For The Property Managers With Big Dreams For Their City

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If you spend enough time in this industry, you eventually meet operators who want more than just "door count." Those who want to drive through their hometown 20 years from now and point to a thriving neighborhood and say, "We helped make that happen."

I’d seen it firsthand with JWB Real Estate Capital in Jacksonville. What started with them improving pockets of “C-class neighborhoods”, has grown into them redeveloping 20 blocks of downtown Jacksonville, and creating a culture that everyone wants to be part of.

It has been an unbelievable story to be part of. It also felt… exceptional. Like something no one else could pull off.

Then I had a conversation with Chris Weidley.

Chris is the principal broker at Redwood Prime Realty in Pennsylvania who is regenerating entire city blocks. He’s focused on filling the need for affordable housing and raising the floor of neighborhoods in his city of Altoona. 

What Chris and what companies like JWB are doing are not separate stories.

They are two halves of the same vision.

Both are driven by the same belief:
That real estate, done right, can raise the floor of a community, not just the returns on a spreadsheet.

But for most PMs, there is a massive gap between that vision and Monday morning reality of proving your worth as a "rent collector," much less a "city builder."

In that conversation with Chris, I uncovered something most property managers never get told.

There is a seat on the city-building bus for PMs who’ve always known they’re more than rent collectors, but the industry hasn’t shown them how to be part of it.

If you’ve ever felt that tension of wanting to make a difference in your city and being part of a bigger vision, this story is for you.

Because buried inside Chris’s frustration was a path forward for property managers who want to make a deeper imprint on their hometowns…

Here is what I learned from Chris about how you get a seat on that bus.

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Why Great Developers Need Great Property Managers

Chris is not simply building new housing units. He is working alongside local governments to solve affordable housing challenges in a way that keeps neighborhoods intact over time. 

These projects are structured as public-private partnerships where cities define the need and developers provide the execution required to meet it.

These projects depend on long-term ownership because cities don’t want buildings that change hands every few years.

They want stability, they want families who can stay, and they want neighborhoods that feel cared for over time.

Chris is clear: none of his vision survives without exceptional operations. He describes management not as a "supporting function," but as one of the three ways developers create equity, alongside buying and building.

Unlike the first two, the "management" way to create equity never stops.

To stabilize a neighborhood, a developer must hold. The tax code rewards this through long-term capital gains and depreciation. But that "Tax Shield" is fragile. It depends entirely on:

• Leasing speed

• The Move-in experience

• Maintenance follow-through

These responsibilities are not separate from the broader mission. They are what allow the mission to continue.

If the front line is slow or the service falls apart, the financial model breaks. The developer loses the tax benefits, and the project stalls. 

When developers talk about their biggest constraint, they aren’t talking about capital or deals. They’re talking about whether the operation underneath the vision can actually carry the weight.

The Problem Developers Don’t Say Out Loud

Developers like Chris can usually find a property manager. What they can’t find is someone who will manage the asset like it’s their own money.

Many developers build, sell, and move on. But those who want to hold (to actually build a community) have powerful incentives to do so.

Holding for 2+ years unlocks long-term capital gains treatment and allows Bonus Depreciation to work for them. This "tax shield" is a magnet for high-income investors (like the doctors Chris works with) who fund these projects.

But here is the fragility: The entire "hold" strategy depends on the operator.

None of those tax benefits matter if the property isn't run at a high level. Chris said it in a way every developer understands:

"You treat your rental car differently than you treat the brand-new sports car you bought."

Developers are terrified that a 3rd-party PM will treat their $20M "sports car" like a commodity "rental car." If leasing is slow, if move-ins are delayed, or if service falls apart, the owner pays the price. Holding becomes unsustainable, especially with high interest rates.

That’s why management isn’t a footnote. In Chris's words, management is the third way developers create equity. Buying and building are the first two, but without operations, the other two eventually break.

Thing Chris Wished He Didn’t Have To Do

At this point, most people assume Chris found the perfect operator. 

He didn’t.

In reality, Chris was forced to build his own property management company from scratch.

Not because he wanted to, but because he couldn’t find a PM he trusted.  So he did the thing he wished he didn’t have to do himself:

He stopped hunting and became an operator because the market failed him.

This is the real lesson.

Developers are hunters. They create value by finding land, structuring deals, and building. Property managers are farmers. They create value through consistency, care, and relentless day-to-day execution.

When hunters are forced to farm, growth slows. When farming is done poorly, everything falls apart. 

That’s why developers like Chris may not necessarily want to become PMs.
They do it because they can’t find partners they trust with their equity, their tax strategy, and their long-term vision.

Until that gap is filled, developers will keep pulling operations in-house out of necessity.

The Big Opportunity For PMs That Want To Be City Builders

I meet a lot of property managers who truly care about their team, about their properties, and about their community. 

Yet they often feel undervalued on that hamster wheel of trying to land new doors under management to reach some sort of magical scale number when their problems go away… except those problems never really stop coming, so they dream of selling the company instead.

This conversation with Chris showed me a new way for property managers  who're tired of selling and uneasy about roll-ups… your highest leverage future might not be “more owners.”

It might be becoming the Operational Co-Founder to a developer who cannot execute their long-term vision without you.

In this partnership, the developer hunts deals and structures capital; you run operations like the asset depends on it, and together, you unlock holding strategies that wouldn’t survive without strong management

This isn’t vendor work. This is shared upside.

The developer gets tax protection, asset stability, and freedom to build.

You get stability, a built-in pipeline of doors, and growth that compounds through partnership instead of pitching. But PMs don’t need to change who they are, only how they’re positioned.

This is how property managers stop being seen as rent collectors and start being invited into the room where cities are shaped. 

For years, this partnership was too risky to attempt. But that’s what changed.

What Chris Leaned Into To Make It Possible (And You Can Too!)

Historically, scaling operations meant scaling people and people introduce variability, burnout, and cost. That’s what made developers nervous about bringing PMs closer to the core.

What changed for Chris wasn’t ambition or philosophy. It was operational leverage. As his portfolio grew, he needed a way to maintain attention to detail without personally absorbing the weight of every maintenance decision.

He shared that Vendoroo helped him de-risk the growing pains of maintenance as his portfolio scaled. That mattered because it allowed him to stay focused on building while knowing the most failure-prone part of operations was being handled consistently.

For property managers, this is what makes the Operational Co-Founder role viable.

When you can use AI to scale maintenance decisions across an entire portfolio, give your acquisition teams predictable costs, and your residents a consistent experience when coordinating maintenance, you can pair with developers that can add 200-400 units at a time.

That’s what de-risks the partnership. It allows a PM to say, truthfully:

“I can scale with you without slowing you down.”

For developers, that’s the missing piece.

Use the tool Chris has used to grow his portfolio without growing pains. 

A Question Worth Sitting With This Week

If you entered this industry because you believed real estate could do more than generate rent—because you hoped it could rebuild blocks, stabilize neighborhoods, and raise the floor of the places people live—ask yourself:

Is there a developer in my market trying to hold assets long-term… who can’t find an operator they trust?

Because if there is, that relationship may be your way into the work you originally hoped this business would allow you to do: turning properties into places that function, helping families stay, and earning a seat on the city-building bus beside the people actively shaping your hometown.

For some operators, impact doesn’t come from building the vision, it comes from being trusted to carry it.

Pablo Gonzalez
Chief Evangelist at Vendoroo