Crossed Paths
A podcast that brings together executives and leaders from mission-driven non-profit organizations to discuss the challenges, opportunities, and evolving strategies within the sector.
E004 | Dr. Jocelynne Rainey
In this episode, host Dine Grullon, CEO of Crewcial Partners, sat down with Dr. Jocelynne Rainey, President & CEO of Brooklyn Org, a lifelong Brooklynite who came into her role with one clear intention: make sure the strategy she built came from community, not just for it.
Brooklyn Backs Brooklyn
A Conversation with Dr. Jocelynne Rainey on Community Philanthropy, Participatory Power, and the Long Work of Equity
“Crossed Paths: Leaders on Leadership” is a podcast that brings together executives and leaders from mission-driven nonprofit organizations to discuss the challenges, opportunities, and evolving strategies within the sector.
In this episode, host Dine Grullon, CEO of Crewcial Partners, sat down with Dr. Jocelynne Rainey, Ed.D., President and CEO of Brooklyn Org (BKO). Founded in 2009 as Brooklyn Community Foundation, the first and only public foundation dedicated solely to New York City’s largest borough, the organization has been reimagined under Dr. Rainey’s leadership as a new model for participatory, community-rooted philanthropy. Since joining in December 2021, she has led BKO through a deliberate strategic evolution: a rebrand, a new strategic plan, and a significant expansion of grantmaking, with the organization surpassing $150 million in total giving. Dr. Rainey is a lifelong Brooklynite, raised in Flatbush and a Bedford-Stuyvesant resident for 26 years; her biography and her institution’s mission are, by design, inseparable.
Why the Evolution Mattered
Brooklyn Community Foundation was already a community-listening organization when Dr. Rainey arrived. What changed under her leadership was the intentionality and depth of that commitment, and the honesty about what even a lifelong Brooklynite does not know.
“Even as a lifelong Brooklynite, growing up in the community, living in Bedford-Stuyvesant and raising my kids there, I also know that I don’t know everything. There are lived experiences that were just not mine.”
She came into the role carrying a specific frustration from her years running nonprofits: foundations that told grantees what they needed rather than asking. Her answer was to go in “eyes wide open,” conducting listening tours across Brooklyn neighborhoods before shaping strategy, hearing directly from residents about what they believed the issues were and what they thought they needed.
The rebranding from Brooklyn Community Foundation to Brooklyn Org in 2023 was not cosmetic, but a signal of reinvention and a new strategic plan oriented around deeper support for nonprofit changemakers and a more accessible model for giving, one that could invite anyone who cares about Brooklyn into the work as opposed to just major donors.
The Participatory Model in Practice
Brooklyn Org's approach to grantmaking is participatory across the board. Funding decisions are made in genuine partnership with community members, not by institutional staff or board alone. The Spark Prize, BKO's flagship annual recognition, awards five nonprofits $100,000 each in unrestricted general operating support and exemplifies this model. Advisory committee members are Brooklyn residents who commit to a two-year process, are compensated with a stipend, and do the work of evaluating and selecting grantees. Every member of the Spark Prize Advisory Committee has asked to stay for another year.
The same participatory structure extends across BKO's broader strategic grantmaking, with advisory committees drawn from Brooklynites closest to each issue area.
Dr. Rainey is direct about the discipline this requires of her, including accepting outcomes that do not always match her own assessments.
“What makes a difference when you’re doing it right and you’re not putting your thumb on the scale is that sometimes someone who you thought was deserving didn’t get chosen in that grant cycle, because there’s so many amazing nonprofits that the committee is looking at as well.”
Reaching the Smallest Organizations
One of the programs Dr. Rainey is most proud of is the micro-grant initiative, which she brought to BKO following her listening tours, which revealed a class of organizations that had been serving tight-radius communities deeply for a decade or more, but whose budgets fell below BKO's traditional thresholds (a farm with a food pantry in Bed-Stuy; organizations distributing clothing, providing childcare, or working with new immigrants in languages other than Spanish). Groups that are essential, hyper-local, and invisible to most funders.
“I went to visit this one nonprofit that has a farm in Bed Stuy, and they have a pantry… and people depend on them. And I was talking to some of the folks that were working with them now, volunteering, and I was like, ‘How did you end up volunteering with them?’ And they were like, ‘They literally changed my life…I’m here because of them.’”
In March 2026, BKO distributed micro grants of $5,000 to $10,000 to 38 grassroots Brooklyn organizations with budgets under $100,000. The grants were made possible through board support and two outside donors, one of them a donor-advised fund holder who had been looking for exactly this kind of pathway to reach smaller organizations.
The Question of Payout and Perpetuity
Dr. Rainey is direct about her view: Brooklyn Org needs to grow, not draw down.
“Brooklyn Org has about $150 million in assets in a city…that has 2.5 million people. That’s not a lot, right? When you think about it.”
BKO has drawn down over a million dollars more in each of the last two years, and the board has authorized continued expansion. But Dr. Rainey’s goal is not just to spend more; it is to grow the platform so that more donors from more, different backgrounds, can participate. The logic is durability: Brooklyn will need BKO past this moment and the institution’s ability to serve the borough depends on its capacity to attract new capital over time.
“I want to make sure that we’re here in order to galvanize more donors and funders to the table, in order to do more for Brooklyn, because even beyond this moment, Brooklyn is still going to need us.”
On Racial Justice as Institutional Posture
BKO has positioned racial justice as a core organizing framework, a stance that carries reputational and, in the current national environment, potential financial risk. Dr. Rainey acknowledges the exposure, but she also insists on making the case rather than retreating from it. Her method is to walk donors through the structural data on criminal justice, education, and labor-market outcomes, explaining what those outcomes cost everyone, not just communities of color, and to draw a clear line between BKO's framework and what is legally impermissible. The framework asks about outcomes, not leadership identity, and in her experience, most Brooklyn donors, people with close-knit neighborhood ties who can see their neighbors' circumstances, are ready to have the conversation.
“What is illegal, I believe, and I’m not a lawyer, is only funding people of a certain race or doing work only for certain people, right? And we don’t do that; we want to give access to everyone.”
The Power Dynamic Between Funders and Grantees
There is a power imbalance in philanthropic relationships, and pretending otherwise does not make it go away. What BKO has built instead is a set of practices designed to make trust possible despite it: being honest about what the organization can and cannot do, keeping grant applications simple and asking for stories rather than numbers, and making leadership personally available to grantees rather than delegating the relationship to program staff.
“One of the biggest compliments I’ve ever heard is a grantee say to me, ‘I know that you do what you say you’re gonna do.’”
The goal, as she frames it, is not to eliminate the imbalance; that would require a different kind of institution. Rather, it is to build the trust and transparency that allow grantees to believe it is safe to be honest back.
What Keeps Her Going
The work has never been abstract. The communities BKO serves are her community.
“I care deeply about my family. My family looks like…the people who participate in the programming that my nonprofits are in.”
She traces a thread through her entire career, from adults with developmental disabilities, to HR work in retail, to the Brooklyn Navy Yard, to GOSO, to Brooklyn Org. At each stop, the through-line was the same: use whatever platform she had to create real opportunity for the people around her. The Navy Yard was the first place she felt she could say that out loud, speaking directly about equity and access rather than working toward it quietly. Brooklyn Org is where that work and who she is have fully converged.
“I am very fortunate to be in a place where the work that I do every single day is aligned with who I am and what I believe. And that’s what keeps me going.”
Key Takeaways
- Listening before deciding should be structural. BKO’s participatory model places funding decisions in the hands of community members closest to the issues, a process Dr. Rainey describes as active, paid, and deliberately insulated from institutional influence.
- The smallest organizations often carry the deepest trust. Micro-grants emerged directly from listening tours that revealed hyper-local nonprofits, below BKO’s traditional thresholds, that had become lifelines for their immediate communities.
- Perpetuity is a form of commitment. Dr. Rainey’s position on payout is rooted in a long view: a foundation that depletes itself cannot keep showing up. Growing assets and growing grantmaking are not in opposition.
- The power imbalance between funders and grantees is real, and honesty is the only partial remedy. Accessibility, transparency about limitations, and relationship (not process) are what allow trust to form across a structural gap.
- Racial justice is argued, not assumed. BKO’s stance requires Dr. Rainey to make the case continuously to donors, walking through structural data, connecting outcomes to shared interests, and distinguishing a framework from a legal or reputational vulnerability.
- Alignment between person and institution is its own kind of durability. Dr. Rainey’s steadiness in a difficult environment comes not from certainty about outcomes, but from the conviction that the work is inseparable from who she is.
Brooklyn Org can be found at brooklyn.org. The organization’s Instagram is active with programming updates, events, and grantee stories. For those interested in participating as a donor or donor-advised fund holder, BKO’s website includes resources on how Brooklyn residents and supporters can engage.
- Permanent capital is an investment structure without fixed timeframes, unlike traditional private equity funds, which require selling assets within set lifecycles. This flexibility allows investors to hold onto assets as long as they find it beneficial, avoiding forced sales regardless of market conditions. By removing these time constraints, permanent capital fosters more strategic, uninterrupted partnerships, focusing on long-term growth rather than the pressure of achieving short-term gains.
DISCLAIMER
This podcast is for informational purposes only and does not constitute financial, legal, or investment advice. The opinions expressed are those of the speakers and do not necessarily reflect the views of Crewcial Partners LLC. Listeners should consult with a qualified financial advisor before making any investment decisions. Past performance is not indicative of future results, and all investments involve risk.
What were some of the main successes of Crewcial Partners last year?
Summary: Most importantly, we maintained our long-term posture through an unfriendly market. Markets have a way of overreacting to events; however, our clients stayed on track and kept their public equity exposure at high levels. Our process ensured we never faced liquidity challenges or any issue that demanded we act in a short-term matter.
Lesson: A long-term bias works but requires discipline, diversification, and an understanding of expectations. Fundamentals and valuation—the price you pay for something— ultimately matters. Crises and difficult times have winners and losers. The winners are ultimately those with the strongest balance sheets, best business strategies, and the most capable manager teams; they win over the longer term because they're better than their competition.
What are your thoughts on sizing in the current environment?
Summary: It can seem contrary to human nature at times; the stuff that does well, you want to see become a bigger and bigger part of the portfolio. However, you should be adding money to managers that have struggled but are poised to rebound, keeping in mind your longer-term return profile. Sizing is important and depends on a deep understanding of diversification and manager volatility profiles.
Lesson: Take advantage of the natural cyclicality within markets, selling at the peaks and buying the bottom is the way to long-term sustainable success. Be proactive when managers have a great year. When Crewcial has a manager that's up 100%, we ensure that we trim back 25-50% so the capital is ready to redeploy into out-of-favor managers with even stronger future prospects.
What are some of the areas that could be improved from 2023?
Summary: We are still trying to wrap our heads around the way markets are actually functioning; the gap between price and fundamental value seems as if it's become unbounded. This creates a problem of balance. If you're constructing a diversified portfolio, one of your underlying assumptions is that it will moderate volatility and some of the short-terms concerns; this should allow you to play offense when things are bad and a little defense when things are really good. But that falls apart if markets are creating high correlations that shouldn't exist between strategies. We’re still learning to better understand which conditions can and will create more of these correlation issues, so that we don't end up constructing portfolios that require truly extraordinary levels of patience to see through.
Lesson: Cultivate a better understanding of correlation among managers. Thinking about managers based on the way they behave in different market climates is important. Prepare for various environments and build portfolios that are not going to have several seemingly distinct strategies reacting to the same market environment. Diversification is ultimately always your friend.
What are some of the insights you’ve gained from your latest year of travel?
Summary: Being back on the road has been one of the great events of 2023. It’s rewarding to physically sit down with people, whether in Europe, Asia, South America, Africa, or the United States, and really hear what they’re seeing on the ground, what they’re doing in their portfolios, and the real-world implications, because markets aren't necessarily the real world. Being reminded how different people see the world differently is immensely important as an investor.
Lesson: Preferable options exist outside indexation; opening up to a global perspective broadens one’s ability to consider truly impactful diversification. The goal is to find differentiated thinking wherever it is. We're not looking for investment managers, we’re looking for thoughtful, engaged people who invest.
What does history tell us for “Magnificent Seven” index funds going forward?
Summary: The index has reached a very high level of valuation concentrated in a group of unbelievably dominant companies. However, while no one is arguing that Apple is a bad business, there is a price for everything and this price seems too high right now. From the 60s through the 00s, people felt the same about many companies that didn't prove to be very good investments. One way to illustrate this is to look at the top five in late 90s, which included Cisco, Intel, General Electric, Microsoft, and IBM. If we exclude Microsoft from the equation, these are all still pretty powerful businesses but they have not been good stocks to own. It’s the inevitable nature of impermanence. We can almost guarantee ten or 20 years from now, the current names will be around, but they probably won't be the most popular or dominant names in the market.
Lesson: Design portfolios to capture the broader economy; while well-constructed portfolios will always have allocations to bigger names, entire swaths of the economy are growing at a much faster rate than these brand-name businesses and are currently being overlooked by investors. Capture long-term opportunities today cheaply.
What is Crewcial excited about for 2024?
Summary: First, ESG, which has unfortunately become a very controversial subject. However, at the end of the day, it's a powerful risk framework; from our perspective, we need to be able to arm both our clients and our research team and consultants with better information on this subject and approach, as it’s a complicated topic. We can't make it simple, but we can identify very specific variables at the portfolio company level to transparently consider which managers and portfolios have a higher level of risk around material environmental, social, and governance issues that affect their viability as good investments.
Second, another big change at Crewcial was our formation of an investment committee. We’re doubling down on our approach, allowing talented team members to focus on what they understand best and follow their passions as investors, but we’re now taking those passions and directing them into somewhat of a more formalized process. It's based on tracking, monitoring, and ensuring individuals get the training they need to scale and fully capture the bigger picture to find the best managers, no matter their initial backgrounds upon entering the firm, while pairing complementary skillsets to bring out the team’s full potential.
Lesson: Don’t be afraid to be different while embracing the fundamental rules of finance. Identify the full scope of everyone’s areas of strength and play off each to build a greater whole. Embrace idiosyncrasies and preferences while being open and honest with feedback and assessments. We do not treat our investment team members as analysts, rather as investors cultivating an owner’s mindset. We're trying to find ways to capitalize on differentiated perspectives to ultimately uncover the difference between market price and fundamental value; seeing things differently, and cultivating an environment in which such perspectives can range openly, is a critical element of that.
We don’t just want the usual suspects from the same handful of schools, we want to expand our collective perspective to include more women, ethnically diverse individuals, and people of all persuasions from different parts of the country or with different educational or experiential backgrounds—talented people come in all shapes and sizes. A diverse team of diverse perspectives is intended to capture the overlooked points of view necessary to uncover the next great idea.
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