How This Nonprofit Raises Money for Its Unusual Approach to Tackling Urban Poverty

Dorchester is a Boston neighborhood that’s a study in contrasts. It’s the home of several venerable local institutions, including Boston College High School, the Carney Hospital, the University of Massachusetts Boston and the Boston Globe. However, the crime rate is 30 percent higher than the national average. Kids often grow up to be cops like New York City Police Commissioner William Bratton—or criminals like alleged thief Arthur “Bucky” Barrett, killed by crime boss James “Whitey” Bulger. 

Since education is a proven way out of poverty, College Bound Dorchesterwas founded four years ago to serve as a national model for breaking the cycle of intergenerational urban deprivation. Its model is unusual. Targeting youth ages 17 to 27 in the worst section of Boston, Bowdoin-Geneva, CBD focuses on young people it calls “core influencers," looking to engage the most "influential and disconnected young people in the community." The idea is that, if you can turn these leaders around—by getting them into community colleges where they can acquire associates degrees and earn a living wage—they can then become drivers of positive change. CBD calls this a "super-user strategy," and sees its goal as "shifting the system," with college becoming the new norm.

This is a challenging mandate. Everyone CBD works with is a low-income student deficient in basic academic skills. Half dropped out of high school, and nearly a third served time in a correctional facility.  

So where does the money come from to make the CBD's work possible?To find out,Inside Philanthropy spoke withMichelle Caldeira the senior vice president of College Bound Dorchester and Simon Taylor a board member who is also president of Comtrade Software.    

“The organization’s budget is close to $7 million every year with about 60 percent of that from public sources from the state and city. The other 40 percent we have to raise via philanthropy, through private foundations and grant proposals,” Caldeira said, laying out the basics.

The biggest foundation backers of CBD are based in Massachusetts including the Boston Foundation, the Hyams Foundation, and the Richard and Susan Smith Family Foundation. Dozens of other foundations have also contributed. The grant amounts aren't huge. It's rare for CBD to get grants over $150,000 and most are far smaller than that. This is a reminder that, while we often cover six- and seven-figure grants at Inside Philanthropy, the majority of nonprofits raising money from foundations are more typically chasing grants of between $10,000 and $50,000.

Beyond government and foundation support, CBD has a keen eye on cultivating individual donors. 

“The annual gala is a huge part of our funding,” Caldeira said. In May, 350 people gathered to honor James Rooneythe Greater Boston Chamber of Commerce President and CEO who has been a big friend of College Bound Dorchester with his dedication to create opportunities for youth.

CBD also does a matriculation event, non-traditionally at the end of summer, in August, because some students take that long to know whether or not they are graduating. “It’s a really great feel good event. For many of our students it is the first time they have put on a cap and gown. Many of them complete their high school credential with us because they have not graduated from high school. The students get to see the people who have invested in their journey.”

And of course, it’s a perfect time to appeal for more funding. “Events are great way to introduce people to an organization, but it’s really the one on one that causes people to make the investment,” Caldeira said.

We hear often from fundraisers for direct service organizations that connecting donors to the beneficiaries of an organization's work can have a huge impact, and Taylor underscored this point: “Every single person I brought into the organization, when they go into the schools to meet the students and experienced firsthand the impact organization has on the lives of people, that is really the biggest driver for having people connect with us.”

Taylor's own involvement in College Bound Dorchester illustrates another important avenue of fundraising. The president of Comtrade Software, Taylor got involved because after living in Europe for years, he re-connected with a fellow alumnus from his high school, Mark Culliton, College Bound Dorchester’s Chief Executive Officer who modestly said “I am going to end urban poverty with my organization.“

“As bold as the claim appears in the beginning, when you actually drill down into what College Bound Dorchester is doing I think it is a case study for a system that actually can end urban poverty,” Taylor said, suggesting that CBD's model of focusing on "core influencers" had unique strengths. “These are the people picking the fights, causing the problems, and really creating disturbances in society. Well, unfortunately almost all the nonprofits in the world are designed to raise money for everybody else, thereby cherry picking the best and brightest in the community and putting them somewhere else. What that does systemically is that it starts to create a brain drain in these already hard-hit or depressed communities so it furthers the problem. College Bound takes the entirely opposite approach.”

Because CBD recognizes that these core influencers are also established leaders in their neighborhoods, it provides education, emotional and social support from mentors who escaped the streets themselves so that CBD students go to college and get the skills they need to earn a living wage, without removing them from their community.

When working with a population like this, though, success is inherently more limited—and that impacts funding opportunities. “We are serving a group of young people that is having the hardest time, young people who have exhausted all other options," Caldeira said. More than 600 students are now in College Bound classes. Over the past four years, more than 150 people have enrolled in college with a retention rate of 61 percent. “One of our challenges in fundraising is that is that much of the philanthropic investment is going to the organizations that could 80, 90, 100 percent success rates,” Caldeira said.

CBD may never get that, but keeps moving forward. “It’s expensive, incredibly expensive, but we’re trying to create change so it is important to stay with them, even if they fall off.”