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Org Design in the Age of AI

This post on org design really resonated.

Most companies today are using AI the way you’d use a faster horse — to make the existing structure run a little better. The companies that pull ahead will be the ones willing to ask a harder question: what would we build if we were designing this organization from scratch, today, knowing what AI can do?

We have to seriously rethink the SDLC, design it from scratch in the context of how our own organizations work. It’s not about a global “right” process any more. The question now becomes “How can the humans in our team, at our company, at this point in time, work best together to serve our customers?”

The peril of laziness lost

Oh, this is very good. On the classic take that the core characteristic of outstanding engineers is “laziness”:

The problem is that LLMs inherently lack the virtue of laziness. Work costs nothing to an LLM. LLMs do not feel a need to optimize for their own (or anyone’s) future time, and will happily dump more and more onto a layercake of garbage. Left unchecked, LLMs will make systems larger, not better — appealing to perverse vanity metrics, perhaps, but at the cost of everything that matters. As such, LLMs highlight how essential our human laziness is: our finite time forces us to develop crisp abstractions in part because we don’t want to waste our (human!) time on the consequences of clunky ones.

The best engineering is always borne of constraints, and the constraint of our time places limits on the cognitive load of the system that we’re willing to accept. This is what drives us to make the system simpler, despite its essential complexity.

This is exactly why I practice Fear-Driven Development, and why everything I do in code includes multiple versions of asking Claude Code “do we need this?” and “is this adding bloat?”

Two small new things on the blog

Now that the site is off WordPress, I can finally start doing a bunch of things I’ve wanted to do for years. Here are the first two:

1. Auto-posting side-project releases

When I tag a GitHub release on one of my side projects — tldl, listentomore, discogs-mcp, and others — a post now appears on this site automatically. Title, tagline, release notes, and a link back to the GitHub release.

I ship a lot of small improvements, and historically none of that work was visible anywhere except the GitHub tab nobody reads. Now it shows up on the blog as a first-class content type.

2. Per-content-type RSS feeds

If you only want the long essays and not my link posts or quotes about other people’s writing (or the release notes, for that matter), you can now subscribe to just those. There are six feeds:

I’ve also updated /subscribe with the full list. And a reminder that RSS is very much alive and well. Get started with What is a Feed?.

Release: discogs-mcp v3.2.0 — Catalog-wide search

Project
discogs-mcp
Summary
Discogs MCP server.
Link
github.com/rianvdm/discogs-mcp

Adds search_discogs for catalog-wide queries beyond your own collection, plus two real-world accuracy fixes: owned-marker correctness across pressings, and exact genre/style matching.

Continue reading →

Release: tldl v2.2.0 — RSS-first monitoring and audio-URL dedup

Project
tldl
Summary
Your favorite podcasts, summarized.
Link
tldl-pod.com

Two meaningful changes since v2.1.0. tldl now detects new podcast episodes directly from RSS feeds with conditional GETs instead of relying on Podcast Index re-crawls, so episodes typically land in the queue within minutes of publication. A second fix catches episodes that get retitled or have their GUIDs regenerated after publication — a surprisingly common pattern in the wild.

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What actually changed about being a PM

I have decided that in this new AI era I will be practicing FDD. Fear-Driven Development. Every time I send a pull request, which happens a lot now, I'm terrified of an engineer sending it back to me and asking me to please stay in my lane and stop sending them slop. So I plan, write specs and implementation plans, test thoroughly, and I don't trust the agent's inevitable confidence.

I'll come back to that, but let me first frame what this post is about. The loudest take on PM work right now is that AI is collapsing the role — that we're one product cycle away from redundancy, or being reduced to prompt jockeys. That hasn't been my experience at all. The job got more hands-on, harder (brain fry is real), but also a lot more fun. What follows is what actually shifted for me over the last 5 months at Cloudflare, what didn't, and a couple of things I got wrong.

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Stand out of our Light

It’s my firm conviction, now more than ever, that the degree to which we are able and willing to struggle for ownership of our attention is the degree to which we are free.

– James Williams, Stand out of our Light: Freedom and Resistance in the Attention Economy

Is Hip-Hop in Decline? A Statistical Analysis

I love this blog and try not to link to it too much, but this one about how fewer people listen to hip hop was especially great.

So, what’s filled the space hip-hop once dominated? A blend of new arrivals and familiar mainstays. Latin music—led by Bad Bunny—and Asian pop, powered by K-pop acts like BTS, have expanded their global footprint. At the same time, legacy formats are resurging: country is booming, driven in large part by Morgan Wallen, while the loosely defined “alternative” category continues to gain share across the charts.

I particularly love how he tries to avoid causation/correlation errors in his hypotheses. Like this one I hadn’t thought about:

Streaming adoption laggards: Hip-hop uniquely benefited from early streaming adopters in the 2010s. Younger listeners—who were predisposed to the genre—were among the first to embrace platforms like Spotify, giving hip-hop an outsized digital footprint. More recently, late adopters—like country fans, older cohorts, and global audiences—have rebalanced the charts, lifting genres like country and K-pop.

I am finally — FINALLY — off WordPress

A quick meta-post incoming! This site has been running on WordPress and Dreamhost for 18 years. It worked fine, but the overhead was really starting to get to me: a MySQL database, monthly hosting costs, plugin updates that arrive every other week, and embarrassing page load times...

I've wanted to move to a static site for years, but it felt impossible. Every time I started to think about it I just gave up. How do I migrate 1,700 posts without breaking almost 20 years of URLs? What do I do about search? The Last.fm widget? Email routing? The existing CSS? There were too many things I didn't know I didn't know, so I never got very far.

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Evals Are the New PRD

Braintrust makes a good case (apologies for the X.com link…) for rethinking how PMs work on AI products: the eval replaces the PRD.

An eval is a structured, repeatable test that answers one question. Does my AI system do the right thing? You define a set of inputs along with expected outputs, run them through your AI system, and score the results using algorithms or AI judges.

The eval becomes both the spec and the acceptance criteria. The directive to engineering:

“Here is the eval. Make this number go up.”

That’s very different to how most teams work today, but I can definitely see the industry moving this way. Product usage generates signals, observability captures them, and evals turn them into improvement targets. The PM’s job is to define what “good” looks like in code and curate the data that reveals what “bad” looks like.

The PM skills that transfer are the same ones that always mattered — discovering needs and opportunities, and making judgment calls about what to build for business value. The difference is that instead of a document that describes the intent, you have a test suite that encodes it.