A Tent in the Living Room: In Conversation with Greg Pensinger

Greg Pensinger is the Director of South Bay, a role he took on in January. This year, he celebrates 11 years at Downtown Streets Team. In that time, he launched new DST communities in San Jose, Santa Cruz, and Modesto.

DST: How did you get into homeless services?

Greg: Chris [Richardson, CPO of DST], introduced me to it. Chris and I were fishing buddies. Back then, I was writing curricula for online colleges and my view on work was very nine to five. Come Friday afternoon, I did not think about work until Monday morning, whereas Chris was happy to take phone calls while we were out on the lake. I asked him what kind of work he was doing that made him perfectly willing and happy to take phone calls on a weekend fishing trip. He described DST to me and I decided I wanted to get involved, maybe volunteer in some capacity. Several fishing trips later, he asked if I wanted to help with DST’s first expansion out of Palo Alto into San Jose. I interviewed and was offered the job of Project Manager in San Jose in 2011. And the rest is history.

DST: Can you give us rundown of that history? I know you were key to launching other communities after San Jose.

Greg: After launching DST-San Jose, I moved into grant writing and development, but office life was not for me. So, I returned to the field to manage Sunnyvale and Palo Alto. In 2017, I launched DST-Santa Cruz; and then in 2019, I moved to Central California to launch DST-Modesto. When the director role for South Bay opened up, I applied for it wanting to return to San Jose and have been the Director of Santa Clara County since January.

DST: What is involved in establishing a new DST community?

Greg: The DST model is really adaptable to the needs of every community, so the first step is to acknowledge that we CAN adapt and then ask HOW we should adapt to best serve the community we are entering. A lot of that work is building partnerships based on the specific needs of the unhoused community and the community in general. We have to determine what resources are available, what partnerships we can build out to enhance the experience of our Team Members. And we have to realize that while DST does a lot, we don’t do everything. We don’t manage shelters, so we need to build a shelter partnership, right. We don’t provide permanent supportive housing, so we need to build relationships with housing programs. Of course, there’s also working with funders and staying on top of compliance and tracking metrics. This is all part of what we call radical empathy, that is understanding the local needs, building them in to our operations, and displaying a strong willingness to collaborate with other problem-solvers.

DST: from your experience, does homelessness take different forms in different cities?

Greg: People experiencing homelessness face a universal set of challenges no matter where you are. Having said that, it’s also true that homeless communities do face unique challenges defined by place. In Santa Cruz, for example, substance abuse services are scarce, so service provision has to take that into account. Or take the example of Modesto. The cost of living is lower in that city, so you might be tempted to think that it’s easier to exit homelessness, but wages are also lower and affordable housing is scarce. So, yes, each city presents unique challenges and opportunities.

DST: From your new post in Santa Clara County, can you observe any trends playing out in South Bay?

Greg: In terms of visible homelessness, we are seeing more encampments. Encampments have become part of the landscape of the whole Bay Area for lack of shelter space and affordable housing. Moreover, displacing or forcibly moving encampments is not an effective solution to the problem and it can have very detrimental results on encampment dwellers. For example, if a case manager or outreach worker has built up a connection with someone in an encampment, and that person is forced to relocate, then the process has to start over in a new location.

DST: Do you see Silicon Valley or Big Tech stepping up in a major way?

Greg: There’s a lot of money in Big Tech—which helps—but even so, it’s hard to say. For example, DST-San Francisco was launched with generous support from Google; and Twitter continues to be a staunch corporate supporter for that community. But, the crisis of homelessness in California is so systemic, that even all the money in Silicon Valley can’t solve it in one go. It’s going to take the coordinated effort of many agencies, both private and public, to build the infrastructure required for large-scale systemic change.

DST: The importance of systemic change reminds me of an anecdote you told once about a tent in the living room? Can you recount that here?

Greg: The story is about Jim, the first person I ever helped get housing. He was the “mayor” of an encampment called The Jungle near Coyote Creek in San Jose. We got him an apartment, but he had been living in The Jungle for several years, and his status, his friends, and his network were bound up in that place. When I showed up at The Jungle to take him to his new home, he didn’t want to come. I practically had to pull him by the ear and pack him and his belongings into the truck.

When I checked in on him a few days later, I found he had pitched his tent in the living room. The tent was his comfort zone, where he felt safest. This was an eye-opening experience for me at an early point in my career. The image of a tent in the living room speaks not only to the need for post-housing case management but also to the need for intentional re-integration. It was unreasonable to think that Jim could adapt to being housed overnight or that he could replace one set of vital relationships for another, or a set of behaviors for another just like that.

There’s a conceptual approach that comes from the mental health field called psychosocial rehabilitation that is relevant here. It’s a model of practice designed to improve the lives of patients experiencing mental illness by teaching them emotional, cognitive, and social skills to help them live within their communities as independently as possible. This is why I believe in the approach that DST adopts in the care of our Team Members. At its core, it’s about building a supportive community – a Team– that models healthy behaviors as a community operating within a larger community. I believe this helps guarantee fewer tents in the living room.