“When we founded Airbnb in 2008 our office was in a three-bedroom apartment in San Francisco, where [co-founder] Brian Chesky and I also lived at the time. The space was packed; there were engineers coding in the bedrooms, we were conducting interviews for new hires in the kitchen; and so restaurants and cafés became our “flex spaces” to have conferences.
One of our first off-site “offices” was Sightglass Coffee – a cool coffee shop in the SoMA area, which launched in 2009 – and we still go there, especially for the affogato [espresso over ice cream] bar. For more meaningful conversations we relied on Rocco’s Café, a family-owned Italian restaurant where the chicken parmigiana is excellent. This is where the early strategic discussions with my co-founders took place and I’ve lost count of the meetings we had there. I still love the atmosphere and daily specials – from pizza with pesto, olives and sundried tomatoes to pasta carbonara with chicken.
These days, I spend a lot of time in meetings in offices, but since our brand is based on the premise of getting out into the world, we try to work outside the constraints of the workplace as often as possible. My go-to spot at home for meeting investors as well as colleagues is Bar Agricole. Everything about it is just right: the food, the atmosphere, the architecture, the vibe of the staff. The all-organic menu changes daily, with things like avocado and marinated beetroot and fennel salad, and farinata – a Ligurian chickpea pancake. I came here recently with retired US army general Stanley McChrystal, a mentor of mine, and talked about leadership over plates of charcuterie and Marin Miyagi oysters, washed down with a rum cocktail.
I like laid-back restaurants, so another local favourite for dinners is Piccino, in the Dogpatch area. I’m a big fan of the converted warehouse vibe and open-air kitchen, and the menu references Italian classics but always in interesting new ways. The burrata, for example, is served with peas, fava beans, pistachios and mint. Everyone always leaves in a good mood.
For half the year, however, I am travelling – identifying new designs, as well as building relationships and focusing on humanitarian work. In the past year I’ve spent a lot of time in Japan where we have been creating Yoshino Cedar House, a shared rental space in the shrinking rural village of Yoshino, in collaboration with design studio Samara. Our conversations with designer Kenya Hara and architect Go Hasegawa began over dinner at the Michelin-starred Daigo, in Tokyo. We sat on the floor and ate delicious Buddhist vegetarian dishes of warm bamboo shoots, sweet potato tempura and soba noodles; there was lots of sake involved. The evening also exemplified two of my dining rules: I always defer to my host when ordering, and I’ll try anything once. This approach can, however, backfire, as at one dinner at Bror, in Copenhagen – a quintessentially Danish restaurant started by two former Noma chefs. The menu is nose-to-tail in the extreme and was, to my American palate, full of outrageous foods. I just had to man up and tuck into chicken hearts and bull testicles.
But challenging cuisine aside, I love places with local colour, such as Fabrica de Arte Cubano in Cuba. It was a real highlight of my recent trip. It’s such an architecturally amazing space – an interactive gallery in a converted olive oil factory in the vibrant Vedado area, featuring a wonderful mix of emerging artists as well as a restaurant, a club – and great mojitos. Best of all, cell phones don’t work in there. The dancing went on until dawn.”