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

Project
TL;DL
Summary
Your favorite podcasts, summarized.
URL
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.

No One Else Can Speak the Words on Your Lips

Ben Roy explains why prompting an LLM to write an essay misunderstands what writing actually is:

People fundamentally can’t prompt good essays into existence because writing is not a top-down exercise of applying knowledge you have upfront and asking an LLM to create something. AI agents also can’t create good essays for the same reason. Even though their step-by-step reasoning is more complex and iterative than human prompting, a chain of thought is still trying to accomplish a predefined goal. By contrast, real writing is bottom up. You don’t know what you want to say in advance. It’s a process of discovery where you start with a set of half-baked ideas and work with them in non-linear ways to find out what you really think.

I will continue to argue that for general business writing LLMs are fantastic if they are given the right context and guidance, and that it can save hours of work (with high quality results). But all my experiments with using LLMs for creative writing has so far fallen flat. Maybe—likely?—that will change within the next few months. But for now, the brain work this kind of writing requires remains. Not a bad thing imo.

Zombie Flow

Derek Thompson goes into the history of the “flow” concept, and how tech and entertainment companies learned to simulate it without any of the substance psychologist Mihaly Csikszentmihalyi originally had in mind:

Algorithmic flow is flow without achievement, flow without challenge, flow without even volition… To be lost in the lazy river of algorithmic media is to be lost the current of life without a mind. Zombie flow.

Ten years ago the question was how to get into flow more often. Now it might be how to get out of the fake version fast enough to remember what the real one felt like.

AI might actually need more PMs

Amol Avasare, Anthropic’s Head of Growth, said on Lenny’s Podcast that maybe PM jobs are not going to shrink as much as we may have thought…

Rather than immediately replacing PMs, AI is currently increasing engineering leverage the fastest, which creates new pressure on PMs and designers. In larger organizations, that may actually increase the value of PMs who can guide priorities, manage alignment, and sharpen decision-making—especially as engineers take on more “mini-PM” responsibilities.

Eight years of wanting, three months of building with AI

Lalit Maganti writes about building a SQLite parser with AI — a project he’d been putting off for eight years, finished in three months. His comparison of AI coding to slot machines is uncomfortably familiar:

I found myself up late at night wanting to do “just one more prompt,” constantly trying AI just to see what would happen even when I knew it probably wouldn’t work. The sunk cost fallacy kicked in too: I’d keep at it even in tasks it was clearly ill-suited for, telling myself “maybe if I phrase it differently this time.”

Also, I agree that this is still true today, but I’m not convinced it will remain true beyond 2026:

AI is an incredible force multiplier for implementation, but it’s a dangerous substitute for design.