How to Make an Inn

by Jay Lesiger

Jay Lesiger is the founder and owner of Chelsea Pines Inn.

I wish I had a dollar for every time a Chelsea Pines guest or acquaintance has said to me, “I’ve always wanted to run an inn. It must be so much fun and so interesting.” Unless I know them very well, I smile politely and say, yes, it certainly is…and then I am silent.

Yes, it is fun, and yes, it really is interesting, but let me tell you, this is 365-day-a-year, 24/7 proposition, and don’t let anyone tell you otherwise! The rewards can be great, but the blood, sweat and tears are very tangible too. Let me take you back a little more than 25 years ago…

My late partner, Sheldon Post, had dreamed of being an innkeeper, something on the order of Mrs. Madrigal, the famed house mother in Armistead Maupin’s “Tales of the City,” complete with life-affirming advice (and maybe an occasional joint or two). And perhaps, in the San Francisco of the 1960s or 1970s, such a thing might have been possible. But New York in the 1980s was not so hospitable and Sheldon continued to purchase various rundown rooming houses all over the Village and Chelsea in the hopes of converting one of them to a gay-friendly guest house. The banks would have none of this; “What was a guest house?”, they would ask. But Sheldon was determined and, although the banks would offer money for condo or coop conversion, he would refuse, resell the building and then move on to the next one (as one acquaintance said of him, he may not have always been right, but he was never in doubt).

At one point Sheldon owned a double-building property on West 22nd Street (trust me, not the neighborhood it is today) and, although both buildings were empty, he could not get financing from the bank. Squatters kept breaking into the buildings at night and setting fires. These 3 am incidents, complete with police and fire department phone calls, drove us to sell and move on again. Finally, we discovered a rundown old rooming house on West 14th Street, a fairly quiet but determinedly unpretty block on the edge of two very rough areas, Chelsea and the Meatpacking District. After some fairly cursory cosmetic work, Chelsea Pines Inn opened its doors to its first guests in 1986.

The first rule of “making an inn” is to have several million dollars in hand for proper renovations. We didn’t have that. We had a bit of savings, an open-ended loan from my mom, and our income from my job (as a benefits manager with Bristol-Myers) and Sheldon’s (as the first openly gay real estate broker in New York). Sadly, Sheldon died in 1988, I lost my job, and here I was as the sole owner of my partner’s “dream”. Not exactly the way we had planned things, but life has a way of “turning lemons into lemonade” when we‘re not looking. The fact that Chelsea Pines eventually became a very tall drink of lemonade has everything to do with the second rule: don’t give up.

Having a pot of money would have been helpful, but somehow we managed without it. Very slowly we began to make more improvements, one of the earliest being the “movie star” theme that has made us recognizable today. Shortly after we bought the building, we began to worry about the sad shape of the walls, both in the common areas and in the rooms. How to spruce this up economically? As Stephen Sondheim once famously said, “You gotta have a gimmick.” As an avid film poster collector (my dad had managed movie theatres throughout Brooklyn when I was growing up and I became very attached to movie memorabilia), it occurred to me that framing my old film posters and decorating the less-than-attractive walls with them was the way to go. Over the years this morphed into the Chelsea Pines “celluloid hero” theme, with each room and common area dedicated to film actor of the “golden age” (where else could the New York Times hotel critic sleep under a wonderfully tawdry poster of Susan Hayward in “Woman Obsessed”?)

But probably the most important rule in the making of an inn is this: keep it personal. We’ve never pretended to be the Waldorf or the Standard and I wish I could tell you that we knew what Chelsea and Meatpacking District would one day become (we did not; we bought what we could afford). But because of our size, our location and the right mix of employees, we’ve become known for our friendly personal service with every guest. Nothing pleases us more than to offer tips about Chelsea Market or the High Line, or to purchase theatre tickets or make restaurant reservations, or give subway or travel advice. We are a inclusively-priced hotel (room rates encompass everything from a substantial breakfast spread to free wifi and local phone calls to concierge service – even a free jolt of espresso to keep you going after a full day of shopping or museums). If we know that a guest is having a birthday or an anniversary celebration, it’s very likely that a bouquet of fresh flowers will be waiting in their room. But the real thing is to have an ongoing dialogue with the guests: how was their day? Do they need airport transportation? Are they looking for the best burger or margarita in the area? In short, how can we make certain that they’re having a terrific time? I think that this is the real key to our success.

So now you know everything about the “making of an inn.” Have I convinced you, or just scared you? It has given me an amazing life for the past 25 years, and I wouldn’t trade it for anything else.

This entry was posted in Anniversary, Films, Guesthouse, NYC and tagged , . Bookmark the permalink.

2 Responses to How to Make an Inn

  1. Hi Jay,

    At this very moment a group of gifted artists (many of them New Yorkers) are preparing to bring “Tales of the City” to the musical stage in San Francisco, so the timing of your blog is serendipitous. It’s thrilling to know that Mrs. Madrigal helped to inspire one of Chelsea’s most treasured institutions. There’s been many a time when I’ve wished someone would tape a joint to my door in NYC — so now I know where to go. (Just kidding, Mr. Bloomberg) Thanks for making me feel part of your rich history by telling this tale of Sheldon’s dream. May Chelsea Pines continue to thrive and bring joy to the free spirits who are lucky enough to discover it.

    Warm regards,


  2. Alan says:

    After staying at your Inn several times over the course of the past decade (or more…) I can certainly say you’ve crafted quite an establishment, and that personal care and kindness has not gone unnoticed or unappreciated. Thank you for offering this safe little haven in the city.

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