“Unreasonable Hospitality” Comes to Property Management

How Reece Register Is Bringing “Unreasonable Hospitality” to Property Management

Listed to the Audio Version

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Last time, we turned the wheel sideways.

We talked about how the org chart is dead, and how the next great property management company will be built, not around tasks, but around trust.
Now, we’re seeing AI giving property managers their time back, handling 95%+ of maintenance tasks for many of our clients..

So now comes the next question:

When AI runs the tasks, what do we, the humans, do with all that time?

That’s the fork in the road we’re approaching as an industry. If Vendoroo alone can deliver automation for something we never thought was possible (maintenance), we have no doubt results like these will become more and more common across the vendor ecosystem..

The value we built our org charts on- "fixing leaks," "answering calls," "coordinating maintenance"- will no longer be a differentiator. They will become table stakes.

So if speed, scale, and efficiency are no longer scarce… What becomes the new, extra source of value?  If tasks are the foundation, what gets built on top of them?

Unreasonable Hospitality as a Competitive Advantage

Few industries are as commoditized as the restaurant industry. Think about it… There are probably a dozen food options within 15 minutes of where you are right now.

Now picture starting a restaurant in New York City… and being awarded “Best Restaurant in the World.” That’s what Will Guidara did with Eleven Madison Park.

In his book Unreasonable Hospitality, Guidara shares the not-so-secret weapon that elevated him to the top of fine dining: transforming service into experience.

What struck me is how many of the leaders I most admire in property management - Jordan Muela, Andrew Smallwood, and others - have read this book, shared it with their teams, and loved sharing their notes on it when I reached out about it.

Because the parallel is undeniable.

Guidara realized the old model of fine dining was built around technical excellence- the tasks. But it was cold. A monologue. His breakthrough was seeing that excellence was just the foundation. The real magic came from the human touches that made people feel seen.

That’s the same pivot property management is facing today.

The “Hot Dog Moment” & the $10 Diaper Box That Changed Everything

In Unreasonable Hospitality, Guidara tells the story that became legend:

One day, he overheard a table of guests at Eleven Madison Park (wealthy foodies on their last night in New York) lamenting that they never got to try a classic NYC hot dog.

So Guidara ran outside, bought a $2 “dirty water dog” from a street cart, and had his world-class chef plate it elegantly.

That moment- the $2 hot dog at the best restaurant in the world- became the defining story of his career.

And it’s the perfect parallel to what Reece Register saw inside Vista PM.

During our conversation, Reece shared his own “hot dog moment.” His team was on a call with a potential new owner who casually mentioned they were moving because they were “having a baby.”

Reece’s team hung up, prepared the management proposal, and then did something no playbook could teach: they bought a $10 box of diapers. When they showed up at the meeting, they handed the diapers to the surprised owner, who signed on the spot and then referred his entire family of investors.

That’s the ROI of a $10 box of diapers.

It’s the difference between providing a service and creating a lifelong memory.

From One-Size-Fits-All to One-Size-Fits-One

Guidara would call that a “one-size-fits-all” moment.  Meaning, it’s highly reproducible.  

At EMP, Will and his team created standard experiences for moments like these, plus developed partnerships and economies of scale around them.  For example, getting engaged at their restaurant was a common occurrence.  So, Will’s team bought champagne bottles in bulk to have ready for the moment, and created a partnership with the Tiffany’s store next door to gift the newly engaged special champagne glasses they toasted with.

Like Reece, any time someone is moving because their family is growing, you could do the same.  You could buy diaper boxes in bulk and even partner with a children’s store for an extra experience.  Heck, you could even partner with a local babysitting service and restaurant to get them a night out.

All these businesses would be happy to get in front of your clients for lifetime value, and you would forever stand out in their eyes.

For companies that focus on accidental landlords, I’d bet marriage and empty nesting are other “one-size-fits-all” moments that you could have an experience ready to go with.

Will and his team also categorized other opportunities as “one-size-fits-some” and “one-size-fits-one” (like the hot dog moment).  It’s the art of noticing what matters most to this person in this moment—and designing an experience just for them.

Reece operationalized that philosophy by simply adding one question to every application form:
“What are your hobbies?”

That single question gives his team the playbook for delight.
It’s not randomness, it’s pattern recognition, built into the business.

And this is where property management is heading.
From process-driven to people-driven. From “doing tasks” to designing experiences.

Culture Is the System

Reece said it best on the podcast:

“Cult is short for culture. You’ve got to create a cult culture around your business so that people want to be a part of it.”

That’s the difference between hospitality as an act and hospitality as an operating system.  It’s not a role you hire for; it’s a mindset you build.

And I’ve seen it firsthand inside JWB Real Estate Capital, where this culture of connection creates loyalty at every level: team, owner, and resident.  It starts with core values, gets operationalized through hiring, and is institutionalized in every all-hands meeting and performance review.  

Once that is installed, that culture becomes the driver of experience for your clients and your greatest marketing asset.

That is the story behind the story of JWB’s $40M community as a marketing channel.

Your Next Step

If this vision resonates with you…

👉 Join “The CX Cult” — Reece Register’s private community for leaders obsessed with building hospitality-driven property management companies.
👉 And if your team is buried in the work that AI can now handle, it’s time to explore Vendoroo. We automate the maintenance maze so your humans can do the work that matters most. Check out exactly how we do that here.

Schedule a demo. Get your bandwidth back.

🎧 And listen to the full episode to hear Reece’s complete story on Property Management Frame Breakers.

Pablo Gonzalez,

Chief Evangelist at Vendoroo

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