Year one
What Claire was wrong or right about, and what she’s ahead or behind on, since she took over last April 16
Our one-year anniversary was something of a disaster. I’d panicked after a work call and rattled Claire, so my pre-planned run to Guido’s for cake, candles, and flowers took on the air of an apology. I stashed them away and met her for dinner at Acqua al 2, which opened a couple months after we got here and has quickly become a favorite.1
While chatting with Valentino there, Claire got a call from Abby, who was distraught: the community event in the Ostrich Room had gotten a bit raucous and broken three of the eponymous eggs in the chandelier.
When I first toured the hotel and saw the chandelier, I thought it was totally custom, one of a kind, a historic and irreplaceable part of the place. It’s not; you can buy one online for $7,800, and it was just put in like three or four years ago. But it is still, locally, for us, iconic. Incredibly, the manufacturer picked up the phone right away; it’d be $275 per egg plus $75, shipping out in a few weeks.
The worst part was that we had a whole Ostrich Room photo shoot coming up in three days. Claire had been planning for months to get the biggest act in town to pack the house for Julie to come and finally get us some good professional photography. It’s already dim and hard enough to shoot in there, and now the centerpiece would be hanging maimed and askew.
Our tavern crowd tends to be tame to a fault, so I was sort of baffled that they’d pulled this off, but when I got back to the hotel it became clear: the Guatemalan Holy Wednesday “Baile de Judas” entails dancing with life-size mannequins on your shoulders. One had a mask a guy had carved from wood from a tree the electric company felled on our hill a few weeks ago. Someone pulled me in to dance. I gotta say, it was great. It was beautiful. But Claire had gone home and I did not bring out the cake.
The previous night, Claire and I had gone out to Olde Heritage Tavern (née Heritage House), where we’d gone on our first day here, and I asked her for lessons from year one.
When you buy a place you think “Surely we can do better!” and bat around a million obvious ideas you can’t believe they haven’t tried — but we always knew we’d be humbled by time. So, first, I asked: what do you now think the Khaghans, the previous owners, were right about?
They were right that you need live music every night the bar is open. Claire tried doing music only on certain nights. Great food, drinks, ambiance — surely we can draw people for other reasons! Maybe that works in town, but we’re a drive away, up a hill, and you gotta justify that somehow.
They were right that it can get annoying when people try to give you ideas. Claire remembers looking at the property and seeing a guest come in and try to give a staffer some ideas and seeing the staffer kind of bristle and wave it off. Claire thought she wouldn’t be like that. And, for the most part, she’s not — but it turns out it really can get grating.
They were right that we don’t need a TV in the Ostrich Room. They took all TVs out of guest rooms, which we love, but we figured we should at least have one on the property, and put one up in the back of the bar — generally off, but, you know, for the Super Bowl, the Oscars; one time a woman came in after a long drive desperate to watch the Tonys. And we could do that for her! But that’s the only time I remember us using it.
Broadly, Claire agrees with how the Khaghans staffed the place: two whole maintenance people; a chef, not just a cook. But Claire broke with them in staffing the front desk. When we got here, the curtains had been clamped shut for, we think, years; guests checked in through an app or something. That might’ve made some sense in Covid times, but it grated on Claire, who started as a concierge back in the day and really values that “touchpoint”. One year in, she feels vindicated. We have a good rotation and it seems to make a huge difference to both guest satisfaction and our ability to manage guest dissatisfaction. And it feels right.
She has gained sympathy for prior owners’ structural struggles. Getting noise complaints from guests? With lovely guest rooms above a beloved tavern, it’s structurally almost unavoidable. Bad reviews? Listen, things will go wrong and some people are just like that. Low winter occupancy? It’s a summer tourism town, of course there’s a winter supply glut.
Last year one of the guys from the Khaghan era came by to visit. We sat in the Ostrich Room and Claire peppered him with questions. Did you ever think about repainting the house? Of course. Landscaping the entryway? Yes. Demolishing the lodge? Naturally. Moving the maintenance gear from the carriage house to the upper parking lot? Yup. Doing more spa facilities? Sure. Building an event pavilion? Totally. I don’t actually remember the questions, I just remember that the answer was always yes. Ideas are not the bottleneck.
There was a period before we moved out here when Claire’s focus was putting together a pitch deck for the property, so I asked her how her investment thesis has changed. Her answer was: not much! She underestimated the supply glut but also underestimated the big-picture potential.
And she underestimated the importance of the niceness of each individual room. When she first visited, they all blended together; now the differences feel huge. The second floor is much nicer than the third. The redone bathrooms are much nicer than the un-redone ones. I asked: but then, wouldn’t it all blend together for the first-time guests? But it doesn’t, because, even if only for a night or two, they’re living in there.
She said she underestimated the difficulty of “messaging the internal consistency of rooms”. We’ve stayed in hotels where each room is unique (shoutout Madonna Inn), and hotels where they’re standardized, and of course we’ve both always felt an affinity for the former. What charm! But that charm is hazy, and the cost is acute: much greater risk of guest frustration due to mismatched expectations; much lower fungibility to accommodate shuffling people around (e.g. because a room has a leak).
You can have a wide range, Claire says — picture the ten grand presidential suite – only so long as you have a high baseline. The higher your floor, the wider the range you can support. Our floor is motel-level. Some aspects of that experience are scoped to the room, but other aspects effectively taint the whole property, which lowers the ceiling we can sustain.2
It’s also easier to communicate your offerings if there exists a single ordering that ranks them in increasing order of niceness along every dimension at once. It is harder when different rooms are nicer in different ways, because you still have to reduce them to a single ordering in the form of the price. That price speaks, and the more subjective the ranking of rooms, the more that one price will mislead people of diverse opinions.
That’s not always how price works! When you shop for well-understood goods (one gallon of unleaded gasoline or 16 ounces of bottled water), you’ll rarely feel that ripped off, because you know going in how the price compares to the value. But a hotel room is harder to understand upfront, no matter how many photos and reviews you consult; you really can’t tell whether you’re going to have an experience worth $200 or $2,000 to you. You have to take the price on faith; the price tells you how good the room is supposed to be. A price of $500 isn’t just an offer; it’s read as an assertion: this is a $500 room. When the value ends up lower than the price, we see reviews like “this is not a $500 room”. (E.g. because a popular concert had driven up the price, and they were not going to the concert.) Whereas you would not see comments like “this is not a $4 gallon of gas”, because in that case, even if the price feels high, no information flows from the price to the understanding of the good.
So because we have no single ordering the maintains monotonicity along every axis, we have to do more explaining. Room 8 is beautiful — but right over the bar! Rooms 11 and 12 are a suite — but up steep stairs and with low ceilings! Isn’t “suite” supposed to mean nicer? It becomes a game of “if you know, you know,” which alienates people.
Before taking over, Claire thought she’d do way more dynamic pricing. Considering common policies like a two-night minimum, she used to think, “I’ll let people stay just one night, I’ll just charge them $1,000!” Don’t leave money on the table; there’s a price for anything! But no. Price complexity imposes the huge burden of maintaining fairness between every pair of prices — the equilibrium of “multiples” that a market constantly computes, but that overwhelms most central planners. You make one room more expensive and the continental breakfast starts looking inadequate. You make another room cheaper and the cocktails start looking too bougie.
And you have to start prices low, because if you ever start them high and lower them, people will cancel and re-book, or complain.
I’ve been personally amazed how much complaints matter to the business, and how many decisions are driven by minimizing complaints. Complaints quickly eat up the marginal hour you could’ve otherwise dedicated to investing in improvement, leaving you treading water. It’s good to listen, but not an unalloyed good; appearing responsive to complaints is sometimes inversely correlated with the sort of long-term investments that attack the root cause of the complaint. Especially when it’s a complaint you’ve heard before, which quickly becomes likely. People love the owner being accessible, but sometimes I can see how guest experience might be better (or rather, get better faster) if the owner were insulated in a large corporate office building in a major city.
Over the last year, some things have happened right on schedule. People had warned us that staffing would be a nightmare, but it came together fast. When the Ostrich Room opened for drinks on June 1 last year, Claire had me print a sign that said food service would start in June 19; I remember feeling that it seemed impossible, and dangerous to promise so precisely, but it happened on June 19 on the dot. (Every individual week felt long and momentous back then.)
Claire has increasingly solid plans for renovations, and good contacts to help her with it, on schedule. We have designs for new branding on schedule, thanks to Larry and Squid, but some pieces won’t come together before the summer season, and it’s hard to know when to “pull the trigger”.
There’s some basic stuff Claire feels behind on, relative to her expectations when she took over. We don’t have a real property map for guests, or a standard handout to give them at check-in, or a curated list of local restaurants and attractions. We haven’t been able to do anything like fresh cookies in the afternoon. The website still has no photo gallery. We haven’t improved the toiletries or replaced the fold-out couch in Room 8. The rooms just have shitty plastic cups in plastic wrapper for water; it should be a glass bottle and two glasses. There’s that station in every hotel; not ours, and it won’t feel like a “real hotel” until we have it.
When we arrived, she took the old one-page history off the lobby mantle because she thought she could do way better — a whole exhibit of mementos, all nicely framed and hung. A year later, she still hasn’t done it.3
We’re behind on financial visibility. We’re nowhere close to knowing our unit costs. And we didn’t get a hot tub this winter.
But the staff has been amazing, with almost zero turnover. Hagai and Adi recently left to move Báladi to a new location (see “Changelog” below), which brings its challenges as we ramp up for the season, but that’s about it so far. We hear from places in the area who’ve gone through like twenty people in six months, and we feel very lucky. Or maybe it’s not luck, and Claire’s just a good boss!
With our second season approaching, we know there’s more we could do with our Tanglewood proximity. A better walking path, a more complementary F&B schedule, maybe even some coordinated events. But, broadly, Claire thinks she overestimated the Tanglewood upside; most of the value of being next to Tanglewood has already been captured, and was in the purchase price.
However, she feels she underestimated the Berkshires upside.
It’s hard to say this without sounding like one of those tourism board ads that invariably just names the area’s greatest insecurity. Like, saying “Boston’s food scene never gets old” is just gonna have people asking a lot of questions already answered by the ad. (Wait, is that our friend Jenny in the entertainment one?!)
But one year of living here — ten months of it without the BSO in residence — has convinced us that there is, in fact, so much more to the area than Tanglewood. We promise! For example:
You know how much we love High Lawn Farm, but there’s also Ioka Valley Farm, 30 minutes away, with animals and treats and seasonal activities like an open sugar house for maple tapping season.
For the anniversary of my dad’s death, Claire brought me to walk the stations of the cross at the beautiful National Shrine of Divine Mercy, ten minutes away.
Christian has been gatekeeping the existence of the beautiful Stevens Glen Trail, a nice hike that leads to a gorgeous waterfall, just five minutes away.
Now, there’s a difference between a pleasant weekend activity that can draw residents out of their living rooms and a world-class institution that can draw tourists from many hours away. So there’s a challenge here.
But Claire thinks maybe the area could develop more of a reputation for music year-round. There used to be a second major institution here, the Music Inn, rowdier and louder than Tanglewood, and there remains a lasting legacy and appetite and a host of great venues. I sort of thought we’d run out of people to play in the Ostrich Room after a couple weeks and it’d just start looping, but it turns out to be an incredibly deep bench; there’s been someone new every week. Last night Johnny Irion returned to play the room for the first time since Claire took over. He’s something of a legend, and built the original Ostrich Room music program, and has a knack for reading and creating vibes, and closed out with a rollicking eight-minute “Pretty Woman”. Neither Claire nor I know music, but this place is doing its best to educate us.
The night after our anniversary was better. Rafi came by, and then Jeremy arrived with his whole wonderful family, and we brought out the cake (and maple cotton candy, Four Seasons–style) and chatted late into the night while Jeremy’s kids sang “Wicked” songs under the stage lights.
Another month has passed since then, and it’s gotten stunningly green; we’d forgotten how green it could get. You could say it’s our first time watching a season change for the second time. The first year, we spent every season fearing the next. In spring we feared the chaos of summer; in summer we feared the comedown of fall; in fall we feared the desolation of winter. But in winter, for the first time, we saw familiar territory ahead in spring. And now we know spring has the charm of things coming together; summer has a thrill of activity; fall brings more pleasantly relaxed visitors; and winter brings a blanket of snow without shutting as much down as we’d feared!
OK, cool it Solomon, to every thing there is a season, we get it.4
The second year will bring the ease of familiarity, but also the burden of standards. “It’s our first year” no longer cuts it. Time brings the possibility of decline, the risk of reaping what you sowed. Inevitably, some things will go more poorly the second time around, and that’ll sting in a new way. We can’t just say we inherited the problems. And we can’t just trundle along in stasis, or with incremental tweaks. Claire didn’t take this on just to run it as-is forever, but because she believes it could be better. Time brings time enough for ambition, and pride, and humbling.
Time brings compounding, and maybe we’ll see some things start to pay off. A year ago Claire had just gotten her liquor license and was desperate to just get a bartender, to get anyone to staff the front desk, to understand how Tanglewood even works. Christian wasn’t here yet. But Claire and Christian have now replaced every part of the “engine” of the hotel — point of sale, accounting, phones, HR, bookings — and in doing so have chipped away at every part of the business they didn’t originally understand. Last year we were often just surviving, and tallying long lists of what we knew we could do better. Maybe this year we can do more of it.
The newsletter has outperformed my expectations, in that it’s still going. Living far from a city, it’s been wonderful to be able to feel closer to all of you. Thank you for reading!
Reader mail
The AI post got some great feedback; thanks to Mills, Nicole, halvorz, Andrés, and others for sharing that one outside my bubble.
Evan says his cousin, a private caterer, is using AI to generate price quotes for private events; he got his response time down from like 3 days to 1 hour. That’s a big bottleneck in our own private events business.
On Twitter, “falafel sir” said, “this is such a great illustration of why the net effect of AGI might be like 2-3% GDP”, and Nicole replied, “to be fair, as a good ex-VC, i think a lot of AI related growth will follow the power law, a ton of duds or negligible (GDP wise) changes to businesses, a few extreme outliers that we maybe even didn't predict just how outsized they'd be”. Nicole later wrote, “going to write a book with the same thesis as more work for mother except… it’s just that for some class of tasks chatgpt doesn’t actually make less work in whole it just expands the normally expected level of work that goes into the whole endeavor”, which I learned from the replies is the Jevons Paradox.
Mills Baker wrote, “It wasn’t until a convo with Chris Best that I realized Hayek was the undisputed king of LLM bears (and this post rules / is a great e.g. of why a Hayekian would have doubts).” This led me to read Hayek’s “The Use of Knowledge in Society” (1945), which is stunning.
Today it is almost heresy to suggest that scientific knowledge is not the sum of all knowledge. But a little reflection will show that there is beyond question a body of very important but unorganized knowledge which cannot possibly be called scientific in the sense of knowledge of general rules: the knowledge of the particular circumstances of time and place. It is with respect to this that practically every individual has some advantage over all others in that he possesses unique information of which beneficial use might be made, but of which use can be made only if the decisions depending on it are left to him or are made with his active coöperation. We need to remember only how much we have to learn in any occupation after we have completed our theoretical training, how big a part of our working life we spend learning particular jobs, and how valuable an asset in all walks of life is knowledge of people, of local conditions, and special circumstances. To know of and put to use a machine not fully employed, or somebody’s skill which could be better utilized, or to be aware of a surplus stock which can be drawn upon during an interruption of supplies, is socially quite as useful as the knowledge of better alternative techniques. And the shipper who earns his living from using otherwise empty or half-filled journeys of tramp-steamers, or the estate agent whose whole knowledge is almost exclusively one of temporary opportunities, or the arbitrageur who gains from local differences of commodity prices, are all performing eminently useful functions based on special knowledge of circumstances of the fleeting moment not known to others.
My mom wrote to point out that Judas in the perfume story is not a strong representative of the EA position, since “our translation noted that Judas was keeping the disciple books and skimming off the top.” The minister made a similar point!
Changelog
The big aforementioned change that puts the “almost” in “almost zero turnover” above is that Hagai and Adi have left to take their brunch restaurant Báladi to a new location, to be announced soon. I previously wrote about the nightmare of categorizing F&B receipts, which illustrates the challenges of running a restaurant “semi-autonomously” inside a hotel, and I look forward to interviewing Hagai again sometime about if that gets any easier!
We now have a fridge for guests to keep their food in the side vestibule. The rooms don’t have minifridges, and people often ask the front desk if they can store food somewhere; this makes it self-serve.
The three broken Ostrich Room eggs have been replaced and reinstalled.
Most of the lobby signs have been reprinted in Taylor Penton’s font Watkins, an element in Larry and Squid’s rebranding. It’s bold and caps-only and works better as a title than body font, so we still have to figure some stuff out.
Alison and Lisa fully rearranged the lobby, ditching the weird overlarge wicker armchairs and moving the long couch over there by the porch, creating room for bookcases between the arches on the back. It feels a lot better, although as the deck goes back into higher use we’ll see how people flow around it.
The lobby space outside the Ostrich Room is now additional dining space. Alice and others used to run the whole first floor as a restaurant, so it feels like a bit of a return, and it works well if you want to hear the music but still be able to chat.
Claire and Sean can now update the Ostrich Room menu on our website by themselves without my help (because it’s just embedded from Google Drive), which is huge, and a good reminder of the value of the sort of CMS I ripped out.
Claire removed the “Please use door to right” sign from the glass door going out to the deck. We put it up last summer because one person tried to go through the door without a ramp and tripped on the step. It’s all too rare that a sign not needed is removed! “There’s your law of precedents; there’s your utility of traditions; there’s the story of your obstinate survival of old beliefs never bottomed on the earth, and now not even hovering in the air!” Good work Claire!
They have locations in a funny three places: Florence; Annapolis; and West Stockbridge, Massachusetts.
How does the quality of the floor “leak out” to affect the ceiling? Some theories: Reviews may not specify which room they stayed in, or which aspects of their experience were due to the room. Prospective guests may not be able to predict how different their room will be; variation creates uncertainty. People don’t like to be around unpleasantness. And the one shared brand has an ineffable aura that’s affected by everything it does.
There used to be a second beautiful old house on the property, the East House. It was demolished in the ’70s because, well, they thought they could do something better. A resort or condos or something. Half a century later, that space is still empty. “One step back, two steps forward” often gets cut short at the one.
I want to make a phenological clock of seasonal scenery and activities for the website.