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Jason

Jason Willems – Building products, exploring the world, sharing what I learn

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I Trust LLMs More When They Tell Me I’m Wrong

It’s strangely reassuring to be told that you’re wrong by an LLM. The further I venture outside my expertise with a model, the more apprehensive I become when it offers no pushback. Is it being lazy? Too agreeable? Overfitting to what it thinks I want to hear? Have we followed one premise so far that the broader context has fallen away? In a recent conversation, a model accepted every premise I…

The Economists and Philosophers of the AI Labs, According to AI

When Anthropic appointed Ben Bernanke to its Long-Term Benefit Trust, I asked ChatGPT which economists most closely matched the worldview of each major AI lab. After the economists, I asked the obvious follow-up: how about philosophers?

Future-Proof Naming: A Magnum Opus Leaves Nowhere to Go

The obvious problem with naming your best model Opus is that you eventually have to build a better one. A magnum opus is supposed to be the work someone is remembered for. Anthropic’s original Claude hierarchy—Haiku, Sonnet, Opus—was memorable and reasonably intuitive. A haiku is short, a sonnet is more substantial, and an opus is a major work (in terms of impact, but that’s often correlated with…

The Five-Minute Fork: The Era of Personalized Software

Good software quietly disappears: it stops feeling like a tool and starts feeling like an extension of how you think. Most software never gets there in large part because it wasn’t built for you specifically. It was built for a market segment. But that rigid constraint is starting to dissolve, and the downstream effects are going to completely rewrite how we think about product defensibility. A…

Acquired: Revisiting A Decade of Tech Predictions

I recently finished listening to the Acquired podcast. Not just the latest episode, but all of them. When I started, I had decided to listen in reverse chronological order, winding my way back through the last 10+ years of episodes. Walking backward through tech history meant listening to predictions from progressively further back with the absolute benefit of hindsight. The show’s 2016…

LLMs: The Fifth Act

You can be deeply familiar with AI and still be skeptical of “agentic AI.” I was. For a while, I dismissed most “agentic” startups as VC-funded cron jobs. An LLM integration wrapped in a thin scheduler, rebranded as autonomy. But there’s something real underneath the hype, and understanding it requires zooming out. LLMs haven’t evolved in one continuous line. They’ve moved in distinct acts, each…

AI Consciousness Is Not an AI Question: What the Debate Reveals About Our Theories of Mind

Dario Amodei, Anthropic’s CEO, recently suggested that their Claude AI models might be conscious. This may seem jarring: large language models generate text by predicting the next likely token in a sequence, a process that appears purely statistical and mechanical. But both the claim and the dismissal miss the deeper question.

AI Is Quietly Reversing 20 Years of Progress Toward an Open Internet

The End of the Crawlable Web : For most of the modern internet, there was an implicit contract between websites and search engines. Websites made their content accessible. Search engines indexed it. And in return, search engines sent users back to the original site. It wasn’t always perfect — news aggregators and social media links were persistent points of contention — but the incentives aligned…

Vibe Coding Didn't Democratize Software, It Tokenized It

As software development shifts from requiring specialized skills—built on multiple layers of technical understanding—to describing intent in plain English (or your language of choice), the act of producing software appears to become accessible to a much wider audience. The people best positioned to excel may not be well versed in software at all, but rather those who are good at expressing ideas…

AI Didn't Break Copyright Law, It Just Exposed How Broken It Already Was

If you paint a picture of Sonic the Hedgehog in your living room, you are technically creating an unauthorized derivative work—but in practice, no one cares. Private, noncommercial creation has always lived in a space where copyright law exists on paper but is rarely enforced. Gift it to a friend? Still functionally tolerated—a technical act of distribution that copyright law mostly ignores at…