Down the rabbit hole…

Picture this: It's 8 PM on a Tuesday. I'm three layers deep into LinkedIn connections, cross-referencing someone's property records with their third cousin's wedding announcement from 1987 in the New York Times. I started the day planning to put together a simple donor profile. Instead, I'd fallen down a rabbit hole.

The donor I was researching? They had connections to four different companies, served on two nonprofit boards, and had a family foundation with a website that looked like it had been built in the same year that MySpace went live. I was living for this puzzle. Every new connection felt like solving a tiny mystery. "Aha! So THAT'S how they know the museum board chair!"

But then reality hit me: I'd spent an entire day playing detective and hadn't made a single phone call, sent one email, or planned any actual outreach. I was the world's most enthusiastic researcher and possibly the world's least effective fundraiser.

If you just nodded so hard you got whiplash, you're not alone.

The Adventure!

I was first offered a glimpse of life outside the rabbit hole one recent summer day when our CEO, Will, reached out and said "If you've ever considered using your fundraising skills at a mission-driven startup, we should chat."

I'll be honest: I hadn't. I’d spent the last few years in development and my nonprofit career felt mapped out: Development Associate to Major Gifts Officer to Director of Individual Giving, maybe Chief Development Officer someday. Foundation work if I got adventurous. But tech sales? That wasn't even on my radar.

Since Will and I happened to be neighbors, grabbing coffee was easy enough. Afterwards, he gave me a trial account to DonorAtlas for a week, and I dove in, expecting to see something similar to other tools I’d used before. I couldn’t have been more wrong–or more sold.

Everything moved quickly after that. I thought that if I’d been soliciting donations from people just because they cared about what we were doing, then surely I could sell a product where they’d get something amazing in return.

Flash forward two months later to me in DonorAtlas’s Chelsea office, working with organizations to help them escape their own research rabbit holes (and only occasionally wondering if my voice cracked while cold calling the CDO of a global nonprofit).

The View from the Other Side

Joining an AI prospect research startup opened up a whole new world for me, but more importantly, it gave me a completely different lens on the whole fundraising ecosystem. As only the second non-technical hire at the company, I’ve come to understand what building this product really takes.

One day, I had an idea for a feature that would’ve changed my life if I were still working in fundraising. I'd spent days if not weeks of my life putting together 50+ person face sheets for events; you know the ones, where leadership needs to know who to talk to and any possible connections they might have. So I asked our CTO how long it would take him to build a face sheet feature that could pull together quick bios, alma maters, job title and company, where they live, highlights about things they care about, and prominent personal connections. Little slices of info, where you could fit 10 people on a page.

He sat back pensively for a second, shook his brain around a bit, and a few seconds later replied while glancing between two other engineers: "We could have it done by the end of the day, I'd say."

I said, "Hm." Just... stunned at how fast they could work.

I think he interpreted my non-response as disappointment, because he started jumping into exactly what they would need to do: "You know, if I stopped working on my current project, I could probably have it done in a few hours..."

Days of my life versus a few hours of theirs. That's when it really hit me: I haven't just switched careers, I've stepped out of the rabbit hole and into a world where the problems that had been eating up my time for years can actually be solved. Suddenly, instead of drowning in inefficiency, I'm alleviating others'. Instead of being frustrated by problems, I am helping solve them.

What AI Actually Does (Hint: It's Not Magic, But It's Pretty Cool)

One elephant in the room when I've told former fundraising colleagues about my pivot to an AI startup: is AI just going to take fundraisers' jobs?

And here’s the truth: it's not going to replace fundraisers any more than calculators replaced mathematicians. What (responsible) AI is is really, really good at is being your incredibly fast, never-tired research assistant who doesn't get bored reading through hundreds of news articles or cross-referencing databases.

The most successful organizations I work with now use AI (in many different ways) to handle the grunt work so their staff can focus on the parts of fundraising that actually require human genius: understanding motivations, reading between the lines of conversations, and building the relationships that transform prospects into lifelong partners.

The Bottom Line

The nonprofit sector is full of brilliant, passionate people who've been making incredible things happen despite having tools that feel like they were designed by people who've never had to use them.

If you're still staring at your screen at 8PM, lost in research that has somehow led you to reading about a donor’s great-aunt's art collection, maybe it's time to take a step back and ask if there's a way out of the rabbit hole.

Your donors will thank you. Your sanity will thank you. And who knows? You might even rediscover why you fell in love with fundraising in the first place (I certainly have).