How Tech Helps Run 500 Rental Properties

This week, I sat down with Tyler Howell, founder and CEO of Whole Property Management in Denver, Colorado. Tyler started the business about a decade ago from a cubicle on the 14th floor of a Denver high-rise, building it up nights and weekends while keeping his day job, since quitting wasn’t an option with young children at home.

Today Whole Property Management manages over 500 rental properties in the Denver area, and Tyler has just joined the Loyalty Brands family (the same franchise group behind CR3 Exteriors) to take the model national. Whole PM is currently at one location, but that is very much the point of joining Loyalty Brands: to franchise the system out to other markets across the country.

We covered how a flat monthly fee beats a percentage of rent when it comes to landing new owner clients, how a nearshore and offshore team keeps margins at 40 to 50 percent, and just how complicated the world of franchising turned out to be once he decided to take Whole PM national.

The Key Takeaways

Below are the most essential insights from my conversation with Tyler that you can apply to your home services business today.

1. He Built the Business From a Cubicle Before He Ever Quit His Day Job

Tyler spent years working a 9 to 5 in a Denver high-rise while building Whole Property Management on the side. With young children at home, quitting his job outright wasn’t an option, so he grew the business door by door until he had 60 properties under management before finally leaving the cubicle behind.

“I sat in a fluorescent lit cubicle on the 14th floor of a Denver high-rise for years. I built Whole Property Management from my cubicle while I was working my 9 to 5. I had young children. Quitting my job was not an option.”

— Tyler Howell

2. Owners Want a Flat Fee, Not a Percentage of Rent

Most property managers across the country charge a percentage of rent, typically 8 to 10 percent depending on the market. Whole PM instead presents owners with a flat monthly fee, for example $229 a month for a single family home in Denver, because prospective clients respond better to a hard number than a hypothetical percentage.

“We’ve found that potential owner clients like to have a flat fee presented to them rather than a percentage, because they like a hard number in their mind rather than a hypothetical one.”

— Tyler Howell

3. Renters Want the Keys, Not a Tour Guide

Whole PM built its tech stack around a self-tour platform, letting prospective renters view a property on their own, 7 days a week from 8 a.m. to 8 p.m., instead of scheduling a walkthrough with an agent. Tyler compares it to test driving a car alone rather than with a salesman in the passenger seat, and it removes the awkwardness and security concerns some renters feel about walking through a house with a stranger.

“Do you really want that salesman in the passenger seat, or do you want them to let you go drive the car for a little bit by yourself? Well, you want the latter, right? And the same is true with a rental tour.”

— Tyler Howell

4. A Nearshore and Offshore Team Powers 40 to 50 Percent Margins

About 55 to 60 percent of Whole PM’s Denver team is offshore or nearshore, including assistant property managers based in Mexico and a bookkeeping team in the Philippines that handles invoices and vendor payments. Combined with the automation built into their Buildium-based tech stack, that staffing model lets Whole PM undercut mom and pop competitors on price while still hitting strong margins at scale.

“We’re able to save a huge amount of money and up our margin, because we’re not paying a US-based person for something that doesn’t really require somebody to drive to a property.”

— Tyler Howell

5. A Two Person Team Handles Every Hundred Doors

Whole PM splits its properties, which it calls doors, into portfolios capped at about 100 each. Every portfolio is handled by a local property manager paired with a nearshore assistant property manager, who fields maintenance requests, dispatches vendors from a rolodex, and coordinates with the bookkeeping team, all communicated instantly over Slack.

“We’ve got a dedicated two person team that’s handling each hundred doors. We’re communicating constantly via instant messages on Slack, so we’re able to knock these things out really quick.”

— Tyler Howell

6. Franchising Turned Out to Be Far More Complicated Than He Expected

Since joining Loyalty Brands a couple of months ago, Tyler has learned firsthand how daunting the legal side of franchising can be. Loyalty’s in-house attorney has been working on Whole PM’s filings for over six months just to prepare the franchise disclosure document and register it across different states, and Tyler is candid that anyone considering franchising alone needs to think long and hard about the undertaking.

“I didn’t have any idea how complicated of a world it is, how difficult it is. If I look back at what has had to be done from a legal standpoint, just preparing the franchise disclosure document is truly a breathtaking undertaking.”

— Tyler Howell

7. He Wants Hands-On Owner Operators, Not Hands-Off Investors

For his first cohort of franchisees, Tyler is looking for people willing to spool up the business themselves, ideally while keeping a day job at first, the same path he took. He points to the recurring revenue model as the appeal: once a management agreement is signed, that door’s income keeps compounding for years, often for a decade or more, unlike most businesses that start back at zero every month.

“You sign the door, and that money is yours for a decade at least. We love folks who have a 9 to 5 or a day job and they’re going to keep that job while they spool up their Whole PM operation. That’s exactly what I did.”

— Tyler Howell

Looking Ahead

Whole PM currently has one dot on the map in Denver, and Tyler says the hardest part of this stage is finding that first validator willing to be the second dot, with potential deals already in the works across a few different metro areas. His advice for anyone considering the model is simple: trust the system, get comfortable with the technology, and be ready to get your hands dirty.

“If you trust the system, the Whole PM system, you trust technology, and you’re ready to get your hands dirty a little bit, then we can create a very, very profitable operation.”

— Tyler Howell