Transitioning from Fortune 200 to Innkeeping 101

Caldwell House Bed and Breakfast

Caldwell House Bed and Breakfast

How’s innkeeping really different from the corporate world? Bed & Brunch pr talks with John Finneran, who runs the Caldwell House Bed and Breakfast, in Salisbury Mills, New York, with his wife, Dena.

How long have you been innkeeping?
Four years, Dena and I bought the inn in late 2011.

What made you want to be innkeeper?
I retired at the ripe old age of 51 from the corporate world. We were living in California and four of our five children had headed out East on athletic scholarships (football, two lacrosse, and water polo). I was originally from the New York area so we thought we’d follow the kids back east, since we figured our future grandkids would be here too (first grandchild due this February)! Dena and I wanted to build a good business together, so we cut up each others’ bucket lists and put the pieces on the table, this “mosaic” developed, and it looked like a bed and breakfast.

How did you find your inn?
I, we, did a lot of research on the Internet. Ironically, I did most of my research in Orange County, California, about Orange County in New York. I have a brother in New York who would go do the initial ‘recon.’ He turned down a few options but as soon as he came to this property he told me to get on the next plane.

What made you choose this inn?
There was an extreme amount of potential here, in the sense of being able to do some expansion work. The previous owner ran it as a four room Inn. Fortunately for us, the house next door, also an original Caldwell property was for sale, too. We bought both properties, thus freeing up the “owner’s quarters” in the B&B. This immediately gave us five rooms to lease. We then added a sixth room to the B&B in 2012.

You have since expanded, haven’t you?
Yes, we have. We saw how successful the new room turned out and decided, in 2013, that we would renovate what was once the carriage house.  We were able to restore it back to its original wood and stone splendor. When completed, we had four new guest rooms, bringing us to a total of 10.

Then, in 2014, lady luck shone down on us. An adjacent property, which had housed the Caldwell barn and family cemetery, was put up for sale. We jumped at the opportunity and bought it. Over the years, it had been converted from a barn to a single-family home. We completely gutted the inside of the original structure and remodeled it, which resulted in the “great room,” where we host weddings and events. We also added a bridal suite and spa, and an adjoining building with four new rooms.

We now have 14 rooms in three buildings, plus a separate home on the eight-acre property for Dena and me. We’ve bought all but one the original buildings belonging to the Caldwell family. It was our goal to a reassemble their estate to the extent that we could. The one missing building belongs to a neighbor… we have our eye on it though.

The inn has such an amazing Irish history. How did you learn its details?
We’re only the fourth owner, and the inn had been in just two families for about 200 years. Several generations of the Caldwell family lived on the property for 150 years. Much of the recorded history was here, in some cases framed in pictures on the walls. In addition, many of the original habitants of the house didn’t go very far! They’re buried in the family cemetery at the back of the property. This is a common site in this part of the country. Many farmers and large landowners had family cemeteries that help keep the history of the area alive.

In addition, John Caldwell Jr., an original inhabitant wrote a 300-page journal that chronicled his whole family’s life. I have a copy of the manuscript (the actual journal itself is with the New York Historical Society). It is a fascinating read.

What’s different between the corporate world and innkeeping?
I went from being Chief Financial Officer of a large energy company that had thousands of employees and a staff on call that could fix or do anything for me to doing it all myself, ourselves. Now, if my computer’s broken, I’m the IT department; if we need to take payments, I’m cash management; if the toilet gets clogged up, I’m the janitorial staff, and I take great pride in being the “greens keeper” – i.e. I love working on the lawn. Having gone from a Fortune 200 company to a mom and pop it’s been different but it’s been a lot of fun. Every job, even the President of the United States, has its tasks that are not fun. When I compare the two experiences; however, this is so much more fulfilling. I get to spend time with such neat people all the time, it far makes up for the day-to-day stuff you have to stay on top of. My favorite time of the day is breakfast where I get to sit with the guests and hear their stories. I joke that I’m practicing to take over for Charlie Rose when he retires!

Any funny innkeeping story to share?
When we first took over one of our first guests, a repeat guest 4 or 5 times now, came to stay for Valentine’s Day. We’d been running the inn maybe two or three months at that point. It was a young couple and they were in essence doing a staycation. They had young kids at home and needed to be close by. They came in with a lot of luggage and I jokingly said ‘Geez, looks like you packed everything you have.’ The husband said they’d been looking forward to getting away, going to their room, lighting the fire, being in the Jacuzzi, and watching adult TV. Well, I must’ve turned redder than red and muttered ‘We, um, don’t have adult TV here.’ Having been a road warrior in my corporate life, I thought they meant ‘adult TV’ in the sense that hotels define it, but they really meant anything butSponge Bob Square Pants. It’s become a running joke when they show up now – I tell them I’m still working on that adult TV thing. We all get a good laugh out of it. 

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