The Robin Hood of the West: Inside the Antipoverty Work of Tipping Point Community

Addressing homelessness has been one priority for Tipping Point Community. JHVEPhoto/shutterstock

Last year, we did a deep dive on the Robin Hood Foundation, founded in 1988 by Wall Street titan Paul Tudor Jones with the ambitious mission to eliminate poverty in New York City. Gotham’s largest antipoverty charity is very much a byproduct of New York City wealth. But on the other side of the country, Daniel Lurie, a former Robin Hood employee and an heir to the Levi Strauss fortune, took some of the lessons he learned and set out to tackle poverty in the Bay Area. In 2005, Lurie launched the grantmaking organization Tipping Point Community, a name he conceived because he was fond of “Malcolm Gladwell’s notion that a few passionate people with a good idea can spark change, big change.”

Since then, Tipping Point has given away some $412 million across areas like housing, early childhood, education and employment. In the past, for instance, we’ve covered Tipping Point’s work supporting foster care youth. The grantmaker rakes in support from a range of high-level donors including Michael Moritz and Harriet Heyman’s Crankstart Foundation, the Charles and Helen Schwab Foundation, and the Anne Wojcicki Foundation. (Wojcicki was recently named to our 50 Most Powerful Women in U.S. Philanthropy list).

After a long tenure at the helm of Tipping Point, Lurie, who is now running for mayor of San Francisco, handed over the reins to Sam Cobbs. I recently connected with Cobbs, as well as Chief Program Officer Ali Sutton and donor Tammy Crown, to find out more about what’s new at Tipping Point. In our conversations, I learned about some of the organization’s latest work, lessons from tackling a seemingly intractable issue through different philanthropic avenues, how Tipping Point has raked in serious support from donors, and what’s in store down the line.

“What he was trying to build”

Before Mississippi-born Sam Cobbs became CEO of Tipping Point, he headed up First Place for Youth, which tackles poverty and homelessness among young people who age out of foster care. One of its first supporters was Tipping Point Community, back when the antipoverty organization was just getting off the ground in 2005. Cobbs met with Lurie, kicking off a longstanding relationship.

“He started to talk to me about what he was trying to build, that all of the funding they were going to give was going to be unrestricted funding,” Cobbs told me, recalling Lurie’s belief in sustained, multi-year support and easing reporting burdens for nonprofits.

A small organization at the time, First Place for Youth had about $1.3 million in overhead. Tipping Point went in with an initial $25,000 grant. But Cobbs said it wasn’t the amount of money that really sold him on Tipping Point, but Lurie’s vision of a new way of doing philanthropy in the Bay Area. “I just realized that he was thinking about and doing it in a different way and I wanted to be part of it,” Cobbs said.

It has all come full circle for Cobbs, who joined Tipping Point as chief program officer in 2018 before becoming president and then stepping into the role of CEO in January 2020. He says that the principles that the organization was founded on still persist, including empowering leaders on the ground who are “proximate to the problem.”

For the first 15 years, Tipping Point’s primary focus was the amount of money it gave away, Cobbs said. This is still an important metric. But over the past five years, Cobbs said he’s proud the organization has been more focused on holding itself accountable to what’s happening in the region. “What has that money done? What has been the return on investment of those dollars?”

Cobbs pointed to the impact of Tipping Point’s five-year, $100 million Chronic Homelessness Initiative (CHI), which aimed to cut chronic homelessness in the Bay Area by 50%, with a particular focus on creating more permanent supportive housing opportunities. And as the initiative wound down, Tipping Point engaged Urban Institute to evaluate CHI’s overall success. One November 2023 finding concluded that CHI’s rehousing effort Rising Up “successfully rehoused 92% of enrolled young people in the evaluation sample, and only 7% exited the program without successfully being housed.”

A newer vision

In 2022, Tipping Point sent out $31 million across its portfolios, with a high mark of $7.4 million going toward CHI and the second-highest total going to its education portfolio at $6.4 million. As Tipping Point moves forward, it has also been focused on policy work. Rather than treating someone for a chronic cough, Cobbs said, Tipping Point is going further upstream to focus on preventing that cough in the first place. For instance, one grantee in its Early Childhood portfolio, childcare provider Kidango, sponsored a state bill called the Childcare and Development Services Act, which has expanded access to early learning and care programs for infants and toddlers.

Chief Program Officer Ali Sutton came to Tipping Point nearly two years ago after a long career in government, including as a senior adviser for the U.S. Department of Health and Human Services. She noted that in government, you’re working with massive scale and resources, but things move more slowly and there’s much less risk tolerance. She said Tipping Point’s homelessness work was a big reason that she joined the organization in 2022.

Increasingly, Sutton has been thinking about the intersections between Tipping Point’s four core issue areas housing, early childhood, education and employment — and finding ways for them to play together. “How are we thinking about employment services for moms that are experiencing homelessness? How are we thinking about early childhood in relation to job training — so really trying to think holistically across the portfolios,” Sutton said.

Sutton also mentioned that Tipping Point is really leaning into the leadership of people of color lately. Today, over 50% of the foundation’s core grantees are led by executive directors of color. Tipping Point has also focused on younger, earlier-stage organizations led by people of color and engaged them via an executive fellowship.

A donor speaks

Self-described “recovering management consultant” Tammy Crown is married to Bill Crown, who is part of the billionaire Crown family of Chicago. The Crown family traces their wealth to Material Service Corporation, founded by Henry Crown in 1919.

“My husband and I have been deeply involved in philanthropy for 20 years now, ever since we got married,” Crown said. The couple have focused on global environmental issues as well as local issues around poverty, inequality and education in the Bay Area, where they live. Through the years, Tammy and Bill Crown have supported places like Jewish Family and Children's Services, St. Joseph's Family Center and Bay Ed Fund, of which she is a founding board member.

Tammy and Bill Crown started supporting Tipping Point in 2016. Part of the beauty of Tipping Point, Crown said, is that it appeals to different kinds of donors. For those who are new to philanthropy, or at least new to antipoverty funding, Tipping Point helps donors understand the space better and identify effective nonprofits. “They identify the best-in-class nonprofits and do deep due diligence… they’re really committed to results,” Crown said.

For an experienced donor like Crown, though, Tipping Point was compelling because of its overlap with the work she has done in philanthropy over the past two decades. While she clarified that the giving she does with her husband is separate from Crown Family Philanthropies, the broader Crown family charity that held some $360 million in assets at the end of the 2022 fiscal year, she is no stranger to that family foundation, including serving on its environmental committee.

Crown sees the added value Tipping Point provides as two-fold. First, she believes it’s important to have a high-level organization in the San Francisco Bay Area that keeps an “eye on the whole ecosystem and all the moving parts.” She likes that Tipping Point brings together private and public partners and knows that for a cause that isn’t particularly sexy — addressing poverty — nonprofits can rely on Tipping Point for constant and steady support.

She also mentioned that she’s been able to call on program officers to learn about a new issue area or get their take on a nonprofit that she funds. “They serve as a kind of check on my portfolio,” Crown said.

Impact on the ground and looking ahead

San Francisco native Shellena Eskridge serves as executive director of Homeless Prenatal Program, one of Tipping Point’s longtime grantees. She speaks powerfully about the impact of substance abuse, mental health issues and other challenges on her family as she was growing up. “You see a lot of things, and experience a lot of hardship, especially within communities of color,” said Eskridge, who went on to earn a master’s of social work from Washington University in St. Louis.

Homeless Prenatal Program is a full-service family resource center that focuses especially on pregnancy and parenthood ages zero to five. Its wellness center provides prenatal classes, transitional housing programs for new or expecting mothers, and more. “We get to do a little bit of everything here,” Eskridge said.

Daniel Lurie originally reached out to the nonprofit’s founder and executive director Martha Ryan, wanting to pick her brain about the needs of families within communities. And from there, Tipping Point became a steady funder, to the tune of at least $4.7 million through the years, Eskridge said. She also credits Tipping Point in helping her get an executive coach and a leadership coach.

Looking ahead, Cobbs calls alleviating and remedying poverty Tipping Point’s “North Star.” For him, it comes back to more targeted and strategic interventions. For instance, while basic income might work for some suffering from poverty, it might not work for others. Or some homeless people might need a case manager, while others might not. Sifting through the unique needs of individuals within populations will be critical going forward, Cobbs said.

Cobbs has also been thinking about what needs to change more broadly among those in power in the sector — and how leaders interact across sectors. He recalls recently being invited to join a panel, but backing out after witnessing a lot of finger-pointing. He said he’s tired of the nonprofit sector blaming government and government blaming the nonprofit sector. “How do we bring people together?” Cobbs asked.