The Art of Turning Curiosity into Brand Equity: Lessons from Ace Hotel to Vacation & Beyond - Ryan Bukstein

In this episode, Ryan Bukstein shares the behind-the-scenes process of how brands like Ace Hotel and Vacation were built, showing how curiosity, experimentation, and unexpected collaborations drove their groundbreaking approaches. Ryan reveals how Ace Hotel thrived by challenging industry norms, embracing cultural programming, and forging authentic partnerships, like its notable collaboration with Converse. He illustrates how these same principles allowed Vacation to redefine sunscreen as a playful, nostalgic experience. This conversation offers a rare look into the strategic creativity, ecosystem leveraging, and relationship-building that made these brands resonate deeply within their communities and industries.
Learn more about Ryan's firm, SMPL, here.
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Music for this show is produced by Clay Bassford of Bespoke Sound: Music Identity Design for Hospitality Brands
Ryan: I worked with Ace Hotel until the pandemic hit and then I left and we had just got a chance to actually bring Alex's dream of a hotel in Japan to life because Ace Hotel Kyoto opened right when the pandemic was hitting. But due to those environmental factors, I think what we were doing with hotels became kind of untenable, my style of it, for at least a few years because you couldn't do event programming, couldn't get together in person, and that was the financial vehicle for why we existed at the beginning.
When you're just trying to break a brand and do your thing with your own money, you can do it your own way, but as you grow, you have to explain why you're investing in things. So our explanation of why we invested in all of the programming and the cultural stuff we did in the cities was because of the events that we threw and those drove revenue.
And so I knew that was going to be on pause for a while, and so I started consulting. Just very lightly exploring what things could look like outside of being at Ace for, I think 15 plus years. So it was a long time at one company. And like you said at the beginning, the hotels were a platform for this kind of brand building and community business. It wasn't really the thing necessarily. And so I didn't want to do, I wanted to try something else to test that hypothesis that what I had learned how to do wasn't just hotels, it was a little bit different. It was more like just a way of brand building and approaching a brand.
And I ended up connecting with an old friend that used to work with us at Ace a little bit, Dakota Green, who was starting Vacation Inc. And through a mutual friend who also had connections to Ace and worked with us for a while. So it was a little bit of that, this community of people that you're building over time that you reconnect with. And that's how I was introduced to Vacation and they had just launched and were gearing up to really grow this idea of making sunscreen fun. And I think that's a good connection to this idea of your brand being a factor of the ecosystem you're in.
And you work with it, but you also work against it if you're trying to bring a disruptor brand in. And so hotels at that point when we opened were boring and there wasn't much going on. And so we had to look outside of hotels to market ourselves and to think about how we market and be contrarian to the industry and do special things.
It was, I think, similar with Vacation where sunscreen had gotten really boring and medicinal. The innovations were all really great, but in beauty in a way that wasn't, that was fun, but not in the way that Vacation had in mind. The nostalgic, going back to when tanning oils were a thing and sunscreen was this sexy, fun thing to do, a party vibe.
And so I really liked their idea. Because it felt very similar to what I experienced with Ace, with this really compelling idea that's totally different. Hiding in plain sight, which is another thing that Alex was really good at. You had talked about Ace Hotel in New York, just the location of that hotel. Nobody thought to put a hotel right in the middle of Manhattan. This neighborhood NoMad was nothing, nothing was there, and it was very strange to us. Naivety. We were like, well, why isn't there a hotel here? And I think it's with Vacation, the same as why isn't there a fun sunscreen brand? That's crazy. And so the founders brought me in to just help entrepreneurially figure stuff out because that was my skillset. I'll jump on calls with Ulta Beauty and figure out how we're going to work with them. And I think that all came from my experience with Ace and learning to ask questions and understand the ecosystem, and that's what I try to talk to team members I get a chance to mentor and remind them that nobody knows how to do things at the start and it's better to learn on the go anyway. And I tell the story of Ace when we were small, so it was anytime something needed to get done, it was who's going to raise their hand? When it was time to do the phones and the TVs and the wiring of the hotels at the beginning stages for Ace Palm Springs, Ace New York.
I would always raise my hand. Because I'm like, well if I have more work, that's great. And I remember I would get on calls with the companies that did that stuff by the third call. I would understand it enough by asking questions. And I think that is how I approach it. And I think the ecosystem that you're in, in a way you can learn from it. Then you learn enough from it to know what you want to do differently and not be tied necessarily to the way everybody else is doing it, but still learn that because that's super important, right? But really the magic comes in when you can find your own voice in that. So I think that's where, for me, the ecosystem can be this great tool for learning and also a really great thing to push back on too. Everybody does it this way, but we shouldn't do it that way because that's not our brand. I learned a lot of that from Vacation team too. Reinforced it, the way that they approached the brand of this is how Vacation looks at CVS or at Target. Doesn't necessarily look like every other brand and it shouldn't, but it's compelling.
Josiah: Well, and I think you told me something earlier, Ryan, that has stuck with me around building brand equity, and there's something along the lines of you need to build it really carefully and you need to spend it wisely. And so I think the building carefully. Like with what you did with Vacation, for example, didn't you have a radio station that was like out of left field? Yeah. But you invested heavily in the brand and you were very careful on how you use that brand equity. But I wonder if you could tell me a little bit about the fun things you did to build brand equity there or elsewhere.
Ryan: Yeah. Well and even with Vacation, that's a good example. Pool Suite FM had been around since 2014 and Marty, the founder, was building that very carefully. He put his everything into that. If you haven't checked that out, Pool Suite FM, it's awesome. Online radio station. Just great music and great design vibes. It's very cool. And anyway, Vacation connected with Marty, the founders, to make Vacation together.
And so it was really where Marty was bringing his brand equity into this idea they had. And together then they built even more brand equity and I think that touches on the power of collaboration in a way too, true collaboration where it is two entities coming together, trusting each other, that they're going to take things to the next level together.
And I think that Ace did a lot of collaboration in that way as well. But yeah, to me that's what it's all about. And I do think if you're taking the approach where you're just trying to do things that are fun and interesting and exciting to you, then it does lead itself to that feeling more, that true brand equity where it feels like this is just, again, trying to put out in the world what you want to be there. It just goes back to why is this happening? Because the people that are doing it want it to happen and feel really passionately about it for collaboration. That's great too. When those things come together.
Josiah: Was that behind some of the collaborations you did because you've done so many over your career, across companies that you've worked with? I remember writing an article in the early 2010s about what you're doing with Ace, and I think what stood out to me then and stands out to me still is the breadth of collaborations you had. And I found it fascinating where you're able to build and refine the Ace brand through collaborations, and you're able to do so much more together with these other variety of brands than you could do just yourself. And it really stood out to me. Was it that curiosity and that sense of hey, we can do more together. That was behind that?
Ryan: I think so, and that curiosity that we can do more together and then that connection to people. One of our biggest first collaborations, which is probably one of the ones you included in 2010, was the Converse that we did. Those were the first major collaborations in that way, I think. Especially with a brand that you wouldn't expect to have its own shoe. And really a big reason that came about was because of the people that were at Converse, Jason, who's still there, doing amazing stuff. He was part of our crew in Seattle and we all worked together on random stuff back in the day in Seattle.
And at the point where we were at with Ace, New York, he was at Converse and we were like, let's do something awesome together.
Josiah: I was going to ask you how do these things come about? And it goes full circle to what you've talked about before around people and relationships. Yeah. And somebody, you're like, let's do a collab, let's do something fun together and look at the output. It's amazing.
Ryan: Yeah. A lot of times. And I think that, of course there, it's changed a little bit. And I don't want to be that guy who's like, oh, collaborations are over. Because it's not that at all. But it is changed, it's a line on everybody's marketing plan now, no matter what, whether it should be there or not, it's there. That's going to change it a little bit, and I think it's a confusing time. Everything is like that. There's a real and a fake version of everything these days. So I don't know. I'm still trying to figure it out myself.
Josiah: You can still collaborate though. You can still work with other people and even if everyone has this aligned in their marketing plan. I feel it's all about the execution. I think it's all about the executions. It's about the origin. How did this come to be? It's about what that exactly looks like.
Ryan: Yeah.
Josiah: So I don't know. I'm still bullish on this. I think there's still opportunity here.
Ryan: No, I am too. I mean, that's what I do, is partnerships and so I do too, and I still think it's fun and it brings brands to life in cool ways, but to me it becomes about that. I guess the people and then the process too. In a way, for us, at least in the early days of Ace, it was really, Alex wanted to figure out how to make a shoe. It goes back to the curiosity, this, I want to do all this stuff because I'm curious about it and interested in it and obsessed with it. So these collaborations give you an opportunity to dabble into these other businesses. That was my take on why he wanted to do a lot of these, and why we all did, because this sounds like fun and exciting way to learn something. So, yeah.
Josiah: I mean, to be interesting you have to be interested and I think that's what it feels like what's behind all of this. I love it.