This week, learn why property managers can make or break your multifamily investment. John explains that once you decide to scale, you cannot do everything yourself, which means your success depends heavily on your ability to find the right property manager, understand what good management actually looks like, and stay actively involved enough to guide performance without getting buried in the day-to-day.
Drawing from his own experience self-managing a two-unit building and later overseeing larger apartment assets, John breaks down the real work property managers handle, from turns and leasing to inspections, vendors, communication, and performance tracking. He also explains why many investors make the mistake of blindly trusting property managers without understanding the basics of the role themselves, and why that lack of knowledge makes it harder to vet, manage, and retain the right people.
If you want to build a stronger multifamily operation, this episode gives you a practical framework for how to think about property management as a core part of the business.
Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.
Key Takeaways
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Understand why property managers should be treated as a critical driver of investment performance, not just a service provider
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Learn why investors need a working knowledge of property management basics so they can vet and guide managers more effectively
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Match your property manager to the property type and business plan, because a strong Class A operator may not be a strong fit for a Class C asset
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Build a repeatable management process around KPIs, meetings, approvals, and communication loops
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Retain great property managers by aligning incentives, giving recognition, and thinking through how your long-term plans affect their career stability
Topics
Why Property Management Matters So Much
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John says investors cannot scale if they try to do everything themselves, and that property managers are essential to driving success across the portfolio
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He also notes that even experienced operators sometimes have to replace property managers because the fit, execution, or staffing changes over time
What John Learned by Self-Managing
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Early in his investing journey, John self-managed a two-unit building with his wife, which forced him to learn the full cycle of managing a rental asset
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That included handling unit turns, contractor coordination, marketing, leasing, applications, compliance, and minimizing downtime between residents
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He argues that this experience matters because investors who have never managed property often do not know what good property management actually requires
Process First, Then People
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John frames most operational issues as either a process problem, a people problem, or a partnership problem
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He emphasizes starting with process, so expectations are clear and performance is not dependent on one person’s instincts or style
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He compares this to the consistency of a fast-food chain versus the variability that can happen when a restaurant relies too much on one chef without strong systems
Finding the Right Property Manager
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John says the first step is knowing what kind of results you need based on the property’s business plan
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A Class A luxury property may require a more polished, service-oriented manager, while a Class C asset may require someone with thicker skin, more hands-on oversight, and experience handling subsidy programs or tougher resident interactions
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He shares an example of hiring a highly respected management company for an eight-unit Class C property in Chicago, only to find that their experience with Class A/B assets did not translate well to the realities of that building
What Managing Property Managers Looks Like
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John recommends frequent conversations, especially early on, often starting with weekly calls and sometimes more often if a property is more operationally intense
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Those meetings should start with key KPIs like occupancy, vacancy, move-ins, signed leases, and financial performance before drilling into maintenance tickets, projects, and operational issues
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He also recommends setting approval thresholds for spending and paying close attention to vendor relationships so managers are not simply hiring friends or using the wrong vendors without oversight
Why Scale Can Improve Management Efficiency
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John notes that larger properties can actually be easier to manage at a high level because they support more dedicated staff and clearer role separation
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On a larger asset, the owner should be managing the manager, not solving individual resident issues directly
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He contrasts this with smaller properties, where owners often get dragged into too many day-to-day details because there is not enough scale to support a stronger operating structure
Why Regional Managers Matter
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When working with a third-party management company, John likes to involve the regional manager in as many conversations as possible for alignment and transparency
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Without that, property managers can get caught between the owner’s objectives and the management company’s internal priorities, which can create conflict or misalignment
How to Retain Great Property Managers
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John says retention starts with understanding motivations, especially compensation and growth opportunities
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He recommends tying incentives and bonuses to the owner’s objectives and the property’s KPIs rather than relying only on static compensation
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He also highlights the importance of praise, recognition, and regular positive feedback because property managers spend much of their day absorbing complaints and solving problems
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Finally, he encourages owners to think ahead about what happens to managers if a property is sold, since uncertainty about job stability can influence retention and morale
📢 Announcement: Learn about our Apartment Investing Mastermind here.
Next Steps
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Explore the Multifamily Mastermind and request more details here.
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Review whether you truly understand the basics of property management well enough to evaluate your current manager’s performance
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Match your management company or manager to the specific class, tenant profile, and business plan of the property
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Create a standard meeting structure built around KPIs, financials, maintenance, projects, and clear follow-up expectations
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Set spending thresholds, vendor standards, and communication expectations so managers know when to act and when to seek approval
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Build a retention plan that includes compensation alignment, recognition, and clarity around future plans for the property
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