Asking for Help Shouldn't Be This Hard
Diaper runs and fixing a $140 billion delivery gap.

Last Monday I was driving to the pharmacy. I was four days into being a Dad and on my first, “baby needs something” run. I had a simple task and the newly minted, somewhat terrifying, and exhilarating clarity that comes with being responsible for keeping a human alive.
As I pull into the pharmacy, my phone buzzes. It’s a call - a request to approve a diaper delivery to a family who needs help. In that moment, my new job as a parent collided with my volunteer job co-running a non-profit. 700 miles away, our program director found a family in need of diapers - they were asking for help with their “baby needs something” run.
The task in front of me was taking care of my own child, it was primal and straightforward. The only thing between me and the pharmacy was a drive. For this family, it was probably their fourth ask - after long applications, arduous income verifications, long waiting periods, and countless denials.
The non-profit is Christmas in the City: an organization in Boston that my family has run for decades, with a single, enduring commitment: making sure that all children can experience some magic around the holidays, regardless of their families’ financial circumstances. We get calls year round to help families and support when we can - including the occasional diaper run.
I’ve been answering those calls my entire adult life. It’s core to who I am and an incredible annual reminder of how to be a human. And the thing that stays with me isn’t the hardship. It’s the courage it takes to pick up the phone and ask. To say: I can’t do this alone, and I need my community to show up for me.
That experience, my experience, of being on both sides of a phone call where someone asks for help is the reason my startup, CivicReach exists.
CivicReach started as a research project. I was trying to understand something simple and close to home: how do people actually access the social safety net in America? How did this family in need of diapers find me?
The answer is all sorts of bad. It’s complicated, often cruel, and inefficient. In a system we’ve created to help people, we make it nearly impossible for people to access help.
The story of social service delivery coming up short is largely rooted in the story of government services more broadly in this country. Jennifer Pahlka spent decades studying how government builds and delivers services, put it bluntly in Recoding America: “Nowhere in government documents will you find a requirement that the service actually works for the people who are supposed to use it.” She found individual projects burdened with 87 documents, 11 stage-gate reviews, and 21 oversight roles. The system - especially the social safety net - was designed to ensure compliance. Not delivery.
In practice, this system built for compliance ignores the humans it’s meant to serve. The agencies and staff delivering services to those most in need are met with relentless paperwork and impossible-to-meet reporting standards. Meanwhile, the families who need help are the ones filling out 20-page applications, gathering pay stubs, and calling back for the fourth time.
I talked to a city housing department who told me that 40, 50, 60 percent of their incoming calls go unanswered. Not because they don’t care, because they have 1 person answering phones for a jurisdiction of 800,000.
I talked to agency directors who spend two months (two months!) disambiguating mandatory federal and state reporting requirements, before they can actually start taking applications to provide assistance.
Caseworkers have told me that with 45 minutes to help a family navigate benefits, they spend more than 20 minutes on intake paperwork they’ve already collected three times.
We see waiting times baked into service programs measured in months and years.
Worst case, this design of the system ensures that it simply doesn’t work at all. Matthew Desmond put a number on it in Poverty, by America: more than $140 billion in government benefits go unclaimed every year. Not because people don’t qualify. Because the system that’s supposed to deliver those benefits has become so complicated that eligible families can’t get through it. SNAP participation rates vary from 56% to nearly 100% depending on the state. This means that whether or not a family eats may have more to do with the social service bureaucracy of where they live than how much they need.
To be clear, the people inside the system don’t drive the complexity, they deliver in spite of it. Caseworkers who chose public service. Agency directors who’ve spent 20 years trying to get their communities the resources they need. Social workers who stay late because a family is in crisis and the paperwork can’t wait until Monday. I have talked to hundreds of these people over the last several years, and they are some of the most dedicated, mission-driven professionals I’ve ever met. The staff working in agencies across the social safety net are stuck in the same system that makes it nearly impossible to do the thing they came to work to do: help their community.
In this country, we argue a lot about how and when our government should help people. It’s core to our debates on taxes, culture, and our identity. But after the politics, policy arguments, and decisions are over - we have agreed upon mandates and budgets to collectively help our neighbors. That’s when it becomes clear that we are remarkably, unforgivably bad at getting that money to solve the problems we said we cared about.
Feeding people. Giving healthcare to people. Covering emergency rent so a family doesn’t end up on the street. Taking care of our veterans. Making sure a senior citizen’s Social Security check shows up. The laws exist. The programs exist. The funding exists.
We are breaking our promise.
Not because of politics.
Not because of policy.
Because of delivery.
Eighteen months ago, CivicReach went from a research project to an earnest attempt to solve the problem - we became a startup.
I brought on a team, raised money, and went to work.
We built a world-class AI to answer the phone for government agencies. An elderly Spanish-speaking resident can call at 9pm and get the same quality of information as someone who calls at 10am on a Tuesday and speaks English. That shouldn’t be remarkable. But right now, it is.
We took on city departments, county agencies, and government-funded non-profits in 6 states. One of the agencies we work with saw a 12% decrease in denials after deploying CivicReach. Something as simple as answering the phone with AI changed the bureaucratic equation and more families received the help they deserved. That's what technology in social services should do. Not replace the humans. Not automate the empathy. Just remove the barriers.
There’s a unique privilege of being a startup founder - every so often you get to show someone a better future and watch their reaction. For the past eighteen months, I’ve continually gotten to stimulate the imaginations of folks across government services and show them a future where they have the tools to help their communities - it’s intoxicating.
The caseworker with 45 minutes and 20 minutes of paperwork - what if she got all 45 minutes back? The city department with 1 person answering phones for 800,000 - what if every call got answered? What if the system actually worked the way it was supposed to?
Last Monday I was in the parking lot and I approved the diaper delivery. I then walked into the pharmacy to give my baby what he needed. 700 miles away another baby eventually got what he needed too. It took me 30 minutes. For the family in Boston, it took months - their diapers came after a chain of people, paperwork, and systems they had to navigate. It shouldn’t be this hard. It doesn’t have to be.

