Benjamin Siegel on Joining Hamilton Jewelers—and the Decade He Spent Building Tech Companies First

By Sam Cooley | August 19, 2026

Hamilton Jewelers has added to its fourth generation executive ranks.

Benjamin Siegel joined the Princeton, N.J.–based retailer on Aug. 3, arriving with 14 years of outside experience and a family rule to thank for it. Hamilton’s approach to getting there is perhaps counterintuitive: Make the next generation prove itself somewhere else first.

Siegel spent 14 years in tech startups and media—fast-paced, rapidly changing industries that rebuild their systems every few years. Now, he is joining a company whose competitive advantage, by his own account, is that key employees stay for decades and clients stay longer.

As director of commercial strategy and operations, Ben will work alongside his father, president and CEO Hank Siegel, and his brother Andrew, the chief operating officer.

What he’s joining is one of the more durable independents in American fine jewelry. Founded in Trenton, N.J., in 1912 and later acquired by Irving Siegel (who then passed the store to his son Martin), Hamilton operates three freestanding jewelry boutiques: one in Princeton and two in Palm Beach, Fla. Their stores carry brands including Rolex, Cartier, Chanel, Chopard, Mikimoto, Breitling, and Bulgari, as well as contemporary favorites such as David Yurman, Roberto Coin, and Pomellato.

Hamilton Jewelers Showroom — *The Hamilton showroom in Princeton (photo courtesy of Hamilton Jewelers)*

He enters the business as the company is approaching two major anniversaries next year: the 115th year of Hamilton and 100 years of Siegel family ownership—all the more impressive considering that only 3% of family businesses ever make it to the fourth generation, according to Cornell SC Johnson College of Business.

Below, JCK talks with Siegel about his early years in tech, his recent experience selling superyachts, how his family handled a fire that ravaged their business in 1957, and what he sees for Hamilton in 2037.

(The interview has been edited and condensed for clarity.)

How did you first get started in your career, fresh out of school?

Between college internships and my first few jobs, I did a little bit of everything—a hospitality management training program, an internship with a boutique commercial real estate firm in New York City, then working on the cutting-room floor in media at Major League Baseball.

I started my career in the early days of social media, when the tech scene in New York was really starting to take off. I volunteered at early-stage startup coworking spaces—that was 2012, 2013—and that’s how I got into what became my career for the last decade. I loved the concept of building from scratch, trying different things repeatedly to find the right success formula.

You’re part of a dynastic jewelry company, but you went off and did your own thing. What brings you back into the fold in 2026?

I have to give a little credit to my dad. Growing up, we had that rule about working outside Hamilton. I don’t remember if there was ever a time frame attached to it, but Andrew and I both would have surpassed it.

What started as exploring different spaces turned into finding something I really loved, which was tech entrepreneurship. That turned into a determination to grow my skills in that field, and then, fortunately, into some success. Then you look up one day and it’s been over a decade, and you start thinking about what could be next. I’m a firm believer that nobody is ever a finished product, especially professionally. At some point I just felt like I was ready.

In the meantime you went into yachting. What did that period teach you?

I’d been brought into Ikonic to apply the operational structure and processes from my previous sales organizations to what is a very, very antiquated luxury industry. As I went through it, my days started to look more and more like what I’d watched my dad and brother do from afar—selling a luxury product, building personal relationships with ultra-high-net-worth clients in South Florida and the Northeast, celebrating life’s milestones.

The biggest overlap is managing brand partners. In yachting we were constantly in communication with the top shipyards, making sure we were positioned to represent them well to our clients. Same at Hamilton. It’s partly the strength of those relationships—built over decades, in some cases—that lets us deliver the experience we do.

*Hamilton’s landmark Tudor-style building on Nassau St. in Princeton (photo courtesy of Hamilton Jewelers)*

Four generations in, what business wisdom got passed down at the dinner table?

My first thought was, Where do I begin and how much time do you have? So maybe it’s easier to talk about themes.

One we heard constantly was that Hamilton wasn’t something we left at the store at the end of the day. My dad would say the business was an extension of our family and our family an extension of the business.

My father and grandfather reminded us that wherever we went, however we treated someone, even how we spoke at a restaurant, we were representing Hamilton. The refrain was, “You never know who’s sitting at the table next to you.”

One story sticks out. In 1957, a fire destroyed our original Trenton storefront—inventory, designs, archives, everything. It happened in October, just before the holiday season. A lot of people who lost everything right before the busiest season of the year would have folded up. Instead the family moved into a temporary storefront nearby, and Hamilton ran a newspaper ad saying the only thing we could take with us was our reputation. I’ve heard that story so many times. It captures the lesson: People entrust us with much more than a purchase.

A century is a long time for a business to last. What’s the secret?

Trust, and everything that goes into earning it locally. But first and foremost, it’s our people.

In a retail culture where it’s commonplace to bounce from store to store, we’ve had some of our most influential team members stay loyal for decades. They’ve grown with us through all our different eras as the industry changed. That gives us institutional knowledge, wisdom to impart on new team members, and the ability to make quick decisions internally.

What was your perspective on the family business at 22, versus today?

I actually led my first letter to the company with this.

I grew up around the company but never worked in it, so I had the pleasure of it being all family and no business. I mean that literally—there are Hamilton team members I consider family, and clients I consider family. As I became more business-minded and my experience became more applicable, it happened naturally: asking my dad more questions, watching Andrew immerse himself. I started seeing Hamilton as more than storefronts and team members, but as operating functions and numbers and brand partner relationships.

What’s something about Hamilton that isn’t true today that you want to be true in 2037?

Hamilton has been fairly successful at using technology to drive efficiencies. My hope is we do better than that—that it isn’t a layer on top of our operating structure but ingrained into it, so you almost don’t feel it. Implementing new technology in luxury retail can feel burdensome, and that’s something all teams are going through as the advancements come quicker.

That said, I wouldn’t over-index on technology or AI. My brother would say the answer goes back to people. We’ve always made sure the operations closest to the client are still handled by a real person. The best way to deliver an incredible experience is still a smiling face on the sales floor.

The real aspiration is proving that local and family-owned and growth and expanded reach aren’t opposing forces. We’re proud that Hamilton is internationally recognized, nationally known, and locally trusted—and that doesn’t necessarily mean more stores or bigger stores.

Success will be measured by whether growth enhances the qualities our reputation was built on. If Hamilton is larger and more influential in 2037 but still feels unmistakably family-led and personalized and local, that means we grew the right way.