In 2024, I quit my job. Under normal circumstances, this might have been an excellent time to rest, reconsider my life and perhaps develop a hobby involving pottery or tennis. Instead, I started quietly studying philanthropy. I had already spent nearly five years building OC Black Moms, so I knew how to build community. I knew how to get women into a room, how to listen to what they needed and how to create something people cared enough about to keep showing up for. What I did not know was whether I wanted to turn any of it into an actual nonprofit, because after discovering that mysterious world in a hotel magazine the year before, I had questions. Many questions.

So throughout 2024 and 2025, while everyone else presumably thought I was taking some well-deserved time to figure out my next chapter, I was doing what can only be described as a private investigation into philanthropy. I looked up organizations. I studied their boards. I watched who funded whom. I started noticing the same names appearing in different places and figuring out which rooms actually mattered. Foundations had program officers. Nonprofits had development directors. Wealthy families had philanthropic advisors. There were consultants advising the advisors and associations convening the people who advised the people doing the giving. And everybody had a conference. Nobody warned me there would be this many conferences. At this point, I wasn’t even sure these were my people. I was simply standing outside the habitat with binoculars, observing their customs.

The first thing I discovered was that philanthropy has its own language, and apparently English was deemed insufficient. I had an MBA and had spent years in healthcare administration, so I thought I had already endured the maximum amount of professional jargon permitted by federal law. I was wrong. In philanthropy, you don’t try something; you pilot an initiative. You don’t want to grow; you scale impact. You don’t need money to pay employees; you need capacity building. You aren’t asking someone to help keep the lights on because Southern California Edison continues to refuse “community impact” as legal tender; you are seeking general operating support.

There were theories of change, logic models, measurable outcomes, collective impact, systems change, sustainability plans, letters of inquiry, requests for proposals, capital campaigns, major gifts, planned giving, endowments, donor-advised funds, restricted funds and unrestricted funds. I discovered fiscal sponsorship, which sounded to me like a nonprofit had been assigned a financially responsible adult until it could be trusted on its own. Then I found the Form 990. Now, this was useful. You mean to tell me the federal government requires nonprofits to publicly disclose financial information, leadership compensation and board members, and then puts it on the internet for me to read? For free? I had discovered federally sanctioned nonprofit gossip. Suddenly this research project had recreational value.

Then I got to the money, and this is where philanthropy became one of the most beautifully complicated ways human beings have ever devised to give someone a check. Foundations have priorities, strategies, geographic restrictions, eligibility requirements and grant cycles. Some want a full proposal. Some begin with a letter of inquiry, which is essentially an application asking for permission to submit the application. Some accept unsolicited proposals. Others very clearly announce that they do not accept unsolicited proposals, which immediately made me wonder who exactly was being solicited and, more importantly, where they were having lunch.

Then I learned about restricted funding. A funder may love the program, the children, the outcomes and the beautiful photographs, but be considerably less enthusiastic about paying the salary of the human being required to produce all of those things. Everyone loves impact. Payroll apparently has terrible branding. Somewhere in the middle of all of this I learned the distinction that made the entire system click for me: need and fundability are not the same thing. You can have a community with an obvious need and a solution that works, but the organization still has to fit somebody’s priorities, geography, timing, budget and theory about how change should happen. Apparently suffering alone does not satisfy the rubric.

And then there were the rooms. Oh, the rooms. Conferences, luncheons, annual meetings, funder briefings, leadership summits, donor receptions, board events and convenings, which I eventually determined is philanthropy’s preferred word for putting people in a room with name tags and sparkling water. I spent two years learning that all rooms are not created equal. Some rooms contained people who could make decisions. Some contained people who knew the people who could make decisions. Some contained people who wanted to meet the people who knew the people who could make decisions. And some contained a keynote speaker, dry chicken and absolutely nobody I needed to know.

This was an expensive distinction to learn. Relationships mattered, which wasn’t sinister; it was human. If someone is responsible for giving away millions of dollars, of course trust matters. But trust is considerably easier to build when you already know where everyone is having lunch. You could spend hours explaining your mission, demographics, outcomes, evaluation plan, financial controls and possibly the blood type of your treasurer, and still discover that one of the most powerful sentences in philanthropy is simply, “I know her. You should talk to her.” That was when I understood that access wasn’t only about money. Sometimes access was knowing which luncheon was worth putting on real pants for.

By the time I launched Held & Rooted in 2026, I understood something I absolutely did not understand sitting in that hotel room in 2023: doing meaningful work and building a fundable institution are two entirely different talents. I already knew how to build community. What I had spent two years learning was all the infrastructure apparently required to convince the government, a board, an insurance company, a bank and eventually a foundation that the community work was occurring responsibly.

You mean I need a volunteer board to govern the organization I founded, bylaws explaining how the volunteer board will govern the organization I founded, minutes proving the volunteer board governed the organization I founded, insurance protecting the volunteer board while governing the organization I founded, and then a grant application asking how the organization I founded plans to sustain itself after the grant ends? Perfect. Very simple. No notes.

But beneath all the absurdity, I finally understood the architecture. I could read a 990. I knew what an LOI was. I understood unrestricted funding. I could walk into a philanthropy conference without assuming everyone else had received a secret orientation packet I somehow missed. The language stopped intimidating me. The rooms became rooms. The important people became regular people wearing conference badges. And perhaps most importantly, I finally understood that knowing the system meant I could use it without allowing the system to become the mission.

But learning how philanthropy worked created a problem I hadn’t anticipated. I had spent two years studying how organizations become fundable, how donors make decisions, how foundations move money and how nonprofit leaders get themselves into the right rooms. Then I launched Held & Rooted and started looking around at the people already showing up for us, and another question began bothering me. I had become so focused on understanding how communities like mine could receive philanthropic investment that I had never really stopped to ask who gets to call themselves a philanthropist in the first place. Because if philanthropy was ultimately people deciding that some portion of what they had should be used to build the world they wanted to see, Black people had been doing that for a very long time. We just had different names for it.

And, as it turns out, considerably better food.

Part Three: Apparently, We’ve Been Philanthropists This Whole Time

Always Have, Always Will ~ Kalie