Week One
If I were properly commoditizing my wife’s dreams as content, I would have started long ago. Maybe two years ago, when I came back from Alexi’s party she couldn’t attend because she was slogging away at Starwood, when she hit some breaking point and figured she was going to have to strike out on her own. Or maybe sometime later, when I didn’t hear from her until 10 p.m. because she’d taken a day trip to research a hot springs hotel in Marin and interview its owner, who turned out to talk a very long time indeed. There were months put into prospects of a cottage colony on Cape Cod; an Italian restaurant in Midtown East; a small new town center; a Hudson Valley Airbnb; and a lot of wetlands with inscrutable zoning. There was a night in October when she felt lost and we talked for hours and mapped out ideas venturing as far from hospitality as a food museum, pool/chimney cleaning, or a salt crystal beer — and as far in the other direction as “getting a real job”.
In November she found a listing for the Apple Tree Inn on LoopNet. That should be, like, Act II of the play. A spark of hope; dare she dream? She tried not to think about it, but couldn’t think of anything else; harried visits; offer in December; months of negotiations, contracts, inspections, rival offers. I, the husband, a man who likes living in the big city, visiting for the first time in the liminal time when the hotel is under contract, almost empty but not quite ours, grappling with whether this will really become my life. Picture the loyal newsletter subscribers along for the ride, building sympathy through ups and downs.
Instead you join us, not quite in medias res, but at the moment of (one) fait accompli. On Tuesday, April 16, almost three weeks ago, I took the day off from work and we drove from our Boston apartment out to Lenox with as many duffel bags as fit in the trunk. We stopped at the pond to take deep breaths; we stopped at the hotel sign on the road to take a photo; and then we met the broker, Jamie, and the sellers, two brothers from New York, Max and James. The sellers respectfully left us to do a final inspection of the property. Jamie represented both the sellers and Claire — not unusual in these small-town deals, but worth noting. I’d heard about his upbeat eager friendly manic nature, and as we did the inspection he greeted every cobweb and broken fridge and tacky couch with a bright idea for how Claire will make it shine. We saw a frog in the basement. “My pet,” laughed Memo, the maintenance guy. Jamie called it a good omen. “It lives in both worlds! Seriously, it lives in the female and the male, the water and the earth.”
As we walked I wondered what it would take for someone to back out now. I guess the mere fact that there must be a final inspection helps ensure there’s no last-minute funny business. And maybe people sometimes use it as a pretext to back out when they’d gotten cold feet for other reasons. But it all looked fine. Not without issues; just not more than expected.
Claire’s mom, Alison, had driven up from New York; she met us and drove us to a quaint lawyer’s house. We entered a lawyerly looking room: dark wood paneling; long wood table; walls completely lined with tomes. A globe, some certificates, some ceremonial shears from some past deal. We and Claire’s lawyer sat on one side; the sellers and their lawyer sat on the other. I belabor this because “the lawyer’s office” is one of the stock images of society, and I had never actually been in one.
I snacked on the chocolate pretzels James had kindly brought us and took notes quietly.
I used to think that the point of meetings was to come up with ideas, discuss them, and decide among them. Then I learned the importance of circulating the ideas ahead of time, and meeting only to decide among them. And I’m still learning about making even the decisions ahead of time, and meeting only to bless them. This meeting was to have no new information, no surprises. The point was to check the math, to confirm the terms, and to sign. The only updates should be to mark to market, if you will: e.g. to update the tallies of guest deposits up until that very moment (no that, no that, I think, like Zeno’s accountant).
Each lawyer passed out documents to their respective clients with a funny symmetry, a little dance of phase-matching, getting them on the same page. The sellers and buyer each took some papers, flipped through, signed them, and moved on. The lawyers pirouetted and exchanged copies and originals like a shell game I quickly lost track of. Like those cryptography things where you pass something through f ∘ g and g ∘ f and ensure they match; like shaking hands with someone’s handshake. They xeroxed things for each other. I work in a digital world of exact and fungible and frequent copies, but they cared a lot about the distinction between copy and original.
The sellers paused on one paper. Why didn’t this number match what they remembered? Their lawyer looked; he flipped through some other papers: ah, it’s simply that this one was more up-to-date. We moved on.
A lawyer asked for a particular tax ID number. Nobody had it on hand. It’s fine; they’ll get it later; we moved on. I was humbled again to realize that law is not code; its gears are greased with fuzzy human pragmatism.
Many of the papers were detailed financial records in small font, all paper. I forget if anyone literally whipped out a calculator. I wondered if these meetings had a lot more of that before all the tabulation was done by machine.
I was conscious that we were probably on the clock and refrained from quips and asides, but as we waited for some xeroxes the sellers asked: so, what’s the first thing you’ll do? We didn’t know. What was theirs? They tore down some tacky vines. We laughed. We’ve been very conscious throughout this process that we are at the start of a road they know and are getting off of. Every feeling — every exhilaration — every ambitious plan — every friend roped in — they did the same just three years ago.
There was no giant John Hancock signature at the end; the lawyers just said we were done. Claire presented Max and James with one of those extra-large bottles of wine, finely wrapped; we took a photo; and we were off. I lamented that I had no service yet with which to tweet before figuring I should probably live in the moment. Alison, Claire and I went out to lunch; I got a steak; Claire hobnobbed with locals she’d already met; we all had a little glass of Prosecco.
Claire brought us by High Lawn Farm, a ten minute drive from the hotel. I had never heard of it and had no expectations, but I cannot overstate how savvy this visit was if she was trying to soothe my anxieties about the rural life. The building itself is beautiful stucco with this tower and cloisters and then you pull aside a big barn door and find yourself alone in a long room of like twenty of the most adorable calves, poking their heads over their little pens, eager to be patted, to lick your hand, to gobble up the hem of your coat. And upstairs they have coffee frappes. I will want for nothing in Lenox.
We got back to the hotel and Claire entered for the first time as owner, unclipped the long-closed curtains covering the front desk, and took her seat behind it.
Over the last couple months I’ve heard a few people say that Claire was “starting” a hotel. But no! She was assuming control of an already-operating hotel, as-is. But aside from the summer, there are basically only guests on weekends, so there was no guest who checked in under one owner and checked out under another. Our first guests were to check in the next day, Wednesday: just one room, two guests. And imagine the full might of us three very excited newcomers shopping for them at Stop & Shop, hitting every aisle.
Claire had already emailed her first few customers to inform them that she’d be taking over — just to warn them to pardon the dust and such, and to make a special effort to cater to their tastes. This first guest had kindly replied that they didn’t like eggs and was trying to eat healthy. The hotel restaurant has been closed for months (and will probably be for one more), but Claire was going to make breakfast for them. Might they want orange juice? Grapefruit? Pistachios? Avocados? Cookies? Popcorn?
For months, Claire’s engagement with a hotel had been abstract. She had modeled insurance, compared seasonality of bookings to comparable hotels in the area, brainstormed marketing strategies and service touches. How did she relate to the long history of the area? How much revenue would come from neighboring Tanglewood’s summer concert season? How could she imagine some countercyclical draws to attract people in the winter? What sort of spa or onsen vibe would she eventually aspire to?
But there in the Stop & Shop we had an exhilarating collision with the reality of: do we know where forks and knives and napkins are? Can we operate any of the stoves? We were partly shopping for our owner’s apartment, but partly for these first two guests. All modeling of profit margin per booking went out the window in the produce aisle! I mean, it’s the first guest, you can’t worry about it. There’s nothing wrong with any of this. It’s just a wild transition from abstract to concrete.
We just snacked that night. We felt crazy.
The next day I went back to work (observablehq.com for all your data visualization needs!) and Alison moved a lot of furniture around and we were all abuzz awaiting the arrival of those first guests. They walked through that door and I heard Claire give them her spiel and I met them briefly and they expressed delight and excitement for her. They had stayed at the Apple Tree before, a few years ago; they loved the building; they were happy to be back, and staying through the weekend for four nights. They went out to dinner and we ate back at the owner’s apartment.
Later, while we were eating, Claire realized she’d missed a text from them like twenty minutes earlier: how do you connect to the Wi-Fi? She quickly replied. We headed back over to the hotel desk.
We were on our laptops in the lobby when the guests came down from their room and said they were going to leave and go home. We were struck dumb. We apologized and they started ferrying their bags back to their car and Claire and I stared at each other in silence for a few minutes.
With the last bag, the woman said goodbye, and we gingerly asked — if they could be so kind — what went wrong. The hotel wasn’t what they remembered it being; it was eerily quiet. There’d been no fire in the fireplace when they got back, no music playing, nobody in sight. Their room was missing the charming clawfoot bathtub them remember. They were just going to go. They wished us luck, but were scared to stay the night. I tried to validate her and relayed how I remembered the eerie quiet of my first visit, and she compared it to The Shining. Though inside we desperately wanted to know every detail they remembered, we had to let them go. Who knows if they were really going home or to another hotel or what.
And they hadn’t even seen breakfast! “This is going to be hard.” Claire hardly ate the next three days.
The next check-in was nerve-wracking. Claire didn’t dare leave her post; we ensured the Spotify never stopped; we stoked the fire like it was an eternal flame. She started briefly explaining the Wi-Fi in every introductory spiel. Her sister Bip and brother-in-law Nick and their dog Nora arrived. Bip made us a playlist so we wouldn’t just have Maggie Rogers or James Taylor on repeat. My friend Alec arrived, having kindly and quietly booked after seeing our tweets. There was the next check-in, and the next; it was now the weekend, and we had several rooms booked, I think 7 on Friday and 8 on Saturday.
We designed and printed menus for the breakfast, branded “Breakeven Café”. Claire and Memo made eggs and bacon and pancakes. Happy couples filled the dining room, a octadecagonal barnacle with a colorful circus-tent roof, formerly run as “the Bellflower”, and before that as “the Omelette Room” — by Alice of Alice’s Restaurant fame, as we’ll have to cover in a future post.
A family with two cute kids gathered around the fire like they never got to see one; they ran around to appreciate the view from all angles; I took some family photos of them on the porch. Everyone was a character. Some teachers. A DEC retiree trying to charge his electric car. Some people checking out Tanglewood even though there are no performances yet. Some here for theater. Lots of people going to the yoga retreat across the street, Kripalu. Old friends who loved to travel together. Sisters getting out of the city. A fellow Toph(er), whom I sadly missed while back in Boston to pack up the remains of our apartment.
We kept waiting for more complaints like those of the first couple, but they have not yet come. They will, of course; there will be more complaints. But not like we feared on that first day. We had feared that the hotel would be intolerable for anyone who was the only booking that night, which would create a real bootstrapping problem for the quiet parts of the year. But other people seem to love to be alone. They just sit by the fire talking deep into the night with a friend they haven’t seen in forever.
We know that we are squarely in the honeymoon period. Everything is a first; even the hard things have the forgiving sheen of novelty. Every problem is inherited, and every idea is not yet falsified. Every guest is thrilled to hear how recently Claire took over. Friends are stopping by for the first time and are happy to book a room. The pivotal summer season has not yet ramped up. We’ve done no marketing. Every expense can be chalked up to start-up costs without concern for the stabilized profit margins. But we can still bask in it.
Yesterday I returned from a week in San Francisco and was immediately greeted by four locals who popped in to use our restroom and ended up serenading us on the piano. Alec and Zoë had driven up to donate a projector and screen from Powderhouse; Danny had thrifted this great old poster of the main lawn at Tanglewood. Our moms and Joe and Lidey were up and Danny grilled burgers outside and we chatted late into the night in front of the fire about plans for the summer with lines of friend and family and guest pleasantly blurred. Sounds like the perfect time for you to visit!
I plan to send a newsletter every Sunday. Feel free to reply or comment with what you’d like to hear about. Our ideas include:
A timeline of the purchase
The three companies that make a hotel: owner, brand, and manager
Thinking in profit margins: if one insurance plan costs $10,000 more, how many more rooms do you have to book?
The service architecture and flow we inherit immutably from the physical structure
Seasonality: how weekends compare to summers, in the Berkshires or on Cape Cod
A guide to the local competition
Astors to Alice: a history of the hotel
Claire’s to-do list
A phenological clock of a hotel: what happens at what time
Bitemporal pace: how far out people book for which times of year
How I learned to stop worrying and love the call center
What Aaron learned from reading thousands of our past reviews
Balancing short-term and long-term investment
Crazy ideas and the practicalities that block them
Interviews with townspeople
Staffing the hotel: maintenance, housekeeping, food and beverage
The interior design visions of Danny, Alison, and Bip
Events we want to host: weddings, murder mysteries, estate sale, and Annie Baker’s “John”
The vintage thrifting scene
Tanglewood’s complicated relationship with popular music
Inferring the implicit interest rate at which gift certificates lend us money
…or whatever you want to hear about!
Announcements
We are urgently looking for a cook and bartender. Email claire@appletreeinnlenox.com if you know anyone!
We’re interested in doing a wood-block logo for the inn and restaurant. Have you done that?
The Tanglewood summer season starts June 20 with John Fogerty (of Creedence Clearwater Revival), followed that month by Roger Daltrey (of The Who), Kool & The Gang, Boyz II Men, and Jon Batiste. Under new leadership, they’ve doubled their “popular” programming this season; for the classicists they’ll have a string quartet workshop on June 26 and an all-day string quartet marathon on June 30.