The Property Manager’s Wealth Mirage & 3 PMs That See Through It

🎧 Listen to the Audio Version Below

This past weekend, I found myself in a room full of property managers, but this was different.  We weren’t there to talk about property management.

I was at a real estate investing mastermind hosted by The PM Systems Conference leadership, Paul Kankowski and Wolfgang Croskey- two guys who have quietly built the most valuable independent event in the industry..

When I heard their next event idea revolved around helping property managers invest in real estate, I knew I had to be there..

Partly because I believe this is a great moment to invest in real estate, and I’m looking to add a home or two to my portfolio. 

But mostly because I explored the need for property managers to invest in real estate in my book, The Property Manager’s Guide to Winning With AI…
but never fully unpacked:

Why should property managers be investing in real estate?
How do you actually get started?
And where does this fit inside a PM company’s business model?

Walking into the mastermind, I expected to sharpen some ideas.

What I didn’t expect was this:

There are way more paths into investing than most PMs realize…
and it takes far less to get started than the industry myth suggests.

But I also saw something equally important- there are real reasons PMs don’t take the leap. 

They think they don’t have enough to get started.  They don’t think their market is right for them.  But most of all, investing in real estate is an intimidating thing with many “insider secrets” and “cautionary tales.”.

All these things aside, there is one unignorable truth:
Property managers already sit closer to opportunity than any other profession in real estate- you see off-market deals before they hit the market. 

That’s what I call “the golden goose of real estate.”

That’s why I wanted to republish the excerpt of my book that shows you 3 approaches used by your peers to integrate building their own portfolio into their PM operation. 

Because once you see how other PMs have integrated investing into their business (without blowing up their operations or losing focus) you realize:

This isn’t a new business.

It’s a better strategy for your existing business.

So let’s go back to a piece I wrote not too long ago.  One that lays out the three paths PMs are using right now to build wealth alongside their clients.

Not Every Climb Is Worth the Summit

Let’s be real:

If you’re running a 300-door PM business, clearing $250K+ a year, living with autonomy and peace of mind… you’re winning. You don’t need to scale to validate what you’ve built.

But if your long-term plan includes a financial windfall—a business that can fund your freedom so you can live life on your terms?

Then you’ll need to be investing wisely… or plan to get acquired by someone else..

And when the latter comes, your two options might be:

1. Take a job at the company that bought you.

2. Start something entirely new.

Most PMs think they’ll be fine with #1 until they’re not.  That’s why Mark’s question should be one more PMs are asking.

Don’t Change Your Business.  Change Your Scoreboard.

If I were running a PM firm today, I wouldn’t be chasing more doors under management.

I’d be chasing doors owned.

Because here’s the truth:
Property managers already sit on the two scarcest resources in real estate:

• Off-market deals

• Operational advantage

You don’t need to invent a new business. You just need to tweak it to gain the following advantages: 

• Better sales conversations by owning alongside your clients

• Higher profitability/ROI by paying yourself as an operator.

• Differentiated experience based on your insights as your own client

It’s what JWB Real Estate Capital did.

Today, they own 400 doors, manage 5,000+, and control 20 city blocks in Jacksonville.  Their (massive) property management operation isn’t the main source of wealth creation. It’s the thing that drives up the value of the wealth created. 

They’re in the same game you’re in.  They just have a different scoreboard

And they’re not alone.

Here are 3 other PMs doing the same, in their own way:

Tracy Streich Turned Property Problems into Equity

Tracy didn’t build his investment model outside of property management; he built it into the heart of his PM process. 

He reframed property headaches as the first step toward ownership.

Step 1: Listen for friction, not just service needs.
When an owner expresses burnout, maintenance fatigue, or tenant turnover stress, Tracy doesn’t just offer support, he sees it as a signal that they’re ready to sell.

Step 2: Offer a solution, not a pitch.
Instead of offering to list the property or refer an agent, he asks: Would you consider selling? Sometimes he proposes creative terms (sometimes it’s a straight purchase).

Step 3: Leverage operational readiness.
Because his team is already managing the property (or one just like it), there’s no friction on takeover. His PM system is his post-close ops plan.

Tracy didn’t add an acquisition strategy to his business. He built one from his business. And now, every painful owner conversation is a possible path to equity.

Listen to Tracy’s full podcast episode here.

Then, here’s Nicholas Cook…

Nicholas is Building Forever Holds from PM DNA

Nicholas didn’t jump straight to investing. He wanted to, but he “didn’t have enough gray hairs for people to trust him with their money.  So he built a property management company instead.

What’s unique is that he intentionally used PM as his proving ground: building trust, refining operations, and crafting a platform that investors could believe in to launch something bigger: a slow-burn fund model.

Here’s his approach to reaching his goal:

Step 1: Use PM to build track record and credibility.
For years, Nicholas focused on running a tight ship. That experience now powers the credibility behind his investment platform.

Step 2: Design a fund that fits the mission.
No flips. No exits on a 5-year clock. His fund structure holds forever, returns capital early (via refi), and includes aligned equity for operators.

Step 3: Create value for everyone involved.
Tenants get stability. Investors get low-risk returns. PM staff gets ownership. The fund isn’t about yield-chasing, it’s about long-term contribution and control.

His investment thesis is slow and durable: acquire assets that cash flow from day one, return investor capital via refinance, and hold for decades, compounding both revenue and operational leverage.

Listen to Nicholas’ full podcast episode here.

Ed Kirch takes it even further…

Ed Created The PM-as-Portfolio Engine Model

When I sat down with Ed, he was really clear about how he feels:

“ When it comes to managing for other people. They're a pain in the butt. They demand a lot. There's not a lot of money in management.”

Ed didn’t scale for clients. He built a flywheel for himself. And now? His PM business feeds his personal investment engine.  Meaning- he owns 220 units of the 300 that he manages.

Ed’s Flywheel looks like this:

Step 1: Treat PM as a deal funnel, not a services business.
Ed isn’t focused on contracts. He’s focused on inventory. PM gives him eyes on undervalued assets.

Step 2: Partner with investors on simple terms.
Forget the fund complexity. Ed co-invests with trusted capital partners—typically 50/50 terms.

Step 3: Use the same systems to stabilize and scale.
He doesn’t reinvent ops post-acquisition. His PM systems are the investment platform. Then, he just reinvests, repeats, builds wealth.

300 units under management. 220 owned. Ed’s not chasing growth. He’s compounding equity one repeatable deal at a time.

LISTEN TO ED’S EPISODE TO GET ALL THE DETAILS

So ask yourself: 

How many of the properties in your portfolio right now are being run better than they’re being owned?

You have the power to do something about it.

The Models Are Working. But the Ground’s Still Shifting

I’m not trying to convince you to wholesale change your business here- just think twice before you rush to sell a property for an owner in distress, think about what you’re passing on- leverage.

The most important thing I’ve learned about rental property investing is that owning them gets better over time, especially when compared to other retirement strategies.

Most people think they need to save, save, save to retire, then spend.

The problem with that is we’re living longer, medical bills continue to go up, and there seems to be weirder and weirder crises taking place more often that are making the stock market feel like an unending roller coaster.

If the roller coaster dips at the wrong time, that magic number you were saving for may not do the trick.  Rental properties have qualities to them that allow you better options in retirement when something goes wrong.

Following Tracy’s lead, or Nicholas’s, or Ed’s Model, will set you up to withstand an ever-changing future…

Especially when the future is changing faster than we can really keep up with… 

You Might Win The Race Just as the Finish Line Disappears

Here’s the part nobody in our industry is really saying out loud:

AI isn’t just changing how you work.
It’s changing what your business will be worth.

As agentic AI reshapes the landscape, the traditional idea of “scale → sell → retire” is getting foggier by the month.  No one can say with confidence what a property management company’s valuation will look like in five years.

But here’s what is becoming clearer:

AI is making the day-to-day job easier—
not just for you, but for the do-it-yourself investor too.

When owners suddenly have AI tools that reply instantly, coordinate vendors, analyze rent comps, monitor maintenance, and keep them informed… the gap between “hire a manager” and “do it myself” shrinks.  That means the managers who rely solely on fee income- without building wealth alongside their clients- will feel the squeeze first.

And the managers who own doors, even a handful, will have a foundation that no market shift, no algorithm, and no AI revolution can take away.

This is why I’m leaning deeper into this conversation.
It’s why I went to the mastermind.
And it’s why I’m going to spend more time learning about and writing about:

• How to start investing as a PM (even with limited capital).

• Creative acquisition strategies that don’t require big cash outlays.

• How to analyze deals the way seasoned investors do.

Honestly, this might end up being the next book I write.  The response from PMs when I first published this (and now Paul and Wolf’s bet on it) tells me the appetite (and the urgency) is there.

But before I go deeper, I want to hear from you.

Are you currently investing in real estate?
If yes, what’s your strategy?
If no, what’s holding you back?

Just hit reply.
Your answers will help shape where this series (and maybe the book) goes next.

And as always—Vendoroo is here to help right-size your workload with AI, so you have the bandwidth, clarity, and capacity to build the future you actually want… not just the one the industry pushes you into.

The next chapter is coming fast.
Let’s make sure you’re building for it.

Pablo Gonzalez, 

Chief Evangelist at Vendoroo