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.
AI Is Making Execution Cheaper. Executive Judgment Is Becoming More Valuable.
We built an AI support agent at Firmspace, named him Ethan, and watched members ask for him at the front desk. Six months later I shut him down. The technology worked. The judgment call was mine to make, and it's the kind of call executives can no longer afford to delegate.
Being There at 2 A.M.: My Conversation on The AI Edge
I went on The AI Edge with Louis Fernandes to talk about Firmspace, and we ended up somewhere better: how a small foundation in Austin built a chat agent that sits with scared people at 2 a.m., in ten languages.
Claude AI for Writing: The Complete Guide for Authors and Content Creators
The rise of AI writing tools has changed how we think about authorship. For most creators, the challenge isn’t whether AI can write—it’s how to make it work with your process, not against it.
After years of building organizations and publishing books, I’ve found that Claude AI (especially the 3.5 Sonnet model) is the first system that feels less like a generator and more like a collaborator. It doesn’t try to be the author—it helps you become a better one.
This guide distills how I use Claude to write and edit long-form projects like The Accidental Nonprofiteer and Mission-Driven Ecommerce. Whether you’re a novelist, nonfiction writer, or content creator, you’ll see how to integrate AI into your workflow without losing your voice or authenticity.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.