INDUSTRY MATTERS: The unstoppable rise of Rolliefest

It seems unbelievable that an event that started just six years ago and has only recently completed its third edition can be the envy of the watch collecting world. Put simply, Rolliefest has become the hottest ticket in town for serious watch collectors across the globe. Geoff Hess, Global Head of Watches at Sotheby’s, and brainchild behind the magic, spoke to Watch Insider’s Daniel Malins about what life looks like on top of the watch world.

Watch Insider: I want to start by asking how Rolliefest originally came about? What exactly is it?

Geoff Hess: Let me take the first part of the question first. I’m 56 years old, I’ve been a watch collector for 35 years, and the watch collector events I’ve been to were held outside of the United States. Those included the Rolex Passion meeting, which was held in the Netherlands for years. 

I was very honored to be invited to so many of those and other similar events. But I was very cognizant that every time I was going to a watch event I was having to get on a plane. There was never any such meeting organized in the US. So, after some urging from friends, I decided to have a party. My Instagram handle is Manhattan Rollie, so I made up the name Rolliefest.

I launched the event in 2019 and we had 110 collectors from 12 countries. The format of Rolliefest has always been the same. A gala dinner one evening; a brunch/lunch the next day, where all the collectors get together and show their watches; and then a farewell cocktail event. For the gala dinner in 2019, I rented the Intrepid aircraft carrier in New York and we had dinner amongst the planes. It was pretty extraordinary. Then the brunch was at the Palace Hotel the next day, and it was extremely well received. 

To answer your second question, the event is about shared passion. It’s a gathering of friends by invite only. I make the invitation list and it’s people that I know specifically. The event is held in secret locations, so people are invited typically six months out, but not told where they’re going until about a week before. And that ensures security, which is paramount – the table during the lunch where people just put their watches down and share them, is worth $20–$40 million. It’s the equivalent of opening a bank without a vault, so security is really paramount. 

In essence that’s the genesis of how it got started and it’s not terribly more complex than that.

I only invite friends and close associates who I know, so the event remains safe and secure. And it’s really just about shared passion and having fun.

The event was so well received in 2019, far exceeding my expectations. I remember CNBC did a 10 minute piece on it. It was really extraordinary. So I said, “Hey, I think I’ll do it again.” I was intending on doing it in 2020, but Covid hit and it ended up postponing the second event until 2023, which was Rolliefest 2. That time, the gala dinner was under the big blue whale at the Museum of Natural History. The ensuing luncheon the next day was at the iconic Rainbow Room. And then I did it again last September. 

It’s non-commercial, there is nothing for sale, there’s no signage, there’s no brand behind it.

Again, there are lots of big watch events, like Watches &Wonders, but those are events hosted, run, and paid for by brands who are seeking to sell you something. This is really just about shared passion. 

I’ll give you an analogy. It’s like listening to music. I can listen to music in the comfort of my home. I can put a pair of headphones on, sit on my couch, and have a great experience. But if I go to a concert and there’s live music, a live band, and hundreds of like-minded individuals listening to the music, nothing can replace that energy. So to me it’s like going to a concert for watches. People have called it the Super Bowl of watches. 

WI: So it’s a biennial event?

GH: Yes. You know, Sotheby’s and I have received messages from all over the world asking how they get invited. There is such a groundswell of support for people just wanting to go and enjoy this event that I wouldn’t be shocked if we do it again next year, despite having done Rolliefest 3 just last year in September. We’ll know soon and maybe we won’t do it in New York. Let’s see what happens.

Rolliefest had 110 people in year one, 175 people in 2023, and for Rolliefest 3 we had 209 people. I can’t see it getting much larger. I think that’s an appropriate size.

WI: But even at that size, do you still personally know each and every one of the attendees?

GH: Yeah, unequivocally. Every single person is known to me. In many cases, they’re very close friends. There wasn’t a single stranger in that room in the One World Trade tower. People feel very comfortable to put their watches on the table and walk away because they know the room is safe and locked down. It doesn’t mean there aren’t men with guns secretly in the room, which there are, but we don’t need it. 

WI: You mentioned the lack of commercial sway, but ultimately it must cost a lot of money in the sort of event spaces that you’re talking about, not to mention the food and drink etc. For the people who are lucky enough to be invited, is there a nominal price to pay, as a way to at least cover your costs?

GH: Yes, that’s a good point. There is a charge each and every year. Last year it was $1,500. I did take sponsorship dollars from Sotheby’s, who have partnered with me for the last two events, and a smaller contribution from WatchCheck, which is the watch servicing partner we have at Sotheby’s. But again, they’re not trying to sell anything. There are no big signs on the wall or anything. This is certainly a not-for-profit, not in the legal sense, but it’s meant to break even. And between the cost of $1,500 a person, contributions from Sotheby’s, WatchCheck, and me personally, it becomes a break even event.

WI: I was going to ask about the separation between yourself and Sotheby’s, because you wear different hats at different times, I imagine. To what extent do you try and keep the two roles entirely separate?

GH: Let me elaborate, because the relationship goes beyond just sponsorship. It’s far beyond just writing me a check. Sotheby’s really embraces the notion of community, and we see this far beyond Rolliefest. One only has to attend one of our watch auctions here in America, and what you’ll see is a room full of cocktail tables and drink carts being pushed around, and sushi stations outside, and hot dog carts. We make it fun and it’s further bolstered by the fact that there’s so much youth coming into our hobby. A third of our buyers at Sotheby’s watches are Gen Zs and Millennials. 

Sotheby’s really embraces that and I consider them to be a real collaborator, more than just a sponsor. They really support it and I couldn’t have a better partner. 

WI: It’s a bit of a crude comparison, but when I think of Rolliefest, it strikes me as being a larger scale and more extravagant version of what RedBar does around the country. In some ways are the likes of you and RedBar ahead of the curve compared with traditional retail? Even the very best jewelers have an environment and setting that can feel quite formal, whereas it sounds like your gatherings are deliberately informal and work backwards from having fun.

GH: Yes, I like to think so. I don’t know if I’d say trailblazer, but it is unique in a number of ways. First and foremost, the list is curated. It doesn’t mean everybody is an expert advanced collector with millions of dollars of watches. We have some of those, and we have some more junior collectors, but the event is curated with really good people. The locations have obviously been wildly iconic and super special. I’ve lived in New York my whole life and I’ve never had dinner in the Temple of Dendur at night. My jaw dropped walking in, and the same thing happened having dinner under the Blue Whale or on top of the Intrepid, so we have these fantastic, iconic locations. We have all the right people who feel very comfortable bringing their best watches and showing them. Again, nobody feels pressure that anybody’s trying to sell them anything. In a sense, it’s really by the collector, for the collector, and that distinguishes it from other events.

So I think between the people, which is really 98% of this, and the locations, and the fact that it’s a secret, and the fact you’re going to see great watches, and that people are paying to be there, it feels like we’re onto a good thing. 

That said, I’ve lost money three times in a row. Maybe someday I’ll get that right!

WI: Compared with the first Rolliefest, there’s now so much hype around the event. There’s a clear excess in demand versus the number of spaces available, so is there now more responsibility on your shoulders regarding how you curate that list of invitees? By what criteria do you go about choosing them?

GH: I definitely feel pressure. The event sells out each time, and in the end I find myself squeezing chairs in. From this past year, I will probably never be able to reply to all the messages that have come in. That sounds like a lack of humility but I’m actually very proud of it. There are lots of messages coming in from all over the world asking how they get invited, so that gives me a great sense of pride. 

The room is mostly collectors that I’ve met along my journey. I’ve always said it, I’m born and bred in New York City and New Yorkers love to say “If you can make it here, you can make it anywhere.” But the truth is, I look back on my childhood and to some degree I feel like I was a sheltered Manhattan city kid. I only knew people that lived in the city, but because of watches I have a bed to sleep in in virtually every major city across the globe. I always love to talk about how watches don’t just tell time, they connect people, and the greatest joy of watch collecting comes, in my view, less from the watch and more from the human element of the owner. It’s all about the people.

For me, and everyone I think, that’s a cornerstone premise of the event. I’ve had the great fortune to have met so many great people from all over the globe, so that’s where the invite list comes from. It’s very international and it’s fun.

WI: Well, my next question was about the international element, because you mentioned not necessarily being beholden to New York in the future. Would you take it on the road in a similar way to WindUp, which now has events in San Francisco and Chicago and New York, or do you feel pressure to take the event overseas?

GH: I’ll never let the spirit of Rolliefest dissipate. You’re never going to see a Rolliefest every two weeks. It’s very different from RedBar, which I love, but that’s very regular. This is meant to be a very special event, but there’s no reason why it couldn’t be hosted somewhere outside of New York and I would love to entertain that notion. I don’t feel pressure to do it, but I sure as heck would love it, it would be a lot of fun.

WI: I’ve got skin in the game, but I think the UK’s had the highest per capita spend on Swiss watches out of any European country since 2000, so there’s a little hint for you!

GH: There are a number of people from the UK that attend. It bears noting that my logo was created by a London company called Bulletproof, the best branding company I’ve ever seen, And the owner of Bulletproof, his name is Gush Mundae, is a huge collector and he’s at the event every year and is one of my dear friends. So I have an added reason to want to do it there. London is definitely in the house, Daniel, I promise you that.

My biggest problem is, after the last event, people said, “Wow, I didn’t think you could top sitting under the whale and being at the Rainbow Room and you somehow managed to do it,” and now people have rightly asked how we’re going to top that again. I’d be lying if I said it’s not going to start to get difficult. I already have crazy ideas in my head, but keeping it at that wow factor level, which is a big part of the fun, is a challenge and a welcome one.

WI: It reminds me of the old Baselworld days with the Breitling parties, which were invite-only. It became a challenge to improve them each year. Do you organize Rollifest all by yourself?

GH: There’s nobody full time on the books on this. I had some administrative help from Sotheby’s and I hired an event planner to help me with some of the logistics, but make no mistake, the vast majority is done by me. It takes about a year, so I start planning approximately one year in advance and there’s no question this is a giant endeavor. All the insurance and the contracts and the hotel rooms, it’s a lot of work. It’s a great labor of love and I’m definitely not complaining.

WI: That’s the interesting point there. I mean, you love the end result of what Rolliefest has become, but stuff like insurance and security and logistics just don’t strike me as very fun.

GH: Well, some of it isn’t fun. But I’m also a lawyer, so I have confidence in my ability on some of this stuff. I always lose sleep about the security, but in a good way. I always have a decoy sign, so the public thinks there’s a marine biology conference or a real estate conference going on. I take security very seriously, and it’s not a coincidence that we haven’t had anything bad happen. 

WI: The nature of the event is that it’s very exclusive and secretive, so to what extent is it a bit incongruous that you’ve also had this amazing press coverage in high profile publications like GQ, the New York Times, the New York Post etc.?

GH: Well, not really, because there is no promotion of any kind in advance of the event. You won’t see anything beforehand. Another rule at the event, and there are signs to this effect that everybody respects, is that there’s no posting of any kind until we leave. So you can’t post from inside the event and everybody respects it. So there is no promotion of any kind before the event, except me maybe doing a teaser saying “Getting excited for Rolliefest,” but that’s it.

WI: Whenever I’m at collector events I’m amazed by the knowledge that people have of the products. When you’ve got a room of VIP collectors at Rolliefest, you must learn so much, even beyond what you know from your job at Sotheby’s.

GH: No question, if you look at the event, in particular the watch sharing luncheon, all the watches are on one long table and people are standing there looking at them and talking about them and picking them up, and they’re learning. There’s no question there is an educational element. There’s also a panel each and every time. We had one in September, it was terrific. We also have giveaways, so we give away six to 10 items, where names are just picked out of the hat and brands are donating these things. So there are people going home with great stuff and that adds to the fun of it. You’re sitting amongst some of the best scholars in the hobby in that room, and it’s a great place to learn. More than anything, it’s a great place to meet new people, you’ll see people you knew before, and it’s virtually impossible to leave that room without having new friends.

WI: That sounds amazing. On that point about the knowledge in the room, is it more about historical knowledge of brands and models, or are these people talking about the current state of the market and their predictions for the future?

GH: I wish it were that complicated, but it really isn’t. This is 200 great great people meeting new friends, sharing watches, and learning. Most of that room is well-seasoned, they know what’s on trend and what isn’t, and we can all make our judgment as to what the future will bring. 

With watch collecting, it’s all about the thrill of the hunt, provenance, stories. The most fun from watch collecting is derived from learning about those stories, asking “Where’d you find that?” or “Tell me about that treasure hunt.” That’s a really big part of it.

WI: Do you have a rule about repeat attendees? Are there some people who have come to all three editions of Rolliefest? If so, would you be hesitant to invite them again?

GH: Yes, there are definitely people that have come to all three. I don’t have any rule. If there’s somebody that’s been to all three, it’s very likely they’ll be invited to the next one because it means they’re sort of in my circle. But there are no rules. Every year there will be some new people that have been introduced to me, but there’s no strict criteria to getting invited.

WI: You mentioned you’re in your mid 50s. Just thinking ahead, if we fast forward a quarter of a century, and all being well and you’re alive and kicking, would you still want to be doing this? It feels like the part of your professional life that’s pure love.

GH: Absolutely. It’s pure love and I have every intention of continuing this. I’m really touched and heartwarmed by the reception. I don’t make money, but wow it’s such a life joy to see so many friends get on airplanes from all over the world and take 10 and 12 hour flights to get here to be at an event where they can share this great passion. It’s everything that I always did for years, and it’s nice to see that we have this in the United States, really for the first time. There are other events here, certainly, but they’re not quite as large. And there are other great events outside of the US and I go to many of them, but they’re just not quite as grand.

WI: Over the past five to 10 years it definitely feels like the States has become the epicenter of the watch industry in many ways. It’s certainly the number one market for Swiss watch exports. So it makes sense to me that WindUp and WatchTime have become so big, and now Rolliefest too, albeit in your own distinctive way. 

GH: Absolutely. Look, when watch collectors really get bitten by this bug, they’ll go to great extremes. A few years ago, I flew to Germany for 12 hours to pick up a watch that I bought. I’ve collected watches in airports and never seen the outside. I’ve gotten off the plane, met somebody at the airport, and turned around and gone through the gate again. People do crazy things, that’s a part of the fun. That’s a part of the craziness of it. It’s so much fun. 

What’s really important is that I just never take that for granted. That’s a big part of why I try so hard to put on a first class event. It’s not lost on me that if somebody is getting on a plane from Singapore and riding 15 hours to be here, it needs to be great. Folks are coming here on my invitation and I want to make sure they have a great time and have an experience that they couldn’t necessarily have in their own hometown, which is why you’re not likely to see Rolliefest in just a hotel conference room anytime soon. It’s got to be fun, it’s got to be different, it’s got to have the right people, and it’s got to be safe. I try to ensure with utmost pride that I’m delivering something that is worthwhile, especially for those that go to such extremes to be here.