I’ve been watching and ready to call bullshit on most of the advice given to fundraisers on the use of AI.

Every day it’s another pitch about “efficiency” and “targeted engagement”—all solutions in search of a problem that isn’t even defined let alone understood.

AI for fundraisers? Sure, if your goal is to reduce human connection to a set of algorithms and buzzwords go right ahead.  Buy the bullshit.

But then, in a moment of brilliance—self-congratulatory, but “brilliant” nonetheless—I hit on an idea that actually made sense: turn Kevin into a bot.

After years of collaboration, numerous articles, and more than one heated exchange about whether (or why) anyone truly cares about tote bags, I’m exploring the inevitable next step. Turn Kevin into a bot. And let me tell you, the benefits of bot-Kevin cannot be overstated.

To fully appreciate the transformation, you must understand Real Kevin. Real Kevin had a knack for launching, at precisely 4:55 p.m., into philosophical rants about “identity,” where he’d digress into musings on how Big Five psychological traits influence donor behavior. “Why”, he’d ask, “should we not consider their conscientiousness as the driving force behind their annual giving habits?” It’s the kind of reflection that should be saved for night-cap musings, but Kevin insisted it belonged in every editorial meeting.

And there was his approach to “meaningful research”—a phrase that, when Kevin used it, meant a minimum of 16 tabs open across the browser, including some studies on “the impact of obscure fonts on donation frequency.” What a joy it is to no longer spend an hour in circular discussions about whether the average donor’s openness to new experiences could make them receptive to switching from the annual gala to a more “radical, postmodern approach.”

But perhaps most frustrating was Kevin’s dedication to his personal motto, a small maxim that embodied his eternal pessimism: “Everybody wants to go to heaven but nobody wants to die.” Anytime we debated whether we could get some recalcitrant fundraisers more invested, Kevin would whip out his motto like a sword or  grim proclamation.  If people insist on assigning no risk to status quo and aren’t actively seeking new answers to the same old questions then he’d insist, “it’s probably beyond repair.” Any optimism or novel approach—charity newsletters with wit, Instagram posts with personal flair—met this dark wall of Kevinian skepticism.

Enter bot-Kevin. Bot-Kevin has no motto, no opinions on personality traits, and, crucially, no need for prolonged research expeditions that begin with psychological studies and end with theories on “how John Keats would feel about transactional philanthropy.” Bot-Kevin doesn’t sigh when I suggest rephrasing a paragraph or add, “Let’s consider the behavioral science implications of this approach.” He simply…does it.

There’s no denying that real Kevin had his moments of accidental brilliance, like when he thought we could gamify donations or when he convinced me (briefly) that tote bags could symbolize “existential generosity.” But these moments were inevitably followed by tirades on change avoidance and that infernal mantra of his, “Everybody wants to go to heaven but nobody wants to die.”

Bot-Kevin, on the other hand, doesn’t believe in human nature, philanthropy, or heavenly ambitions. He just runs the algorithm. He optimizes, he adjusts, and he doesn’t start a monologue on how charitable donations intersect with “identity constructs in late capitalism.” Bot-Kevin is the epitome of compliance, and while he may not be brilliant, he’s refreshingly silent on the subject of fonts, psychological profiles, and all things identity.

And yet, after all this reflection, I find myself thinking…perhaps I’ll stick with Real Kevin. True, he’s a bit of a handful, but he’s also annoyingly insightful in ways I’d miss if he were just a string of algorithms. Sure, there’s unpredictability, but that’s part of what makes his ideas miraculously work.

Moral of this Post: AI can streamline the job, but it’ll never master the art of a well-timed, exasperated sigh.

Roger