TALKING SHOP: Greenwich means time

Having already established a successful restaurant business in New York, Italian-born Roberto Chiappelloni relocated to Greenwich, Connecticut, in the mid-80s and started buying and selling watches. Through some connections and some good luck — not to mention a whole heap of skill, judgment, and hard work — today Manfredi Jewels occupies prime locations, offering one of the biggest ranges of independent watch brands in America, along with a significant selection of pre-owned timepieces. Watch Insider’s Daniel Malins paid the store a visit and sat down with Chiappelloni to discuss what still makes him tick. 

Watch Insider: How did you go from running a restaurant in Queens to running a jeweler up in Connecticut?

Roberto Chiappelloni: The restaurant, like most of my life, was either a consequence of opportunity or an opportunity that set everything that followed in motion. I went to a trade high school in Italy, which was hotel management, and then I decided to get a major in languages, thinking I’d go on to work for a travel agency or a hotel concierge or something like that. In the process, I always worked in restaurants, which was the easiest paid work opportunity there was. First it was in Geneva, Switzerland, then I went to England to the School of English and Commerce, and on and on until I did a stint on a cruise ship.

Then I decided to spend time at New York University and work in a restaurant for maybe six months in New York. One time I was with a friend of mine in this tiny little restaurant in Queens in Forest Hills and a gentleman that was probably about my age now, 75, was on the phone speaking in Italian with his attorney saying that he had to get out of the restaurant because he needed major surgery. Out of curiosity, I asked him how much he wanted for the restaurant. It was a negligible amount so I decided to buy a restaurant. It was an opportunity and that was that.

I worked very hard in that restaurant and fixed it up. I was young and I introduced to that neighborhood a true Italian restaurant. We became successful in no time, so much so that less than three years later I relocated to a larger premises where I was able to buy the building.

Also at that time, the whole mechanical watch industry was in the doldrums. Anyway, there were two gentlemen who owned a pawn shop that would eat in my restaurant a couple of nights a week and they knew I loved watches and they would always show me what they had bought. My passion for watches came when I lived in Geneva but back then I probably couldn’t even afford a watch strap.

The restaurant was doing well so I started collecting some very beautiful timepieces and I was able to purchase a lot of those watches, not thinking that I had some great investments or anything like that. I just bought it for my own pleasure. In the mid-80s, I moved to Greenwich, Connecticut. All of a sudden, watches that I bought for $700 or $800 were now worth $4,000. That gave me an impetus to look a little deeper and I saw this opportunity.

I had some connection to the jewelry industry. A very good childhood friend of mine, Julian Manfredi, was a very successful young creative designer who had shops around the world, including a beautiful store on Madison Avenue that I had helped establish in a small way by talking about the lease, getting an accountant, things like that. One summer while I was in Italy, we were spending time together and he said: “Why don’t you open one of my stores?” and that’s how we got the name Manfredi. I said if I was to do anything then I wanted it to be in the watch business. He told me I could do whatever I wanted but that I just had to represent some of his jewelry. So I did. My entire career and my investments were never really planned, they were just things that happened, all just at the right time and seeing an opportunity and taking it. I had four or five restaurants by that point and I could afford to make some mistakes, and I did. 

I built a beautiful little store, and the first brand was IWC, then Piaget, then Vacheron [Constantin]. But my passion as I started attending Basel[world] was always the small independents. I would go to the back of the room before I visited anybody else. My first independent brand was Franck Muller, and then pretty much every small independent that we could get our hands on. Nowadays the micro brand or the small independent are very well accepted but back then it was not the case. You had to believe it, you had to romance it, you had to explain and compare and contrast so much. Why would somebody buy a Franck Muller over a Vacheron Constantin?

WI: If you had your time again, would you have made more money by being a Patek Philippe, Rolex, or Cartier authorized dealer? Or do you think it’s good that you went in a different direction and carved out a niche for being one of the very few in the tri-state area to be putting your faith in these independents?

RC: Well, I don’t think I had a choice in my town. Those established brands were already taken, so there was a moot decision because it certainly would have been an easier path. But I loved that I was able to represent F.P. Journe, Richard Mille, Kari Voutilainen, and Laurent Ferrier. I love Lauren Fourier — for four years, we were the only dealer they had in the US and Canada.

People want a sure thing, but we’d say: “Take a look.” The independents had spectacular quality, and amazing passion is expressed in every thread of the watch. It was part of my passion, my love for watchmaking, my respect for these men that very often committed every dollar they had to their dream and passion to create a watch under their own name.

I mean, we were dealing with Gérald Genta, Daniel Roth, Max Büsser — all of these people were friends, we spent time together, and their love for their profession and their dreams were very alive. I feel very fortunate that I worked with and met these people. 

WI: It’s often a closer relationship because you were dealing with the owner of the brand. Do you think that’s changed much today because some of them have gone on to be so successful? Or do you still feel like there is a strong sense of camaraderie in that segment?

RC: Well, I lost some, like Richard Mille and F.P. Journe. When they go on to become boutique-only you lose the connection. It’s a big difference when they ask: “Could you buy another watch? Can you prepay some of it? Can you help me and take a couple more pieces?” It’s a give and take, one believes in the relationships and commits to it, not just out of charity but because we all, at least in my case, really believed they deserved the space and the help because of their talent. I’ve not just purchased them for resale but I’ve owned every single one of those brands by myself, so the belief was there that they are who they claim to be, and they are the talent that I wanted to represent.

WI: By what criteria are you judging these brands and which ones would be appropriate for your store? Is it gut instinct? Is it the personal relationship? 

RC: It’s a bit of a combination of different values. Superficially, it’s like when you see a beautiful girl before you enter into a conversation and you have that visual attraction. Then you speak and you decide to learn how it is made, who made it, what pieces come from where. You’re figuring out whether you can tell their story. Does the value correspond to what’s in it? 

I think it’s a gut instinct too, but more of a thought-out process at that stage of the game. I like money just like the next guy, but it’s never the first ingredient that goes into it.

WI: When you look back, do you think there was a period of time that was particularly transformative for the business?

RC: I certainly caught a very good time in our industry at launch. Mechanical watches were being respected again, but also we had a fairly healthy economy. It was 1987 when I really started putting my store together, opening in 88. That was a time where you could speak on a regular basis with brands. Your watchmaker was able to go to their headquarters in New York, go to Patek Philippe, go to Rolex, and come home with parts, service a watch, and three weeks later the watch would be on the client’s wrist without any extravagant expense or weight.

So, it certainly was a time that you felt more of a partner. You’re still an authorized retailer and there are rules, but we had give and take and we had real relationships. These relationships seem to have disappeared more now. Today it’s “I need this or that, and, if not, you’re out.” 

WI: Do you still have the restaurant?

RC: I sold most of them except the original one and in 08 when I expanded the jewelry store, my sister, who always participated and helped me with the restaurant, said: “Can I continue with the restaurant?” and so she did until the end of 22 and then we sold everything — the restaurant, the building.

WI: Before you sold it, had it got to the stage where one business was helping the other? For instance, customers who would buy watches would come to the restaurant and vice versa.

RC: No, it was very separate. Of course, some clients that knew me would visit the jewelry store, but really it was two completely different worlds. But the restaurant was very instrumental in financing the jewelry store. 

WI: So you had the Greenwich store and for some people that would have been more than enough. But some business owners always want to do the ‘next thing.’ Were you ever tempted to create an empire for Manfredi jewels?

RC: No, because I was always very much into the ability to mesh family life and being home at 5:30 at night and raising my wonderful daughter with my wife. We open 10am to 5pm and typically half an hour later we’re home. Our staff is all together and they get off at the same hours. We would have had to sacrifice too much for an expansion that was doable. But especially with the brands we represented, we could certainly have done a lot more. Now I don’t know what my daughter will do, but she seems to have the same view — she wants a bunch of children, she has a wonderful ability to be a mother and a business owner, and the two can live very well together without the expansion.

WI: And does your daughter have complete autonomy with your New Canaan store?

RC: I let her be because I feel that she’s capable, she’s made her own success in her world. She went to law school, got a masters in international law, worked in a major law firm doing mergers and acquisitions and all that, and then made the decision to come into the family business so that she could have more of a family life, as she’s married and has a young child. All of that gave me confidence in handing over to her as a managing partner and she purchased a percentage of the business and hopefully she’ll continue until she owns the whole store. 

If she asks me, of course I’m more than happy to give her my thoughts. But if she doesn’t, I’ll let her make her decisions. She’s younger, she has a better feel for fashion, where I’m more critical on quality, on the gem quality. I think a lot of the younger generation are more focused on trends and fashion and all that.

WI: With your daughter taking care of the New Canaan store, but is your view that whilst you’re passionate and healthy, you’ll keep going and going yourself? Or do you have retirement in your mind at some point?

RC: No, I really enjoy my current situation and my work environment. It’s nice knowing I do not have to make a decision, because let’s say something happened to me — she can easily continue until she decides what to do with it [the business]. Whereas before, maybe I’d have had to make some plans so that I don’t leave a mess! Now I work and I really love what I do, so it’s not an effort for me to come to work but also take a lot of time off. In the winter, we go to Naples, Florida, and then come back and go again for three months. And after Geneva, I went to Italy for almost a week. At the end of July, I’ll be gone for a month to Italy again and possibly Paris. I’m doing what I wish to do, what I want to do, and I’m enjoying my business.

WI: Is it easier or harder to make money buying and selling watches today versus when you started out? What’s changed?

RC: Well, I think what has changed is the financial climate. It’s live and well. There is amazing wealth that is available and trickles down and puts us to work, all of us. In 08, we all know what happened — we had to tighten our belts, we had to be aware. Then we had Covid and we thought that we would be shut down. Our governor kept our state open and we benefited from the surrounding — New York, New Jersey, Massachusetts — who were flocking into a town where restaurants were open, schools were open, businesses were thriving. So what we thought would be a very challenging time actually became a bonus time.

The ingredients should always be: do you have a product that has value? Do you have a service that has value? Are you listening to the noise that surrounds you, in terms of what your client thinks of what you deliver? I mean, we sell stuff that nobody needs, but if you talk to 100 people, 95 will share something celebratory or special that happened recently — a birthday, a graduation, a baby, a promotion. A store like ours is ideal because we truly connect to our client. It’s not: “Hand me that Cartier watch, here is my credit card.” We compare and contrast with the 37 brands we carry in the store.

Today, pre-owned watches are the rage and we’ve done that from the day we started, so it’s nothing new for us. People say: “This watch is a bit out of my price range” and we say “I bet you have a watch at home that you haven’t worn in 10 years. It has value, you can trade it in, it can offset the cost of getting you the watch that you really want to own.” We have that flexibility, we have all of these ingredients, and of course we have beautiful jewels, estate jewels, gems. We do it all. It doesn’t matter if it’s a battery for a watch, a watch strap, or a watch repair — as long as we’re able to get parts for a particular watch, we’ll repair almost anything.

All those things are really what determines if you have a business, because the flexibility of caring and taking the time to take care of that client really brings us to another level.

WI: You’re a man who’s owned many watches in your time, both in your personal collection and for your business. If you had to keep one watch for the rest of your life, which would it be?

RC: Let’s say two watches. One would be one of my independents that I love — Kari Voutilainen. He’s such a gentleman and he’s a friend and has been with us for almost 20 years. I was the only retailer he had in the US.

The other would have to be a sports model, you know, a basic Rolex Oyster Perpetual. The most basic watch because it’s easy to wear for someone my age, which has no date. For that matter, it could be another brand, but just a basic sports watch. I own a lot of watches, but I can’t even read half of them at this stage! I still love them and I still wind them and I’ll put them on. And honestly, I’m still buying watches. I just treated myself to a beautiful, ultra slim Breguet — beautiful enamel dial, no date again, just the epitome of an elegant, beautiful watch.

WI: Was that pre-owned or new?

RC: In that case it was new, but a large majority of my watches were purchased pre-owned. From the beginning, from the times before I had a store.

This article was first published in the June 2026 edition of Watch Insider.