Insights on Building Mission-Driven Organizations
Practical lessons from 15+ years of leadership across nonprofits, real estate, and healthtech. Topics include AI implementation, nonprofit operations, business systems, and what it takes to scale organizations without losing your mission.
A Few Notes From 2025
I didn’t really plan to write a year in review.
This is more me noticing a few patterns that kept showing up.
Most of the things I worked on this year, across writing, nonprofits, real estate, and tech, kept circling the same questions:
What actually holds up over time?
What quietly breaks?
What needs a human, and what really just needs a system?
That framing ended up shaping more of my thinking than any single project.
Kenny’s 2026 Tech Stack
People often ask what tools I rely on day to day. The honest answer is that my stack is less about novelty and more about reliability. I care far more about whether something fits into my operating rhythm than whether it is the newest thing on Product Hunt.
This is a snapshot of the tools I’m using right now, how they show up in my work, and where I’m seeing real value versus diminishing returns.
The Rise and Flux of the Chief Automation Officer
When I first wrote about the Chief Automation Officer a couple years ago, it felt like a defining role for the next decade. Someone had to connect the dots between all the apps, processes, and platforms that were supposed to make work smarter. And for a moment, that was true — automation was the next big thing.
But in tech, “the next big thing” doesn’t stay still for long.
