Yesterday I had breakfast with a financial advisor I respect and have known for over 30 years. He’s got a great reputation, works with high net worth clients, and is the kind of person other advisors point to as doing things the right way.

He described a standard move when a client has a large liquidity event, a business sale, an IPO, an inheritance: His firm creates a donor advised fund.

But then he shared the punchline: He works with the donor to schedule pre-determined distributions over a period of 25 years.

Not 5.

Not 10.

Twenty-bleeping-five.

And because the money goes into a DAF, the donor gets a tax deduction immediately, but the actual grants to IRL nonprofits trickle out over a quarter century. And for 25 years, that capital sits in an investment account instead of a program budget. And for 25 years, it generates fees for the advisor managing it.

So I asked him a direct question: Did he encourage his client go to any of their favorite organizations and ask what those organizations could do with that money now, or over 5 years, or over 10? Could they hire staff, expand a program, buy a building?

I also asked: Wouldn’t it be more fun for his client watch a program grow from scratch into something that family legacies are built upon?

And then: Surely there are creative projects out there within ambitions high impact organizations dying to put that money to work?

He looked at me like I had just mounted a donkey while wearing a top hat… and nothing else.

The question simply hadn't occurred to him but candidly he shared that my questions were not typically part of the conversation his firm has with clients.

The incentives are the problem

Most advisors who set up DAFs get paid on assets under management. The longer the money stays in the fund, the longer they collect a fee on it. A 25-year payout schedule isn't a donor's spontaneous preference. It's a product design that matches the advisor's revenue model.

Meanwhile the charitable tax deduction is claimed the day the gift goes into the DAF, not the day it reaches a nonprofit. The public treasury absorbs that cost immediately but public benefit shows up years or decades later, if the schedule holds at all.

DAFs now hold well over $350 billion in charitable assets nationally. Unlike private foundations, which must distribute at least 5% of assets each year or pay an excise tax, DAFs have no legal payout requirement. A sponsoring organization can hold a gift indefinitely and never be forced to move it.

Maybe it’s time to revive the ACE Act?

Yeah I know, we’ve been here before on this blog… but remember back in June 2021 when Angus King and Chuck Grassley introduced the Accelerating Charitable Efforts Act, known as ACE? A companion bill followed in the House from Reps. Ro Khanna, Chellie Pingree, Tom Reed, and Katie Porter. It was genuinely bipartisan.

The bill created two new categories of DAF. A qualified DAF, or QDAF, would cap a donor's advisory privileges at 15 years from the date of contribution. If the fund still held assets after 15 years, whatever remained would go to a preselected charitable beneficiary, and the sponsoring organization would owe a 50% excise tax on anything left undistributed.

Cute and tidy.

A second option let donors set up a 50-year fund instead, but with a catch: no charitable deduction until the money actually left the fund and reached a working charity. That reversed the current order, where the deduction comes first and the grant comes whenever.

Cute, tidy, and also quite reasonable.

The bill also created a qualified community foundation DAF category, which required a minimum annual payout of 5% of fund value, the same standard private foundations already meet.

There were exemptions built in. Community foundation DAFs under $1 million were excluded from the 15-year rule entirely, a concession meant to protect smaller, locally rooted funds from the same pressure aimed at commercial gift funds warehousing money for high net worth donors.

But you know what, it went nowhere

The ACE Act never got a vote because DAF sponsors argued the 15-year rule would create unwieldy reporting burdens. Community foundations, many of which run endowed DAFs with their own long payout horizons, pushed back hard, even with the carveout protecting smaller funds. And most nonprofit sector associations stayed quiet. Almost none campaigned for a bill that would have moved a large amount of money toward the organizations those associations represent.

(Note to reader: there is no doubt in my mind that this is the sort of platform that artificial intelligence was made to manage. I have no doubt that you could create individual bots to manage single donor advised funds for compliant and payout requirements. It is simply a question of political and technical will)

Today the bill is effectively dead and it seems that Angus King’s sole output as Senator from Maine has been to stump for his son’s failed run for Governor (Angus King III came in 5th out of 5).

Since 2021 ACE and similar DAF reform efforts haven’t been reintroduced with real momentum, and recent tax legislation has focused on deduction limits and AGI floors, not payout timing.

The warehousing problem the ACE Act targeted is still exactly the same today as it was in 2021. Only DAF assets under management (AUM) are over $200B higher.

What this means for the sector

I don't think the advisor I spoke with is doing anything illegal. I think he's doing something the system currently permits and financially rewards, which is a different problem and possibly a worse one.

Every year a dollar sits in a 25-year DAF instead of reaching a nonprofit is a year that nonprofit doesn't have it. Staff don't get hired. Programs don't scale. Waitlists don't shrink. The donor already took the deduction, the public already paid for it, and the only party still collecting on the arrangement is the asset manager.

If your organization works with major donors who use DAFs, ask the direct question I asked at breakfast.

Ask what the payout schedule actually is.

Ask why.

If the answer is a number like 25 years, ask whether that number came from the donor's stated wishes or from the advisor's fee structure.

Absent legislation, the only leverage the sector has is asking the question loudly and often enough that advisors have to answer it before the gift is structured, not after.

Because if the ACE act is dead, the only way to unlock DAF assets is for fundraisers like us to be really, really, really good at their jobs.

Worrisome.

Not because the people behind it aren’t smart. They’re really freaking smart: Tom Kalil, Kumar Garg, Ronit Kanwar. These are serious, accomplished people with genuine records of impact in science policy and philanthropy. That’s precisely what makes this so concerning.

Let me explain.

Renaissance Philanthropy’s core argument is that philanthropy is where investing was in the 1940s: slow, generalist, and structurally incapable of evaluating technically complex bets. Their solution is to build expert-led philanthropic funds modeled on venture capital, where donors act as limited partners and field leaders make the calls.

It’s a seductive analogy.

Venture capital works because failure is baked into the model, because you only need one investment to “pop” for the fund to generate returns to its LPs. But for all the pops, there are countless other bets that breakeven or are total losses. And those losses are not just tolerable, they’re expected because in VC land, failure IS the asset class.

Now, is that the same for philanthropy? I’m not so sure.

Because nonprofit and social impact organizations don’t work that way. There is no “pop.” There is no exit. There is no 100x return that wipes failure from memory. Because when a social impact or philanthropic initiative fails (I mean like really fails, publicly, with names attached) it doesn’t just damage that initiative. It damages the donor’s relationship to philanthropy, the reputation of the administrator of the gift (no matter how misguided or even well intended), and the morale of the research teams involved.

In my experience working in and observing this space for a long time, I have watched donors go apoplectic over a single failed initiative.

And not just withdraw from that cause, but pull back from philanthropic engagement entirely, even going so far as to threaten careers and livelihoods. And yet Renaissance Philanthropy explicitly celebrates funding “non-consensus ideas” and “riskier bets.” One of their case studies is called Impetus Grants and is praised precisely because it funds ideas that “many would fail.”

That’s fine for a biotech portfolio.

But it could be a catastrophic posture for a sector already struggling to maintain donor confidence and public trust.

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The Risk/Reward Problem Nobody Is Talking About

Here is the argument that is conspicuously absent from the Philanthropy 2.0 framework: who actually bears the risk in this model, and what do they get for it?

In venture capital, the risk/reward relationship is at least theoretically rational. LPs accept high failure rates because they are seeking financial returns. GPs build reputations and carry interest and everyone in the structure has a clearly defined upside.

In the thesis-driven fund model, donors bear all the financial risk….but receive no financial return. The “field leaders” who manage the funds build professional reputations and career capital. The RenPhil piece is admirably honest about this: one of the explicit advantages of the fund model, they argue, is that it creates “legible track records” for talented people who might otherwise go into government or industry.

In other words, a significant part of the value proposition of this model is career development…..for the fund managers.

That’s a cynical observation, I’ll admit. But in practice it means that donors and (frankly) research and nonprofit leaders are being asked to absorb VC-level risk with zero financial upside, while the professionals managing their capital build a shiny résumé. That asymmetry should be front and center in any honest accounting of what this model is (and also what it isn’t)… but it’s nowhere in the RenPhil white paper.

The Real Problem Is Velocity, Not Architecture

The deeper issue with Philanthropy 2.0 is that it diagnoses the wrong disease. Renaissance Philanthropy, Emerson Collective, Bridgespan… all of these organizations are, to varying degrees, trying to build a better mousetrap: How do we deploy donor capital more intelligently? How do we find better research leaders? How do we build more coherent theories of change?

These are real questions.

But they are secondary to the primary problem, which is this: there is an incomprehensible amount of philanthropic capital that is structurally incentivized to go nowhere.

And while those entities sit around handwringing about how to allocate it “efficiently” or “effectively” or in novel ways (and with truly good intent, I think), they unintentionally create barriers to its actual deployment.

Why? Because their careers and reputations depend on them always, and I mean always, being right.

So they slow play. They obfuscate. They analyze. They write white papers and speak at conferences. They author impact reports. But despite the kabuki theatre of it all, in reality these entities are profoundly risk intolerant. They simply cannot be wrong when allocating the capital of their billionaire philanthropist boss.

On the other end sits university and foundation endowments who collectively hold trillions of dollars governed by spending policies that were designed to preserve capital in perpetuity…not accelerate impact. Donor Advised Funds alone now hold more than $324 billion, growing faster than distributions. The average DAF payout rate hovers around 20-25% annually, meaning the majority of that capital is parked, sometimes indefinitely, in financial instruments while the problems it was ostensibly designated to address continue to worsen.

This is not a build a better mousetrap problem. It is (as I have stated in several posts) a monetary velocity problem. And no amount of elegant fund architecture solves for capital that has been structurally incentivized not to move.

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The comparison that actually fits here is not banking in the 1940s. It’s the CDO market in 2006. Collateralized debt obligations, synthetic CDOs, CDOs-squared — these were instruments designed by genuinely brilliant people to solve what looked like a capital allocation problem. The models were sophisticated. The theses were compelling. The pedigrees of those involved were impeccable. And the complexity of the instruments served, whether intentionally or not, to obscure the underlying fragility of the system.

Long-Term Capital Management is an even sharper analogy. LTCM was run by two Nobel laureates and a team of quantitative geniuses. Their models were right … until they weren’t. And when they failed, they very nearly took the global financial system with them, not because their ideas were stupid, but because their confidence in their own models caused them to underestimate the knock-on effects of them being wrong.

I am not predicting that Renaissance Philanthropy will cause a systemic collapse. But I am saying that a model built on elite pedigree and sophisticated framing attracts significant “smart donor capital” (and RenPhil’s own white paper explicitly targets UHNW donors with $50M+ in assets). This targeting drains capital from the existing philanthropic ecosystem while its own thesis-driven funds work through their inevitable failure rates while building resumes for their managers.

But remember: the organizations and communities that depend on that capital don’t get a bailout. They wait, and wait…while RenPhil plays out more ivory tower modeling.

There Are Solutions, but They’re Less Glamorous

The good news is that the velocity problem has actual levers. They are just less intellectually exciting than building a new fund architecture.

DAF platforms are increasingly developing tools to accelerate deployment, and there is growing regulatory and advocacy pressure to raise minimum distribution requirements.

Some foundations have made binding commitments to spend down their endowments entirely (the Stupski Foundation being among the most notable examples, having made an explicit decision to deploy its full resources within a defined timeframe rather than manage a perpetual institution.)

That decision did not require a new theory of philanthropy. It required a commitment to urgency over institutional preservation.

Foundations like RenPhil could make voluntary commitments to increase their payout rates above the 5% minimum required by law (a policy threshold that was set in 1969 and has never been updated to reflect either inflation, the scale of contemporary challenges, or the hollowing out the public services).

Because the gap between what is legally required and what is morally adequate has never been wider.

These are not exciting interventions. They don’t require field leaders with deep domain expertise or compelling theses or anchor donors. They require institutional will. And that is exactly why the philanthropic sector’s thought leaders aren’t talking about them: because “spend your money faster” is not a conference keynote. It doesn’t build a consulting practice. It doesn’t create a new class of expert intermediaries with legible track records.

The Hardest Question

The hardest question for Renaissance Philanthropy and the broader “new philanthropy” ecosystem is one they don’t ask in Philanthropy 2.0: who are you accountable to when the thesis is wrong?

In VC, the answer is clear. You’re accountable to your LPs, who will or won’t reinvest based on your returns. In government, DARPA program managers (whom RenPhil invokes admiringly) are accountable to Congress, to the public, and ultimately to the taxpayers whose money they’re deploying.

But not really, right? Right?

The same is true in a thesis-driven philanthropic fund: the fund leader is accountable to the anchor donor, who vetted the thesis and then agreed to act like an LP and defer to the fund manager’s judgment. That’s a closed loop. And when the thesis fails (as many of them must, by design) the people whose lives were affected by the underfunded alternatives have no seat at the table.

That’s not a new problem in philanthropy. But Philanthropy 2.0 doesn’t solve it. It institutionalizes it, with better branding and a more sophisticated vocabulary.

The sector deserves a real conversation about velocity, accountability, and what it means to be genuinely connected to the communities you’re trying to serve and the problems you’re trying to solve.

That conversation starts with a lot less hubris in those creating new models, and more urgency about getting capital to the people doing the actual work.

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So….there’s this piece circulating on Substack that makes an ambitious albeit back-of-the-napkin claim: that AI wealth is about to generate somewhere between $37 billion and $100 billion in new annual philanthropic spending, and that the sector’s main challenge is building enough organizational capacity to absorb it.

The piece has generated responses from the Chronicle of Philanthropy and even the New York Times. Its one of those things that could gain traction as the truth. That’s because the author seems credible: A Harvard educated Stanford MBA whose career stops include Uber (author’s note: as many of you know, I think Uber is a criminal enterprise that lost $52B on its way to destroying the taxi industry), Parthenon Group (private equity, of course!) and Stripe (Internet’s financial plumbing/taxing authority. Not many know this but Stripe sort of works like a successful version of the failed virus algorithm from Office Space - they siphon off a teeny fraction of a penny from every single e-commerce transaction. Turns out if you do that well…voila: you’re an instant billionaire (see also, the Collison Brothers). Interesting what those brothers are doing with their billions BTW….)

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“Train a model on your content!”

“Your AI avatar: always on, always you.”

These “let AI be you” posts are everywhere and I’ll be honest: I sort of get it. Let agentic AI do all the work that you might otherwise do at a keyboard. And this should work because you like to write and you’ve spent years developing a sharpened point of view and a recognizable cadence.

So why not bottle it? Scale it? Let it work while you sleep? Write stuff as you all the time, all day long, 24/7/365. Always on, always creating, a constant stream of you.

But every time I see it, I get (I dunno)….sad.

Because that thing being sold as your “voice”? It’s a steroidal autocomplete function imagining your typical sentence structure, preferred adjectives and the way you open paragraphs.

Those are like your writing fingerprints, or maybe your author’s DNA, but they’re not You.

Because while some might see it otherwise, AI can never pin that down. Because what you write is the accumulation of everything that has ever happened to you, everything you’ve read, or felt, or argued about. It’s every time you’ve changed your mind or left a city or ended a relationship or triumphed at work. It’s a composite of every personal failure that quietly rewired how you see the world.

But it’s more than that.

Because AI models trained on your content have no conception of your existence. It doesn’t know about your childhood, your heartbreaks, your formative embarrassments, the teacher who said something that stuck, the book you read at exactly the right moment.

So it might have your writing patterns. But it isn’t you.

Sorry, Claude.

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And even if AI could replicate some version of you, you’re not the same person you were when you created the model. Hell, you’re not even the same person you were when you started reading this very amateur blog post.

Because even if an AI could perfectly replicate you as you sound right now, it would already be falling behind when you wake up tomorrow.

And tomorrow, when a newly rested version of you wakes up, AI you is already obsolete.

Sorry, Claude.

Because your perspective on the world is constantly being revised by new experiences, relationships, evidence, grief, and joy. The person you are right now is different from the person you were five years ago, and meaningfully different from who you’ll be five years from now.

Truth? I would not want an AI version of 25-year-old Brad Smith bopping around for eternity with all his certainties and blind spots firmly intact. No thanks. I’ve worked pretty hard to outgrow that shit.

To illustrate, here’s a very recent example of what AI could never digest.

Last week I took my teenage daughter to the hospital. And because she and I had binged The Pitt recently, of course we called the attending “Robby” and our 3rd year medical student “Huckleberry”.

(Author’s note: Those monikers were fun, but not very accurate. First the attending was old (late 60s) and not particularly attractive. Our earnest 3rd year medical student did not come from a farm in Nebraska nor did he have a comically horrible mullet. But then again he was genuinely kind in a “I don’t fully know what I’m talking about, but I want you to believe me” sort of way, so for him: Huckleberry it is.)

But our doctor duo was only part of the experience. There were the scared parents curled up in the ER with their sobbing toddlers. A kid wearing a neck-brace, immobilized after some sort of sporting accident, surrounded by his teammates and family. A patient’s angry sister frustrated by the lack of snack options. And on top of that: the incessant thrum of a wall mounted video game console installed in the pediatric waiting area.

(Memo to Maine Med: That thing needs to go.)

I marveled as clinical care teams moved between patients with empathy, love and concern. I watched jovial CNAs dutifully clean rooms between patients. I watched a nurse roll an elderly man past kids in hall beds and parents on cell phones, trying to find an empty, private restroom. All while feeling deep gratitude for the concern and care directed towards my own daughter (who is fine, thanks for asking).

It was so profoundly, powerfully human.

And you know what? AI will never get that.

Because a trained AI avatar is digital taxidermy. Recognizable from a distance, or mounted on a tavern wall. But it will always miss the thing that made you worth listening to in the first place.

BTW, this is not an argument against AI. I use AI. It helps me organize, distill, and analyze. But AI models and their proponents underestimate how much the daily human experience shapes out voice, and LLMs will never keep up.

Sorry, Claude.

Invest $1 in fundraising, get back $5.

It sounds like a law of nature. It gets cited in board presentations, repeated in consultant decks, and handed down from executive directors to development directors like scripture.

The problem isn’t that the ratio is wrong, the problem is that it’s average, failure, and aspirational all at once.

A Number Without a Birth Certificate

Try to source the origin of the $5:$1 ratio. Go ahead. Follow the citations back through AFP publications, through consultant white papers, through conference keynotes and LinkedIn posts.

What you will find is a chain of aggregated data blessed as universal truth.

This is how professional mythology works. First a consultant presents a compelling case study. Another cites it as a benchmark. A third drops the original context entirely and presents the number as settled science. By the time it reaches your board chair, it has the weight of settled wisdom but feels more like that grapevine scene from the movie Johnny Dangerously.

The $5:$1 ratio is not a law of fundraising. At best, it’s a sector average validated by longitudinal research, but unfortunately it has become an expected outcome laundered through decades of repetition into something that feels true.

And we sort of let it happen.

Here is where it gets uncomfortable.

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The $5:$1 ratio has not been equally convenient for everyone. For boards and executive directors managing tight budgets and anxious finance committees, the ratio functions as a ceiling as much as a promise. If we expect five dollars back for every dollar in, then a $60,000 development director salary should generate $300,000 in revenue.

Anything less is underperformance. Anything more is gravy.

And this math has a seductive tidiness. It also happens to justify chronically low compensation for development professionals, especially at smaller organizations where the director of development is often single person responsible for donor relations, grant writing, major gifts, events, communications, and board management….all at once.

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There is a version of the Major Gifts Officer (MGO) role that most people in advancement have never experienced. It’s the version where a fundraiser works with a donor and his or her family over years (and in some cases, decades) learning their values, their family history, their philanthropic ambitions. This is where a gift conversation emerges from a place of mutual trust, and where the fundraiser is not so much managing a “portfolio” so much as tending to a community.

That version of the MGO role still exists. But it is increasingly hard to find inside institutions because many have reorganized their advancement operations around metrics, pipelines, and portfolio assignments that would feel familiar more to a mid-market insurance sales team. At those institutions, the dashboard won.

This is worth examining not to romanticize a past that was imperfect in its own ways, but because the current model is failing donors, failing gift officers, and ultimately failing the institutions it is meant to serve.

How the Model Changed

The shift toward metrics-driven fundraising was born of a reasonable impulse: Accountability. Advancement offices were being criticized for being relationship-rich and results-opaque, so naturlaly came under pressure to demonstrate that the significant investment in staff and travel was producing identifiable, traceable and commensurate returns.

Leadership wanted to know: what are our gift officers doing, and how do we know it’s working?

The consensus: Activity metrics. Dashboards. Visits per month. Proposals submitted. Dollars moved through pipeline stages. Portfolio coverage. Qualification calls completed. All concrete, trackable, and reassuring in a spreadsheet. And achieving high output in these variables made the career of many a Director of Major Gifts.

But there was a profound miscalculation at the center of this transformation. It was subtle but consequential. Activity metrics measure what gift officers do. But they say almost nothing about what donors are ready to do.

And in major gift fundraising, donor readiness (the presence of genuine philanthropic motivation, life-stage alignment, and institutional connection) is not another metric.

It’s the entire game.

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The Donor’s Experience

Consider what the metrics-driven model feels like from the donor’s perspective. A loyal alumna who has given annually for fifteen years receives a call from someone she does not know, representing an institution she cares about deeply, who has been assigned to qualify her for a major gift portfolio. The gift officer is following process and doing exactly what their manager expects, while spending precious institutional resources to travel the country meeting with people just like her.

The stakes for that meeting are insanely high.

But the donor experiences something different: an unsolicited approach from a stranger representing her alma mater who wants to assess her “Capacity” and “Readiness” IN PERSON.

This is not a hypothetical.

This situation has me anecdotally documenting a growing and striking trend: donors are asking explicitly not to be contacted by gift officers at all. Others are quietly redirecting their giving to institutions that approach them differently. Even more cynically, these donors have spurred a proliferation of donor-advised funds where they gain an objective win (tax deduction) and still retain control of the distribution.

But let’s say the quiet part out loud: Donors don’t want to be managed.

They have built wealth through their own judgment and initiative. They give on their own timeline, for their own reasons. A cold qualification call (no matter how however well-scripted or well-intended) signals that the institution does not understand their origin story or (worse), thinks that sending a thirty something rando to their home or place of business is somehow part of the standard philanthropic journey.

Worse: It signals that the prospect has become a target, not a potential partner.

But what about the Gift Officer’s Experience?

If the metrics-driven model is hard on donors, its become unsustainable for the people asked to execute it. Major gift officer turnover has become one of the most persistent and expensive problems in advancement. The average tenure in many programs is now eighteen months to two years (and often less). Some gift officers stay just long enough to close one significant gift (something to anchor a resume) before departing for another institution.

Some burnout and leave the advancement field entirely.

Because when the work consists primarily of outreach to donors who did not ask to be contacted, measured against activity quotas that bear little relationship to actual philanthropic intent, the role becomes demoralizing in a particular way. You know what I mean: the kind of grinding, purposeless work that corrodes your sense of professional identity.

Yeah, that kind of work.

And because altruism is what tends to draw gift officers into advancement in the first place, that friction risks eroding their faith in the entire profession.

High potential fundraisers don’t become fundraisers expecting to cold call alumni and “manage a portfolio”. Most entered it because they believed in the transformative power of philanthropy and wanted to help facilitate that human impulse. The metrics-driven model takes this altruism and buries it under contact report requirements, and increasingly, the cynicism of donors, CDOs and CFOs at every institution.

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A Different Kind of Career

I have been thinking a lot about the MGO role recently, mostly because a former colleague of mine is retiring after serving in that role for over thirty years. Thirty two to be exact. He helped facilitate hundreds of millions of dollars in donations while partnering with donors he genuinely knew.

And better yet: they knew him!

The relationships he built over that career are extraordinary, and they’re anything but transactional. They’re partnerships forged through consistency, curiosity, and care. He built a career on something the current model systematically destroys: the time required to become a fundraiser that most donors actually want to work with.

Because you cannot manufacture trust through qualification calls and moves management. Trust accrues by showing up year after year with genuine interest and without an agenda other than to understand, then advance the philanthropic intent and ambitions of potential major donors.

But I also see his career as a proof of concept. It demonstrates what the role can be, when institutions are structured to support it and gift officers are empowered to practice it.

The question worth asking is why we intentionally engineered the philanthropic concierge out of so many institutions, and whether we are willing to design it back in.

It Does Not Have to Be This Way

The good news is that there is a coherent alternative. It does not require abandoning accountability or discarding data. It requires pointing those tools at something more meaningful than the kabuki theatre of metricized volume.

The first principle is achieving a CLEAR SIGNAL before a gift officer ever reaches out to a prospective donor. This requires analysis of data (behavioral, relational, or otherwise) that signals a donor is ready to engage. This is not a radical idea. It is how the best relationship-based fundraisers have always worked. We paid attention to what donors were showing them, and donors responded to our curiousity about those signals rather than imposing their “cultivation” onto some kind of schedule.

The difference now is that we have access to significantly richer signal data that can surface readiness. And not just individual readiness: Readiness at scale.

The second principle is redefining what it means to be IN PORTFOLIO. Because not every major prospect, no matter how capable, belongs in a gift officer portfolio. In fact, it could be argued that only prospects in active cultivation or in discussion about a major commitment should be “in portfolio”.

So what are you to do with the hundreds or even thousands of newly portfolio-less prospects? You deploy tools that invite deep, meaningful conversations without the expectation or burden of in-person meetings.

(Editor’s Note: Automation is NOT the same as AI. In fact, it’s anything but. That’s because AI’s LLMs can access far too much information about a prospective donor. And applying that much information to the engagement/cultivation process is manipulation. And fundraising may be a lot of things: but it’s not manipulation.)

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Sorry for the digression, but what does this look like in practice?

Well, first it means that initially, major gifts might emerge more slowly. Second, it acknowledges the reality of what’s known as Dunbar’s Number: specifically, that a human being can only juggle 150 total relationships at a time.

And that includes family, children, partners and friends. Sort of makes you wonder why are Major Gift Officer portfolios are often 200 names or more.

Second Editor’s Note: Many have attempted to debunk the logic of Dunbar’s Number, and admittedly it’s not a law of nature, like gravity or magnetism. But it is a healthy approximation in my mind.

What this means in practice is that major gift officer “portfolios” are only those that are driving towards a substantive gift conversations and not cold calls for qualification. And as I shared in an earlier post in this Newsletter, those cold-calls now represent nearly 2 months a year of a MGO’s time.

It’s why they’re quitting in droves.

The third principle here is critical: AN INVESTMENT IN TENURE. Programs that churn through gift officers every eighteen months are not just paying replacement costs, they are destroying accumulated relationship capital. On more than one occasion I suggested to MIT’s CFO that the Institute consider business interruption insurance on top fundraisers past a certain tenure threshold (say, five years) because their accumulated relationship capital was so valuable.

Structural changes that make the MGO role more sustainable, more professionally meaningful, and better aligned with the actual conditions of major gift fundraising are not squishy soft ideas. Rather it acknowledges that hiring an MGO or building a team of MGOs represents a strategic investment in developing a reliable, long-term revenue stream: individual major and planned gifts.

The fourth and final principle is the acknowledgment of DONOR AGENCY. The most productive major gift relationships are ones where the donor has chosen to engage, and where they have, in some meaningful sense, opted in. Designing advancement programs around a donor’s agency does not mean being passive. But it requires being strategic about when and how initial outreach occurs, and ensuring that when it does, it is welcomed and not resisted.

The Path That Is Still Available

Major gift fundraising is one of the most best jobs in advancement. It sits at the intersection of institutional mission and private generosity, facilitating the transfer of resources toward purposes that matter. The people who do it well are not salespeople running a quota.

They are advisors, connectors, and trusted stewards of relationships that can span generations.

That version of the work is still possible. My former colleague’s thirty-two-year career demonstrates that possibility. But it can also be a deeply rewarding and mutually reinforcing experience for the fundraiser, the donors, and for the institutions they serve. The metrics-driven model almost entirely obscured this possibility, and in doing so, drove away many of the people most capable of practicing it.

The institutions that figure out how to reclaim the spirit of the MGO model (not by abandoning rigor but by reorienting it toward activities that produce major gifts) through signal generation will have a advantage in the years and decades ahead.

Because the great wealth transfer is underway.

The question is whether advancement programs will meet their constituents as partners or continue cold-calling them with a revolving carousel of high strung, hyper metricized MGOs.

It worked well enough for long enough that institutions built entire staffing structures, compensation frameworks, and technology stacks around it. But while the conditions that made this model work have shifted dramatically, the portfolio model of major gifts fundraising endures like that stack of CDs you just can’t get rid of.

This is not a critique of the people doing the work. After all, major gifts officers are my peeps, and rank among the most under appreciated and interesting professionals at any institution: master integrators connecting prospective donors to institutional projects that have the potential to change lives for the better.

The problem isn’t the people.

The problem is structural, and I recently concluded that the portfolio based major gifts model has outlived the logic that justified it.

The Pipeline Assumption No Longer Holds

Portfolio-based fundraising rests on a core assumption: that donors can be meaningfully segmented by capacity and readiness, assigned to an officer, and moved through a predictable engagement arc toward a closed gift. That assumption requires relatively stable wealth profiles, predictability about where family assets will land, and most importantly: a captive population receptive to a relationship with a member of your organization’s fundraising staff.

Each of those conditions is eroding.

The most significant disruption is that, despite relentless focus on the billionaire class, we happen to be in the early stages of the largest intergenerational wealth transfer in history. And while some organizations pursue billionaire donors at all costs, the amount of money being moved over the next 20 years is beyond staggering:

In fact, estimates from Cerulli Associates (founded by a fellow Colby College alumnus, holla!) estimate that $84 trillion will move from Baby Boomers to younger generations over the next two decades.

For fundraisers, that number is not a windfall. It is a signal.

Still: Principal Gifts Have Changed the Math

The emergence of dedicated principal gifts programs at major research universities has quietly and unintentionally reshaped the existential “why” of the major gifts program. Because when an institution is seriously pursuing eight- and nine-figure commitments, those relationships require a fundamentally different approach: longer time horizons, multilayered, multi-partner engagement, deep family-office-level relationship management, and a cultivation horizon that operates well outside the typical eighteen-month solicitation pipeline.

The consequence is that major gifts officers are increasingly caught between two worlds: UHNW and HNW donors with transformational gift potential and who require sustained, unhurried, highly personalized attention, and the standard identify/engage/solicit model outlined above.

But in my experience, metricizing the principal gifts function is patently absurd: Who cares about total visits if a gift officer is spending all of his/her time working towards $10M+ gifts? Moreover in this environment, visits, touches, and pipeline reports are kabuki theatre for Advancement Committee meetings or for that ambitious AVP’s shameless resume building efforts.

Worse, they are awkward proxies for what truly effective cultivation actually requires.

And when institutions try to manage both through the same staffing and portfolio structure, they typically underproduce at both ends: the prinicipal gift donors don’t get the depth the relationship demands, and the standard major gift donors don’t get the consistent love and affection they deserve.

The Stewardship Demands are Real

The second reason that the portfolio model is dead is that let’s face it: Higher Education and major healthcare institutions have been in permanent Campaign mode for the last quarter century. Those institutions have an enormous accumulated donor base that necessitates deeply personalized, creative stewardship.

Donors who made gifts a decade or more ago (particularly those who made endowed commitments with ongoing fund activity) should still expect meaningful, informed engagement.

They want to know what is happening with their gift.

They want to meet the students.

They want updates on the research.

They want to feel remembered.

Most major gifts officers are not set up to provide that level of after-the-sale service. That’s because most MGO performance frameworks reward qualification calls, asks, and closed gifts, not the stewardship of prior donors. In fact, deep, personalized stewardship competes for time with prospecting and cultivation.

Why? Because the rational MGO knows that the only way up is to close gifts.

And this focus on top line “closing” creates a chronic backlog of un-stewarded relationships that institutions know they should be investing in but don’t, because they’re constantly chasing and qualifying new leads.

But that approach is running into a demographic and cultural buzzsaw.

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Donors Are Skeptical of Being Managed

There is a growing cohort of philanthropically sophisticated donors (many of them in their 40s and 50s) who are either equity compensated leaders or next-generation wealth holders who matter to institutional pipelines. Those Gen X prospects are increasingly cynical about being assigned to a fundraiser because they are aware of what the relationship is about and don’t have the time or the interest in being “cultivated”.

They recognize the bland choreography and insincerity of that model.

The maddening rise of donor-advised funds reflects this cynicism. DAFs give donors control over timing, pacing, and the relationship with recipient organizations. The donor decides when they are ready to engage and at what level. That arrangement is structurally incompatible with a model premised on having an MGO managing the relationship arc.

Fundraising programs that have not updated their approach to today’s digitally fluent, time constrained, and philanthropically autonomous prospect pool aren’t just leaving money on the table. They’re unintentionally putting distance between their institution and the alumni donors they will need in the future.

Worse, MGOs are becoming a terrible investment. Why? Well let’s do the math shall we?

A Major Gift Officer earning $95,000 in base compensation, with $30,000 in benefits and a $25,000 travel budget, carries a fully-loaded annual cost of $150,000. Against a goal of 150 qualification meetings, that’s $1,000 per meeting on paper, right?

But the real number is higher. To land 150 meetings, an MGO typically has to make 15 attempts per meeting, generating 2,250 calls and emails along the way. At just five minutes per contact, that’s over 187 hours of outreach activity (nearly five full work weeks) just spent on attempts that will never result in a conversation. Factor in the staff cost of that dead time and the true price of each qualified meeting climbs closer to $1,100, before a single flight is booked or a cup of coffee purchased. Add in the industry standard 18-month tenure for the typical MGO, and you end up with even more unproductive staff time.

While nobody is going to say “stop qualifying donors!” it does tell us why typical major donor prospects are cynical about being in portfolio: They’re literally under siege by a rotating carousel of gift officers.

Compensation Models Are Shifting

For decades, major gifts officer compensation has been structured around base salary plus performance bonus, typically tied to predefined metrics. That model reflects a particular theory of the job: it is a production role, and production can be measured in meetings or closed gifts. But as the function becomes more complex, requiring longer time horizons, multi-stakeholder (internal and external) engagement, and real stewardship depth, the gap between what the compensation structure rewards and what the role actually requires keeps widening.

More progressive institutions and some nonprofit intermediaries might consider experimenting with equity-adjacent structures, long-term incentive frameworks, and compensation tied to portfolio quality rather than closed volume. These would be novel, early experiments to be sure, but they would signal something: that the sector is quietly acknowledging that the major gift metrics based model does not accurately capture the value being created by MGO work or the time horizon over which that value is created. So something is amiss.

And yes my friends: Something is definitely amiss.

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What Comes Next

None of this means that dedicated major gift focused relationships are obsolete. They are not.

What is obsolete is the idea that a portfolio built on assumptions about a defined donor pathway with fixed wealth assumptions, measured through short-cycle pipeline metrics is the right container for those relationships.

What institutions need instead is some sort of demand signal-based model: one that automates donor engagement and delivers consistent donor readiness signals rather than a bland portfolio assignment. This model should also monitor and account for the sensitive timing of intergenerational wealth movement, and also create space for deeply intentional stewardship.

But make no mistake: a demand signal from your prospective donor pool is the essential ingredient in this new model.

What that allows is the kind of deep, unhurried cultivation that major donor relationships actually require, without constant MGO outreach to cold leads. This has lead me to conclude that the MGO portfolio as a management tool is past its prime, but I also think that there is another way.

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Yeah, that guy.

The piece reads like a memoir and actually tilts sympathetic: Ross reckons with his choices while trying to enjoy a quiet retirement in Beacon, New York. Ross is conducting what the reporter calls “his own accounting.” He claims to be “mortified,” and “ashamed.” He has resigned from his positions. He has apologized, publicly, more than once.

And yet…

The emails between Ross and Epstein, released as part of the Justice Department’s massive document dump in early 2026, tell a very different story.

For example, when Epstein was released from jail in July 2009, Ross emailed him: “a welcome home! Glad the nightmare is over, Jeffrey. It was an undeserved punishment foisted upon you by jealous creeps.”

Uh, what’s that David?

An email like that is not a lapse in judgment. It’s the posture of a man who had consciously decided that Epstein and his pipeline of donor access (and by extension, Ross’s own professional success) was worth more than the weight of what he knew about Epstein.

To Ross, Epstein the sex offender was a friend and fundraising asset. And those people who punished him and put him in jail? Jealous creeps!

More examples: In September 2009, after watching a deposition video of Epstein taken as part of a civil lawsuit brought by his victims, Ross wrote to Epstein: “Sorry to have seen this… but I know how tough you are, and in fact, it probably bothers me as your friend more than it does you. Thinking of you.”

Read that again.

A man who had been convicted of soliciting a minor for prostitution was being comforted by a nonprofit leader, because watching the victim’s deposition must have been hard on Epstein.

(The victims, the actual humans harmed, are not mentioned in Ross’s email.)

The Times piece frames Ross’s behavior in the context of what is now referred to as the “Epstein Class”: a global circle of billionaires, academics, political leaders and (yes) fundraisers who did not participate in Epstein’s sex or trafficking crimes but openly and willingly laundered his credibility and reputation.

They cashed his checks, hosted him at galas, and mingled their reputation with his own. That framing is 100% accurate.

But where the article falls short is in accepting Ross’s stated rationale: that fundraising culture created the conditions for this blindness, as something approximating an explanation rather than a rationalization.

Ross himself said, “I became my job, and I lost track of myself.”

Yeah, it’s a funny thing that whole “losing track of yourself” excuse. And it comes up a lot in Epstein rationalization land.

Case in point: When I was at MIT in the early 2010s, I worked with a fundraiser at the MIT Media Lab who regularly name-dropped Epstein and his connections to billionaire Leon Black. This fundraiser and his boss (disgraced tech leader Joi Ito) didn’t care what Epstein had done because Epstein had access to a billionaire.

And wasn’t turning a blind eye worth it for a billionaire?

(BTW, the MIT Student Newspaper has done a remarkable job cataloguing the Epstein connections to Leon Black’s donations to MIT, but also donations made to MIT by another Epstein pal, Bill Gates.)

And just like Joi Ito at MIT, David Ross treated Epstein as a friend. And to accept Ross’s argument that engaging with Epstein was just part of the job, we allow the fundraising imperative to supersede all moral and ethical judgment.

And doesn’t the relentless pursuit of a check absolve or explain anything?

I’ve watched this form of rationalization unfold just up the road at Bowdoin College, alma mater of two famous Epstein pals: George Mitchell ‘54 and Jes Staley ‘79 (the latter as probably the most notorious financier and friend of Epstein himself).

What I find remarkable about Staley’s case is that it took Bowdoin nearly 15 YEARS to oust Staley from the College’s board of trustees.

(BTW, if you want to read some outstanding coverage of the Epstein files, follow the Bowdoin Orient, who shows how rationalization works in practice. Case in point: Jes Staley put his own daughter Alexa in direct touch with Epstein and used Epstein’s connections to advance her own career. Put aside the fact that Staley connected his OWN DAUGHTER to a child sex offender, it’s her acquiescence that floors me even more. Epstein’s assistance meant that she got involved with the LIGO Project. So much for meritocracy!)

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This level of rationalization is not a fundraising virtue. It’s a path to moral bankruptcy.

And this matters beyond David Ross and that college up the road. It is a symptom of something more corrosive at organizations being led and operated right now. It’s a study in what happens when an organization or an individual substitutes motion for judgment, hustle for strategy, and access for values.

It’s what I refer to as “flailure”.

Flailure is what happens when an organization (or person) moves so fast in so many directions all at once that he/she sets the organization on the path to long term destruction or hardship.

But make no mistake: Flailure is not akin to laziness. Quite the opposite, actually. It’s the product of a culture that has absorbed the “move fast and break things” ethos of the blitzscaling era and applied it to contexts where that ethos doesn’t work: mission driven organizations, cultural institutions, higher education, or any nonprofit whose raison d’etre depends on trust, generational impact, or long term credibility.

And on the path to flailure, speed feels like a competitive advantage. Aggressive pivots seem virtuous and might even be “data driven”. But at a museum, a university, a foundation, or a social change organization, speed without clarity or conviction is not an advantage. And at worst it’s theatre for personal ambition, or accelerates the kind of drift into rationalization that the Ross story illustrates.

Because when you move quickly towards every open door, you stop wondering whether the door should be opened at all.

In my experience, “Flailure” has a signature look:

• Four or more “strategic pillars” running simultaneously.

• A development office with more than five “fundraising priorities”.

• A board that approves a new initiative every quarter because saying yes feels like leadership.

• A leader who speaks eloquently about impact yet cannot tell you what his or her organization does not do.

• Several, sometimes dozens, of open “Associate Director” jobs but no commitment to administrative support.

Organizations in a state of flailure are always very busy. But they are almost never effective.

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There is an antidote to flailure. And despite my emphasis on pacing, it doesn’t mean that you have to slow down. Rather, in my experience coherent organizations making real progress share three defining characteristics.

1. Clarity of mission , not a mission statement, but an operational understanding of why we exist that is specific enough to guide actual decisions. If your mission can justify almost any new initiative, it is not a mission; it is a permission slip.

2. Sustained messaging , the willingness to say the same thing, in roughly the same way, for years. Not because the world does not change, but because trust is built through consistency and eroded by constant reinvention. Every time an organization rebrands, relaunches, or pivots its narrative, it is asking its donors, partners, and stakeholders to start over. Most of them don’t. They just quietly disengage.

3. Defined impact areas: Explicit, public clarity about what you do and, just as importantly, what you do not do. This is the hardest discipline for mission-driven leaders, because saying “no” to good or meaningful work feels like a betrayal. But diffusion kills organizations. Focus compounds them.

David Ross did not wake up one morning and decide to cozy up to a predator. He drifted. He rationalized because in his mind\ he was cultivating access, opening doors, building relationships (all the things the fundraising culture rewarded him for BTW) and at some point that drift carried him somewhere he should never have gone.

But the job also had some sweet perks: Private jet flights. Private viewings at the Sistine Chapel. Access to the most famous and powerful people on earth.

Was David Ross selfish, or selfless? Yes to both.

But more importantly: David Ross represents flailure at the individual level.

And sadly, Ross has an institutional parallel nearly everywhere you look: In advancement shops that declare “everything is a priority” and in boards that mistake saying “yes” to everything as real progress.

Organizations that want to avoid their own version of this story have to build something different. Not a culture of speed, but a culture of discernment. Not the widest possible aperture on revenue, but a disciplined, values based, grounded view of who you are and who you are not.

The fundraising imperative is real. Revenue matters. But it cannot be the organizing principle of every mission driven enterprise.

Because if it becomes that, you don’t just risk your reputation.

You and your organization risk becoming unrecognizable.

Which it is, partly.

(Editor’s note: I attended a Thiel talk at MIT back in 2015. He talked for an hour and with 100% sincerity about why people like him should live forever.)

But buried inside it is something more important: a quiet admission that the Giving Pledge was more about optics than outcomes. And that admission opens a door to a much bigger conversation.

Because the conversation we should be having isn’t about whether billionaires keep their dopamine-generating, image burnishing philanthropic promises. What we should be talking about is the fundamental plumbing of American philanthropy, and why so much charitable money sits idle while the world is on fire.

So we might as well say It: The Pledge Was all PR.

When Warren Buffett and Bill Gates launched the Giving Pledge in 2010, the idea was simple and elegant: get the world’s wealthiest people to commit, publicly, to giving away more than half their fortunes. No legal obligation. No enforcement mechanism. Just a moral commitment and a letter.

In the first five years, 113 billionaires signed. In the next five, 72. In the five years after that, 43. Last year: four.

Now Peter Thiel is privately lobbying signers to walk away, calling the whole enterprise an “Epstein-adjacent, fake Boomer club.” Elon Musk is reportedly out. And a damning 2025 report from the Institute for Policy Studies found that of the $206 billion given away by 2010 signatories, 80% went straight into private foundations. Plus that those same 32 original American signatories are now, in aggregate, nearly *three times wealthier* than when they signed. Combined net worth: $908 billion.

Read that again. The people who pledged to give away their fortunes are three times richer than when they made the pledge and are giving their money back to themselves.

(Editors note: When is it OK to call this “hoarding behavior”?)

The Giving Pledge isn’t the only commitment that’s been conveniently ignored. In 2012, the general partners of Andreessen Horowitz (one of the most powerful venture capital firms on the planet) publicly pledged to donate at least half of all income from their VC careers to philanthropy over their lifetimes. It was a bold, unambiguous commitment. I was working with one of the six A16Z GPs at the time and it was exciting to imagine the good he would be able to do with his comically huge portfolio.

But what do you think happened instead?

Yup, in 2023, Marc Andreessen published his Techno-Optimist Manifesto and quietly rewrote the terms of philanthropy. His argument: technological innovation is inherently philanthropic because technology creators capture only about 2% of the economic value they create, with the other 98% flowing to society as “social surplus.” Therefore, building tech companies *is* the philanthropic act. The pledge didn’t need to be broken it just needed to be reinterpreted out of existence.

But he can fuck all the way off. Aren’t all wealth creation exercises, from real estate development, mining, manufactuiring, transportation, retail (but not finance, I’ll tackle that nonsense in a future post), ultimately about creating social surplus and making the world cheaper, more efficient, or more livable while also becoming fabulously wealthy?

And shouldn’t that wealth creation come with civic or moral obligation to support the same system that allowed you to create that social surplus in the first place? If not, the only solution is a massive wealth tax to extract the “capital surplus” created by innovative extraction experts like Andreessen.

Yeah, like I said: Andreessen and his ilk can fuck all the way off.

Here’s what I think happened across all of these cases: the pledge solved a perception problem for the ultra-wealthy. It gave them an answer to uncomfortable cocktail party questions, “I signed the pledge and am giving it all away” without requiring any action whatsoever. The pledge had no payout schedule. No timeline. No consequence. It was, as Buffett himself said, “just a moral pledge.” And moral pledges, it turns out, are great for reputations and terrible for nonprofits.

This isn’t entirely cynical. Some signers gave generously and urgently. But the structure of the pledge made urgency optional. And that optionality, when you’re worth $40 billion and surrounded by advisors who want to protect your assets, tends to mean later.

And in the case of many billionaires, “later” tends to mean “never”.

The Real Problem: Charitable Capital Has a Velocity Problem

Here’s the thing Schleifer’s piece doesn’t quite get to: the Giving Pledge isn’t the exception. It’s a perfect expression of how American philanthropy is structurally designed: to park money, not move it.

I studied economics in college. I loved the field, but wasn’t very good at it. But I do know the concept of *monetary velocity*: the rate at which a dollar circulates through an economy. A high-velocity dollar changes hands frequently, funds wages, buys goods, creates jobs. A low-velocity dollar sits in a savings account and does nothing. The same principle applies to charitable capital: and by that measure, American social services and nonprofits are expected to run on sub-optimized velocity.

Consider the numbers. There are currently $326 billion sitting in Donor Advised Funds. These are accounts where donors have already received their tax deduction, meaning they’ve signaled, legally and financially, that this money is for charitable purposes.

And yet, in any given year, approximately 75% of it goes nowhere. It just sits there, earning returns, warehoused in accounts at Fidelity, Schwab, and Vanguard while the food banks run out of money and the affordable housing waitlists grow.

Then there are private foundations, which are legally required to distribute just 5% of their assets annually. Five percent. Most university endowments (Harvard’s is $53 billion, Yale’s is $41 billion) distribute similarly modest percentages while sitting on assets that dwarf the GDP of small countries.

We have, in this country, more than $1.5 trillion in charitable capital that is nominally intended for public benefit and functionally inaccessible to the organizations that need it.

That is not a fundraising problem.

That is not a nonprofit capacity problem.

That is a velocity problem.

The question isn’t whether the wealthy care about giving. Because many of them genuinely do.

The better question to ask is how we build systems that increase charitable velocity?

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Two Levers We’re Not Pulling

There are two obvious interventions that the philanthropy sector has been too polite (or too captured) to demand seriously.

The first is mandated payout reform. Congress has been content to let foundations distribute at 5% for decades, a number set in 1969 and never meaningfully updated. DAFs have no payout requirement at all. The result is predictable: donors and their advisors, incentivized to minimize distributions and maximize asset growth, do exactly that. You can’t blame them for responding rationally to the rules. But you can change the rules.

A modest increase in the mandatory foundation payout (say from 5% to 7% or 8%) applied to large endowments above $1 billion, would unlock billions of dollars annually for direct charitable work. Similarly, introducing a minimum spend down requirement for DAFs (say, all funds distributed within 5 years) would immediately free tens of billions of dollars that are currently warehoused. These aren’t radical ideas. They’re what a serious country would do if it actually wanted its charitable sector to function.

The second lever is structural innovation. While we wait for Congress to act (stop laughing), there is meaningful work to be done at the product level. The charitable sector needs new vehicles that create velocity by design: mechanisms that make it easier, faster, and more joyful to move money from intent to impact.

This is where I think the most interesting work in philanthropy is happening right now: not in legacy foundations or giving pledge letters, but in participatory models that give donors a reason to act, rather than defer.

Giving circles are a perfect example. Rather than parking a DAF contribution for years while deliberating alone, a donor joins a community, nominates causes they believe in, and watches their gift pool with others into something collectively meaningful. The velocity is built into the structure.

There’s something else giving circles do that traditional philanthropy doesn’t: they make giving social. And social giving moves faster than solitary giving. When 500 people are deciding together, in real time, where the money goes, the friction that keeps individual donors paralyzed (which organization? how much? Is this the right time?) dissolves.

The community absorbs the cognitive decision load and the money flows.

If you believe, as I do, that charitable velocity is the central challenge in American philanthropy, then the numbers become clarifying rather than overwhelming.

Accelerate just 1% of total DAF assets toward active giving activates $3.3 billion — and you’ve created more annual grant making than most foundations dream of in a decade. Move 5% ($16.3 billion) and you’ve changed the funding landscape for the entire nonprofit sector. Do this consistently, at scale, over ten years, and a 10% acceleration of the existing total DAF pool represents $32.6 billion in additional charitable capital reaching real communities.

That would make this decade’s giving circle movement the largest philanthropic distribution vehicle in history: not by pledging, but by building something that moves money by design.

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What the Giving Pledge Backlash Gets Wrong

Schleifer’s article spends considerable time on Peter Thiel’s critique: that the Giving Pledge is politically captured, that its money funds left-leaning institutions, that it’s a cultural artifact of a philanthropic era now passing.

Thiel is right that the Pledge failed. He’s wrong about why.

The problem with the Giving Pledge was never ideology. It was structure. A voluntary moral commitment with no timeline, no mechanism, and no accountability will always produce the same result: a lot of impressive letters and very little change. It doesn’t matter who signs. It doesn’t matter what they believe. Without velocity, charitable intent is just charitable intent: and intent doesn’t feed anyone.

The billionaires who are walking away from the Pledge aren’t the story. The story is the $1.5 trillion sitting still while the problems the Pledge was supposed to address get worse.

If we’re serious about fixing philanthropy, we stop building monuments to intention and start engineering for movement.

We stop celebrating hollow feel good pledges, and build better pipes instead.

Everybody has heard of the Stanford Marshmallow Experiment - more colloquially known as the “marshmallow test” - right?

It’s the experiment that tested whether kindergarteners could avoid eating a single marshmallow placed in front of them, or wait for a reward of two marshmallows later, testing the idea of how humans deal with delayed gratification. Follow on studies asked a rather provocative question:

Does the ability to delay gratification as a 5 year old serve as an insightful predictor of success later in life?

And when the test was conceived in 1970, this was an interesting hypothesis. Because some kids “failed” the test and ate the marshmallow. Others “passed” the test, and waited for the reward. Then the kids who took the test were tracked and studied in order to understand whether their innate ability to delay gratification corresponded to success later in life.

Published follow on studies were pretty clear, too: There was a positive correlation between the ability to delay gratification at Age 5 and higher SAT scores, higher lifetime earnings, and even a perception of those children as being “highly competent”.

So since then (and maybe since the beginning of time), delayed gratification has been defined as being a “good thing”.

We save for retirement and plan for college.

We scan the horizon for threats and strategize against them.

We prepare and ready ourselves for these threats with the hope that things will be better tomorrow, because the rewards of waiting outstrip the delight we know that we will experience if we choose immediate gratification.

Right? It has to be that way right?

Lately, I’m not so sure.

In fact it seems that today’s gratification and tomorrow’s reward are both under significant threat.

Frankly, it’s possible that all of the marshmallows will disappear entirely. They might be taken away by a nefarious actor, or be subject to an e coli outbreak at the manufacturing plant, or they might fall on the floor and be eaten by a cat.

It’s also possible that the marshmallow sitting right in front of you is not actually there, and was never there to begin with.

So while there may have been a time when delaying gratification primed a person for a more successful adulthood, that’s only the case in a trust-and-effort based world, where robust savers, better workers, honest people could delay gratification and expect that future rewards will be reliably available.

I am not sure that’s the case anymore.

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I’ve listened to Mark Carney’s brilliant speech at Davos several times, and in his view the historical bargain of delayed gratification as key to success is being ruptured, and those who believe in delayed gratification as the key to success may be making “performance of sovereignty while accepting subordination.”

In fact, my hypothesis is that the students who ate the marshmallow are now far better equipped to survive in this new, bargain-less world we live in.

Let me explain.

We live in a world where trust of authority is at or near its nadir. Our government lies to us, manipulates images on social media then calls it the truth even in the face of overwhelming evidence to the contrary, fails to accept the consequences and results of free and fair elections, and prosecutes those are disagree with or openly oppose its policies.

In that environment, who in their right mind would delay the rewards of labor, when the likelihood of receiving those rewards depends on whether or not you abide by the rules set by those in power?

Said another way, have we reached the point where the continued belief in a future reward, or some future higher state of being, might make you insane?

Do you really believe that tomorrow is going to be bett

er, or should we just eat all the marshmallows now just in case there are no more marshmallows coming, like ever?

OK OK, that’s pretty bleak.

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I’ve been thinking a lot about careers lately, and I’ve been thinking about them in thirds. Not rungs on a ladder, promotions or titles you post on LinkedIn. Not in financial achievement or public recognition.

Just fractions. Just Thirds.

Because when you sand down the LinkedIn gloss and fancy resume titles, most of us don’t live one career. We live thirds. And if you look really closely, those phases tell a very powerful story about who we are and what we were thinking about at that time in our lives.

The First Third: I Need This.

The first third of your career is about needing. You need to prove yourself. You need a foothold. You need something that screams, “I belong”. In my own case I also needed money to pay off student loans and many of my early career decisions were driven by (what I felt at the time) was an existential financial need: to avoid default.

And for many young adults, myself included, this is unproven territory. Yo…

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Automobiles, kitchen appliances, jumbo jets, the George Foreman Grill, and of course: Furbys. Remember those things? Terrifying bubbling and furry, and despite their Gremlin-esque look and positively creepy eyes human beings made and distributed over 40 million Furbies from 1998-2000, truly a manufacturing and distribution phenomenon.

OK, now think about our remarkable system of industrial distribution: Roads, bridges, canals, railroads, ports, airports, highways. Now think about what it takes to maintain those systems. Need a hint? Well, it generally involves a mix of private investment, government funding (federal/state/local), and specific local and state funding agencies. I did a time-sucking dive into how railroads are maintained: turns out, freight railroads are largely self-funding via revenue reinvestment …

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Each morning, I check LinkedIn. Yeah I know, that’s kinda lame. But it’s become a habit and often times there are things in my daily feed that catch my eye as either a) thrilling, b) infuriating, c) sad, or d) all three.

This morning qualified as a natural hat trick when I saw several openings from our local minor league soccer team, the Portland Hearts of Pine. The team is a bona fide sensation: huge crowds, great sponsors, unique and inspiring merch, even a newly announced 501©3 Foundation (presumably as a tax-advantaged destination for their profits, great PR, or both).

The Club is advertising for the senior role of “Senior Director of Finance and Administration”. It reads like a CFO position, with responsibilities to match, such as “Excellent analytical, problem-solving, and communication skills, with the ability to present complex financial information to Board members and other stakeholders.”

The JD even tosses in t…

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Steve Pagliuca and Michael Dell are good at some things, but they’re “ignoramus gigondas” when it comes to understanding the time scale and mechanics of successful basic research.

The world learned this last month when Pagliuca-and-Dell-funded Arena BioWorks abruptly ceased operations so that “everyone could move on freely in their separate ways”.

That this venture’s failure hasn’t been more fully covered in the media is either tremendous PR or deeeliction of duty.

What makes this such a spectacular failure is that it had all the ingredients: people with bottomless capital reserves, access to the Cambridge MA biotech talent ecosystem, and a network of billionnaires to sell their vision.

It had founders who believed so wholeheartedly in their ability to build a better mousetrap that they committed $500M (a small fraction of their personal fortunes mind you) to one-up the university research engine.

Not a casual undertaking.

And Pagliuca…

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Recently, I learned about a concept known as a "demand signal"—the sign that a product or service being developed is well-received, desired, and ready to be consumed. But in the marketplace of ideas, knowing whether anybody is listening - or even cares - isn’t always clear.

I know this all too well. I’ve built and launched a consulting firm, a 120,000-person nonprofit community, a job board, this blog, and even a small “Academy”. Most of these things I’ve done out of a desire to be productive and generally useful. But until now I’ve mostly ignored or overinterpreted the “demand signal”, and even clung to my own ideas like some sort of existential life raft—insisting that demand would just, well: materialize.

Spoiler: it didn’t.

So what do you do when the signals go quiet, or when the enthusiasm you hoped to see doesn’t simply appear? What do you do when a project or idea you poured your soul into lands like a flop, instead of taking off like a rocket?

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Earlier today, The Current administration sued my home state of Maine for not complying with the government’s push to ban transgender athletes in sports, escalating a dispute over whether the state is abiding by a federal law be allowing two (yes, 2) transgendered athletes to compete in sports.

But regardless of where you stand on the issue of whether transgendered individuals should be allowed to participate in a sport of their identified gender, the government is threatening to pull $150M from our entire state’s education budget to make a political point.

Yes, that’s right: They are targeting kids.

But this shouldn’t be too surprising, because bullies love targeting the weak and powerless. After all, it seems like an easy win, an easy and …

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Tomatoes, peppers, cucumbers, beans. Our kitchen floor and our fingers ended up covered in dirt, and for the rest of the afternoon, we smelled like potting soil.

Meanwhile, the world feels like it’s been set on fire.

I don’t mean that metaphorically, although I wish I did. The climate crisis is accelerating, and there seems to be more fires than ever. But this is a nonprofit newsletter and - well - we’re all under attack. Universities are being financially carpet-bombed, my friends in the sector are burning out, and all around us, the people and systems built to guide us forward seem to be unraveling before our eyes.

It’s tempting to throw your hands up. To doom scroll. To despair. I’ve done my fair share of all three (especially the doom scrolling. I’m wicked good at that.)

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But this weekend, my wife and I did what we always do in April: we planted seeds. Not because it was the practical thing to do. Honestly, a part of me felt absurd …

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About a month ago I went to the Museum of Fine Arts, Boston to see a tremendous Henry Moore/Georgia O’Keefe retrospective. What can I say? I’m a former football player who likes museums.

And while the Moore'-O’Keefe exhibit was fine, I left most excited by the “Power of the People: Art and Democracy” exhibit - specifically the gallery of posters made by students at the School of the Museum of Fine Arts in May of 1970, addressing contemporary political events and movements such as civil rights, Black Power, and women’s rights

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The current Republican Administration has started calling Diversity, Equity, and Inclusion (DEI) an existential threat to meritocracy. But if they believe that society before current DEI efforts rewarded only qualification and talent, they be plain crazy.

Because for centuries our country’s elite institutions have operated on a system of preferences and mores that had nothing to do with merit.

The Myth of the “Most Qualified”

One of the loudest arguments against DEI is that it lowers standards by admitting or hiring people who aren’t the “most qualified.” But let’s ask a fundamental question: How have we historically defined qualification? For those ardently opposed to DEI, the “most qualified” are usually white men like them who come from semi-privileged (or downright rich) backgrounds, worked in the right companies or attended the right schools.

But for generations, America’s elite colleges have disproportionately ad…

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