DEV Community: Jarrod Cabarubio

DEF CON Was Different This Time, Maybe Because I Was Different... <☠/>

Jarrod Cabarubio — Sat, 15 Aug 2026 17:28:46 +0000

The first time I went to DEF CON, I spent most of my time doing challenges. That was the mission. Find something interesting, sit down, start digging, and see if I could figure it out. I loved it. There is something incredibly satisfying about disappearing into a problem for a few hours and eventually getting to the other side of it.

This year was different.

I still love that deep-dive side of DEF CON. CTFs and technical challenges are part of what makes this community what it is, and there is a reason so many incredibly talented people spend hours working through them.

But this year I realized that what was scarce for me wasn't screen time. I can always find time to go deep on a technical problem. What I couldn't recreate at home was being physically surrounded by this enormous concentration of knowledge, creativity, technology, companies, researchers, builders, hackers, and people obsessed with things I may have never even heard of.

I wanted to see what was out there.

So I walked.

Following Curiosity

DEF CON is difficult to explain to somebody who has never been. Yes, it's a cybersecurity conference, but that description doesn't really capture it.

There are villages dedicated to specific areas of security, people working through CTFs and challenges, hardware being torn apart, locks being picked, wireless signals being investigated, social engineering, AI, physical security, embedded systems, privacy, infrastructure, and countless things that seem to exist somewhere between all of those categories.

What struck me this year wasn't any single technology. It was the density of ideas.

You can walk ten feet and find somebody who knows an incredible amount about something you barely knew existed. Walk another ten feet and it happens again. There is something energizing about realizing how much you don't know.

Instead of making me want to retreat into the things I already understood, it made me want to keep moving.

I started following whatever caught my attention.

Sometimes it was security. Sometimes it was a product or a demonstration. Sometimes somebody had built something that immediately made me wonder what else you could do with it.

That's where my brain tends to get me into trouble.

One idea becomes another idea. That one connects to a problem I've seen somewhere else. Then I'm wondering whether the same approach could work in an entirely different environment.

Before long, I wasn't just looking at what people had built.

I was thinking about what could be built next.

More Than the Technology

Something else caught my attention that I wasn't expecting: how companies were presenting themselves.

My company is entering a period where marketing is becoming increasingly important. Marketing isn't my job, but apparently my brain doesn't care much about job descriptions when it finds an interesting problem.

So I started watching.

What made somebody stop at one booth and walk past another? How were companies explaining complicated technology? What made a demonstration memorable? How did they turn something deeply technical into something another human being could understand in thirty seconds?

I started looking at DEF CON partly as an engineer, partly as somebody interested in security, partly as somebody interested in products, and apparently partly as an accidental marketing researcher.

That ended up being one of my favorite parts of the trip.

It also made me realize that the things I find interesting increasingly seem to live between disciplines rather than comfortably inside one of them.

The Conversations

Then there were the people.

I met a penetration tester working in the same state where my company operates. I unexpectedly met the social media person from one of our channel partners. I talked with vendors, builders, security people, and people working on technologies that sent me down entirely new trains of thought.

Those conversations mattered.

Not because every conversation resulted in some immediate opportunity. Most didn't. They mattered because talking to somebody who sees the world through a different technical lens can change the way you look at your own problems.

That's hard to reproduce sitting behind a computer.

And this was probably where my experience diverged most from my first DEF CON.

The first time, I wanted to solve what was in front of me.

This time, I wanted to discover what I didn't know was there.

Neither approach is better. They're just different ways of using the same incredible environment.

For me, this year, the second one felt right.

Paying Attention to Where My Mind Goes

I've been thinking about that since coming home.

I'm a test engineer, and testing has shaped the way I think more than I probably realized. It teaches you to question assumptions, look for what isn't obvious, understand how systems interact, and investigate the distance between how something is supposed to work and how it actually works.

I love that mindset.

But I'm also starting to notice that my curiosity doesn't stop at testing.

Lately I've been increasingly interested in designing solutions, architecture, AI, scaling systems, communicating ideas, connecting technologies, and taking something that exists in one place and imagining what it could become somewhere else.

I'm not ready to put a title on that.

Actually, I don't think I want to.

I'd rather pay attention to it.

There is a difference between deciding who you want to become and noticing what you naturally move toward when nobody is telling you where to go.

DEF CON gave me an interesting opportunity to observe the second one.

Nobody told me which booth to visit. Nobody assigned me a project. Nobody told me which conversations to have or which ideas were relevant to my job.

I had an enormous playground of technology and knowledge in front of me and complete freedom to choose where I spent my attention.

Looking back, where that attention went might be one of the most valuable things I learned on the trip.

I'm documenting this journey as it happens, the things I'm building, what I'm learning about AI and systems, the people and ideas that challenge the way I think, and occasionally experiences like DEF CON that move the whole thing in an unexpected direction.

Someday I want to be able to look backward and see how the pieces connected.

This was one of them.

One more for the books. Until next time, DEF CON.

The problem was never intelligence, it was continuity.

Jarrod Cabarubio — Tue, 04 Aug 2026 22:40:37 +0000

Building an AI Operating Layer
Entry 2
The Problem Was Never Intelligence. It Was Continuity

Somewhere along the way I realized I had been asking the wrong question.
I kept obsessing over intelligence.
Bigger models.
Better reasoning.
More capable agents.
Better tools.

It seemed obvious. If the models kept getting smarter, everything else would fall into place.
Then one day it hit me.

None of that matters if the next conversation has to start over.

Think about that for a second.
You spend two weeks finally understanding a problem.
You make decisions. You reject bad ideas. You discover patterns. The architecture starts making sense.

Then a new model jumps in.
Or another engineer joins the project.
Or six months pass.

And everyone starts rebuilding the same understanding all over again.

That felt crazy to me.

I thought memory was the answer.
Save the chats.
Store the documents.
Add vector search.
Summarize everything.

Those ideas help, but they don't solve the deeper problem.

Memory stores information.
It doesn't tell you what still matters.

That was the turning point.

I stopped thinking about memory and started thinking about continuity.

What if the important thing wasn't remembering everything?
What if it was preserving understanding?

That single question quietly changed the architecture.
Today the project looks very different.
Instead of asking how to give an AI more information, I'm asking how to prepare the right understanding before any reasoning begins.

That has led us into knowledge models, governed context, project reconstruction, and architectural boundaries.

Some of those ideas will survive.
Some probably won't.

That's okay.
This journal isn't here to prove I was right.
It's here to document how the thinking evolves.

Where I am today
I no longer think the hardest problem is building a smarter AI.

I think the harder problem is making sure understanding survives.
If we can solve that, maybe intelligence stops starting over.

Maybe every project gets a little wiser than the last.
I don't know yet.

But I think that's a question worth chasing.

Building an AI Operating Layer - Episode 1: Why I Didn't Start Sooner

Jarrod Cabarubio — Wed, 29 Jul 2026 21:04:03 +0000

Building an AI Operating Layer

Episode 1
Why I Didn't Start Sooner

Most engineering projects begin with an idea. This one began with a question.

For months I found myself watching the explosion of AI tools, frameworks, models, and agent platforms. Every week there seemed to be another breakthrough, another library, and another opinion about where everything was headed. I could have started building immediately. Part of me thought I should have.

But I realized something, and it kept bothering me. I wasn't afraid of writing code. I was afraid of solving the wrong problem.

When a new technology appears, it's easy to jump straight into implementation. Pick a framework. Choose a model. Build something. Ship it. I didn't want to start there because I had a feeling there was a much bigger picture that I wasn't seeing yet.

So I waited.

I spent my time reading, experimenting, asking questions, and trying to understand how all of these pieces connected. The more I learned, the more I realized I wasn't actually interested in building another AI application.

What fascinated me was the system behind the systems.

What happens when you stop looking at models, memory, orchestration, tools, policies, and execution as separate ideas and start seeing them as parts of a much larger ecosystem?

That question became the beginning of this project.

This isn't a story about predicting the future. It's a story about trying to understand it. I'm sure some of my assumptions will be wrong. I'm sure parts of this architecture will change. If they do, you'll see that too.

I don't want this journal to only show the polished results. I want it to capture the discoveries, the wrong turns, the redesigns, and the moments where a better idea replaces an old one.

At the center of this journey is a project I'm calling the AI Operating Layer. Today it's mostly architecture, documentation, research, prototypes, and a growing collection of ideas. Maybe that's exactly where projects like this should begin.

I'm not interested in rushing toward a finished product. I'm interested in building understanding first. If the understanding is solid, everything that follows has a stronger foundation.

One realization has already changed the way I think about this project. I originally thought I was building a sophisticated synthesis engine. Now I think I'm trying to understand what it means to build a living knowledge ecosystem that can continuously learn, integrate new capabilities, and grow over time.

Whether that idea survives the journey is something we'll discover together.

This isn't a launch announcement. It isn't a product reveal.

It's an engineering journal.

Welcome to the journey.