Why I Built Cottagr...it's personal

I sat there mouth open staring blankly ahead. If someone was filming the scene, it would have been comical had it not been so serious.

Sitting at our family cottage in Nova Scotia last summer, I was on the phone with the local municipality about a mundane issue. Canada Post had failed, yet again, to deliver a package despite getting within 200 feet of the cottage (shocker). I was calling to confirm that our rural address was correct.

It was.

Then the woman on the other end of the line asked a question no one wants to hear.

“Do you know you have back taxes owing?”

Uh, no. I assumed it was a timing issue. Maybe a payment was late. Maybe a notice had been missed. As the tax information wasn't sent to me, I didn't know.

“How much do we owe?” I asked.

The number almost stopped my heart. I knew immediately that things had to change.

In hindsight, the situation was completely predictable and avoidable. The cottage had been inherited years earlier by three middle-aged brothers scattered across the globe and none of us lived close by. I use the cottage the most so I assume most responsibility. One brother uses the cottage a few weeks a year, and my other brother lives in Australia and rarely sets foot on the property (but it's happy times when he does). In the aftermath of settling the estate, responsibilities defaulted rather than being decided explicitly - you know, who paid which bills. Who handled maintenance. Who kept track of what.

Most of it defaulted to me, but not all of it and some things were never explicitly managed or agreed. Others were assumed. And without re-litigating the emotional dynamics of any estate wind-up, the reality was simple. We had no shared understanding of what was happening at the cottage.

In that moment, it became painfully obvious that none of us had a single source of truth related to matters of the cottage.

Maintenance knowledge lived mostly in my head, with closing instructions written on a pad of paper left at the cottage. The one with water stains on it. Property surveys, legal documents, appliance manuals, insurance information (you name it) were scattered across email inboxes, filing cabinets and drawers around the world. Expenses were paid inconsistently, and no one had visibility into due dates, let alone accountability.

These are hard issues to address over text or phone.

We had been lucky in one respect. Booking conflicts were not an issue because the cottage sat empty much of the year. But that luck was starting to run out. We had begun discussing renting the cottage to friends and trusted contacts to offset costs.

That raised a new question.

How do you manage a cottage responsibly when ownership is shared, expectations are unclear, and information is all over the place? Each of us own one-third of the property. The management problem is not trivial.

So I built Cottagr.

Not as a startup idea, and not because I wanted to build software, but because I never want to be on the wrong end of a phone call like that again. Ignoring a problem is a recipe for disaster.

We needed a single place where ownership was explicit, expenses and due dates are visible, and knowledge is shared and accessible so cottage information does not live in one person’s head. We also needed a simple way to manage who is using the cottage and when, and a private way to allow trusted people to book time without putting our cherished family property on a public rental site.

In short, we needed Cottagr.

Cottagr is still under development, and I am intentionally not focused on monetization until I get a market signal. Right now, it exists to solve the exact problem that blindsided me that summer afternoon. The one that started with a routine call about mail delivery and ended with a number that could have cost us the cottage altogether.

The irony is that nothing about that moment was dramatic. No storm. No fire. No sudden disaster. Just a quiet administrative failure that happened because three well-intentioned people assumed someone else had it covered.

I built Cottagr so the next call with the municipality would be boring again.

If you are dealing with shared ownership, inherited properties, or the slow drift that comes from “I thought you were handling that,” I would encourage you to try Cottagr. And I welcome your feedback. If nothing else, it helps to know I'm not alone here. Feel free to reach out.

Colin

colin@cottagr.com