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X Marks The Spot

Chris asked if I could jump on a quick call a few weeks back. I’ve developed an annoying peccadillo of diving into whatever topic is on my mind at the beginning of a call, without first confirming with the caller that this is in fact the subject they are calling about; and so, as we connected I immediately launched into app feedback responses with barely a pause for air. Chris waited…

An AI Agent Restores A Sailboat

If your algo has even a dash of AI in it, always-on agents have probably flooded your feed harder than cauliflower-based hors d’oeuvres at a Lululemon company offsite. Everyone seems to have a personal robot that handles every aspect of their lives - from screening emails to scheduling oil changes, nothing says “I AI better than you” than beach meditation humblebrags while your…

The Pull Request Needs To Die

This month marks one year of ubiquitous agentic coding in the software world. Early adopters may have dabbled with pre-harness harnesses (remember Cursor? Github Copilot?) going all the way back to 2021, but agentic coding as we know it was really birthed late February of 2025 with the launch of Claude Code. I struggle to find an accurate historical analog for the rapidity and completeness in…

Bad News About Those Vanishing Barriers

There is an old Doug Stanhope bit where a news channel polled their viewers “ Will there be a terrorist attack at this year’s Olympics? " and the results were: 70% no 28% yes 2% I don’t know. The punchline is that none of these people know , and what the survey really tells us is that 98% of people will have strong opinions about things they can’t possibly know anything about. This is what it…

GDD: Generative Driven Design

Reflective generative AI software components as a development paradigm Nowhere has the proliferation of generative AI tooling been more aggressive than in the world of software development. It began with GitHub Copilot’s supercharged autocomplete , then exploded into direct code-along integrated tools like Aider and Cursor that allow software engineers to dictate instructions and have the…

Of Ducks, Types, and Identity

A Duck, Typing In 1967 computer scientist Melvin Conway made an observation that came to be known as Conway’s Law . Organizations which design systems (in the broad sense used here) are constrained to produce designs which are copies of the communication structures of these organizations. Conway’s Law is why you often find rigid, silo’ed tables modeled into the data architecture…

The Hindsight Guide to Replatforming

I was sketching out architectural recommendations for a client project that, after a successful POC, was ready for the prime-time of production software. I stopped to ask myself why the new arch diagram I was creating looked vastly different from the architecture of the existing concept software; even when my answers seemed solid (they included specific measures of reliability, speed, scale, and…

GenAI Sanity Check

For a little while now our LinkedIn feeds have been littered with AI Takeaways; a highlighted, prompt-toned text blurb wedged under selected posts and adorned with a little star (to let you know this is an important new feature). Premium users can click on the prompt and be treated to what “an AI” has to say on the subject at hand. Here’s one now! Note: the lopsided toast is not…

Restoring the 'Product' in AI Products

grounding your ML development lifecycle in commercial reality If you subscribe to the Gartner predictive model for AI impact and adoption (a.k.a the “AI Hype Cycle”) we are still far from peak (inflated) AI expectations. Casual observation supports the Gartner timeline; every week it seems a new Generative AI breakthrough sends techno-pundits and content creators into a frenzy. This…

50 First Dates With MemGPT

preamble The drive home from the movie theater was not going well. My then-girlfriend sat arms crossed in the passenger seat, the red glow from the traffic light matching her mood. “You can’t just let it be romantic. Why do you have to ruin everything!?!” We had just seen 50 First Dates , a classic Sandler/Barrymore romance about a woman who’s brain injury prevents her from…

An Indian Summer for Old Programmers

History The most money I have ever made was my years spent selling motorcycles. Software Engineering is by all means a lucrative profession, and I’ve never been the starving artist developer who prizes a compelling mission over a compelling paycheck. But the years I sold motorcycles - between 2003 and 2008 - coincided with a wave of temporary insanity in the US real estate market. Heretofore…

Langchain is a Ticking Timebomb

Let me preface this by saying that I very much appreciate the entire Lang* ecosystem. At my shop we rely heavily on Langfuse for development as well as the tagging interface for our training strategy. More than a few platforms have tried to be the framework for language model applications (think Guidance, Haystack etc), and the Lang* team has arguably made the most headway, and done it OSS…

Prompt Engineering

The world never ceases to be filled with new things, and that is exciting. New things are great, but as they come with a learning curve - not the least of which is the language surrounding them. Like when the first coffee shop opened in the little town where I went to college in the late 90s, and we learned to order “express-o” (which was named that, logically, because it was like coffee but…

Caffeine

There is a well-warn platitude that “debt is stealing from your future self.” The logic follows that instead of (or worse, in addition to) spending the resources you currently have, debt is the act of spending against resources you will have down the road. Debt functions on highly optimistic principals, namely that future you will be so very well off that not only will that version of…

The one where a picture of your dog broke your CD pipeline

It starts out innocent enough, on a frozen New Year’s Eve afternoon. You are doing some final documentation cleanup - because it is New Year’s Eve and not the best time for the team to be rolling out fresh feature code, and because updating the repo docs is usually a worthwhile endeavor in moments like this as part of good code hygiene. Being the clever and hilarious documentation…

Fun with SQLAlchemy Mapped forward refs

SQLAlchemy has nifty declarative mapping type support with the Mapped typing descriptor. If you are in the habit of typing your Python, this is a welcome tool that reduces boilerplate while still feeling quite natural: class Banana(SqlalchemyBase): is_squishy:Mapped[Optional[bool]] = mapped_column(server_default=text('TRUE')) picked_date:Mapped[datetime] belongs_to: Mapped['User'] =…

A Complete Containerized CD Pipeline With AWS and Cloudflare for 2024

Recently I went about standing up a fresh Continuous Delivery pipeline for a new project. The project is a relatively standard containerized stack with nothing exceptional to speak of, and as our exploratory work was already in AWS I decided to launch this CD in AWS CodePipeline. Furthermore, we wanted to dogfood our long-term infra management (this project is infra abstraction/automation…

On Having Enough Time

It is difficult to argue substantially that there is not enough time if there is a TV on your wall or TikTok on your phone.

Data Science Nomenclature

I have a working theory that most of the Data Scientists working today developed their naming conventions by watching Star Trek: The Next Generation in the 90s.

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Open Source

My contributions to Open Source Software

Photo Transformer for Web

Transform large, randomly named photos into web-ready images with meaningful names. Supports individual photos or ZIP archives for batch processing. When processing multiple images, you’ll receive a convenient ZIP file containing all transformed photos. Perfect for content creators who need to process multiple images without manual work.

Set Sail

Innovation does not live in a cubicle