Greg Flynn Bets on San Francisco’s Comeback with Major Investments

Greg Flynn, whose restaurant and hospitality empire spans the U.S., is banking heavily on San Francisco’s recovery. The founder of Flynn Properties was recently named one of the city’s 2025 San Franciscans of the Year for his ongoing commitment to local development, including the renovation of the historic Huntington Hotel and the transformation of Market Center on Market Street.

Speaking from the headquarters of Flynn Group in the Financial District, Flynn described his efforts as both a business decision and a vote of confidence in the city’s future. His recent acquisition and overhaul of two major properties reflect his belief that San Francisco, despite current challenges, is poised for resurgence.

The Huntington Hotel, located atop Nob Hill, is undergoing a full renovation that Flynn said will make it “by far the best hotel in San Francisco.” Built originally as an apartment building, its large rooms, classic Georgian facade, and panoramic views give it unique character. Flynn said the renovation costs are more than double the purchase price. He added that the Big 4 Restaurant—once a signature San Francisco institution—is being restored as it was, and a new bar named Arabella’s will provide a more intimate setting. Arabella was the second wife of Collis Huntington, the 19th-century railroad magnate for whom the hotel is named.

Flynn also recently purchased Market Center, previously known as 555 Market Street. He’s repositioning the two-tower complex as a hub for modern office tenants. Plans include a range of new amenities: an indoor-outdoor public bar, a basketball court, pickleball courts, a 30-foot climbing wall, a golf simulator, and private lounges. Flynn says his goal is to turn it into “the funnest building in San Francisco,” with renovation costs around $18 million.

Flynn emphasizes that both projects are long-term investments made at lower purchase prices due to current market conditions. He said cycles in San Francisco’s office market are predictable, and timing is critical. “I believe San Francisco is in the process of coming back from its downturn,” he said.

While Flynn’s projects aim to turn profits, he said they also serve a bigger purpose. “I love The City,” he said. “These projects feel like I’m giving back to The City a little bit in a way that I enjoy doing.”

He described San Francisco as a city driven by variety, creativity, and natural beauty, adding that his appreciation of the city informs his business approach. “If you are the kind of person who likes variety and interesting stuff and newness and challenge and enjoy meeting people with different lifestyles and different perspectives — this is a great place.”

Flynn’s current favorite restaurant is Sociale, a neighborhood bistro in Presidio Heights where he said he enjoys the food, the service, and the sense of community.

By revitalizing high-profile properties and adding leisure infrastructure to commercial spaces, Flynn hopes to model a path forward for San Francisco. “You can get almost everything right, but if you get the timing wrong, you’re in a bad place. You can do a lot of things wrong, but if you get the timing right, you’re in a good place,” he said.

With his latest moves, the city’s largest private restaurant owner is betting that the right time is now.