Claire

I am originally from just outside New York City — a town called Pelham — and though this makes me technically a New Yorker, I have always had a weird “thing” for Massachusetts. I grew up as a big Red Sox fan thanks to my Massachusetts-born dad, attended boarding school in Massachusetts, and spent two months every summer in Massachusetts. It was just icing on the cake when I married my husband Toph, who has many great qualities, only one of which is being a Massachusetts native.

During those Massachusetts summers, I spent a few seasons working at the Chatham Bars Inn, a beautiful old hotel on Cape Cod, which is where I fell in love with hospitality. I worked as a concierge and loved sitting at my desk in the great, wood-paneled lobby, watching the guests go to and fro, all with their own lives and stories. The hotel was a fun, grand production every single day and, to me, represented the intersection of so many of the best parts of life: food, history, architecture, intriguing backstories, teamwork, nice views….

After I graduated from college, I worked at a couple of jobs — in real estate development which I liked, and in edtech, which I did not — and had been at business school for a couple of months, still not totally sure what I should do with myself, when I had my “Eureka!” moment: I had loved my summer hotel job so much, and had liked working in real estate development, why not try to work in “hotel real estate development”? Felt too good to be true. Does such a thing exist?? I wondered.

It took me a little while to figure it out, but it turns out that it does! So I spent the balance of business school taking every real estate and finance class they offered, meeting every hotel-related person I could, and working as an intern in development finance at a luxury hotel company called Rosewood. I was rewarded at the end with a prize I could hardly believe — a job offer at a very intense and analytical hotel investment firm called Starwood Capital Group.

Having never done Excel financial modeling professionally before, I spent every day of my first year there afraid that I was going to get fired. But by the end of three years, I couldn’t believe how much I had learned and how much the company seemed to like me. That appreciation is what gave me the confidence to act on the whisper in my head to do it, to go out on my own. It sure is comforting to have some understanding of how hotel financials work when you buy a struggling, seasonal inn in a remote area, and for that, and for many things, I am eternally grateful to the people at Starwood.

I started my hotel search in Cape Cod because of my familiarity with it, but discovered after some months that anything remotely nice on the Cape was going to be just too expensive for me. When brainstorming alternatives, I thought: What about the Berkshires?? Toph and I had gone to see the Boston Symphony Orchestra perform at Tanglewood one weekend in Summer 2023 (thanks to our friend Gene’s wedding present!), and we had absolutely loved the show, the Tanglewood campus, and the whole area. But, we had only been there once, and for only two days at that, so it did not seem like the most reasonable thing in the history of time to pack up our lives and go buy a hotel there.

However, I discovered that the Apple Tree Inn was on the market so I went to look at it and it was love at first sight. The views, the history, the arches in the living room, the graceful front porch, the moldings, the wood paneling in the Ostrich Room, the working fireplaces, the wallpaper, the music wafting up from Tanglewood, the acres of woods in the back, the fact that it had just been connected to town sewer, I mean, come on, this was it! I made an offer that day, and the rest, as they say, will unfold in future email newsletters!