Rhinecliff Hotel: from the starting line
Behind the scenes of opening a hotel
I can’t even begin to share the number of tasks we’ve completed in the last two weeks. At some point, I’d love to tally them all up, if only for my own amusement.
I want to share this process because it’s every bit as fascinating from the inside as it is from the outside. And as someone who has dreamed of having a hotel of my own, I want to document the experience for anyone who shares that dream (which, as I’ve learned over the past few weeks, is more of you than I realized), or for anyone simply curious.
The footnote version: it’s a lot of work. But I probably didn’t need to tell you that.
Barry and I have officially rejoined the 100-hour-work-week club, gleefully, as we embark on the project of a lifetime. Nonetheless, tired.
Someone asked me, what motivated you to take this on?
Why not? What else am I going to do with this one wild and precious life of mine? I am here to create. To build. To follow my curiosity wherever it leads.
I am built to stretch. I want to become the version of myself that can hold and has the capacity for a lot. because growth lives at the edge of our capabilities. A more expansive life requires a more expansive self. And in order to become that person, I have to be willing to do difficult and sometimes scary things.
There is also something deeply compelling about hotels to me, particularly at this scale. They can become little jewel boxes of discovery, connection, inspiration, and remembrance. Travel expands us. It reminds us, on a cellular level, that there is more. More beauty. More possibility. More ways to live.
While the primary activity of a hotel may be sleeping, I want our property to be stimulating. I want to create a place that helps people return to themselves; a place that sparks imagination, unlocks new horizons, encourages meaningful connection, and is carried home with each and every guest.
We are OFFICIALLY taking bookings for this summer in our phase 01 rooms!
Know anyone traveling to the Hudson Valley this summer? or craving a change of scenery? USE CODE: ‘SUBLOVE’ to receive 10% off your booking (this discount is exclusive to my readers because I love you).
Note: We are currently operating as a rooms-only property as we plan our commons (to include community gathering “living room,” coffee bar, and full restaurant/bar) for a summer 2027 opening.
The challenges this week
Industry folks will know this already, but if you don’t: the hotel booking and distribution world is completely nuts. I feel like I’ve learned five new languages in the last two weeks alone. We chose to use a channel manager (we went with ‘Little Hotelier’) which allows us to list our rooms across multiple booking platforms while managing everything from a single dashboard.
In theory, it’s brilliant. In practice, there is still an astonishing amount of manual work happening behind the scenes. Rates don’t always map correctly, room inventory occasionally develops a mind of its own, payment preferences selected by guests don’t always transfer cleanly from one platform to another, guest messaging systems promise to centralize communication, but often seem determined to do the opposite. What appears to guests as a simple, seamless booking experience is actually a web of connections between booking engines, channel managers, payment processors, websites, online travel agencies, and property management systems - all speaking slightly different dialects and occasionally refusing to speak to one another at all.
[The platforms I am all-too-intimately-enmeshed, aka my tech-stack: Little Hotelier, Booking.com, Expedia.com, Airbnb, HotelsTonight, Whatsapp (which I’ve learned is owned by Meta), Instagram, Facebook, Stripe, Squarespace, Google Business, Gmail, Quickbooks … with only more to come as we hit our stride]
The good news is that every day the system gets a little cleaner and a little more automated. The bad news is that I now find myself casually using phrases like “channel mapping” or “PCI compliance” in everyday conversation.
We’re currently locked out of our Google Business listing. If you’ve ever had the pleasure of navigating Google’s user experience, you’ll understand the challenge immediately. Google doesn’t exactly have a customer service department you can call when things go sideways. As a result, when someone searches “Rhinecliff Hotel” or even “hotels in Rhinebeck” our property is currently showing up as Permanently Closed. Not ideal.
Most guests are reassured once they hear from us directly, but I completely understand the hesitation. If I booked a hotel and Google insisted it no longer existed, I’d probably have a few questions too. The unfortunate reality is that we’ve lost some reservations because of it.
The fortunate reality is that the hotel is very much open, our guests are very much arriving, and we’re slowly working our way through the labyrinth of verification requests, ownership claims, and support forums required to convince Google of this fact. In the meantime, if you happen to search for us and see that we’re “permanently closed,” I can assure you that both the hotel and its owners are very much alive.
We sprung a leak in the office. The source isn’t obvious, which means we’re currently gathering bids from plumbers who will likely need to open up portions of the ceiling and play detective until they find the culprit. Thankfully, it wasn’t in a guest room, so bookings and operations could continue uninterrupted. Small mercies.
What we’re beginning to appreciate on a very practical level is the reality of managing a property of this size. There is always something demanding attention: landscaping, mechanical systems, repairs, preventative maintenance, vendor management, inspections, and the thousand small details that guests never see but that make a property function. Both Barry and I are no strangers to managing brick-and-mortar hospitality spaces, a 12,000-square-foot commercial property? Different beast.
Every day seems to present new puzzles to solve, a new system to understand, or a new skill to acquire. It’s equal parts exhilarating and humbling.
Fortunately, I seem to enjoy learning things the hard way.
Alongside the hotel opening, I am continuing to work closely with a small group of private Creative Strategy clients.
Balancing client work with the realities of opening a hotel has, unsurprisingly, had me burning the candle at both ends. My clients have been extraordinarily patient, supportive, and understanding as we’ve crossed this threshold, for which I am deeply grateful.
One of the things I value most in my work is presence. I want to show up with energy, attention, creativity, and genuine care. And if I’m honest, dividing my attention between a small hotel opening and my client work has stretched my nervous system and overall capacity more than once over the past few weeks.
That said, I wouldn’t necessarily see it a negative thing. I often talk about the importance of expanding our capacity, and it would be a bit hypocritical if I only believed that in theory. Growth requires friction; new levels of responsibility require new levels of resilience. While I certainly wouldn’t choose to operate at this pace indefinitely, there is something valuable about discovering that you can hold more than you thought you could.
Thankfully, beginning Monday, we should settle into a more sustainable rhythm. The property is largely prepared for summer guests, many of the major opening tasks are behind us, and we can begin shifting from launch mode into management. At least until the next surprise arrives.
Wins this week!
We passed our fire inspection on Monday, passed our health inspection on Wednesday, and then moved straight into a sold-out weekend on Friday (e!x!h!a!l!e). Not a bad way to start. The reality, of course, is that hospitality is a game of consistency, not just busy weekends. In order to reach our financial targets, we need to fill rooms Monday through Wednesday as well, and reaching a sustainable 50% occupancy rate remains a primary focus.
That said, we’ve already received more than 50 bookings through the summer within just a few days of opening. For a project that existed only in our imaginations a matter of weeks ago, this has felt incredibly validating.
Building anything new requires a certain amount of faith. You make decisions with incomplete information. You invest time, energy, and resources long before there is evidence that anyone will care. Fifty bookings doesn’t mean we’ve figured it all out but it does feel like a wink from the universe that we’re onto something.
Right now, we’re prioritizing learning. We’ve intentionally priced the rooms below market. At this stage, the rooms are not yet what they will become, and while we have a much larger vision for the property, many improvements are still ahead of us. Because of that, our strategy this summer is simple: sell the room before we optimize the room.
Or, as the hospitality industry likes to say: heads in beds.
We want guests in the building. We want feedback. We want to understand who is coming, why they’re booking, what they love, and where we can improve. The encouraging part is that the feedback so far has been remarkably consistent. Guests have described the rooms as bright, clean, and comfortable. Nearly everyone comments on the river views and convenient location. And perhaps most validating of all, several friends and guests have independently mentioned that they would have expected to pay closer to $250 per night for the existing experience, compared to our current baseline rate of $165.
They are small but meaningful signals that the value people are experiencing already exceeds the value we’re currently charging for. And that’s exactly where we’d hoped to begin.
Perhaps one of the most unexpected, positive, learning curve has been learning how to work together while also being in a relationship together. Barry is a verbal processor (he likes to talk through everything in detail ahead of time); I am a feeling processor (I feel and sense my way into things intuitively in the moment); oy.
You can imagine how well this works at times. Or doesn’t. The reality is that opening a hotel together has accelerated our communication lessons considerably. There is nowhere to hide when you’re making hundreds of decisions a week, solving problems in real time, and sharing both a business and a life.
We’re learning each other’s operating systems, discovering when one person needs more discussion, when the other needs more space, and how to meet somewhere in the middle. And we’re truly getting the hang of it!
Anyone who has ever built something alongside their life partner knows that this piece is foundational. The quality of the communication affects everything else (the business, the stress, the joy). The hotel may be the visible thing we’re building, but behind the scenes, we’re building new ways of understanding each other, too.
Perhaps the greatest surprise of the last three weeks has been the outpouring of community. Both locally and online, our world has expanded overnight. Creatives, hoteliers, investors, artists, entrepreneurs, neighbors, friends, and complete strangers have emerged from the woodwork to offer support, encouragement, introductions, advice, resources, collaboration, and genuine enthusiasm for what we’re building.
There are long hours, endless decisions, and plenty of moments where we’re simply hoping we made the right call. What I didn’t fully anticipate was how many people would lean in to say, “I’m rooting for you.”
THANK YOU. THANK YOU. THANK YOU.
While I plan to share much more of the design inspiration, creative vision, and renovation process in the coming months, this particular letter is mostly administrative, because well… that’s the reality.
The truth is that entrepreneurship often looks a lot less like mood boards and grand visions, and a lot more like spreadsheets, inspections, plumbing leaks, software integrations, permit applications, and running to the hardware store 10 minutes before a guest is set to arrive.
Social media has conditioned us to only share the polished parts. But I’m increasingly interested in the messy middle! That’s is the real-real, baby!
Thank you for being here with us at the beginning.
If you’re not following us already, show us some love on the gram.
xx MC
The messy middle is often the best part! So excited for you guys and can't wait to come check it out soon
Hang in there!!!