Everything in this book is invented. The company doesn’t exist. Neither do the people, the town, or the lake.
However, everything in this book is also true in the sense that every problem in it has happened, repeatedly, to companies we work with. We made up the names and combined the stories. We didn’t have to exaggerate any of it.
Ballard House Vacation Rentals manages 112 units and wants to manage 250. That’s not a large company, but it is a specific kind of company. It’s past the point where one person can hold the whole week in their head, and not yet past the point where the systems can hold it for them.
If that describes your business, you’ll recognize people here.
Each chapter opens with a scene, then steps back to look at what was actually breaking underneath it. The opening scene of each chapter stands alone, and it’s marked. The section that follows gives additional context in a straightforward, business-minded way.
The story runs September through March, because that’s the calendar this business already runs on.
Dana Ballard, 41, president. Took over from her father in 2021. Her last name is on the sign, which is a good thing about half the time.
Ray Ballard, 74, founder. Started Ballard House Realty in 1994 with six cabins and a landline. Comes in most Tuesdays. Knows the name of every owner’s dog.
Marisol Vega, 58, accounting manager. Nineteen years. Built the linked workbook everyone calls The Book, which produces every owner statement the company sends.
Theo Okonjo, 34, operations manager. Ran restaurants before this. Manages housekeeping, maintenance, and a whiteboard he photographs every night.
Kavita Raman, 29, revenue manager. Hired fourteen months ago from a regional hotel group. Very good at her job, currently unable to do most of it.
Wes Doyle, 46, reservations manager. Six agents. Loves guests. Hates the phone system with a purity that borders on art.
Char Nguyen, 24, reservations agent. Fast, curious, and about to cause a problem that turns out to be a gift.
Ruben Ortiz, 51, lead housekeeper. Has cleaned more units in Ridgewater than anyone alive.
Plus: Gerald Pfeiffer, a homeowner who reads every line and prefers paper. Nina and Marcus Amaro, tech-savvy owners who prefer digital platforms. Summit Ridge Collective, the competitor buying up the valley.
The whiteboard in the boardroom still had August on it.
Theo hadn’t erased it, which was unusual, because Theo erased the whiteboard every night at 7 p.m. the way other people brush their teeth. But the last week of August had been the kind of week where you stop doing the small things that keep you sane, and now it was the Tuesday after Labor Day and the board was a wall of red marker nobody wanted to look at.
Dana looked at it anyway.
“Walk me through the red,” she said.
“Late turns.” Theo didn’t get up. “Red means the guest checked in before we were done.”
“How many?”
“On the board? Nineteen I think.”
“For the week?”
“For the week.”
Dana counted them herself, because that’s what she did, and got twenty-one. She didn’t mention it.
“Mmm,” she said. “How many for the season?”
The room got uncomfortably quiet. Wes stopped scrolling. Kavita looked up from her laptop. Mari, who had come in for the coffee and stayed for the meeting, set down her cup.
“I don’t know,” Theo said.
“Best guess.”
“Dana, I really couldn’t guess. The board gets wiped every night. I’ve got photos on my phone going back to June, but half of them are blurry and some nights I forgot.” He rubbed his face. “I could probably reconstruct it. It’d take me a couple days.”
Dana looked around the table at five people who between them had roughly eighty years of experience in this valley, all of whom were very good at their jobs, none of whom could answer a question a competitor could answer in four seconds.
“Does everyone see the problem?” she asked.
They all did.
The confusing part was that it had been a good summer.
Revenue was up eighteen percent. They’d added twenty-two units since March, including a nine-door building on the north shore that Ray had been courting since 2019. Occupancy held through August. The reviews were, on average, excellent.
And yet everyone in the room looked like they’d been reprimanded.
Dana spent her 20-minute morning commute trying to name what she was feeling and had landed on something uncomfortable: the business was no longer knowable. Not long ago, she could arrive on a Monday and hold the entire week in her head. Every arrival. Every problem unit. Every owner who needed a call.
That version of her job had petered out sometime around unit one hundred. At some point, she started arriving on Mondays feeling like a consultant and not the boss. It felt like they needed another headcount. An ops coordinator, maybe. Someone to herd the cats. That was still in the back of her mind as a possible solution.
“Let’s do this properly,” she said. “Everybody tell me what broke this summer. Not what went wrong once. What broke and stayed broken. Don’t hold back.”
Theo went first, because Theo always went first.
“For me, it’s turns,” he said. “Ruben’s crews are the best in the valley, but I find out about changes too late. Guest extends a night, that shows up in the reservation system, and then somebody has to tell me. Usually Char, by text, while she’s on another call. Some nights I don’t find out at all. Then we clean a unit that isn’t turning and miss one that is.” He shrugged. “Now that I look closer, that’s twenty-one reds, which Dana clearly knew.”
She laughed in spite of herself. “I did.”
“I know.”
Wes went next. “Inconsistent information. Guests get different answers depending on who picks up. I’ve got six agents and six versions of the late checkout policy. That would be on me, but I’ve written it down twice. It doesn’t stick because when a guest is upset the agent does what feels right and what feels right depends on the human.” He paused. “Also, I had a guest last month, sixth year in a row, same week, same unit. The agent treated her like a brand new caller because to the system, she was.”
“Not good,” Dana agreed. “Kavita?”
“I spend a solid hour Monday mornings copying numbers out of three systems into a spreadsheet so I can tell you on Tuesday what happened last week. By Wednesday, it’s out of date. My job is to price 112 units dynamically but I’m functionally a data entry clerk with a hotel background.”
She said it evenly. That was somehow worse than if she’d been angry.
Mari said nothing.
“Thank you. Mari?” Dana said.
“The Book is fine,” Mari said.
“That’s not what I asked.”
“No problems on my end,” Mari said again, and picked up her coffee. “Sorry, it’s my day to pick Lindsay up from daycare.” And that was the end of that.
Dana ended the meeting early, as much to let the heavy air settle as the fact that their predicament was painfully clear.
Ray came in a few minutes later and found her still staring at the whiteboard, tapping her pen on the table like she did when something vexed her. His hands were shoved into the pockets of his ubiquitous down vest.
He studied it for several long seconds.
“Red’s bad, right?”
“Cute, Dad.”
“Your grandfather had a ledger book,” he said. “Green cover. He’d sit with it every Sunday night at the kitchen table. Six cabins. Took him an hour, but he’d have bet the farm it was right. And it always was.”
“Is this the part where you tell me it was better then?”
“God, no.” He laughed. “It was terrible. I lost a whole season’s worth of receipts in 1997. Your mother still brings it up.” He tapped the board. “But he knew. Every Sunday, he knew exactly where he stood. That’s the only thing worth keeping from back then.”
She looked at him like she had a million times in her life. He’d watch her try and fail again and again just to swoop in and deliver the solution like a classical hero.
“You don’t know,” he said. It wasn’t unkind. “That’s the thing to fix. Not what’s in red.”
“Do you ever get tired of being right?”
“Nope,” he said brightly. “Which is why I’m going to humble myself by going fishing.”
Dana’s company was experiencing something specific, and it happens to nearly every property management company at around 100 units. That’s when your operations and processes will either buoy you along to the next growth milestone or bog you down.
The tools and habits that produce success at smaller scales don’t degrade gradually. They work until one day, they don’t. It doesn’t usually point to just one thing.
Below 100 units, this business runs on ease of use and personal knowledge. The software needs to be simple. The team needs to be good. That combination is genuinely sufficient, and many excellent companies were built on it.
But above that line, efficiency, automation, and accounting rigor become load-bearing. Same team, same tools, different result. The key is to ensure that the way your business runs is at least as professional as you and your fellow team members aspire to be. A professional team working with amateur tools can’t shine its brightest.
Professionals in this industry generally aspire to:
However, if your operations weren’t built to handle the growth you’ve experienced, cracks will appear in that foundation, and a patch job won’t do.
Four failures show up, roughly in this order:
Dana’s first instinct was a normal one: hire an ops coordinator to bridge the gaps and keep her from having to be quite so hands-on.
That would’ve worked — for a few months.
Adding staff and point solutions to a foundation problem is tempting, but it produces drag. Every new tool is another source of truth, another login, another set of numbers to reconcile. Your team gets very good at moving information between systems, which is work that produces nothing. Reporting becomes an autopsy. By the time you can see what happened, it’s over.
Most platforms weren’t built for this level of complexity. They were designed for ease of use at small scale or a legacy kind of “formula” that asks you to change your workflows to fit the software. Then, over time, they tighten around the business like skinny jeans at Thanksgiving dinner.
Vanishingly few platforms are built to flex with the evolving needs of complex operations, especially as you need to scale. Fewer still actually reward your loyalty by continually adding innovation and value.
The rest of this book follows Ballard House through the next six months. They evaluate systems in the fall, make a decision in November, and go live in February, which is faster than comfortable and slower than they wanted.
Track is the platform they choose, so it’s the one you’ll see named. What matters more than the name is the standard they eventually learn to hold vendors to, and it comes down to three questions:
Is the accounting a true, native, double-entry general ledger, or a reporting layer on top of something else?
Can the product run your business your way, or does it force you into canned workflows?
Is there a named person accountable for your long-term success, or do you file tickets into a queue?
Dana didn’t know to ask any of those in September. She learned them the way most operators do — by something starting to break.
“You don’t know” is the correct diagnostic.
Not “what’s broken.” Every operator has a list. The useful question is which things you can no longer see, because visibility is what you lose first and what everything else depends on.
Dana’s twenty-one late turns were a symptom of a larger disease in which the number lived on a whiteboard, in photos on one man’s phone, and nowhere else.
If you enjoyed reading about the Ballard House in Growing Season and would like to hear more about their journey, please provide your email address to receive the downloadable eBook.
