I was running more than ten properties through Hostaway and spending hours a week on things that had no business being manual.
Listing rewrites. Any time I needed to update a description, make it more SEO-friendly, sharpen the appeal for a new target guest, or tweak the opening line after a slow conversion month, I started from scratch in a text editor. Copy the existing copy, open a doc, rewrite it, paste it back. Then do it again for however many listings needed the update.
Guest reviews. Hostaway keeps detailed records on every stay: what the guest booked, how long they were there, whether they followed house rules. Writing a personalised review from that data should take thirty seconds. I was spending five minutes per checkout, and when you're moving ten or more guests through a week, that adds up.
Then there was daily ops context. Quick questions that should have instant answers (what's the occupancy rate across all properties this month, which booking has the earliest check-in tomorrow, what are the cleaning notes on that property) meant clicking through a PMS that wasn't designed for fast retrieval. I didn't want a different PMS. I wanted to talk to the one I had.
Those three problems were the product. I just didn't know it yet.
The fix came before the product
I'm not someone who sits down and decides to build a SaaS. The pattern is: I hit a problem hard enough, I build a solution for myself, and somewhere in that process I realise the solution has a shape that other people might pay for.
Here, the fix was connecting Claude to my Hostaway data. I wired Claude into the account directly so I could query it conversationally. "What's the occupancy this week?" "Draft a review for the guest who checked out this morning." "What do I need to update before the school holidays?"
It worked straight away, and it was obvious that it worked. The friction that had been bleeding time out of my daily ops dropped to almost nothing.
So the question moved from "does this work for me" to "how many Hostaway users are doing this manually right now?"
Based on a few conversations in STR operator forums, the answer was almost all of them.
90 days
I set a loose constraint: first paying customer in ninety days or I park it.
The wedge was the two problems with the clearest before-and-after: listing rewrites and guest review automation. Both had obvious inputs and outputs and a direct line to time saved, and hosts were already doing them manually every week without a good alternative.
I did not build a clean product in ninety days. I built a version that did the thing. Listing rewrites were slow. The review automation was fragile at the edges. Onboarding was me sending an email and a Loom recording.
The first customer paid anyway, because the output was better than what they were doing manually, and they were doing it manually every single week.
That first payment is a specific kind of signal. Enthusiasm is one thing. Someone deciding this is worth money compared to the alternative is a different thing, and the second one is what matters at day ninety.
The thing I over-built
Somewhere between the working prototype and the first paying customer, I built a full multi-property dashboard.
Nobody asked for it. I built it because I could see what the product was going to be, and I wanted the shell ready. I had a clear mental model of RentalStack as a platform: a place where an operator with ten or more properties would come to understand their portfolio at a glance, then act on it. The dashboard already existed in my head, so I built it.
It sat unused for two months. The users I had weren't managing ten properties. They were managing three. They didn't need the dashboard. They needed the automations to be faster and more reliable.
I don't regret building it, though. The work forced me to understand the underlying data model in depth: how properties relate to bookings in Hostaway, how availability is structured, where the edge cases live. When it came time to extend the product properly, I already knew that structure.
Building it was fine. Counting it as progress was the mistake.
What the product is now
Three things.
Listing rewrites. Feed in your current listing, select what you're optimising for, and get back a rewrite that's ready to publish. You can push it directly rather than treating it as a suggestion or a rough first pass.
Auto guest reviews. Hostaway knows everything about a stay. RentalStack turns that data into a personalised review after every checkout, with no copy-pasting and no starting from scratch.
Hostaway data connected to AI. The workflow I built for myself, querying and acting on Hostaway data without going through screens, is where the product is heading. The customer is the operator who has to click through three menus to answer a question they need answered twenty times a day.
What's being built next
The biggest friction point left in STR operations is onboarding a new property, more than managing one once it's live.
Right now, a host adding a property to any PMS goes through a mostly manual process: fill in fields, write descriptions from scratch, upload photos without context, hope the listing lands. The AI tools that exist mostly help you edit after the fact. Nobody has made the onboarding itself fast.
That's what I'm building into RentalStack next. A full property onboarding workflow where the host drops in photos, works through a structured checklist, and the AI analyses the images, pulls in the relevant context, and writes the listing from that instead of from a blank prompt. The output is a listing ready to go live, not a draft to refine.
There's more attached to it. When a property gets its first booking, the owner gets an email. When there are gaps in the onboarding checklist, the system emails them and asks for what's missing. It ends up as a light CRM layer around the onboarding process rather than a form: tracking what's been provided, what's still needed, what's happened since the property went live.
That gap exists in every PMS I've looked at. The tools are good at managing properties once they're in. Getting them in is still mostly a host copying and pasting into text fields at 11pm.
The pattern that keeps repeating
I've shipped enough products now to recognise the shape of the ones worth continuing.
RentalStack has it: I needed it, I built it, it worked, others needed it, they paid. That's the whole story. The products that don't make it usually fail at the second or third step. Either the build never produces something that works well for the builder, in which case you're shipping hope, or it works for you but you're too unusual a user for the problem to generalise.
The direct Hostaway connection I built for myself is an edge case. Most STR operators aren't going to wire Claude into their PMS account. But the problem it solved, slow and manual interaction with data they already own, is completely general. What the product sells is the outcome, less time on operational copy and more accurate information when you need it, and the technical implementation underneath doesn't matter to the customer.
That's the translation work, from what I built for myself to what someone else would pay for. The first version is about the builder. The product has to be about the customer.
What I'd do differently
Start charging earlier.
Pricing is a forcing function. It changes what people say. Free users give you enthusiasm. Paying users give you requirements.
The dashboard I over-built would have stayed in the backlog if I'd been talking to paying customers from week four instead of week ten. They would have told me what they actually needed, and it wasn't a portfolio view.
Everything else (the over-build, the fragile first version, the Loom onboarding) was fine. You have to build something, and the first build is always rougher than you want it to be. Rough and working beats clean and hypothetical.
The first ninety days of RentalStack looked nothing like a startup. They looked like an operator fixing a problem, then checking whether other operators had the same problem, then charging them to use the fix.