Vendor Portal
When you hear the words “$20 million portfolio,” most people imagine someone in the game for decades. But for Wyatt Simon, that success came in just a few years—through grit, strategy, and a lot of BRRRR deals. In this episode, Wyatt joins us to talk about how he used the BRRRR method (Buy, Rehab, Rent, Refinance, Repeat) to scale a massive portfolio in a short period, and the systems he created to make it sustainable.
Whether you're a new investor, an experienced Chicago property manager, or someone looking to transition from single-family to multifamily, this episode is a blueprint for how to think bigger and work more efficiently.
Questions We Answer in This Show
Q: How can Chicago landlords use the BRRRR method to scale?
A: Wyatt breaks down his process of buying distressed assets, rehabbing them smartly, renting to quality tenants, and refinancing to pull out capital. For Chicago property managers, this method can unlock rapid portfolio growth while maintaining strong operational systems.
Q: What systems are needed to support a growing real estate portfolio in Chicago?
A: Property management software, vendor networks, and automation. Wyatt shares how he systematized rent collection, maintenance coordination, and communication with lenders to make scaling manageable.
Q: What mindset helps when scaling a property management business in Chicago?
A: Resilience and clarity. Wyatt explains how focusing on long-term goals over short-term pain allowed him to persevere through evictions, contractor issues, and funding challenges.
Q: Should new investors become property managers too?
A: Not necessarily. Wyatt distinguishes between owning real estate and operating a property management business. He advises landlords to understand the difference and consider outsourcing to a professional Chicago property management company if they want true passive income.
Q: What’s the first thing a new Chicago investor should do before buying a property?
A: Build your cash machine. Wyatt recommends stabilizing your income stream before diving into real estate. It allows you to withstand unexpected issues and grow with confidence.
Q: What overlooked resource does every Chicago investor need?
A: Community. Wyatt credits much of his growth to being around other ambitious investors. Whether it’s a coaching program, a meetup, or a solid network, surrounding yourself with smart people accelerates growth.
Q: How can landlords use real estate to create a freedom-based lifestyle?
A: Through intentional planning. Wyatt shares how becoming a father reshaped his goals. He now focuses on cash flow, systems, and building a team so he can stay present at home while the business runs smoothly.
Q: What role does mindset play for property managers and investors?
A: It is everything. Wyatt talks about visualizing his funeral (inspired by Stephen Covey’s “Begin With the End in Mind”) and designing his life from that perspective. For Chicago property managers, that means building a business that serves your goals, not consumes them.
Q: What advice does Wyatt have for new property managers in Chicago?
A: Don’t try to do everything yourself. Invest in training, lean on experienced mentors, and don’t be afraid to delegate. The faster you build repeatable systems, the faster you can grow.
BRRRR in Chicago: A Framework for Scaling
Chicago’s diverse housing stock—from distressed two-flats to underutilized small apartment buildings—makes it an ideal city for BRRRR investing. Wyatt used this method to build his portfolio from scratch, turning neglected properties into income-generating machines.
For Chicago property managers, this strategy also highlights the importance of post-rehab operations. It’s not enough to renovate—you have to lease quickly, screen properly, and manage proactively.
The BRRRR method is most successful when the property management piece is airtight. That means having a strong move-in process, clear lease language, and systems for maintenance and rent collection.
The Property Manager’s Role in Scaling BRRRR
Wyatt makes a clear distinction between being a property owner and running a property management business. Too often, landlords blur the lines and burn out trying to do both. He encourages investors to treat property management as its own discipline.
In Chicago, that means understanding local ordinances (like the RTLO), managing turnovers to align with peak leasing seasons, and proactively addressing tenant concerns.
For landlords not interested in managing the day-to-day, partnering with a Chicago property manager who understands value-add properties and stabilization strategies is key. The right manager doesn’t just collect rent—they help preserve your rehab work, prevent vacancies, and protect your NOI.
Operational Systems to Support Growth
Wyatt emphasizes systems—something every good Chicago property manager should be obsessed with. He broke his book into three sections: how to buy, how to build systems, and how to scale.
Some of the systems that helped him succeed:
Vendor scheduling & oversight: Avoiding delays and cost overruns
Property dashboards: Tracking performance across multiple buildings
Communication SOPs: Making it easy for tenants and contractors to get what they need without overwhelming the owner
Property managers who implement these systems early on give themselves the edge—especially in Chicago where building compliance, taxes, and tenant relations can eat up your time.
Lessons for the Chicago Landlord
Know your role: Are you investing in real estate, or running a real estate business? The answer shapes your daily actions.
Systematize early: Don’t wait until you're overwhelmed. Build your systems while you’re small so they scale with you.
Visualize the end game: Design your portfolio based on the life you want—not just the properties you can get.
Use professional property managers: If you want passive income, hire a Chicago property management company that aligns with your goals.
Stay in your lane: Wyatt’s success came when he stopped trying to be good at everything. Focus on your strengths and delegate the rest.
Be visible: Social proof is powerful. Documenting your journey can lead to partnerships, deals, and long-term trust.
Don’t ignore education: Wyatt invested over $150K in real estate education—and credits it for accelerating his curve.
Serve others: His 7-Figure Mastermind is built on the idea that we rise by lifting others. That’s true in investing and property management alike.
Show Notes
00:00 – Introduction: How Wyatt went from solo deals to a $20M portfolio
01:32 – Becoming a father and re-aligning his business with life goals
03:45 – Why Wyatt created his 7-Figure Mastermind
05:10 – The real reason behind writing his book
07:45 – Posting on social media to build credibility and connections
10:20 – How to buy 20+ deals a year using BRRRR
12:30 – Three-part framework: Buy, Systematize, Scale
16:00 – Competitive Advantage: Relentless belief and persistence
18:40 – Clarifying your role: Investor vs. Operator
21:00 – What to do before buying your first property in Chicago
23:10 – Using property management systems to free up time
26:15 – Book recommendation: The Seven Habits of Highly Effective People
28:00 – How “Begin With The End In Mind” changed Wyatt’s trajectory
30:45 – Finding community with Jake & Gino and learning from mentors
34:30 – Connect with Wyatt: @wyattbuysbuildings and wyattsimon.com
37:41 – Chicago Fact: Average annual snowfall and seasonal trivia
Guest Info
Guest Name: Wyatt Simon
Connect: @wyattbuysbuildings / www.wyattsimon.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,
Mark Ainley
Founder, Partner, Podcast Co-Host, and Investor
