Everything here rests on one bet: that clearer thinking makes everything downstream — the work, the story, the decision — better.
I'm Dave Hail. For twenty years in fundraising and advancement, I watched the same pattern: whenever a tool or a story or a system genuinely helped, it wasn't by adding more — it was by making something clearer. So I keep building things that try to do exactly that.
It shows up in five questions I can't stop asking.
How do we think more clearly?
Fundraising intelligence, strategy, and clear systems.
Deployed at
Why do some stories endure?
Fiction, story development, and creative tools.
Also:
How do we make wiser decisions?
Frameworks for reflection and judgment.
How do we find direction?
Leadership paths, orientation, and smarter travel.
Also:
Part of
What makes us human?
Story, memory, and meaning
Writing
All essays →Current Questions
- 01
Can software make fundraising more honest instead of just more efficient?
Most fundraising technology is built to extract. I'm interested in whether it can do the opposite: help people understand why giving matters before we ever ask.
- 02
Why do some stories keep working long after the moment that made them?
It isn't simply that they were written better. Something deeper separates a story that endures from one that was merely told well.
- 03
How do people actually become wiser?
Information compounds on its own. Judgment doesn't. We keep building better ways to collect data and almost no ways to reflect on it.
- 04
How do you keep becoming the leader you hope to be?
Not through a breakthrough. Through thousands of ordinary decisions, made a little more thoughtfully, over years no workshop can teach.
- 05
Can software explain its own decisions well enough to be trusted?
Most systems that decide for you are opaque. I'm building one that has to show its reasoning for every call it makes — and testing whether that transparency is what turns automation into something you'd actually trust.