Caitlin Gilman

The Millennial Side-Hustle


Airbnb Superhost


I’m most proud of the Boston Public Market project because I'm able to see the direct result of everyone loving that space.  It’s a space that everyone can join, that's open to the public, and working on a public project like that was really rewarding.










By Abigail Bliss

The latest installment in our Millennial Side-Hustle series offers a fresh take on the way the gig economy affects communities today: Caitlin Gilman, architect and Airbnb Super Host, forges connections and finds community via the Airbnb platform.

As an architect, Gilman has shaped public spaces throughout the city of Boston, having worked on the Boston Public Market interiors and contributed to city planning and preparation in the face of climate change.  As an Airbnb Super Host, she’s received five-star reviews across the board and hosted travelers from all around the world in her Jamaica Plain home.  Her two pursuits allow her family to tread water financially and leave her uniquely poised to understand the changing concepts of home, workplace, and community in the 21st century.

I recently sat down with Gilman at her home in JP, her toddler sleeping upstairs and Airbnb guests in the adjoining unit, to learn how Airbnb is revolutionizing the way people travel today and why sustainable design is particularly important in the city of Boston. The main takeaway?  How can every voice, regardless of profession or background, can be a part of the critical conversations shaping our city today?

What attracted you to architecture?

I was always interested in design. When I was younger, I would keep a notebook of t-shirt designs. In undergrad, I studied Art History and Humanities and thought, maybe, I wanted to teach. Then an opportunity came up where I could be the buyer for a clothing store my friend was starting. I went into fashion that way, and then I realized I wanted to be on the design side of it, and I wanted the creativity with more parameters and more rules, and I wanted it to be more structured. I thought, 'Architecture has both.' It has the creative side, but it’s also very technical. There's a lot of math. You're beholden to physics. The building has to stand. 

I had never done anything architecture related: I hadn't taken any architecture classes other than Architectural History so once I graduated, I did a summer program at Harvard called the Career Discovery Program. It's this immersion where you can just try it out, an intensive summer course with lectures and real assignments. I fell in love with it. I couldn't leave the studio. I was up all night dreaming about the designs and dreaming about the work. From there, I went back and to get my master's degree, and became licensed a couple years ago.

What kind of architecture do you practice?

When I went back to school, I knew I wanted to focus on sustainable design. If we're going to be making new buildings, we should design them intelligently. We can do it better than we have in the past. I went to the University of Oregon because their focus is sustainable design and then onto Boston in a firm focused on 100% sustainable design. We’ve done work everywhere – from net zero buildings that don't require any energy from the grid, to the Boston Public Market interiors. I've since switched firms and still focus on sustainable design. I work on a broad range of projects, from schools to high-rises in Jersey City in New York.

I’m most proud of the Boston Public Market project because I'm able to see the direct result of everyone loving that space.  It’s a space that everyone can join, that's open to the public, and working on a public project like that was really rewarding.

What challenges are the field of architecture facing today?

Because my focus is sustainability, I think that's a huge issue that a lot of architects need to address. The field is getting better at making sustainability a focus, but it's often a side note, or architects will have one or two projects where it is a priority. Buildings are a huge contributor to climate change, and if we really want to combat climate change, every building needs to be thought about in a sustainable way.

For Boston in particular, another project I worked on and was really proud of was the Boston Living with Water competition, put on by the City of Boston. It is an international design competition, open to people worldwide, with the goal of coming up with solutions to help fortify the city against rising tides. If you look at a flood map, most of the Boston that we know will be underwater by 2100. Sandy only missed us by five hours; if the storm had been five hours earlier, it would've hit Boston, and the damage that would've caused to buildings around the coast and to Back Bay – that is huge. For any new building that goes up in Boston, we need to be thinking not only about energy use now, but also resiliency and how we can build so that we're fortified against something like Sandy.

I recently saw a new map showcasing vulnerability to climate change in and around the Boston area, and it’s pretty alarming, even for areas not directly on the water.

Yes, it's crazy! You probably know that most of Boston is infill. If you compare those recent maps to the original maps of Boston, they look almost identical. Back Bay is essentially all infill, and even though it’s not necessarily on the water, it’s all going to be underwater again. Everything that’s filled in is just going to be back underwater again, and it is alarming; the city’s almost being restored to its original land mass. Next time, look at the two maps side by side.

How has residential design changed in the past ten years?

There is an interest in building homes that are more energy efficient because there's a direct cost benefit for the owner. As oil costs go up, heating costs go up, and you start to see the impact on your wallet. Homeowners in the past might not have cared if homes were sustainable or not, but now they might be seeing the direct cost in their pocket and are looking for ways to save energy through sustainable design.

Why did you decide to start hosting through Airbnb?

My husband and I used Airbnb for a really long time and loved it. And, we had bought this house, which is multi-family, so we were already renting space out to tenants. Then a friend from Germany came to stay in our little basement apartment, which was a bedroom with its own private bath, and it also has a sink and some cupboards and its own entrance around the back of the house, and we realized that this guest could come and go as he wanted; it’s totally private. That’s when I thought, “This could actually be an Airbnb.”

We decided to put up a listing to see if we got any hits. Now, we're booked out almost full time. My parents have a hard time visiting. I’ll tell them, ‘You have to book six months in advance because there’s no openings when you want to come stay.’

It started out as side-income. Because we own the place, there's a high mortgage. This house was built in 1898, and there are a lot of repairs and projects that we want to do.  Having that supplemental income has been huge, and it’s become bigger than we had hoped and has allowed us a freedom to do projects and a security with our property that we didn't have before.

You're now a Super Host. What does that mean?

The Super Host has specific criteria. You have to get five stars in every category –cleanliness, location, friendliness, etc. For a long time, we had five stars in almost everything, and our rating was like 4.9, but location was the one where we couldn’t quite get five stars. We're located near the T, so we get really high reviews from some people, but other people wish they were closer to Boston. I think because there's such a high volume, we eventually had enough five star reviews, and we're now a Super Host. We try to put a lot of care and a lot of thought into our unit.

Who do your Airbnb guests tend to be?

Surprisingly, there's a really big range. We see some of the tourists we expected, but we found that we fill a niche that we didn't really know existed: people who want to come to Jamaica Plain. There aren’t really hotels or a lot of accommodations here that are nearby, or even affordable. We've had first-time grandparents visiting their son who lives a couple streets down with a new baby, or families that have other friends or other family members in the neighborhood. We do get a fair number of one or two-night tourists that are here to see Boston and want to do it more cheaply; the hotels in Boston are so expensive. We actually have some commuters who live farther out, but want to have a night out in the city and take public transportation. So, they'll actually just take the train to our house, spend the night and then go home in the morning. Airbnb fills a larger need than we realized in the city.

Are your neighbors open to your guests coming and going?

Yeah, we haven't had any issues. Because it's a private entrance, our guests aren’t bothering our direct neighbors at all, and everyone we've rented to so far has been great. Airbnb has a really good online community.

Tell us about that community.

When you hear about Airbnb, there are always these horror stories. And, I know those exist, but as a whole, Airbnb is full of people that want to travel differently, that want to look for interesting spaces or maybe cheaper places, that have interesting stories, that are coming from all over. One of the features in our apartment is a map of the world, and everyone puts a pin where they’re from. It's amazing to see where everyone has come from.

Why do you think Airbnb has been successful?

They allow people to be their own entrepreneurs, which is huge. You can get extra income while being your own boss. People have property taxes and mortgages for their houses when family moves out. Airbnb allows them to meet those.

Also, Airbnb has done a good job of fostering an online community. Their rating system is really good. As a traveler, it’s really easy to use. They set up messages like, ‘check in with your guest,’ or, ‘check in with your host.’ They’re starting to branch out, too; they’re now offering experiences instead of space rentals. Someone could offer a pottery class for twenty dollars a visit, or a photography class on portraits around the city of Boston. You can make income by giving the guest a more personal experience around the city rather than simply doing the touristy things. Vacation rentals have always existed, but Airbnb is different because of that online community. They're always I think thinking of new ways to make the traveling culture better.

As an architect, when do you think design will start incorporating these new demands of technology today? Will we start seeing lanes dedicated specifically to Ubers, or a surge in in-law units intended specifically for Airbnb?

I want to say ‘yes,’ but I think it's easy for architecture, at least, to get stuck. I’ve seen this with sustainable initiatives – addressing flooding, for example – where there are codes that make it difficult to enact certain changes. For example, if the zoning code says that the ground floor has to be retail – well, if the first floor is going to be underwater, you don't want to put a retail space there because it's going to be flooded. Maybe you want to put parking there and move everyone up and elevate the street level and have it a little bit higher, but the zoning code won't let you do that. I'd like to see advances like lanes dedicated for Ubers, but there’s always slow change in implementing those kinds of things. I do think there would be a lot of interest in creating other apartments knowing you can rent out through Airbnb. I think that might be driven by developers. It’s a huge selling point.

How has the gig economy changed the concepts of workplace and home?

I think it's changed the workplace in that people are seeing that they can have more freedom – and actually earn pretty good income doing side jobs. I work full time.

We have an eighteen-month-old boy, and my husband has been able to be home with him. The only way we could manage this is the Airbnb income. It's given us freedom to have a holdover period

while my husband tries to build up his company. And, we now have this young toddler, and we're trying to make that work, and we haven't found a daycare that we like yet… It gives us room to tread water. I think it's created a much better work life balance that people can't quite find in a traditional job setting.

It seems people are putting off buying a home: One third of Americans between the ages of 18 and 34 live with their parents. Will people, at some point, just stop owning homes?

In cities, maybe. I think nationally, no – only because there's still part of our country that really focuses on, ‘This is my land. I want my space. I need my home.’ But for people that live in cities, it's becoming so expensive, and a lot of people don't want to be tied down. They want to be able to travel. They want to be able to move where their job takes them. You can work anywhere for certain jobs, so why be tied to one place?

I also think that part of that is tied to the fact that home prices have become so expensive. It's so hard to buy, whereas even for my parents' generation, the ratio of the cost of homes to their income was much less, comparatively.

What about college tuition?

Yes, and college tuition. Maybe some people really don't want to buy, but I think a lot of people can't. The gig economy might help with that, especially with Airbnb, which very nearly pays for our mortgage. It's pretty amazing.

Whose hands do you think are instrumental in the shaping of Boston as a city?  Are there any prominent architects or planners?

There's the BRA [Boston Redevelopment Authority, now The Boston Planning & Development Agency], the big overarching arm that decides what does or doesn't get built or is or is not approved. I think I'd like to say, ‘the people,’ only because there are opportunities where you can voice your opinion. You can go to hearings. People can speak out if they're seeing certain codes that aren't being implemented that need to be, either sustainability-wise or zoning-wise.

I've been to some planning meetings. I've been to hearings about Airbnb, specifically, in Boston. A couple of years ago, they were trying to decide what regulations, if any, they wanted to impose. Did they want to go the way of New York and San Francisco? It was an open forum, and people from all over the community stood up and said if they supported Airbnb or why they didn't and why not. There were people from both sides, and the mayor and his team were there taking notes. They were listening. I think it's easy to sit back and say, ‘What can I do? I'm just an average person. I have no say,’ but if enough people go out and speak up, they can be the hands that mold the city.

How can non-architects and planners get involved in the conversation?

I think the hardest part for non-architects, and even me as an architect, is sometimes you get lost. You just don't necessarily know when things are happening, what's going on, what changes are taking place. Maybe the city could do a better job of communicating certain policies that are affecting specific neighborhoods, but I think it's the knowing that's the hard part.

What is your favorite piece of architecture in Boston?

I think my favorite space to be in is the Boston Public Library. It's a classic. There's this moment where there's the old Boston Library and the addition, and in the floor, the architect demarcated where the addition starts and where the old building ends, and the line where they meet is a really – I love that point in the Library, where the old meets the new.