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Meet Amy Michaelson Kelly, the powerhouse co-owner of The Radical, Asheville’s gritty-luxury hotel masterpiece. While she spends her days championing local street artists and historic preservation, Kelly is also—surprise!—a lawyer by trade. We caught up with her to chat about how she balances a passion for creativity with the tight financial discipline of a legal mind. Spoiler alert: you can build a tight capital stack and still stay fiercely devoted to your neighborhood.
—Interview by Jennifer Glatt, edited by Bianca Prieto

What was the original spark for the concept of The Radical, and how did you pressure-test whether it would resonate beyond your own instinct?
I didn't know The Radical would resonate here. My partner Jason and I were just kind of committed to the fact that we wanted to incorporate the neighborhood and arts into it. That—and the preservation of the historic building—was foundational.
The Radical is an industrial building, but we didn't want it to be that Southern industrial warehouse that you see so much. During design, everyone creates a design story, and ours got super out there. In short, we wanted The Radical to feel like it was an abandoned building that had been vandalized and that heirloom-quality textiles, art and furniture were layered on top.
If you had come to The Radical before we bought it, you would have seen graffiti on every wall, basically as high as the human hand could touch. You would see something different every time you were here—people's poetry, people's heartbreak, people's political beliefs. We wanted the design to honor that experience of discovery through the art and soft textures. The industrial components are part of the story, but the real story is the art and the River Arts District.
How has your legal training shaped the way you structure deals, manage risk or negotiate partnerships in hotel development?
Once you're a lawyer, you're never not a lawyer. As a company, we try to do things in a really creative way, but we are also, at heart, nerds. We like all this creativity and culture, but we want our financials to be tight. And I think that background does allow us to proceed in a capital-raising context with a little bit more comfort, so we can achieve the creative things we want to achieve. There can be a tension between being creative and being institutional. There is some give and take there, but if you're comfortable with both, then you can proceed with confidence.
Practically speaking, The Radical is the kind of project that doesn't happen without historic tax credits, which is a type of capital we have experience with as lawyers. It's just too expensive to make penetrations through concrete. (This was a bomb shelter in the Cold War for the city, so it's very solid.) The project needed a little bit of attractive capital to make that work, and our backgrounds helped us get over that hurdle and get the project capitalized.
Creative vision and financial discipline are often a tightrope that independent hotels walk. What’s one decision where protecting the concept cost you in the short term, but paid off operationally or financially later?
I wouldn't quite say it costs us in the short term, but we're very committed to our neighborhood, and there are times when we, like many small business owners, have made decisions to forego financial benefit in the interest of the neighborhood. We sometimes host free events here because the larger neighborhood needs that in order to be successful at recovery from the hurricane. [Flooding from 2024’s Hurricane Helene caused widespread damage in western North Carolina].
We also have a gallery downstairs. We get asked to do paid activations in that space, but we are committed to reserving that space for the neighborhood. We do a quarterly cycle to introduce new art there, and it's a big event for the neighborhood, and the artists sell artwork right off the walls. We take no commissions, obviously. We just have a commitment to being that initial connection place for the artists, and hopefully, it's helped us build trust among our neighbors.

The Radical. Photo courtesey Jennifer Glatt
As a soft brand that benefits from Hilton's distribution but avoids full standardization, where have you deliberately pushed back against brand expectations to preserve identity, and how did you navigate that conversation?
The Radical was an independent hotel when we opened, until spring of last year, when we converted into a Tapestry [Collection by Hilton]. During construction, we hired a fire, life and safety consultant that brands sometimes use, so we could flag the hotel someday with minimal cost if we wanted to. (It was maybe the lawyers in us that told us to do that.)
When we decided to join the Tapestry Collection, we were committed to keeping editorial control of the property. For what it's worth, Hilton did not flinch at that at all. Honestly, they've been so supportive of everything about our hotel. Tapestries are supposed to be neighborhood hotels. That’s a pillar of that brand. And we just kind of fit right into that. Hilton has so much firepower on the distribution, and that gets more people to the [River Arts] District.
Looking back, what’s a constraint (budget, site conditions, neighborhood dynamics or even timing) that initially felt like a limitation but ultimately became essential to what makes the hotel successful today?
It is a priority for us to have the trust of our neighbors. That was important to us from the jump, and we've taken the time to build a lot of great relationships. Asheville is not a transactional town. You know, some towns can be that way. It's like, ‘I give you this, you give me this.’ Asheville is not like that. It's very relationship-based.
Hotels have a mixed reputation in a lot of tourism towns, including Asheville. So, as a hotel, we had that to overcome. And then, specifically, in the RAD, we just wanted to be an asset. But having the credibility to engage with people and have them feel that you're additive and not extractive, that's something that we really wanted to achieve, and we didn't know if we could. We have a lot of great relationships with our neighbors. And I think those relationships are essential to us, and hopefully, our neighbors feel like we are essential to them.
Photo credit: Hatteras Sky
Mint Pillow’s Take
Every square foot of a hotel usually has a strict revenue target attached to it, but what happens when you turn that corporate logic completely upside down? Dedicating a prime piece of real estate—like a lobby gallery or an activation space—entirely to local creators without taking a single penny of commission flips traditional hospitality economics on its head. By choosing not to take a cut, you’re using your physical footprint to pour money right back into the local creative economy. Prioritizing long-term trust over quick transactional wins is a beautiful way to prove to your neighbors that you're there to genuinely protect and celebrate the community, not just profit off it.



