Joe Callinan spent twenty years in software before he ever got into the short-term rental industry. The first decade of that was at Intuit, where he built a version of QuickBooks for solopreneurs. He later built an accounting product at LegalZoom, holds an inactive CPA license, and does the books for every company he owns.

In April he bought a Casago Sea Ranch & Gualala franchise covering 210 units across two markets on the Sonoma County coast. He had Guesty running as his PMS, QuickBooks Online for accounting, and Breezeway for operations.

Within weeks, he realized the cost of manually managing the finances was only going to get worse. He had two do-it-yourself options in front of him, and he turned both down to partner with Topkey.

The Challenge: A Fragmented Financial Operating System

Joe took over 210 units without having thought much about how the financial operations would actually run. The properties, the guests, and the housekeeping schedule demand attention first, and the money follows behind.

No way to attribute spend to a property

Roughly 20 corporate cards were already out with his field team when Joe arrived. Transactions landed in QuickBooks Online the way they always had, which meant he could see what had been spent and almost nothing about why.

Categorizing a charge was never the hard part. He had done that for fifteen years across his own companies. The part with no answer was everything after it. "The whole attributing it to a particular property and then determining whether it's billable to the owner or not," he says, "I had no way to do that."

Often he could not tell what had been bought at all. Amazon was the worst of it, because Amazon is one merchant for everything a property needs, and a charge arrives with an amount and a merchant name and nothing else. Someone on the team knows what it was, which house it went to, and whether the owner should pay for it. None of that reaches Joe. In this business, the difference between a light bulb for a specific home and office supplies for the company is the difference between an owner billable and a cost Joe absorbs.

He had a better manual process worked out, but it was going to live in a spreadsheet, and as he puts it, "it still would have been horrendous." At 210 properties with 20 cards in the field, manually keeping a spreadsheet current would have been a full-time job and Joe didn't have the time.

Joe was running a fragmented financial operation system. Guesty held the properties. QuickBooks Online held the accounting. Breezeway held the housekeeping work. A spreadsheet held whatever the first three could not, and a set of checkbooks paid for all of it.

Each system knew its own piece, none of them could hand that piece to the next one, and Joe quickly realized he was becoming the connective tissue between all five. The result was him spending more time on the books than talking with owners and growing the business.

The obvious fix was to make QuickBooks carry more of the load, so before he knew Topkey existed he worked out whether it could. QuickBooks has classes and locations, and the standard approach is a class for every property. Joe ran the math at his scale and rejected it. A class per home would not be sustainable to maintain, and it would not give him the reporting he wanted, because he needed markets at the top level with properties nested underneath.

The person concluding that QuickBooks could not do this job spent a decade building QuickBooks. If there were a configuration that made it work, he would have found it.

Paying vendors meant rebuilding the record by hand

Both halves of Joe's vendor spend had the same defect. The information already existed somewhere. It just had no way to reach the payment.

Breezeway tracked the work. Departure clean tasks were assigned, completed, and carried a predefined cost, because Joe negotiates a housekeeping rate on every individual home. Turning 93 completed cleans into fifteen vendor payments was a separate job, and Joe did it by hand the first few times because he wanted to see the numbers himself before trusting anything to produce them. Vendor by vendor, counting completed jobs to work out what each one was owed. Four hours, for one week of cleans.

The invoice side was worse, because it was already running before he could design it. He had handed his general manager a set of physical checkbooks, and she was writing a check for every invoice that came in, photographing it, and texting him the picture with a note about which vendor it was for and which house it belonged to. "And of course," Joe says, "in the middle of the week, that's not helpful."

A photograph arriving on a Wednesday is not a record. It is a message, and messages get buried. By month-end she was spending a couple of hours going back through her own notes to reconstruct what each check had been for and why.

They built a spreadsheet to hold it together, which produced a steady stream of back and forth between the two of them. Joe stopped there. He was not going to run a 210-unit operation on a system where paying people meant reassembling the reasons after the fact.

Every answer had to come from the owner

Underneath all of it was the problem that made the others unfixable.

The work could be spread across the team. The accountability could not. His general manager could write a check, but the reason for it lived in her head until Joe went and extracted it. The field team could spend, but nothing captured what they had spent it on. Whatever the team did, Joe was the layer that turned it into something an owner statement could use.

That is not a criticism of anyone. A capable team without a system has no way to hand off a decision, because there is nowhere to hand it to. Every purchase became a question, every question routed to one person, and that person also happened to be responsible for running operations across two markets.

It was slow at 210 units. It was also the thing that would decide how much bigger the business could get.

The Solution: A System His Team Could Run without Him

Letting the field team code its own spend

The bottleneck broke the moment the reason for a purchase got captured by the person making it.

Everyone on Joe's field team has a card and a Topkey login. They code their own transactions at the point of sale, choosing the unit, category, and marking whether the charge is billable to the owner while the purchase is still in front of them. Joe reviews the categories and classes afterward because he wants the P&L a specific way, but he is no longer the person doing the capturing. "I love that I don't have to follow up with any of the team," he says. "They know that there's either billable or non-billable."

The change was never about the people. His team had always been spending correctly. What they had not been given was a system where recording the reason took ten seconds instead of having to remember to take a picture of the receipt and send him a text message.

Invoices route the same way. Whoever is responsible for a group of properties approves any invoice attached to one of them, and Joe pays once it clears. Receipts are required on every card transaction, so each line traces back to a real purchase without anyone chasing it.

One rule holds the whole thing together, and he states it plainly to his team, "every payment runs through Topkey so it can be tracked."

Connecting Guesty, QuickBooks Online, and Breezeway

A coding habit only works if the systems underneath it agree on what a property is. That agreement is what Joe did not have, and it is the first thing Topkey gave him.

Guesty: Joe describes it as a real-time connection to his PMS, always pulling down the list of properties, which means nobody maintains it by hand. When a charge is marked billable, Topkey posts it back into Guesty as an owner charge with the amount, date, description, and receipt attached, which is the piece Joe had no way to do before.

Breezeway: The negotiated rate on every home syncs every Monday, and completed tasks import into Topkey as work orders that already carry the property they belong to, so nothing needs re-tagging on arrival. Each one keeps its notes and timestamps, which matters when an owner asks what a charge was for. Joe filters, matches the count, and turns them into bills in bulk. Nobody counts tasks by hand anymore.

QuickBooks Online: Coded transactions and approved bills push across in bulk with their GL codes already mapped, so nothing is entered twice. Joe also finally got the structure he had worked out on paper but could not build, using classes as markets with properties nested underneath, which is the reporting shape a class-per-home approach could never have given him.

The shape of it matters more than any single connection. Joe used to be the thing standing between five systems, translating what one knew into something the next could use. Topkey holds that position now. Spend gets coded once, against a property Guesty defines and work Breezeway tracked, and it reaches QuickBooks with the GL code already attached. Nobody types anything twice.

Every dollar attached to a property

Joe did not have to give anything up to get this. He kept the Chase Sapphire rewards card his team was already using and connected it along with the other twenty, so the rewards kept accruing while Topkey expense management ran on top.

Property tagging and the billable decision now happen at the moment of spend instead of being reconstructed later. His team buys a fair amount through Amazon Business. Orders import with their line items, Topkey matches each one to the card charge and attaches the itemized receipt without anyone uploading anything, and the purchase order number or delivery location tells it which property the order belongs to. The three questions that used to need a person now answer themselves. "Who bought the grill? What house was it for, and can I bill for it?"

Corrections still happen. Someone codes a light bulb as office supplies and Joe fixes it in a few seconds. What he does not do is chase anyone. Every transaction reaches him already tagged to a property and already marked billable or not, so his job is to review it rather than investigate it. That is what makes it possible for him to close out month-end in just a few hours.

Paying fifteen vendors in ten minutes

Bill pay starts before Joe touches anything. A dedicated AP email address forwards vendor invoices straight into Topkey, so vendors send directly and nothing sits in a person's inbox waiting to be noticed. Joe does a first-pass categorization, the approval workflow routes it to whoever owns those properties, and he pays.

The weekly housekeeping run is the piece he rebuilt most deliberately. He filters Breezeway for completed maintenance tasks and takes the count. He filters the same view in Topkey, checks that the two totals agree, then creates and pays the bills in one action. Last week that was 93 completed departure cleans across 15 vendors, nine of them housekeeping, and roughly $20,000 in spend.

When a vendor calls to ask about a balance, Joe pulls up their bills and reads back what is paid, what is in progress, and what is still in draft. "Topkey is my source of truth," he says, and he means it literally. It stopped being a question he had to research.

Straight onto the owner's statement

Owner statements are where all of it has to land. Every purchase the team marked billable belongs to a specific owner, and every one has to appear on that owner's statement with something behind it if anyone asks.

Topkey posts those charges straight into Guesty as owner charges, carrying the amount, the date, the description and the receipt with them. Joe controls when they go, which matters to him, because he tidies up descriptions before an owner ever sees them. Guesty builds the statement out of what arrives.

The Result: A Connected Financial Operating System

90% less time spent on financial operations

The 90% is measured against the manual process Joe adopted when he bought Casago Sea Ranch & Gualala. What he is comparing to is QuickBooks Online, a spreadsheet, and himself sitting in the middle of five systems that did not talk to each other.

That version is worth picturing. Twenty cards coded by hand with no property attribution. Breezeway tasks counted manually and turned into payments one vendor at a time. Invoices tracked in a sheet that someone has to remember to update. Month-end assembled out of all of it, after the fact, from notes.

What replaced it is not one task done faster. Coding happens at the point of sale, work orders convert to bills in bulk, invoices arrive through a dedicated inbox and route themselves, and everything pushes into QuickBooks with its GL codes already mapped, so nothing gets entered a second time. The manual alternative was a dozen slow jobs stacked on each other, and the 90% is the time that comes back when all of them are seamlessly connected.

The estimate carries weight because of who made it.

15 hours per month saved on vendor payments

The four hours Joe spent counting Breezeway tasks by hand was the most avoidable work in his week, and the first thing to go.

He audited every line at the start. Vendor by vendor, task by task, making sure the numbers were right. Then he noticed he was solving a problem that had already been solved. If the Breezeway count and the Topkey count matched, the individual lines had to match too, so he stopped checking them. "A thing that took me probably four hours the first time," he says, "takes me 10 minutes now."

Ten minutes a week against four hours is roughly 15 hours a month returned to him, and the shape of that saving matters as much as the size. The old process got slower with every new unit added. The new process lets you add 50 units and still pay your vendors in 10 minutes.

Hours instead of days to close month-end

Everything in the attribution problem comes due at month-end, which is why for most property managers month-end close is an event. Days of chasing receipts, hunting down what a charge was for, and holding owner statements hostage to a transaction nobody can explain.

Joe's owner statements go out in hours instead of days.

The reason is structural rather than clever: because every transaction was coded at the moment it happened, there is no backlog waiting at the end of the month. There is nothing to reconstruct because nothing was left unexplained. He sits down for a few hours to review and approve the transactions and he's done. His own summary of month-end is about as flat as it gets. "The end of the month is actually non-eventful."

Confidence first, then freedom

Joe used to be the only place an answer could come from. Getting out of that seat took longer than installing the software did, which is how it should work. Trust in a financial system is earned by watching it be right, repeatedly.

The first owner statement was nerve-wracking. On the second, he verified everything against his bank statements line by line, because he wanted to be certain the numbers agreed before he trusted them. By the third and fourth he had stopped checking. He is confident every owner billable is being captured, and reaching that point took him 45-60 days.

What he does with the time is the part that matters to his business. Joe owns operations for the franchise, and a day in the life of a short-term rental operator is dictated by whoever is complaining that morning. Having his financial work handled means he can spend time with his team working out how to stop the complaints from happening at all, which is work that gets overlooked when month-end is consuming the calendar.

Why Topkey

Topkey is a small team, and Joe gets direct access to them, including the head of customer service and product. He names this as a benefit rather than a limitation, pointing out that he is getting time with people he probably will not get in five years.

What he values most is what happens after he gives feedback. "I'm sharing the feedback and I know it's getting to the people," he says, "because he's sending me back like, hey, just refresh your page. It's there."

The contrast came to him unprompted. He had spent two hours on the phone with Booking.com the day before, and described that team as very much the opposite, the kind that tells you it does not do that and apologizes. For an operator who has built software himself, the difference between a vendor and a partner is measured in whether feedback is taken and incorporated.

Month-End, Made Boring

Ask most property managers about month-end and you'll hear about the chasing. Joe's is non-eventful. He sits down for a few hours, reviews, approves, and he's done. See what that looks like for your portfolio.