If There’s One Thing I Can Help You With, It’s This…

You probably heard about SFHPM 2030, the virtual summit on AI and the future of property management.

We had 600 registrants, nearly 300 people tuned in for hours, and the conversations were incredible.

But THIS—the subject of this newsletter—is the single most important thing you need to take away from that event.

That’s why it was the opening keynote. (LISTEN TO IT HERE ON OUR PODCAST.)

The truth is, I’m not a property manager. Never have been.

But I’ve spent years obsessively studying industries that have been exactly where property management is today.

Industries that woke up to find themselves in a collision between external shifts and new technology.

Industries that assumed they had more time than they actually did.

And while every case is different, the pattern is always the same:

Some companies recognize the shift early and move forward—and they win.
Others cling to the way things have always worked—and they disappear.

Which brings me to the most important thing I can share with you today.

The Landmine Property Management Is About to Step On (But You Can Avoid)

There’s an invisible trap in every industry facing massive change.

It’s not a competition.

It’s not regulation.

It’s something far more dangerous: the belief that what’s working today will still work tomorrow.

That’s the landmine property management is about to step on—or avoid.

It’s what’s known as The Innovator’s Dilemma.

And it’s why great companies don’t just lose—they implode.

Because the real threat isn’t moving too fast.

It’s standing still.

The Landmine That Took Down Your Local Video Store

Disruptive technology doesn’t just improve industries—it redefines them.

But companies don’t fail because they don’t see change coming.

They fail because they hesitate at the moment they need to commit.

Take Blockbuster.

Most people think they ignored Netflix and stuck with their old model until it was too late. That’s not what happened.

Blockbuster actually launched its own online DVD rental service—and for a while, they were outpacing Netflix in customer acquisition.

But they couldn’t let go of their old success.

• Their KPIs were wrong. They measured store revenue per sq. ft. — instead of keeping track of market share.
• Their finance teams resisted the shift. Short-term revenue looked better in retail, so they complained.
• Their franchise owners fought against change. They were making too much money from in-store traffic.

Blockbuster didn’t lose because they failed to innovate.

They lost because they measured the wrong things—right up until the moment it was too late.

Why This Matters for Property Managers

The name of the KPI will be different, but the concept is still the same.  

Property managers aren’t tracking store revenue —but A.I. The decision will challenge your existing KPIs.

One example is for property managers that make money on maintenance. If maintenance is driving profit per door, someone on your team may argue that you shouldn’t have AI troubleshoot maintenance issues for your residents.

But A.I is also able to prove dollars saved on maintenance deferred, and that could keep owners with you longer, increasing average customer lifetime value.

And just like Blockbuster, this can make you hesitate at the moment you need to commit.

AI is shifting property management right now. Owners are starting to ask different questions.

If you’re still answering the old ones, you’re going to fall behind.

You Can’t Avoid The Minefield- You’re Already In It

If the Innovator’s Dilemma is the landmine, then the changes in context have created the minefield.

It’s no longer possible to stand still—the context around you is changing in two ways.

1. Wall Street Is Here—And Property Managers Are No Longer “Under the Radar”

For decades, property managers operated quietly. Their work was important, but it wasn’t in the spotlight.

Not anymore.

Institutional investors have flooded the market, bringing with them:

• Professionalized property operations—data-driven, tech-enabled, and profit-focused.
• High-performance expectations—managers must now prove value, not just maintain properties.
• Government attention—housing affordability has become a national issue, meaning more regulations, more scrutiny, and more pressure to adapt.

The perception and scrutiny of our industry has officially changed.  Everyone has an opinion now.

2. The Great Generational Wealth Transfer Is Changing The Client

Millennials and Gen Z investors are inheriting real estate portfolios.

They have different expectations than their Boomer predecessors:

• They want transparency. They’ve never had to wait for an answer for anything, so they’ll want immediate insights into their properties.
• They want automation. They are used to hitting a button and getting anything they want delivered, so they expect things to happen quickly.
• They want strategy, not just service. They were parented more closely than any generations before them,  they expect guided experiences.

The next generation of property owners won’t settle for their parents’ property management.

They’ll either work with property managers who align with their expectations… or they’ll do it themselves.

Especially because they are more likely to be aware of the disruptive technologies that are now available.

But it’s not all bad news, if you embrace the new context.

Not Just a Way Out—A Way to Win Big

Most people look at disruptive technology and think only about survival.

But the real winners don’t just adapt—they create a new way of doing it, they create a new category.

If you look at the biggest winners in these types of shifts- the Netflixes, the Amazons- you see companies that dominate their market and are way more valuable than the companies they knocked off.

This means you have a chance to adapt to the new reality faster, knock out your biggest competitor, and completely dominate your market.

But that’s not all.

In both examples- Amazon and Netflix- there was one giant winner, but there has also been an explosion of small winners:

• Amazon made the 1 person, $1M business possible
• Netflix made the solo director with a passion project rich
• Property Management will have a version of this, meaning- a much lower overhead, less painful, more profitable version to make a living of.

And that’s the big AHA- Innovative Disruption isn’t a zero sum game.  

There is an opportunity to become the new Amazon of property management- aka. a highly tech enabled, dominant market player.

Or become the straight to consumer e-commerce business of property management- aka. a highly profitable, low overhead business that creates a great lifestyle.

Unless you get taken out by the Innovator Dilemma landmine.

A Roadmap Through The Mine Field- My Proposal

Using information from the Innovator’s Dilemma and my own personal experience from talking with property managers, I’ve created a checklist to aid you when asking yourself tough questions like -

“Am I staying in the past or am I building the future?”

Here’s it is:

• Mitigate Fear Of “Switching Costs” - switching costs are real, but your cost of inaction is your biggest vulnerability.  If you are already thinking of switching your PMS (or starting new) make sure you build on systems with an “open” philosophy.  Softwares like Rentvine get this, while others are purposely trying to keep you locked in.

• Keep An Eye On Your KPIs - As you evolve your business model to fit this new reality, make sure you redefine what winning looks like for your and your team.  Remember that valuing their $/sq.ft. is what stopped Blockbuster from adapting to the new reality.  Keep in mind that data like the PM OPS Standards is a great snapshot of the past, but add your own vision of what winning looks like in the future.

• Insert Generative, Test Agentic - There aren’t a lot of fully functional agents yet, but every single one of your processes can benefit from some level of generative A.I.  It’s important to map out these opportunities, inject generative A.I. into low hanging fruit, and test the agentic A.I. solutions that are ready for you.  Having 1 teammate own this A.I. roadmap is a great idea.  Ideally, it’s an owner or director of operations, but if that person isn’t passionate about this, Jay Berube and BetterWho are creating AI-certified RTM’s that would be perfect for this role.

Don’t Forget This – We’re Living in Exciting Times

Despite what some people might have felt in the moment of transition, great changes almost always lead to a lot of positive upside for society.

And we’re at the cusp of a change the likes of which our world hasn’t seen before.

It’s okay to be worried about the future. Some stress is inevitable, because, as you see, there’s a real danger engulfing the property management space.

But what can’t also be denied is there’s also an even bigger opportunity - the pie will not shrink, but grow. We’re headed towards a future of abundance.

If you want to make the transition to the AI-driven future of property management as smooth as possible, Vendoroo would love to help you out.

Join the AI-driven movement today, and let’s start building the future of the industry together.

Pablo Gonzalez, Chief Evangelist at Vendoroo.

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