there are three big categories of barriers. The application barrier, the interview barrier, and the document barrier. And that’s what we spent most of our time iterating on and building a system that could slowly learn about those barriers and then intervene against them.

The application is asking, “Are you convicted of this? Are you convicted of that? Are you convicted of this other thing?” What is that saying to you, as a person, about what the system thinks of you?

Often they’ll call from a blocked number. They’ll send you a notice of when your interview is scheduled for, but this notice will sometimes arrive after the actual date of the interview. Most state agencies are really slammed right now for a bunch of reasons, including Medicaid unwinding. And many of the people assisting on Medicaid are the same workers who process SNAP applications. If you missed your phone interview, you have to call to reschedule it. But in many states, you can’t get through, or you have to call over and over and over again. For a lot of people, if they don’t catch that first interview call, they’re screwed and they’re not going to be approved.

getting to your point about how a website can fix this —  the end result was lowest-burden application form that actually gets a caseworker what they need to efficiently and effectively process it. We did a lot of iteration to figure out that sweet spot.

We didn’t need to do some hard system integration that would potentially take years to develop — we were just using the system as it existed. Another big advantage was that we had to do a lot of built-in data validation because we could not submit anything that was going to fail the county application. We discovered some weird edge cases by doing this.

A lot of times when you want to build a new front end for these programs, it becomes this multiyear, massive project where you’re replacing everything all at once. But if you think about it, there’s a lot of potential in just taking the interfaces you have today, building better ones on top of them, and then using those existing ones as the point of integration.

Government tends to take a more high-modernist approach to the software it builds, which is like “we’re going to plan and know up front how everything is, and that way we’re never going to have to make changes.” In terms of accreting layers — yes, you can get to that point. But I think a lot of the arguments I hear that call for a fundamental transformation suffer from the same high-modernist thinking that is the source of much of the status quo.

If you slowly do this kind of stuff, you can build resilient and durable interventions in the system without knocking it over wholesale. For example, I mentioned procedural denials. It would be adding regulations, it would be making technology systems changes, blah, blah, blah, to have every state report why people are denied, at what rate, across every state up to the federal government. It would take years to do that, but that would be a really, really powerful change in terms of guiding feedback loops that the program has.

when you start to read about civic technology, it very, very quickly becomes clear that things that look like they are tech problems are actually about institutional culture, or about policy, or about regulatory requirements.

If you have an application where you think people are struggling, you can measure how much time people take on each page. A lot of what technology provides is more rigorous measurement of the burdens themselves. A lot of these technologies have been developed in commercial software because there’s such a massive incentive to get people who start a transaction to finish it. But we can transplant a lot of those into government services and have orders of magnitude better situational awareness.

There’s this starting point thesis: Tech can solve these government problems, right? There’s healthcare.gov and the call to bring techies into government, blah, blah, blah. Then there’s the antithesis, where all these people say, well, no, it’s institutional problems. It’s legal problems. It’s political problems. I think either is sort of an extreme distortion of reality. I see a lot of more oblique levers that technology can pull in this area.

LLMs seem to be a fundamental breakthrough in manipulating words, and at the end of the day, a lot of government is words. I’ve been doing some active experimentation with this because I find it very promising. One common question people have is, “Who’s in my household for the purposes of SNAP?” That’s actually really complicated when you think about people who are living in poverty — they might be staying with a neighbor some of the time, or have roommates but don’t share food, or had to move back home because they lost their job.

I’ve been taking verbatim posts from Reddit that are related to the household question and inputting them into LLMs with some custom prompts that I’ve been iterating on, as well as with the full verbatim federal regulations about household definition. And these models do seem pretty capable at doing some base-level reasoning over complex, convoluted policy words in a way that I think could be really promising.

caseworkers are spending a lot of their time figuring out, wait, what rule in this 200-page policy manual is actually relevant in this specific circumstance? I think LLMS are going to be really impactful there.

It is certainly the case that I’ve seen some productive tensions in counties where there’s more of a mix of that and what you might consider California-style Republicans who are like, “We want to run this like a business, we want to be efficient.” That tension between efficiency and big, ambitious policies can be a healthy, productive one. I don’t know to what extent that exists at the state level, and I think there’s hints of more of an interest in focusing on state-level government working better and getting those fundamentals right, and then doing the more ambitious things on a more steady foundation.

California seemed to really try to take every ambitious option that the feds give us on a whole lot of fronts. I think the corollary of that is that we don’t necessarily get the fundamental operational execution of these programs to a strong place, and we then go and start adding tons and tons of additional complexity on top of them.

In their quest for social change, givers like Arnold are reluctant to support “causes”; they want to “solve problems—big ones,” as Callahan puts it. But, in Arnold’s case, lessons had to be learned along the way. His early forays into philanthropy, including an effort to reform public pensions, were scorned, with critics noting that Enron’s collapse had resulted in the loss of billions of dollars in pension funds.

Moskovitz and Tuna weren’t keen to embrace traditional development organizations, which they are inclined to view as lethargic and bureaucratic. For them, grant making is akin to venture-capital investing: they want to act decisively and disrupt traditional models and structures. They have contributed $32 million to a group called Give Directly, which is not interested in vaccinating children, digging wells, building toilets, and creating schools. Rather, it gives cash handouts to the poor, who are free to spend the money as they wish. Callahan is skeptical of the ideology guiding Moskovitz and Tuna—who favor Silicon Valley mantras such as “empower individuals over institutions”—but he knows they are too influential to ignore. The couple will give away hundreds of millions of dollars every year. They are not yet thirty-five years old.

There are growing concerns about the influence and reach of the superwealthy: “Philanthropy is becoming a much stronger power center,” Callahan says, “and, in some areas, is set to surpass government in its ability to shape society’s agenda.” The state has retreated; the givers have advanced.

in many U.S. cities, elected officials are overwhelmed by debt obligations, and as a result have precious little money to spend on parks, museums, and other public services. The givers have no such constraints. In Boston, the Barr Foundation has done much to shape the city’s arts, culture, and political milieu. In Houston, Richard Kinder is helping to forge a massive network of urban trails. In Detroit, the Kresge Foundation is contributing funds for a new light-rail system. In New York, the Leon Levy Foundation has helped to revitalize a pair of Brooklyn landmarks, the Brooklyn Public Library and the Brooklyn Botanic Garden. These are worthy endeavors, but Callahan is right to express concern about a fundamental shift of power from a “hollowed-out public sector” to elite private givers who are not fully accountable and operate in dark corners.

In 2008 Stephen A. Schwarzman, another cofounder of Blackstone, gave $100 million to the New York Public Library at a moment when the Library was secretly undertaking a dubious real estate and construction scheme. For nearly a decade, the NYPL refused to reveal how Schwarzman’s money was being utilized. Only in recent months did the Library account for the gift’s use: the $100 million formed part of the endowment and will soon be used for new renovation projects.

Under an initiative backed by Broad and like-minded funders, L.A. could add hundreds of new charter schools in a decade. Broad is quick to refute allegations that he is overreaching: “I think everyone is getting heard,” he informed Callahan. “We’re getting heard, the philanthropists. The unions and administrators are getting heard. Overall, we’re creating debate.”

That may be so, but increasingly the debate is among people who already agree. The Givers makes a persuasive case that the superwealthy are expanding their influence at a moment when many Americans are bolting from civic and political life. The author, drawing on the scholarship of Theda Skocpol, evokes an earlier era when mass-membership organizations such as trade unions flourished, giving ordinary citizens a certain degree of influence vis-à-vis elite power structures. These days, he writes, “We’re fast moving toward a future where private funders, not elected officials and the citizens they answer to, choreograph more of public life.”

Of the top eighty American foundations, only twenty-six post detailed information about their current grant making on public databases. The Susan Thompson Buffett Foundation, endowed by Warren’s wealth, “has no real website and the information available on its grant making through tax returns is always a few years out of date,” Callahan notes.

The Givers is alive to these and other contradictions in the philanthropic sector and poses thorny questions for elected officials and nonprofit leaders: why is a check to a right-wing think tank tax-deductible but a check to a conservative senator is not? Why are many large foundations spending a mere 5 percent of their assets each year when they can easily afford to spend more? Why do so many foundations exist in perpetuity, instead of “spending down” and closing their doors? Why is the sector so lightly regulated by government, particularly the IRS? Finally, what exactly is the public getting in exchange for colossal tax breaks granted for philanthropy, which mainly go to rich people?

The Givers, which went to press before Donald Trump was elected, concludes with a stark and prescient warning: the nonprofit sector should initiate its own reforms, before politicians do it with a heavier and more mischievous hand. “It’s not okay,” he warns, “to settle for a status quo in which the foundation world remains forever a black box.” His proposals for change—the creation of a new U.S. federal office of charitable affairs, a reevaluation of what should qualify for tax-exempt status, trustee boards that are more inclusive and transparent—are not likely to be embraced in Trump’s Washington, however.

Katz, writing after Trump’s victory, argued that Callahan has sidestepped the central issue: Our current dire political situation is the product of both traditional American anti-statism and a very different and deliberate assault on the state by plutocrats. We do not have so many billionaires, and thus mega-foundations, because we now have a larger and more adept entrepreneurial class, but because the structure of (mostly federal) economic policy has been captured by people of wealth, who have rewritten the laws to enable themselves to become extraordinarily rich…It seems to me that the new plutocrats are in fact the problem, and they are quite unlikely to be part of the solution, as Callahan contends.

My own wish is that Callahan had confronted, in a more pungent way, the structural features of the behemoth that looms before him: the grant-making model itself, upon which modern American philanthropy rests. Foundation leaders advocate transparency, inclusion, and equality, but they operate in a strikingly hierarchical manner. They are a cloistered elite.

Does this top-down model—in which grantees spend immense time and energy chasing cash—inhibit the growth of dues-paying organizations, which may be more vibrant and democratic than nonprofit organizations dominated by an aloof board of trustees and an executive director? Passages in The Givers suggest that Callahan has pondered these matters, but he stops short of a full critique.

There are now more than ninety thousand private foundations, whose assets total $700 billion. These foundations supply money to more than a million tax-exempt, nonprofit organizations. Some of these nonprofits are financially secure, but many chafe under immense anxiety as they await annual grants from their masters in the foundation suites.