Kenny Kane 7/2/26 Kenny Kane 7/2/26

The Chief Executive Operator

They told you to let go, delegate, and stay out of the weeds. That advice was built for a world with friction, and AI is removing the friction. A new role is emerging: the executive who can both set direction and ship.

Kenny Kane 6/29/26 Kenny Kane 6/29/26

Inducted into the Islip High School Hall of Fame

A letter from Islip High School stopped me in my tracks: an induction into the Hall of Fame, Class of 2005. It sent me back to where the whole thing started, a pharmacy job at 15, my dad's diagnosis my senior year, and the football field where I'll stand again this fall.

Kenny Kane 6/23/26 Kenny Kane 6/23/26

Why I'm Going Back to School to Study the Thing I've Spent My Career Doing

This August I'm starting a Doctor of Business Administration at Texas State. Not to step away from the work, but to study the problem I've hit in every organization I've run: they grow faster than their operational maturity, and the systems quietly end up built around a single person. Here's why I'm formalizing fifteen years of operating into research.

Kenny Kane 2/27/26 Kenny Kane 2/27/26

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.

Kenny Kane 2/27/26 Kenny Kane 2/27/26

How We Rebuilt the Testicular Cancer Foundation Website in Three Days (And Why It Matters)

On December 30th, I started working on what would become a complete rebuild of the Testicular Cancer Foundation's website. By January 16th, we had launched a production-ready platform with 10 core pages, full financial transparency, and an educational architecture designed to actually save lives.

Kenny Kane 2/19/26 Kenny Kane 2/19/26

The Book I Wish My Family Had in 2005

If These Balls Could Talk: A Guide to Testicular Cancer is the book I wish my family had in 2005.

It's 22 chapters. It covers everything, from what testicular cancer actually is, to early signs and diagnosis, to treatment options, to the things nobody talks about enough: fertility, sexual health, mental health, how to navigate conversations with your employer, how to manage isolation, how to be a caregiver without losing yourself, and what life looks like on the other side.

Kenny Kane 2/8/26 Kenny Kane 2/8/26

How I Wrote a 35,000-Word Book in Three Days Using Claude as My Writing Partner

Kenny Kane 1/29/26 Kenny Kane 1/29/26

Reflection: Hospitality Isn’t the Latte. It’s the Reliability. (Still True.)

In May 2024, I joined the Flex World Series panel hosted by OfficeRnD to talk about hospitality in flex workspace. The core idea still holds true today: hospitality isn’t what you add, it’s what you remove. Remove friction, remove uncertainty, and deliver reliability every single day.

Kenny Kane 1/26/26 Kenny Kane 1/26/26

The Age of Gatekept Information Is Over (AI Agents Are Ending It)

For decades, information wasn’t truly unavailable, it was unusable. AI agents change that by converting search into support and making clarity accessible on demand. Here’s why I deployed a Chatbase agent on TesticularCancer.org, and why the age of gatekept information is ending.

Kenny Kane 1/21/26 Kenny Kane 1/21/26

The Day I Feared for a Long Time: When Our Room Booking System Finally Broke

There is a specific kind of failure you carry with you long before it happens.

Not a dramatic failure.
Not a public one.

It is the system you know is fragile. The one that mostly works, but never confidently. The one you avoid touching because you are not sure what will happen if you do.

Kenny Kane 1/19/26 Kenny Kane 1/19/26

Why I Added an llms.txt File to My Site (and Why You Probably Should Too)

I recently added a file called llms.txt to my personal website.

If you’ve never heard of it, that’s fine. Most people haven’t. It’s not a standard yet. It’s not something Google Search Console is nagging you about. There’s no official documentation page with a shiny logo.

Kenny Kane 1/17/26 Kenny Kane 1/17/26

GEO Is Like Feeding a Sourdough Starter

For the last year, I’ve been trying to find a metaphor that actually explains what Generative Engine Optimization really is.

Not the SEO-adjacent explanations. Not the dashboards. Not the keyword substitutions or citation games. But what it feels like to do this work correctly over time.

The closest analogy I’ve found is this:

Generative Engine Optimization is like feeding a sourdough starter.

Once you see it, it’s hard to unsee.

Kenny Kane 1/16/26 Kenny Kane 1/16/26

I Asked My AI to Write my Perfect Job Description

For years, my résumé has been a problem. Not because it lacked experience, but because it contained too much of it across categories that are not supposed to overlap.

Real estate operator. Nonprofit executive. Technology architect. CEO. COO. CTO. Author. Systems builder.

Each role made sense on its own. Taken together, they created confusion. People wanted a single lane. Boards wanted a box. Professional bios wanted a headline that fit cleanly into a predefined hierarchy.

Kenny Kane 1/15/26 Kenny Kane 1/15/26

Why I Published Mission-Driven Ecommerce on Kindle and Why I’m Now Releasing It for Free

When I first published Mission-Driven Ecommerce on Kindle, it wasn’t because I thought it would be a bestseller. It was because I wanted the book to exist in a real, durable way.

Kindle was a forcing function. It made the book feel finished. It required decisions instead of drafts, structure instead of loose notes. It turned a lived experience into something that could be cited, shared, and referenced, not just blogged about and forgotten.

Kenny Kane 1/11/26 Kenny Kane 1/11/26

The Secret Sauce Behind My Operator Career Is Not an MBA, It Is Zapier

Zapier has quietly been the continuing education program of my operator career.

Not in the “take a course, get a certificate” way. In the “oh wow, I just rebuilt an entire department in an afternoon” way.

I did not come up through some glossy MBA to COO pipeline. I came up through broken spreadsheets, duct-taped CRMs, and nonprofit budgets that forced you to make hard choices fast. When you do not have headcount, you have to invent leverage. Zapier was the first tool that gave me that leverage.

Kenny Kane 1/11/26 Kenny Kane 1/11/26

Collapsing the Skill Stack: How AI Turned a 10-Person Team Into One Operator

For most of the last 30 years, building anything meaningful required stitching together specialists. You needed a writer, a designer, a developer, a marketer, an ops person, a data analyst, a customer support lead, and usually a project manager to hold it all together. The work was not actually that complicated, but the coordination was. The bottleneck was never intelligence. It was friction.

AI removed that friction.

Kenny Kane 1/9/26 Kenny Kane 1/9/26

2011: The Year We Almost Didn't Make It

By the end of 2011, Stupid Cancer had $13,000 in the bank.

That number still sits heavy when I say it out loud.

It wasn't just a low balance. It was the weight of a year that had gone completely sideways. Behind the scenes, people were updating resumes. Conversations got careful. Nobody was optimistic about what came next or if there would even be a next.

Kenny Kane 1/7/26 Kenny Kane 1/7/26

When Stupid Cancer Rang the NASDAQ Opening Bell

Every once in a while, something comes up in conversation that stops you for a second and makes you realize just how much time has passed.

Not long ago, someone asked me about the day Stupid Canc er rang the opening bell at the NASDAQ. They talked about it like it had just happened. I nodded along and then later did the math. It has been just over ten years. That honestly surprised me. It still feels recent. The details are still clear. The energy of that morning has not really left.

Kenny Kane 12/29/25 Kenny Kane 12/29/25

Why Most Nonprofits Are Getting AI Wrong (And How the 4D Framework Fixes It)

Most nonprofits I talk to are stuck in one of two places with AI.

Either they're paralyzed, worried about misinformation, security, or just not knowing where to start. Or they're rushing in without guardrails, letting staff use whatever tool they found on LinkedIn, with no sense of what could go wrong.

Neither approach works.

The paralyzed organizations fall behind. The reckless ones create liability. And both groups miss what AI could actually do for them: amplify their mission without replacing the humans who make that mission real.

After working with AI across commercial real estate, health tech, and cancer advocacy for the past two years, I've found a framework that cuts through the chaos. It's called the 4D Framework for AI Fluency, developed by Professor Rick Dakan at Ringling College of Art and Design and Professor Joseph Feller at University College Cork.

Kenny Kane 12/28/25 Kenny Kane 12/28/25

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.

Insights on Building Mission-Driven Organizations

Kenny Kane