnerships with shared responsibility.

Q: How can landlords automate their way to growth?
A: Use software for rent collection, maintenance tracking, and communication. Automate savings into reserves. Set up recurring reminders and calendar systems. Automation helps you scale without burning out.

Q: What habits helped Wonderful become financially free through real estate?
A: Waking up early (the 5AM Club), budgeting every dollar, reinvesting profits, tracking expenses monthly, and constantly networking with local property managers and investors.

Q: How does Wonderful approach risk when expanding his portfolio?
A: He sets aside reserves for each property, avoids over-leveraging, and focuses on predictable, stable cash-flowing properties. He evaluates each deal with conservative estimates and long-term exit strategies in mind.

Q: How can a new immigrant or first-generation American start investing in Chicago real estate?
A: Begin with education, budgeting, and setting a clear vision. Use FHA loans or partner with experienced investors to reduce risk. Wonderful emphasizes trusting the process and finding mentors early.

Q: What systems can property managers use to manage time more efficiently?
A: Property management platforms like Buildium, AppFolio, or RentRedi can automate rent collection, lease renewals, and maintenance tickets—freeing up time to focus on growth.

Q: What are some early red flags in multi-family investing that new landlords often miss?
A: Underestimating repair costs, ignoring tenant history, and assuming rents can rise too quickly. Wonderful advises conservative underwriting and planning for worst-case scenarios.

Show Notes

00:45 – Wonderful’s backstory: immigrating from Ghana and early financial struggles
04:28 – A personal tragedy sparks a total mindset shift
08:11 – First 3-flat purchase through house hacking in Chicago
11:33 – Navigating lending as a foreign national
15:22 – Budgeting, saving, and reinvesting every dollar
19:47 – Using automation to manage rentals and time
24:05 – Key lessons and risks while scaling to 20 units
29:40 – The 5 AM club: how waking early led to more deals
32:16 – How to manage contractors and cash flow wisely
35:12 – Final thoughts: advice for landlords stuck at 2-3 units
39:00 – Using community knowledge to unlock deal flow
42:05 – Finding undervalued properties and building teams
45:30 – Scaling responsibly in uncertain market conditions
49:20 – The mindset of doing hard things early to enjoy freedom later
53:40 – Realistic expectations vs. social media glamorization of real estate

Takeaways for Chicago Property Managers and Landlords

House hacking remains the top strategy to start building equity and experience in Chicago.
Community support and mentorship are key accelerators of growth.
Systematization and automation reduce stress and enable portfolio expansion.
Delayed gratification and long-term thinking are essential for wealth-building.
You don’t need perfect conditions—just consistency and resourcefulness.
Chicago landlords can benefit from local real estate meetups and investment groups.
Avoid over-leveraging and build reserves to withstand market changes.
Use your W-2 job as leverage: consistent income opens financing doors.
Understand your "why" before scaling—your mindset drives every action.
Working with investor-friendly real estate agents can help spot undervalued properties.
Never underestimate the power of one good deal—it can fund the next five.
Build relationships with small, local lenders—they often have more flexibility.
Practice patience: real estate rewards those who think in decades, not months.
Always run your properties like a business, not a hobby.
Find your investing tribe. The right community can cut years off your learning curve.

Guest Info

Name: Wonderful Togbey
Instagram: @mrwonderfulinvests
Website:Wonderful's Linktree

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,