Pine Street Inn’s CEO Lyndia Downie on Solving Homelessness

by Karen Lieberman-Daly

Senior Vice President

Posted March 9, 2020

Development Guild is proud to have called Pine Street Inn a client for over 30 years. The largest homeless services provider in New England and a nationally recognized leader in the space, Pine Street provides a comprehensive range of services to nearly 2,000 homeless and formerly homeless men and women every day.

In the midst of the organization’s $50 Million, 50th anniversary campaign, and fresh off the news that the Boston’s Way Home Fund surpassed its $10M goal two years ahead of schedule, our Senior Vice President Karen Lieberman-Daly sat down with Pine Street’s President and Executive Director Lyndia Downie to reflect on Pine Street’s growth, the issues that persist today in solving homelessness, and what comes next.

Karen: 2019 marked Pine Street Inn’s 50th anniversary. What has changed in this time?

Lyndia: In our early days, all we could really offer was a place to sleep, maybe clothing, and on a good day when we had received donations, a meal. There was this belief that, as long as we provided shelter, that was enough – that people would be able to solve their homelessness on their own. This is true for some people, but for those who might be living with serious mental health issues, battling substance abuse, and/or are medically frail, providing shelter isn’t enough.

Today, we recognize that people need more than shelter. We have shifted our strategy to be more data-driven and informed by national research and trends. We focus more purposely on how long people have been homeless, and we’ve expanded our supportive housing units so they outnumber our shelter beds. In addition, we have an entire arm of the organization dedicated to housing search so we can help people move out of shelters permanently, and we have clinicians in our shelters and supportive housing units. We recognize that homelessness does not have a one-size-fits-all solution.

Throughout all this change and growth, what has remained the same?

While how we achieve our mission has changed, our mission itself remains the same. We continue to be the place where, no matter what the situation or obstacles, we will take you in and do everything we can to help you solve your problem – whether it be a short-term issue, like you don’t have enough money to pay rent this month, or a more long-term issue, like you have no income and you’re struggling with mental health issues.

Pine Street is still one of the few places where people can go when everything has fallen apart, and I believe the hallmarks of our founding—acceptance and respect—remain front and center in everything we do.

When you recently spoke with the Boston Globe, you discussed the challenge of housing those in need while average rent costs in Boston continue to increase. This is happening in almost every major city across America. How are Pine Street Inn and the city of Boston addressing this challenge?

Besides the extremely wealthy, access to affordable housing is an issue for everyone in Boston no matter who you are. While the city and the number of jobs have grown substantially, housing options—at all levels—have not kept up.

elderly woman sits on bedHowever, what I would point out is that for the fifth year in a row now, Boston has had the lowest street count of the 30 largest metropolitan areas in the country. Only 2% of the city’s homeless population sleeps outside. Of course, we’d like that number of be 0%, but when you compare it to places like Florida, Texas, or the West Coast (50% of San Francisco’s homeless population sleeps outside), you understand the success of our efforts.  And some people may point out that it seems logical for the street count to be higher in warmer regions, but even if you double our percentage, we’re nowhere near 50%.

And it’s not just about weather – it’s about a deliberate effort to connect with and help people living on the street. Having people living on the street is horrible for many reasons; it negatively impacts neighborhoods, businesses, hospitals. The longer people are on the street, the more likely they are to visit an emergency room, to end up in an inpatient bed, so we’re focused on helping those who have been dealing with long-term homelessness. Our street outreach team is out on the streets 365 days a year, and every person in Boston who has been homeless for more than a year is added to a master list for housing vacancies and logged in a common, shared database. Members of our outreach and housing placement teams meet with other housing providers in Boston on a weekly basis to review the database and identify barriers that are keeping these people from being housed.

Is this approach unique to Boston?

Other communities are taking a similar approach, but I believe the level of coordination and the relentless determination we possess to recognize and help those who have been homeless for an extended period sets Boston apart. There are people living with significant disabilities who often remain homeless for years and contribute substantially to homeless rates in cities, and we’re committed to helping this population. There’s a collective acknowledgement that if we don’t help them, no one else will.

How can someone like me or the person currently reading this interview help?

Beyond volunteering and providing financial support, people can help by questioning and battling stereotypes about homeless populations. In Boston and Brookline, Pine Street owns 35 buildings. Most people in those communities have no idea we own the properties or that the residents living there are formerly homeless. However, we are constantly facing pushback and zoning issues when we attempt to build more housing due to unfounded fears people have about homeless people.

When the citizens of Boston help us dismantle these stereotypes and spread the word that supportive housing is a sustainable solution to homelessness, it makes a difference.

Tell us more about the Boston’s Way Home Fund.

The Boston’s Way Home Fund was started by Mayor Marty Walsh. When he was first elected, instead of having an inaugural celebration, he came to us and said he would rather that money go towards housing homeless people. Together, we came up with the idea of creating a fund that would help us build 200 additional units of supportive housing in Boston.

man washes dishes while smilingWe were able to raise $10M from private funders, which will cover the cost of our supportive services. I call this the ‘glue’ of supportive housing – it’s the staff who are committed to helping people find housing and stay housed. We had a retention rate of over 90% in our supportive housing last year, and that’s absolutely due to the work of our supportive housing staff. You and I and most people we know have a support system when we face challenges in life, but many of the people we work with don’t. Our supportive housing staff provide that assistance.

We’re thrilled at the response we’ve received for the fund. We are meeting with the zoning board next month with the hope of starting construction on a site in Jamaica Plain in 2021.  

You’ve been with Pine Street for over 30 years. When you look forward, and especially given that it’s the start of a new decade, what energizes you the most about the future?

There a few things I’m excited by. The fight to continue developing housing for the lowest-income and most vulnerable people will always be a top priority for Pine Street. Of course, there will be challenges, but we have to do it.

Second, I’m excited by the possibility of stronger coordination, not just at the city level, but also with state partners and private partners. How can we connect the disparate systems and services that the people we work with need? For a lot of the people we serve, their lives tend to fall apart during moments of transition – they complete detox, but can’t get a follow up placement, or they get a follow up placement, but it only lasts a month. How do we invest in long-term solutions? Does this person need first and last month’s rent, or an opportunity to stay with someone for six months while they look for a new job? I am excited about some simple interventions we can use to help people.

I also think we can use our data to better inform our next set of programs and responses to homelessness. While we currently have a lot of data about how long people stay homeless, there is an opportunity to do more predictive analytics going forward. We need to know who is coming through the door, what the likelihood of them being homeless long-term is, and, most importantly, how we can intervene now. While we’ve made some progress in this area, there is a long way to go.

 I want to shift gears a bit and ask what advice would you share with CEOs on how to partner effectively with their organization’s development team?

I would remind them it’s mission first – if your mission matters, you can’t achieve it without money. Philanthropy offers a chance to do things that the public sector can’t or won’t do. At Pine Street, we have been able to use philanthropic dollars to start programs and track outcomes, which has enabled us to then bring this data to the public sector, display the program’s value, and request they fund it at scale.

I’d also say that philanthropy has to be embedded in the business and mission just like everything else you do. It has to be a core part of an organizations’ culture. It’s not just about raising money – it’s about raising support from the community. To achieve social change, you need the ability to scale and ample support to scale – philanthropy helps provide the path.

When you think back on Pine Street’s first comprehensive capital campaign in 1990 in comparison to the current 50th Anniversary Campaign, what lessons did you learn along the way?

Our first campaign was an enormous learning experience. We were starting literally from square one. I remember Meg Morton [retired-Senior Vice President at Fidelity Foundation] came to Pine Street and asked us about our feasibility study, and I told her we were working on it. When she left, I turned to a colleague and asked, “What’s a feasibility study?”  And that question brought us to Development Guild! But I will forever be grateful to Meg for helping us recognize what we didn’t know. Since then, we’ve learned a lot:  how to get our vision on paper; how to recruit a board and campaign committee who will help make our vision real; and how to be more intentional when we ask donors to partner with us – in general, to do a better job aligning our aspirations with our donors’ aspirations.

Ultimately, you have to have a strong vision to be successful. Nobody is going to buy into something that isn’t inspiring and visionary. It’s the President’s job to inspire that vision and help execute it by making sure staff have the tools they need, and the organization has enough support.

Read our Pine Street Inn client story to discover how multiple campaigns have positioned the organization to fulfill its mission of making permanent housing a reality for all.


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