The Soul of San Francisco and the Art of Hospitality: An Interview with Entrepreneur Jack Handlery

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Driving the economic, social, and cultural pulse of San Francisco are not just Silicon Valley giants or major tech multinationals, but a dynasty that has made a century-long mission of caring for people. Jack Handlery represents the fourth generation at the helm of Handlery Hotels and is today one of California’s most authoritative, influential, and respected entrepreneurs. Leading the iconic Handlery Union Square Hotel—founded by his great-grandfather Harry Handlery in 1928 and proudly remaining the oldest family-owned and independent hotel company in the State—Jack oversees daily operations by combining an uninterrupted family tradition with a modern vision of business and destination management. Featuring 377 rooms and suites, a rare outdoor heated swimming pool in the heart of the metropolis, and a prime location a stone’s throw from the theater and shopping districts, the hotel embodies a philosophy best synthesized by its historic corporate mission: “to make sure every guest never asks why they chose to stay here, but why they didn’t do it sooner.”
In this exclusive interview, Jack Handlery takes us behind the scenes of his city, addressing the challenges of the post-pandemic recovery, the relationship with the new administration, the impact of artificial intelligence, and the secret to a success that rejects standardization to preserve the warmth of a true home.

Mr. Handlery, San Francisco is a city accustomed to reinventing itself: from the Gold Rush and the great earthquake of 1906, to the silicon revolution and recent post-pandemic transformations. Having had a privileged vantage point on Union Square for four generations, how have you seen the architectural and social soul of this neighborhood change, and what do you believe its next urban face will be?

Dr. Pepe, fortunately, the new mayor of San Francisco, Daniel Lurie, is a huge supporter of our tourism industry. He recognizes that if the people who come here do not have an exceptional stay and do not experience an exceptional city, it will create negative repercussions on a global scale. So the new Administration, fortunately, has brought about drastic changes to the streetscape, introducing new events and new conventions coming to San Francisco in the coming years. The new city policy is therefore attracting a huge influx of AI companies to the city, for example: they understand that this is the central hub and this is where everything will happen. As for Union Square, we are witnessing a major shift in the area’s retail sector, and this is offering a new image to our guests. We are seeing a new San Francisco rising from the ashes of COVID, which really put the hospitality industry to the test.

Mega-metropolises often tend to create “bubbles” for travelers, detached from real city life. Walking through the downtown streets today, where do you think one can still breathe the true rebellious, bohemian, and multicultural spirit that made San Francisco a myth in the global collective imagination?

It is a very simple answer: Golden Gate Park. It is larger than New York’s Central Park and offers so much. Whenever I have guests arriving at the hotel, whether traveling with family or solo, they ask what to do. Of course, I recommend the restaurants, shopping at Union Square, the cable car, Fisherman’s Wharf, but I believe everyone traveling in major metropolises loves to take refuge in natural, wooded areas. In Golden Gate Park, you can see bison grazing freely, visit the Conservatory of Flowers, and find running paths. There are small food trucks, and it is truly a jewel of the city. It is the place I always recommend going.

San Francisco has recently undergone profound transformations and complex urban challenges, from the post-pandemic era to drastic changes in the retail sector. How has “doing business” changed in the city?

I cannot speak much about the retail market, but I can tell you how we have adapted: mostly through events, focusing heavily on weekends and packages. Today’s traveler is very experience-driven: they are not just looking for the cheapest rate, but want to know what they are getting in return. People gladly pay a little extra if they know they are getting a tour, restaurant packages included, or a complimentary bag. For example, we introduced our shopping package in partnership with Macy’s, the department store right across from Union Square: we offer a room discount, 50% off parking, coupons, and perfume samples like Valentino and Dior. Our guests love it. We were among the first to do it, and now I see other hotels imitating us because they see it works. That is how business works: if an idea works, you follow it. It means we are doing the right thing.

Today San Francisco is the global epicenter of artificial intelligence and technological innovation. How is this strong “tech” footprint changing the social and cultural fabric of the hotel industry? Specifically, the hospitality industry is moving rapidly toward automated check-ins, AI, and the dematerialization of services. How does a company that has always built its success on human contact and personalization innovate technologically without losing its nature?

Regarding AI, it has been a huge revolution in San Francisco, with companies like OpenAI and Anthropic being headquartered here. We use AI, both in San Francisco and San Diego, from a marketing perspective: to understand how to promote ourselves better, reach international markets, and analyze performance statistics in places like Italy. But once guests are here, AI needs to step aside. At Handlery, we will never do fully automated check-ins. We still have a switchboard with real human beings answering the phone. Robot deliveries are fun, but they make the guest feel like a number. If a customer asks for extra towels, we prefer sending one of our team members who knocks on the door and says, “Hello, do you need anything else?” Looking another person in the eyes with a smile changes everything. We use technology for invisible efficiency, but human warmth remains at the center.

Italian tourists are often considered very demanding. What are the typical peculiarities or requests of your Italian guests?

I have a funny memory from when I used to work at the front desk. Italian guests loved the room very warm and wanted the heating ready to go. I remember a guest who kept repeating that she wanted it even warmer: I walked into the room and it was incredibly hot, and I thought, “Just how high can we turn up the temperature?!” Jokes aside, every guest has their preferences, regardless of nationality. Just when you think all Italians want it hot, a group arrives wanting the room freezing cold. You can never generalize, but one thing is certain: Italians immensely appreciate authenticity and the human factor.

In Italy, the tourism business fabric is made up almost entirely of family-owned companies, but passing the baton between generations is often the most critical moment. You have successfully reached the fourth generation: what is the secret to passing down the vocation for hospitality, preventing it from turning into cold managerial administration?

A very simple answer: loyalty. I have the privilege of working closely with my father, who is our president and CEO. The key is loyalty to the team, suppliers, and guests. If there is no trust and loyalty within your own team, you have already lost, because it will reflect on the guest experience. When you see reviews praising our team by name, you understand the value of a stable team. We have had loyal guests who insisted that the same housekeeper, always clean their room. You won’t find that in a large standardized chain. If you are just looking for a bed, go elsewhere; if you are looking for a family, come to Handlery.

In a global hospitality market increasingly cannibalized by major hotel chains, Handlery proudly maintains its independence as California’s oldest family-owned hotel company. What is that “genetic trait” of your hospitality that a large group can never replicate or standardize?

It is truly the stability and dedication of our team.The average tenure of our team is 12 years. In our housekeeping department the average tenure is around 20 years! In our family—and my father and grandfather did the same—you start working at 13 starting out in housekeeping, then moving around to front office, accounting, reservations, engineering, etc. I myself have worked alongside many of these people my entire life. We do not come here just to punch a clock and collect a paycheck; we do it because we love the hotel, what our family has built, and the people we work with. This family component is our true DNA.

Why should a tourist choose to stay at the Handlery Union Square Hotel and the Handlery Hotel San Diego?

As I said: if you just want a bed, go somewhere else. But if you want to feel part of a family, you must choose Handlery. Our mission, since 1928, is simple: to make sure every guest never asks why they chose to stay here, but why they didn’t do it sooner. We offer an unbeatable location just steps from shops, restaurants, and theaters, beautiful heated outdoor swimming pools in both properties, impeccable cleanliness, and affordable rates. But what makes the difference is the human factor. When you travel, you always remember who made you feel cared for and welcome, who warmly asked what you came to do in the city. Our staff is the reason people return year after year. At Handlery you will always find that authentic warmth that no large corporate brand can replicate.