CHERRY ON TOP 🍒 is our monthly newsletter exploring the ins and outs of everything that modern businesses need to truly shine. We dive into topics that live at the intersection of our two companies – ORCHARD STREET, a venture studio + angel fund & DALY, a comms+ agency – as both help founders get the best ideas out into the world, through outstanding operations, comms, and culture-building.
Alex here! I’ve been thinking a lot about taste lately. Who has it, who thinks they have it, and (maybe most interestingly) what happens to it as companies grow, more people get in the room, and a singular vision slowly becomes a shared one.
Which brings me to hotels.
There are hotels you walk into and immediately get. The lighting is right. The music is right. Someone clearly cared about the little bouquet in the corner. You can feel the vision and the culture without anyone having to explain it to you. And then there are the very expensive hotels where everything is technically “nice,” and yet you could be…anywhere.
I first met Brooks Reitz at a dinner I co-hosted with Colin Nagy at Prune, and have followed his particular way of looking at hospitality ever since. Brooks is a restaurateur, entrepreneur, writer, and, importantly for today’s purposes, someone who notices things: the tiny choices that make a place feel singular, and their absence when it doesn’t.
When we asked him to write for Cherry on Top, we originally floated the question: what makes something feel good?
He came back with something better: an argument for why the best places (and, really, the best businesses!) have a point of view, what happens when that vision gets diluted, and why culture is built in the details.
Over to Brooks!
Brooks: I just returned from a summer out West, meandering from LA up through Northern California, bouncing between rented homes, Airstream camps, our favorite winery’s private lodging for friends, a cottage on a conservancy, and – for work – a few high-end hotels where prices began at $1,000 and soared northward. In each case, mercifully, I was being hosted, or my rate was heavily discounted.
I don’t, in theory, have an issue with the $1,000 a night room – or much more! A truly excellent hotel experience inspires me in the same way that great art can, leaving me open to possibility, wonder, and awe; I’m happy to pay for that feeling. But in a lot of hotels, excellence has been harder to find, average seems to be the flavor of the day, and outsized rates have become depressingly common for increasingly poor experiences.
I’ve paid handsomely for stays at many excellent hotels over the last decade: Ett Hem, Chiltern Firehouse, and Heckfield Place are a few that come to mind. What these hotels have in common (or had: the Firehouse is rebuilding after a fire, a painful bit of situational irony) is a singular owner with the ideas, dedication, money, and drive to bring a spectacular, singular hospitality experience to life.
Inside the Chiltern, Andre Balazs’ maniacal attention to the most minute of details was evident. The rooms oozed sex, taste, elegance, and just the right amount of danger. There wasn’t a corner that had not been obsessed over, a moment that had not been telegraphed, or a situation not planned for. Cocktail waitresses wore custom dresses from Emilia Wickstead. DJ’s pulled selections from the bar’s deep collection of interesting records. Barmen poured the finest Negroni in the land. The result was a world-class city hotel with the sophistication of the best parts of London itself.
At Ett Hem, Jeanette Mix’s commitment to building a hotel that operates like a home, with a warm, natural service-style that doesn’t draw attention to itself, is evident in the easygoing manner with which your days unfold. Guests are invited to take their meals anywhere they’d like, to put on a record, settle in with a book, or mix a cocktail from the well-stocked honor bar. Service is engaged but not sycophantic. Visually, her commitment to celebrating the best of Swedish and Scandinavian design, alongside the precision of Ilse Crawford, resulted in a one-of-a-kind experience that has been referenced many times since, but will never be equaled.
And at Heckfield Place, the Georgian manor house is dressed in the finery of a world-class British art collection, the outcome of the studied and tasteful sensibilities of Dr. Gerald Chan, not to mention the furniture, which celebrates the best of British craft and design across the property. When you settle into an expansive George Smith sofa, set your drink atop a PINCH table, or read a novel in the deep Rose Uniacke chairs, you understand more fully the place you are inhabiting. In the kitchens, cooks deploy local ingredients, many grown on property. There is a subtle story being told across the property – one of place – and you are invited in.
Outside of these increasingly rare and distinctive properties, the luxury hotel market has been flooded with too many corporate chains sporting luxury price points without the real luxury of a point of view, creativity, or taste. Nearly every hotel I’ve encountered that is the product of a large hospitality entity, where decisions are diced up and shared among a handful of stakeholders, struggles to deliver the kind of stay that should be required to command top dollar. There are simply too many voices at the table. Without the roadmap of one strong-minded hotelier leading the way, experiences get watered down, value-engineered, or designed by committee.
The result is that many hotels at the highest end of the price spectrum are difficult to differentiate, void of defining characteristics that anchor them, give them a sense of place, or a point-of-view. You could be in Dallas, San Francisco, Nashville, or Charlotte – increasingly, it all feels the same. The beds are comfortable, the art is always bad, and no one can figure out how to work the lights. In many cases, I’d prefer to stay in a budget hotel, where at least no one is under the assumption there is something special happening.
Hotels, like many businesses, need vision. And vision can’t be workshopped in a boardroom. It must be championed by someone who has lived a bit of life, is willing to take some calculated risks, and sees the roadmap ahead. The best experiences have always been a delicate balance of art and commerce. Increasingly, it feels the recipe is out of balance: the fiscal imperative has completely overshadowed the guest experience. What we need is more sex, good music, softer lighting, and better art. Invite in the artists, the weirdos, the music-fiends, and the obsessives – someone with a real sensibility – and let them get to work!

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Cherry on Top: Hotels are a business, and the finances have to work. But for impactful, soulful lodging experiences that command top dollar, there should be a balance of art and commerce. Independent hoteliers are often the ones leading the way, because they are playing a longer game; larger brands would be wise to welcome more creative voices into early stages of planning, giving them influence over the music, art, design, or tapping into the local culture. When a hotel is grounded by the place it’s in, drawing meaningful connections to the area, the experience is richer and everyone wins.
Brooks Reitz is a Charleston-based entrepreneur.






