A study of a San Francisco nonprofit’s $100 million effort to reduce chronic homelessness by half in five years shows the effort fell significantly short of its goal. But the Urban Institute’s analysis of Tipping Point Community’s ambitious quest holds valuable lessons for philanthropy.
Specifically, the study illuminates how hard it is for philanthropy to fix a big and seemingly intractable problem like homelessness in a relatively short period, especially if there isn’t sufficient collaboration with municipal government.
While the 2017-2022 Chronic Homelessness Initiative helped build housing for the homeless, the program couldn’t keep pace with the number of people becoming homeless and flowing into the system just as others were getting housed. The Covid-19 pandemic brought unexpected challenges as well.
Tipping Point CEO Sam Cobbs says his nonprofit overlooked the importance of focusing on broad systems that work to prevent or stop homelessness before it starts, and miscalculated what it would take to build positive relationships with the city’s government agencies.
“We really underestimated how difficult it would be and how long it was going to take to build trust and the positive relationships that we needed to have with our partners in the government,” Cobbs says. “Philanthropy is great, but it doesn’t have enough money to scale anything. You really need your government partners to do that.”
The Urban Institute study found that five years wasn’t enough to cut in half the number of people experiencing chronic homelessness in San Francisco, and that the Covid-19 pandemic significantly affected the effort’s timeline and government and nonprofit partners’ abilities to reach the program’s goals. It also found that Tipping Point officials erred in publicly announcing the Chronic Homelessness Initiative before building strong relationships with government agencies that had more experience on the issue. This caused tensions with government partners and made it harder to plan strategies and programming.
The report goes on to say that the jargon Tipping Point used to describe how it planned to work with its government partners, such as “optimizing the public sector,” angered some city employees. Even so, relations between Tipping Point and San Francisco government representatives improved in the latter part of the partnership with the achievement of some program goals.

Tipping Point spent nearly $100.7 million on 32 programs between 2017 and 2022 aimed at halving chronic homelessness, which the federal government defines as people grappling with mental illness, a physical disability, or substance abuse and who have experienced homelessness for at least one year or repeatedly over time. A government survey found about 6,800 individuals experienced homelessness in San Francisco in 2017; by 2022, the number grew to 7,750.
The Tipping Point effort guided 595 chronically homeless people into permanent supportive housing. It also moved an additional 373 people, already living in supportive housing but ready for more independence, into market-rate housing through a voucher program.
A spending breakdown shows that the Chronic Homelessness Initiative devoted nearly $69 million to creating housing and about $12.3 million to programs that work to improve San Francisco’s overall response to chronic homelessness. A further $10.3 million was spent on programs aimed at preventing people from becoming chronically homeless, while operations, staffing, and evaluation cost more than $9.1 million.
A bright spot, Cobbs says, was the planning and construction of Tahanan, a 145-unit apartment complex, developed in collaboration with the Housing Accelerator Fund, a nonprofit that raises private and government money to build and protect affordable housing.
The Tahanan project took only three years to complete, about half the time such a process usually needs. Cobbs says his organization worked to get 11 other parking lots in the city zoned for such housing, although he said there isn’t yet a timeline for when construction on those lots will be completed.
Insufficient Data
Among the challenges for Tipping Point’s Chronic Homelessness Initiative was the lack of up-to-date, reliable data on how many people were experiencing homelessness or entering into homelessness — what experts call “inflow” — says Samantha Batko, who led the Urban Institute’s evaluation.
“You can maximize placements — even exceed goals on placements — but if you’re not preventing people from entering chronic homelessness, you’re going to continue to struggle as a community,” Batko says. “Even now, five years later, we still don’t have a great sense on inflow [in San Francisco] and it’s still a challenge to understand the pathways into chronic homelessness specifically, as well as the number of people who would traverse those pathways in any given year.”
Go Deeper
-
Nonprofit Effectiveness
How Much Good Can $100 Million Do? Sesame Street and IRC Put a Big Bet to the Test
One of the few regular sources of national data is the Department of Housing and Urban Development’s Point-In-Time Count survey. This national head count tallies both sheltered and unsheltered people who are experiencing homelessness on a single night in January. The count isn’t published sometimes until a year later, so it is out of date when it reaches those working on solving homelessness. Its generalized and anonymous nature makes it unhelpful as well, says Rosanne Haggerty, who leads Community Solutions. Her nonprofit won the MacArthur Foundation’s $100 million 100&Change award, in 2021 for its successful approach to speeding an end to homelessness in 75 U.S. communities over five years.
Haggerty points out that HUD’s survey was not designed to help nonprofits and other government agencies understand who is unhoused in real time. She says it is primarily a part of a “billing system” where communities that receive HUD homelessness funds are required to enter their data.
“Any kind of sophisticated problem solving, name any field, involves specific real-time dynamic information, and communities don’t have that,” says Haggerty.
Philanthropy’s Role
Tipping Point was founded in 2004 by Dan Lurie, an heir to the Levi Strauss fortune who stepped down as the nonprofit’s CEO in 2019 and is now running for mayor in San Francisco’s 2024 election. Fourteen donors contributed to the Chronic Homelessness Initiative, which became the city’s biggest private endeavor to reduce chronic homelessness.
But the $100 million in philanthropy pales in comparison to what San Francisco has spent to reduce homelessness between 2016 and 2022: over $2.8 billion, according to an analysis from the Hoover Institution. The Urban Institute report underscores that, though smaller, philanthropic dollars can play an important role, particularly in testing, identifying, and advocating for what works.
“Government funding has a lot of restrictions that private funding doesn’t necessarily have,” says Cobbs. “The big infusions of private capital can do things that the government dollars can’t do because of all of the requirements, all of the bureaucracy around them. What the private dollars can do is show that it works and then advocate to the government.”
Amanda Andere, CEO of Funders Together to End Homelessness, a coalition of grant makers (of which Tipping Point is a member), says while directing philanthropic dollars toward building housing and related programs is important, she thinks philanthropy should focus more on advocacy, organizing, and coalition building.
“It’s going to take real big investment to build or give people access to housing, Andere says, “but at the same time it’s also going to take us looking into how folks get into housing, who is getting into housing, who’s been historically marginalized or prioritized. That doesn’t happen just with an investment into the housing piece.”
She says the limitations of Tipping Point’s five-year effort show that solving the problem of homelessness requires widespread systems change — and an end to the affordable housing crisis.
“Every time we try to program something, we are trying to tweak around the edges instead of getting to the crux of the issue,” says Andere. “Affordable housing solves homelessness, but we are in a housing crisis, and that housing crisis is due to decades of not investing in the right things like [ending] structural racism. Where philanthropy can play a role is in thinking about a systems change rather than a program intervention.”
Reporting for this article was underwritten by a Lilly Endowment grant to enhance public understanding of philanthropy. The Chronicle is solely responsible for the content. See more about the Chronicle, the grant, how our foundation-supported journalism works, and our gift-acceptance policy.