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.

Ten Years Ago, I Was Writing About Ecommerce Apps
Ecommerce Kenny Kane Ecommerce Kenny Kane

Ten Years Ago, I Was Writing About Ecommerce Apps

A decade ago, I was folding t-shirts. Not metaphorically. Literally folding t-shirts (hundreds of them) in the back office of Stupid Cancer, figuring out how to run an online store in real time and apparently talking about it enough that BigCommerce invited me to write for their blog. I recently dug up those five posts through the Wayback Machine. Reading them a decade later is a strange, warm kind of nostalgia.

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A Few Notes From 2025
Technology & Digital Strategy Kenny Kane Technology & Digital Strategy Kenny Kane

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.

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