Four years running a scholarship foundation
Introduction
For anyone reading this who doesn’t know me personally: hi, my name is Phillip. Most of my friends call me RPC, and if you want to be my friend then that’s something you can do too.
I’m the founder and chairman of the American Leadership Foundation, a 501(c)(3) nonprofit that issues scholarship grants and provides ongoing mentoring support to students graduating from large public high schools.
I filed the paperwork to incorporate the ALF in September of 2019, which is just over four years ago now. Building and running the foundation has been a big journey, and I feel like I’ve learned along the way; I have some hope that I’ll be able to share some of those lessons here in a way that people find useful.
More than that, though, running the foundation has proven to be important to me in a way that is hard to summarize, and I have some hope that people who read about the experience might find something in it thought-provoking.
When I filed that paperwork in September of 2019, I was 25 years old — which now strikes me as preposterously young. I could list any number of things that I might have focused on instead, not the least of which would have been my career and personal savings. I definitely wasn’t “ready” in the way that people talk about these things; I had no experience starting an organization like this, non-profit or otherwise. Everything involved in running the ALF ended up being an area of growth for me, and I’m deeply grateful for that.
There’s this quote from Garson Kanin[1] that I think about a lot:
When art critics get together they talk about content, style, trend and meaning, but when painters get together they talk about where can you get the best turpentine.
It’s one of those vague-but-pithy framings that people use to say all kinds of things, but I like to read it as a comment about what we choose to focus on. There are all kinds of intellectual exercises you can dive into as part of your desire to better appreciate art, but the actual business of creating largely deals with concrete, definite problems. It’s surprisingly easy to get caught up in the former and not realize you’re neglecting the latter; you need to find an outlet through which you actually make contact with the world and face the challenges of reality.
For me, the ALF has been that outlet and more. Working to build the foundation has been both humbling and inspiring, and it’s brought me tremendous clarity. I don’t worry about finding meaning in my life because I don’t have the time. I worry about the annual application cycle and our students’ internships, and I don’t have the energy left for anything else after that.
There’s always more to do, and there are always things I could be better at, but I have the peace of knowing I’m doing everything I can. I don’t ever lack motivation in my main career, because I always have something obvious I can do with more money. And the lessons I learn running the ALF don’t just make me a better chairman — they usually make me a better person in the other aspects of my life, too.
It’s nice to focus on turpentine.
What is the American Leadership Foundation?
The ALF is a scholarship foundation. We issue grants and provide ongoing mentoring support to students graduating from large public high schools.
At the time of writing we’re still entirely focused on our pilot grant program (the Deo Kujirabwindja Memorial Scholarship) working with students from Montgomery Blair High School (my alma mater), but we have plans to expand to more schools with additional grants as we figure out how to best scale our model.
My original idea for the foundation was simply focused on the pain I felt the most when I was a student: money. Paying my own way through college, I was splitting my time between work and classes, and I would be frustrated by small grant offerings on the order of $500. If I had been able to aggregate a lot of those, apply in large batches, and had confidence in my odds of receiving any given one, the small face value wouldn’t have been an issue — it’s free money, after all. But I had real bills I definitely needed to pay and a limited amount of time, so I focused on work.
When I thought about that experience later in life, I wanted to set up a program that would appeal to someone in a similar situation. One that issued larger grants, paid out in lump sums, would both give the recipient a meaningful boost in purchasing power and justify the speculative effort of applying. That was the origin of the Deo Kujirabwindja Memorial Scholarship, whose primary grant recipient is awarded $10,000 just as they graduate from high school, giving them a financial cushion when they need it most and have the most time to apply.
The mentoring program grew quite naturally out of the grant program. The applications gave us a chance to get to know very impressive students that we would then financially invest in; it’d be silly to not stand behind that investment with career assistance, networking help, and so on. Even the $10,000 award of the primary grant could be easily beaten by the $12-25k a student might make in a summer at one of the more compelling internship opportunities, and those internships turn into full-time jobs and career paths.
In the spirit of figuring things out as we go, the grant program has evolved to offer secondary and tertiary awards as the mentoring program has become a more primary focus of the foundation. As of 2023, we have awarded 17 scholarship grants summing to over $60,000, and all recipients have access to the foundation’s board of directors for any help we might be able to provide.
Building a foundation
An old manager once told me that his only real job as a manager was to figure out how to fire himself.
His constant goal, he explained, was to understand all the tasks he was responsible for, create job roles that would cover all those tasks, and train other people into those roles, freeing him up to take on new responsibilities. He would know he had succeeded when he was no longer needed by any part of the organization he created.
I’ve thought about that conversation a lot over the past few years — I think that core skill of management has been the single biggest area of growth I’ve had to focus on, and I’m really grateful to have had it broken down so clearly for me.
A necessary first step is simply diving into a problem and trying to figure out what’s going on. Those early stages of understanding the space you’re operating in are fundamentally chaotic, and are filled with a lot of concrete, procedural challenges. For starting the ALF that meant learning about how to get 501(c)(3) status from the IRS, setting up some kind of process to get our first applications, getting the word out so students would actually know to apply, etc. Starting from zero, all these things just kind of hit you at once; I think the best approach is to just try to figure them out one by one.
Over time, though, I started to think about the foundation as having 3 main “parts” that we had to work on, and separating tasks into these 3 buckets helped a lot with organizing board meetings and thinking about how to budget time and energy. They are:
- The annual application cycle
- The ongoing mentoring program & alumni network
- Organization-level concerns (governance, funding, etc.)
I’ll examine each of these pillars in a moment, but I want to pause here to emphasize the importance of the structure itself.
It’s not enough to understand what needs to be done and be able to explain it to others; you need to be able to explain it so well that the person you’re explaining it to can explain it to some third party.
That might seem like a small distinction, but I’ve found that one extra step requires an entirely different mental muscle group than what is needed for building personal understanding. I’ve also found that last step to be one of the most important for being an effective leader in this role. The foundation is a part-time effort for everyone involved — all of the board members have other jobs, and we go weeks or months between discussions depending on the application cycle. Deeply distilling the understanding of what needs to be done is essential to building continuity across those time gaps.
Creating this structure for the foundation’s activities is also how I make progress towards firing myself. A key personal goal I had when starting the ALF was that I wanted it to be more than just a vanity project, I wanted the foundation to be something that could outgrow and outlive me. That was why I took the title of “Chairman”, to act as a small cue to myself to focus on organizing things so that they could be done without me.
At this point I would say I spend about 15-20% of my time on the annual application cycle, 60-65% of my time in ongoing mentoring, and the remaining 20-25% focused on org-level concerns. That’s about what I think the long term split should be for the board, though I would hope that the time and attention paid to org-level concerns falls below 20% over time, leaving 80+% of the focus on the core work of actually helping students.
The application cycle
“The application cycle”, as a bucket of work, includes figuring out how to structure the application process, getting people to apply, and reviewing the applications received.
Structuring the application process has generally been pretty straightforward. Pretty early on we figured out a core structure that gave us pretty good signal on the applicants while being easy enough to handle a potentially large number of applications:
- An open call for applicants, who must submit a written essay
- Every essay is read by at least two board members who each give it a yes/no vote. Applicants with that get double “yes” votes are shortlisted for further consideration
- All shortlisted applicants are asked to provide a letter of recommendation from an adult non-relative (usually a teacher, but employers etc are welcome also)
- Every shortlisted essay and recommendation letter is read by every member of the board. Each board member individually stack-ranks the applicants, and finalists are chosen on the basis of ranked-choice voting.
- Finalists are interviewed by the board (2 interviews, each interview with one half of the board)
- The board conducts a final review that considers applicants’ initial essays, rec letters, and interviews. Grants are awarded by ranked-choice voting.
Nothing here is really new or exceptional in any way, and I’m happy leaving it like that. It’s important to be picky about where you feel like you have unique insight and really want to invest the time and energy into being innovative, because otherwise you’ll stretch yourself too thin. For the ALF I just don’t think it’s that important for our application process to be groundbreaking, especially since students are still finishing their senior year of high school when they apply.
I will note two decisions that have definitely been helpful even if they aren’t groundbreaking, though. One was using ranked-choice voting at multiple stages in the application review process. That has been very helpful both in making sure everyone’s point of view is represented and focusing conversation where it’s most productive — cases where an application causes high variance in reactions, or where there’s a tough choice between two candidates at a certain stage in the process.
The one other point I’d call out here is that our essay prompt asks students to choose from a selection of films and compare or contrast themselves with their choice of character in that film. This was a very deliberate decision to push students to write in a way that expresses their personality more while still giving them enough structure within the prompt to help their writing. At 17-18 years old, most people will struggle with writing into a totally open-ended format; giving them choices within a defined structure can help focus their thinking and actually bring out more of their personality than asking them to just talk about themselves.
With the above structure in place, reviewing the applications is just a question of putting in the time each year to follow the process outlined. We do reflect a bit each year on what went well or poorly and make some tweaks to things, but the core structure has worked pretty well and remained roughly the same for all four years.
Most of our time and energy in the application cycle bucket is currently focused on promoting the scholarship and getting students to actually apply, and I expect this to continue to be true.
Go-to-market is always harder than people expect it to be. I see this all the time professionally, of course, but I’ve been aware of the core issue since college when I was participating in student organizations.
People will have an idea — for a product, for an event, even just for a party — and are consistently surprised by how hard it is to get anyone else to notice.
The fact is, people are busy and there’s a lot competing for their attention. You can’t just mention something once and have people latch onto it; you have to introduce the idea, remind people about it, and make it easy for them to participate.
The experience can be extremely discouraging! It can feel frustrating to have to put so much effort into getting people’s attention. If you’ve already invested a lot of time and energy into an idea, the last mile of getting the word out about it can feel like an overwhelming hurdle after an already exhausting journey. But that’s not a productive way to think about things. Some problems you can’t avoid, you just have to invest into solving them.
Go-to-market is something that we’re still solving at the ALF, and will be a place where we’ll need to keep coming up with fresh solutions over time.
For the Deo Kujirabwindja Memorial Scholarship, we set up a registration process where students sign up to get the application info emailed to them, which also lets us send follow-up emails as the application deadline gets closer. The ALF website also uses Google Analytics so we can try to gauge interest and can see the effectiveness of certain outreach attempts — e.g. how many views an email from the guidance counselor’s office can send our way.
I’m happy we have these bits of infrastructure in place, but there are a few obvious areas where we could easily do more. Social media presence is a big one — at the time of writing, the ALF still has no Instagram or TikTok or anything — and we haven’t had flyers, which are how a lot of student events are shared. If I compare our outreach to that of Blair’s principal, who is prolific on every social media platform of note, I find us sorely lacking.
The mentoring program
The vast majority of my overall time working on ALF development is spent on the mentoring side.
Concretely, this has meant having regular meetings with all our various grant recipients at different times throughout the year to catch up, hear about their lives, and give input on anything they ask about.
Every board member contributes time to the program. Personally, I’m currently averaging about three meetings a month, generally lasting somewhere from 1-2 hours, with text follow ups and ad hoc discussions as needed, e.g. for certain internship application deadlines. I’ll typically talk to any given grant recipient somewhere between 2-6 times a year depending on their circumstances, with the general trend that I hear less from students as they get situated into a major and career path that they’re happy with.
Long-term, I expect the mentoring program to be the single most important facet of the ALF, though it’s also been the most ambiguous and challenging to figure out.
Like I said earlier, the entire idea was an organic development from simply having the infrastructure of a scholarship foundation in place. We identified promising students, invested in them financially… Now what?
Some things are pretty straightforward. When a student knows what field they want to work in, it’s not too hard to help them figure out what internships they should be applying for, or who someone on the board knows that might be able to help them get their foot in the door. I also feel very lucky that I was able to recruit a board from different aspects of my own life, as we have a variety of life experiences represented that translates into pretty good coverage of various career paths students might be interested in.
Helping with things like writing résumés and cover letters, doing mock interviews for internships, or figuring out good budgeting strategies are easy wins that help develop the relationship with our students while also delivering simple benefits.
What’s trickier, but still worth doing, is coaching students on bigger topics of personal development.
The cross-over points tend to be pretty obvious and intuitive. We can help students find and get internships when they know what field they’re interested in, which inevitably leads to some students asking what they should be interested in.
When you’re just graduating high school and don’t have much or any work experience, even the question of what to major in can feel vague and daunting. Some students definitely do come to us having a pretty clear plan of what they want to do and why they want to do it; talking to them, you can feel a certain level of conviction in them and realize all you have to do is support them in their vision, maybe pointing out some tips or shortcuts along the way. There are other students that benefit a lot from someone talking to them in an open ended way about different possibilities — one major distinction of the ALF vs other scholarship programs is that we don’t have any focus on students going into certain professions, which means we’re well positioned to have those open ended conversations and help people pursue anything that’s right for them.
I don’t go into any of these conversations with any set agenda in mind. I keep notes while we talk, mainly as a way to cue myself to actively pay attention, and I’ll have threads from previous meetings to follow up on, but I try to focus on these discussions being as useful of a service to the student as possible. That usually means trying to listen and be reactive to the life circumstances of the day rather than proactively lay out how they should be living their lives.
A reactive approach is especially important because of the age we meet these kids at — 18 to 22 is a period of pretty dramatic personal growth and reinvention. When we first started the ALF I was somewhat bewildered by the first cohort of grant recipients, any one of whom would be a completely different person every six months. From semester to semester it was like they were replaced by body doubles, with entirely different goals, hopes, fears, and preoccupations on their mind when we next talked. Over time, I found this to be pretty typical for their age, with freshmen being the most extreme and variance gradually reducing with age.
Even without a set agenda, though, there are definitely core themes in my conversations that come up repeatedly with many different students. Points of emphasis include:
- Developing an internal locus of control
- Executive functioning skills
- Growing in confidence and assertiveness
- Focusing on what’s important, not just what’s salient
Any one of these could be the subject of an essay unto themselves; I might follow up with separate writing on these themes if I can figure out a way to present the information in a general way that’s still useful.
One of the most interesting and most challenging aspects of the mentoring program has been the difficulty of isolating what really delivers impact in student lives. From a purely material perspective, almost all of the benefits and best outcomes stem from a very small set of the conversations I have with a student. A single conversation where I push a student to be more ambitious in what internships they’re applying to might account for all of the concrete benefit that the mentoring program provides to them.
Putting numbers to it, it’s probably less than 10% of my time talking to students that is directly responsible for virtually all of the positive outcomes. The tricky part is just that those 10% of conversations usually rely on the relationship we develop during the other 90%. Building trust and mutual understanding is fundamentally a time intensive process, but you need that trust and understanding to have a real impact in someone’s life rather than just address surface-level details.
From a personal perspective, getting better at developing these relationships has been a major area of growth for me — one I’ve found both difficult and rewarding. Talking with young people has a strange quality to it, because they’re usually able to perceive a lot more than they can express. Trying to understand their thoughts and point of view can take more effort than you put into other conversations, but they can be lightning sharp on noticing whether or not you’re putting in that effort. I’ve found I tend to have best results when I take up to 10 minutes before a call with one of them to mentally prep myself, checking back on notes from previous conversations just to clear my mind of anything I’m thinking about from my own life so that I can be fully present with them. I can take a call with one of them “cold”, especially if it’s one of the older students I already have a rapport with, but it can lead to conflict and misunderstanding if I don’t really cue myself to focus on the conversation from the start.
Of the 17 grant recipients, I’ve had my connection with 3 of them fizzle out over time. I mostly attribute those cases to inherent differences of personality — you can never get along with everybody — but reflecting on those experiences has been useful for finding ways I can continue to grow.
One small thing that’s been extremely helpful has been making a point of finding out every student’s birthday in one of my first conversations with them. I add each one to my calendar and make it a top priority to send some kind of well wishing text at least. (I do this with ordinary friends, too.) Everyone likes to be remembered, and it adds a no-pressure touch point with each student every year. Some large percentage of my happy birthday texts end up leading to us scheduling a catch-up call when a student has been busy with classes and clubs etc.
The last point that I want to note briefly here is that there is incredible variance in output with students this age. I might write more about this later, but even though we run a competitive application process that selects very motivated individuals, there can still be a big gap in efficacy between them when we first meet. A common case will be that students will get great grades and be active in clubs, etc, but need a fair bit of hand-holding when it comes to applying for jobs — usually because it’s an all-new process to them which is inherently intimidating. I can think of one student in particular, though, who literally had more than 20 internship interviews in the Autumn of their sophomore year, and whom I had to push to be more selective and focus on just the best opportunities. Truly, there is always someone who sets your personal best as their baseline.
I have some hope that, as the ALF gets older and we have a larger “alumni” pool, we can foster more peer-to-peer connections that will help these students inspire each other and bring them all up to that highest level. There’s certain things you have to see someone similarly situated do before you can believe you’re capable of them, too. I think developing more peer-to-peer support is also just generally important for making the mentoring program more scalable, as I and the rest of the board only have so many hours in a week.
The organization
I’ve tried to be as thoughtful as I can be when planning the ALF as an organization, but this is one area where time will be the most important test.
My initial focus was just on building up enough structure for us to receive tax exempt status. There’s a lot of important table-stakes stuff in there: recruiting a board of directors, putting together a core group of corporate bylaws, etc.
When you start reading about these things, though, you realize there’s a fair amount of diversity within the “tax exempt organization” umbrella. Do you want to start a public charity? A private foundation? A social welfare organization?
We ended up being recognized by the IRS as a 501(c)(3) “private operating foundation”, which has favorable tax treatment for donors (donations are deductible up to 50% of donors’ adjusted gross income, instead of the 30% limit for other private foundations) while allowing a level of flexibility in board control and fundraising that was essential for us getting started.
I’ve generally been very happy with this structure as it allows us to run the foundation, essentially, as a start-up. Instead of worrying about fundraising campaigns, I’ve been able to fund all our initial grants myself while we figure out a good working structure and answers to all the other challenges I’ve outlined here. It’s been a strategic de-risking. Now we can raise money knowing that we already have something that works, and start to make longer term plans about how to scale and grow from here.
The high level concerns remaining for me at this point revolve around funding and longevity.
For funding, we have two main options open to us. We should probably build our capabilities in both, but currently have expertise in neither. First: our structure allows us a lot of flexibility in fundraising, but we don’t actually have any organizational experience there. Second: we can carry an endowment and pay for grants through investment proceeds, but we haven’t built out that expertise yet, either. A focus in the next few years will be developing both of these skill sets so that we’re not fully reliant on either one and maintain flexibility.
I will note that one big advantage we have on the funding side of things has been our grant structure. The lump sum approach I was attracted to from a student-empathy perspective is also much easier to fund, as it removes the asset-liability matching issues that other foundations hit when they pay out grants over longer periods of time. That simplifies the endowment planning process considerably; we’ll always know how much money we have available to deploy in any given year.
Our extreme efficiency in general is helpful as well. With an all-volunteer board and outreach that goes directly through partner schools (rather than relying on any kind of advertising), our expenses outside of the grants themselves are generally pretty negligible. That’s been a win both in easier accounting and financing.
My concerns about longevity are a bit more vague but I think they’re important to keep in mind. The most pressing one is the “bus factor”: making sure that I’m replaceable. I think I’ve made progress on that front — this writing is part of that effort, even! — but I’m still less than confident that the foundation would be able to thrive without me.
One thing I’m trying to work on is delegating more of the foundation’s day-to-day work to other board members and/or looking for other volunteers to help with basic administrative tasks like keeping the ALF website updated. In a normal business setting, these would be easy things to hire for, but in the non-profit context it’s more difficult. I have some intuitive sense that, beyond having the tasks broken down, people have to have some reason to care about the organization and the mission. It’s not enough to be a great manager; you have to be a great storyteller, too. I’m still a work in progress on both points.
Concretely, we’ve just re-elected the board of directors and organization officers for the next three years. During that time I expect we’ll mainly be focused on continuing operation improvements and developing expertise in the two areas of funding I’ve outlined above. At the end of those three years, though, I’m hoping that we’ll be in a place where I can start to transition my own role further away from day-to-day operations, potentially bringing in someone new to focus on the application cycle and mentoring program — maybe one person for each. And though I’m deeply grateful to everyone on the board who has helped this journey so far, the first board seat replacement will also be an important milestone for us.
Like I said, these concerns are vague, but I think it’s important to worry about this kind of thing early.
A funny contrast between non-profit work and business is that you have a lot of different ways you can succeed in business. Your company doesn’t necessarily have to become a behemoth and IPO on the New York Stock Exchange — being quietly acquired at some multiple of invested capital can be a great outcome for everyone involved. With non-profits that’s a lot less true. You either build an institution that endures or you end up winding yourself down and dispersing the funds to other people who did. And you can’t build an institution without eliminating your key man risk.
Closing thoughts
If you’ve read this whole thing, I want to first thank you for your time and attention.
There’s a lot of heavy detail in here, but part of why I wanted to write all of this out is that I think the details matter.
For me, one of the most fascinating parts of running the foundation has been the emotional experience of it. When I started out wanting to do this, I thought it came from a very altruistic place — I wanted to give back and help kids from my old high school, what’s better than that? And I think there always was a core of true altruism in there — I stuck with it, after all. But it’s also just been a lot of work.
I’ve written with a ton of detail here because there were a ton of details I had to figure out to make any of this happen, and there are still many more challenges to face and questions to answer.
Our first cohort of grant recipients is graduating from college in 2024, and the early successes there have been a huge confidence boost for me. I feel like I’m seeing that effort come to fruition in a way that’s more deeply satisfying than I can explain. But I would feel negligent if I gave you the impression that I never had doubts. Preparing a 50 page application for tax exempt status was never my idea of a good time; trying to improve our application process and figure out how to get our applicant numbers up is always stressful; trying to show up and be my best self with every grant recipient in every mentoring meeting can be utterly exhausting, even when it goes really well.
There are still times when I get a little nagging voice in my head that asks me why I bother with any of this stuff. What am I trying to prove? Who am I trying to impress? Truthfully, I basically never interact with anyone in my day-to-day life who cares at all about the foundation. It’s not even been a helpful résumé entry for me.
But it’s not about me — that’s the point.
To the extent that it is about me, it’s about my desire to genuinely be an altruistic person and a net-positive presence in the world. That means putting in the work; that means getting stubborn, digging in, and solving real problems; that means telling the little nagging voice to shut up if it’s not going to be helpful.
If you get nothing else at all from reading about this experience, I hope you can take away something from that. You have to believe in yourself in order to be the best version of yourself.
It can be really easy to feel lost in the world’s problems like some great lake. You just have to get your feet underneath you and look for a bit of sand. Refuse to drown. Find a foothold and push.
Many thank yous to Aviva Mitchell and Claire Boston for reading early versions of this work.
He attributed it to Picasso (and that's how it's often remembered), but it probably was original to him. ↩︎