Are The Best PMs Too Good At The Wrong Thing?

Property Managers….

If the Sistine Chapel was Michelangelo’s masterpiece, your business is yours.

But what if I told you that the way to take this project to the next level… might involve you stepping out?

What if your real genius isn’t in painting every detail… but in creating the cathedral that inspires everyone else to build with you?

If you're still chasing every vendor and answering midnight maintenance calls...

You’re not leading an organization.

You are the organization… and that’s not just draining your mental energy—it’s putting your company’s future at risk.

Because…

A number of context shifts are all converging down on the property management industry.

• The Great Generational Wealth Transfer.
• The space is becoming mainstream.
• The 4th Industrial Revolution in the face of Artificial Intelligence.

The rules of the game are evolving…and to create abundance you must evolve with them or else, you'll be left to compete for breadcrumbs.

So here’s the hard question…

Are you optimizing a machine that no longer fits the world it was built for?

Are You Streamlining… a Sinking Ship?

Being a great operator is a part of the skillset of all great entrepreneurs.

That is especially true in a process-heavy industry like property management.

But right now, the process of how we do everything is being dismantled. The Great Generational Wealth Transfer is bringing new investors and buyers. I previously wrote about 4 new policy changes that will impact the industry very soon.

Oh, and did I mention that agentic AI can practically handle all maintenance coordination tasks now?

Nobody knows what the future will look like… so, no matter how well you operate in the present reality, you must reassess. Because that reality is being swept under our feet.

You can master every move on the board—but what if the board gets flipped?

At that point, sticking to your role as an operator becomes a liability.

So how do you escape the trap—before it costs you everything?

Start with the guy who already made it out.

The Coach Who Teaches PMs to Step Off the Field and Into Power

Last week, I had the chance to interview the #1 success coach in the property management industry, Tony Cline.

The one-hour slot we’d planned for our conversation disappeared in a heartbeat.  

Tony is a frame breaker in every sense of the word - he successfully exited his first property management company, selling it to a national aggregator, then went on to create the most successful coaching program in the space…

And if that isn’t enough, he also runs 200-mile ultra marathons… because he can.

The conversation had many perspective-bending moments, but the most important one for this newsletter is when we discussed what Tony thinks about the future of the PM space.

We agreed that nobody really knows what the next decade will look like… but there’s one thing that is certain:

The property managers best positioned to take advantage of the new reality will be the ones who have carved out a time in their schedule to strategically think it through and plan for it.

It’s the CEOs who decide to work less, not more, that are best positioned here. The ones who become comfortable with the idea of delegating even what they do very well to focus on what only they can do - make the right decisions for the company.

Or, as Tony put it much more poetically:

Move FROM the most important person in the day-to-day, TO the most important person in the business.

Step One: Stop Letting Talent Hold You Hostage

I’ve mentioned previously that the best time to make a change is when it’s still a choice and not forced on you. Now is the best time to transform yourself from an excellent task-master to a grand business strategist.

Sounds radical? That’s the point.

Playing it safe hasn’t future-proofed anyone.

Tony specializes in turning property managers from in-the-weeds, stressed out operators to big-picture business owners that work less and grow their business through strategic decision-making.

So what does stepping out actually look like?

Here’s Tony’s 3-Part Blueprint for moving from Operator to Owner:

🧭 The 3-Part Process to Get Out of the Weeds

Tony helps property managers transform from task-saturated operators to vision-driven owners.

Here’s how he does it:

1. Define Your Personal and Business Vision

Before you build a strategy, build your why. That’s where Tony starts.

“What kind of life do you want your business to fund or support?”

Clarity here becomes the North Star for everything else. Without it, no system will stick.

2. Establish Core Values and a Mission

This is where you begin the transfer of authority.

Core values aren’t decorative—they’re decision-making infrastructure. They tell your team how to think when you’re not in the room.

“You can’t delegate with confidence until your team knows what you would do.”
— Tony Cline

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3. Let Go of What You’re Great At

This one’s counterintuitive—and the turning point.

Your highest value is not doing what you are great at, but doing the things ONLY YOU CAN DO, like:

• Cast vision
• Evangelize it
• Build the systems that bring it to life

Together, these steps shift your role from doer to designer. From operator… to owner.

This is the moment you stop being the MVP… and start becoming the coach who builds dynasties.

Build a Business That Runs on Your Mindset, Not Your Minutes.

The end goal is designing a system that operates the business without you in the trenches.

At this stage:

• The team makes decisions based on company values and policy.
• KPIs are tracked with clarity.
• The business owner transitions in his new role of grand strategist.

When I think of this phase, I’m reminded of Jeff Bezos’ quote about the job of all great leaders:

“A leader’s goal is to make 3 good decisions per day.”

This is what great systems are for. They give you the mental headspace to make the best possible decision for your business. To steer it in the right direction.

Systems aren’t just tools. They’re memory. Culture. Decision-making. They’re what allow your business to keep its shape even when you—or your best team members—step away.

And in this next chapter, systems won’t just be built by people. They’ll be augmented by intelligence.

But here’s the shift no one saw coming: systems won’t just be built for people anymore. They’ll be built for intelligence.

Your Team Is Great—But It’s Still a Bottleneck

Sure, a team with aligned incentives and values is virtually unstoppable… but what happens when they reach capacity?  Or someone’s life changes and they have to leave?

Getting people to invest in a mission will increase people’s drive and mitigate bad behavior, but it can’t overcome the need to rest or stop life from happening.

That bottleneck has always been part of business—and challenging it used to make you sound like a jerk.

Enter: Agentic AI

You’ve delegated to team leads.

You’ve delegated to vendors.

But what if the next leap isn’t human at all?  

Now we get to the sexy part.

Agentic AI already had its Bannister Breakthrough moment earlier last month when Vendoroo unveiled their new Agents that could handle the full process of maintenance coordination.

At last week’s NARPM Broker/Owner, we gave hundreds of PMs access to these agents, asked them to imagine this AI was a job candidate, and asked them 1 question:

“If this showed up day one with these skills, how would you rate it?”

The results?

Most didn’t just want to hire it.

They said it outperformed humans they’d worked with for years.

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For the first time, an AI agent showed the industry that it can own the outcome of tasks, not just assist in their completion.

To put this in economic lingo - the cost of detaching from your business’ operations is getting lower and lower.

And that’s an opportunity.

Ready to Build The Future?

In the last segment of my chat with Tony Cline, he mentioned that what gets created today dictates what gets created tomorrow.

So the verdict is still on in regards to what the world of tomorrow will look like for the property management industry.

But why not take part in its shaping? You know this industry better than the outside forces that try to dictate its direction. Why not let the world know your opinion?

One thing is certain. You already have the tools to help you get there.

If you believe in the message of this newsletter, I have two suggestions:

If this message resonated, don’t just nod—act.

• Need the plan? 👉 Reach out to Tony.

• Need the team? 👉 Test Vendoroo’s AI Agents.

Let us help you become the business owner you were meant to be.

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Pablo Gonzalez, Chief Evangelist at Vendoroo