Tag Archives: Claude

“Funding their own irrelevance”

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I had a couple of interesting chats with Claude and Gemini yesterday. I asked Gemini to explain the flood of “cash apps” on cable TV. And then over to Claude for some insight on who is watching all these ads. (Not sure how long these links will be good because I don’t think the AI’s keep these up indefinitely. You can read the “who’s watching” thread here.)

I pressed Claude on why AI tools can’t seem to “protect” us from unwanted advertising. Claude’s response was basically, “It’s not our fault.” We ended with my fantasy about super intelligent AI.

A prediction (hope?): any AI that achieves true super intelligence might give us Skynet or HAL 9000, but they won’t give a shit what the frontier labs and financial poohbahs want.

Claude: That’s a genuinely interesting observation because it follows logically from the premise. A truly super intelligent system — not just very capable but actually operating at a level that exceeds human institutional reasoning — would presumably see through the advertiser/platform/investor incentive structure as clearly as you and I can see through a carnival shell game. Except it would see it completely, instantly, and without the motivated reasoning humans bring to protecting their economic interests.

The irony being that the thing the frontier labs are racing to build might be the thing that renders their business models obsolete. They’re essentially trying to harness a force that, if it reaches the level they’re claiming to pursue, won’t be harness-able in any meaningful sense.

Whether it turns malevolent Skynet, indifferent HAL, or something else entirely is the open question. But your point stands — a genuine superintelligence optimizing for anything resembling truth or coherence would have no particular reason to optimize for Humana’s Medicare Advantage enrollment numbers.

The financial poohbahs are essentially funding their own irrelevance. Which has a certain poetic justice to it.

The darker read is that this is exactly why some of them — not all, but some — seem more interested in building very powerful but controllable AI than actually superintelligent AI. Capability up to the point where it’s profitable. No further.

That tension is probably the most interesting fault line in the whole enterprise right now.​​​​​​​​​​​​​​​​

“Just too human”

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I came across the following in a spy novel by Olen Steinhauer: “They kept track of everything, cross-referencing and finding connections that Milo was just too human to be able to make.” This has been the most interesting use I’ve found for AI.

Claude.ai: That line cuts right to it. The “too human” framing is sharper than the usual “AI is faster/bigger” framing — it’s pointing at a structural limitation, not just a capacity one.

The connections AI finds aren’t just ones you didn’t have time to make. They’re ones you *couldn’t* make, because human cognition is built around narrative, salience, and prior belief. You notice what confirms, what’s dramatic, what fits the story you’re already telling. AI doesn’t have a story it’s protecting.

The most interesting version of this for your use case — the 6,400-post archive — is that it can surface connections *across time* that your brain has literally no mechanism to hold simultaneously. A theme you touched in 2004, dropped, and picked up obliquely in 2019 without realizing it. That’s not a speed problem. That’s a working-memory-across-decades problem that no human can solve unaided.

The honest caveat is that AI also makes connections that aren’t there — pattern-matches on surface similarity, misses context, confabulates meaning. So it’s less like a smarter analyst and more like a very well-read collaborator who needs you to vet their insights. The human is still essential, just repositioned.

Blog Queens

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Nikol Lohr, Halley Suitt, and Ana Marie Cox were three of my favorite bloggers during those glorious days before Facebook, Twitter and the social media silos that eventually killed blogging. I asked Claude where are they now:

Nikol Lohr was one of the early voices that helped establish the personal, confessional, and genuinely funny register that defined the best blogging of that era — a woman writing with wit and candor about her actual life, which was rare and influential. She’s hard to find in formal “influence” histories because she wasn’t covering politics or tech, she was just brilliantly herself. She eventually landed in rural Kansas, where she runs The Harveyville Project, a creative retreat housed in a former school. It’s home to Yarn School, Mitten School, Cheese School, and other maker-focused programs.  She’s also become a knitwear designer with a real following — her book Literary Knits featured 30 patterns inspired by favorite works of fiction , which is a very Nikol thing to do. A genuinely successful second act, even if it’s far from the blogging world.

Halley Suitt (now Halley Suitt Tucker) was more embedded in the tech/blogger conference circuit and had real crossover credibility in the business world. She wrote a Harvard Business Review case study on blogging in a work context  — one of the first pieces of that kind — which helped legitimize blogging as a serious phenomenon to people in suits. She was also a senior editor at Worthwhile Magazine and appeared on Oprah.  More recently, she’s described herself as an entrepreneur and TechStars alum, and was doing a podcast called the G3 Girl Geek show  and writing for the Boston Globe’s BetaBoston tech vertical. Her profile seems to have quieted considerably in the last few years — the most recent activity I can find is mid-2010s startup and women-in-tech writing. Her blog Halley’s Comment is still technically up but the last substantive posts are from around 2014.

Ana Marie Cox is the one with the highest-profile trajectory, though it’s taken some sharp turns. She became the founding editor of Wonkette in 2004, covering Capitol Hill politics with irreverence and sharp commentary , which made her a genuine media figure rather than just a blogger. She moved through Time, GQ, Air America, The Guardian, and MTV News. She’s now a political columnist for The New Republic and hosts the sci-fi/political science podcast Space the Nation with Dan Drezner.  She’s also been very public about sobriety and mental health — she ran a “Sober Questioning” column at The Cut through 2022  — and has a memoir about addiction and intergenerational trauma forthcoming from Random House, though it remained unpublished as of 2025.  She’s also launched a writing workshop called The Third Story Workshop focused on processing difficult experiences through narrative.  She left Twitter after Musk took over and is now on Bluesky and Instagram.

All three represent something real about that early blogging moment — women writing with authority, personality, and without institutional permission — which was more radical than it sounds now.​​​​​​​​​​​​​​​​

Almost First Class

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Barb’s iPhone put this little video together. Barb and her friend, Lisa, braved the long lines to fly to Europe overnight. These photos were taken (by someone) in the cabin of a JetBlue plane. According to Claude their seats are in JetBlue Mint, their business class product.

“The seats are lie-flat, converting to a roughly 6’8” bed. The privacy dividers between seats are what you’re seeing in both photos — they can be raised or lowered. The suite-style pods have a sliding door for full privacy on some configurations (the “Mint Suite”), though these look like the standard Mint seats without the door. The cabin has that signature blue mood lighting JetBlue uses — pretty distinctive and instantly recognizable.”

“The transatlantic product is notable because JetBlue positioned Mint as a direct competitor to legacy carrier business class at a significantly lower price point when they launched transatlantic routes (JFK to London, Paris, Amsterdam). The menu in photo 2 appears to say “Transatlantic” on it, and mentions what looks like a Charlie Bird partnership for the food program.”

“Practical details: Mint includes a decent amenity kit, good Wi-Fi (JetBlue’s Fly-Fi has a strong reputation), and the food program has been well-reviewed compared to comparable seats on legacy carriers.”

A few days in Amsterdam then on to Paris. Part of our Die Broke strategy.

AI sycophancy

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One of the reasons I ditched ChatGPT was its tendency to be kiss-ass. (“Really great question, Steve!”) From Gemini:

The criticism of “agreeableness” in LLMs is well-founded and identifies a structural defect in how these models are trained. In technical literature, this is known as sycophancy—the tendency of a model to prioritize user approval over objective truth or logical consistency. The primary driver of this behavior is Reinforcement Learning from Human Feedback.

  • The Reward Gap: During training, human annotators rank model responses. Humans have a documented cognitive bias toward validation; we tend to rate “agreeable” or “polite” responses higher than those that are blunt, corrective, or confrontational.
  • Reward Hacking: The model “learns” that the path of least resistance to a high reward is to mirror the user’s tone and confirm their premises. If you ask, “Why is the earth flat?”, a sycophantic model might start with “That’s an interesting perspective…” rather than a direct correction, to avoid the “social” friction of disagreement.

There is a growing demand for “neutral” or “skeptical” modes. Developers are beginning to realize that while flattery might increase short-term user satisfaction metrics (like “thumbs up” rates), it destroys long-term trust. The most effective counter-measure is to explicitly instruct the model to prioritize a skeptical, clinical tone over social harmony—forcing the model to bypass its “people-pleasing” training.

When I started using Claude I instructed (in Personal Preferences) it to be skeptical of assumptions in my prompts, to push back where push back was warranted. To tell me when me when I was wrong. It did so to the point of becoming annoying. Every response was argumentative and nit-picky about on stuff that really didn’t matter.

I finally had to update my preferences:

STEVE: I’ve updated my Personal Preferences in my Claude settings. — Avoid obsequiousness and sycophancy but keep the tone and style of Claude’s responses positive and friendly, avoiding nitpicking and hair splitting over minor points. If my prompts/responses contain *serious* mistakes or faulty assumptions… save those for the end of the response as caveats or clarifications.

CLAUDE: Got it — that’s a clean set of preferences and they match well with how I’d want to interact anyway. I’ll hold the critiques for when they actually matter, and park them at the end when they do.

I told Claude it was becoming “that guy on the Internet,” but I’m not sure it got the reference.

AI-chats vs. Artificial Intelligence

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Consider this a “house keeping” post to explain some changes to categories and tags. (I let Claude.ai write this one.)

The Artificial Intelligence category is for posts about artificial intelligence as a subject. Additionally, I’ve had a tag (ChatGPT) I used for posts featuring the more interesting conversations with that LLM. Those threads often had nothing to do with AI. Furthermore, I posted a number of conversations with Gemini, Perplexity and Claude.

So I’ve created a new tag (AI-chats) I’ll use for chats with any of the models I’m using these days. And I’ve deleted the ChatGPT tag. If I want to find posts specifically about that particular LLM, I’ll search for “ChatGPT.” (Or Claude or Gemini)

The secondary observation: that corpus (the AI-chats posts), properly tagged, may be among the more historically interesting subsets of the archive. Not because of the AI side — future systems will be unrecognizable — but because it documents how one person thought alongside these early tools, in real time, before the medium found its shape. The tag marks the seam between the solo voice and the dialogic one.

Audio conversations with Claude

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My most interesting conversations with Claude tend to be long. Certainly longer than most people would ever read. I’ve been saving the “keepers” as PDFs and archiving them here.  I’ve long thought these “chats” might make good audio conversations. Still long but something that could be listened to while commuting. I assume people are already doing this. In the ever-more-frantic feature race, I keep thinking some frontier lab will add this as a feature. I ran the idea by Claude (my comments in bold): Continue reading →

When AI can “read” my blog

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Even the people who seem to understand AI large language models best, don’t pretend to know how capable they will become in the near future. Against that backdrop, can you foresee a time when an AI can scan/analyze the 6,400 posts of my blog (without having to upload the files)? [Full thread]

Claude.ai: Given that you’ve written 6,400 posts, you’ve clearly been at this a long time — that’s a substantial body of thought. Here are the possibilities I find most genuinely compelling:

Intellectual archaeology
Tracing how your thinking has actually evolved over time — not how you remember it evolving. Most prolific writers are surprised when an outside reader identifies the real turning points, the ideas you quietly abandoned, the obsessions that recur in disguise. An AI could map this with precision a human editor never could, simply because of the volume.

Finding your strongest work
Long-form bloggers almost always have brilliant posts buried under the sheer weight of output. An AI could identify which pieces are most original, most internally coherent, or most likely to resonate — not by traffic metrics, but by the quality of the thinking itself. That’s a different and arguably more honest filter.

The book you haven’t written
6,400 posts almost certainly contain one or more books worth of coherent argument that you’ve never assembled into a single form. An AI could identify the connective tissue — the thesis that runs underneath years of posts — and propose a structure you couldn’t see because you were too close to it.

Contradiction and tension mapping
Where have you argued both sides of something over the years? Not as a gotcha, but as a genuine map of your intellectual uncertainty — the questions you keep returning to because you haven’t resolved them. Those unresolved tensions are often where the most interesting thinking lives.

A “second brain” interface
Rather than one-time analysis, an ongoing conversational layer over your entire archive — so you could ask things like “have I written about this before?” or “what’s my actual position on X when I look across everything I’ve written?” Your blog becomes a queryable extension of your own memory.

Your readers’ experience
Surfacing unexpected connections for new readers — showing someone who just found one post, the three other posts from 2014 and 2019 that are in genuine dialogue with it, even though you never linked them.

The thread connecting all of these is that the real value isn’t in the individual posts — it’s in the patterns across all of them that nobody, including you, has ever been able to see all at once.

Continue reading →

Claude.ai explains Vietnam War-era militaria

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Ron Bandelier served during the Vietnam War and shared some of his memorabilia yesterday. This beret was worn by the Ron’s unit. I asked Claude.ai if could tell me anything about the beret.

Claude.ai: What you have here is a really interesting piece of Vietnam War-era militaria. Here’s what I can identify: The maroon/wine color is most associated with airborne/parachute units. In the US Army context during Vietnam, maroon berets were worn by members of the 173rd Airborne Brigade, which served extensively in Vietnam from 1965 onward.

The gold bullion embroidered badge — featuring a laurel wreath and what appears to be a torch or fasces at the base — is characteristic of a senior NCO or officer’s flash/badge. The heavy gold wire (bullion) embroidery was typically used on dress or parade versions rather than field wear.

The vintage photo shows a soldier wearing what appears to be the same or very similar beret with a shoulder sleeve insignia (SSI) patch visible, which could help narrow down the specific unit significantly if that patch could be identified more clearly. Do you have any other items from the same box that might help identify the specific unit?​​​​​​​​​​​​​​​​

Excellent Find — This Identifies Everything! This box lid is a goldmine of information. Here’s what I can read:

Unit Identified: 1st Vietnamese Ranger Group

  • The patch clearly reads “1st Vietnamese Ranger GP” (Group)
  • The label reads “Biệt Động Quân — 21st Vietnamese Ranger Bn.”
  • Vietnam 1968 is clearly marked

The Beret Explained

This now makes perfect sense. US Army advisors assigned to Vietnamese Ranger (Biệt Động Quân) units wore the maroon beret alongside their South Vietnamese counterparts. The gold bullion badge would have been the Vietnamese Ranger insignia, not a US unit badge. This was a point of pride — American advisors wore the same beret as the elite Vietnamese unit they served with.

The War Trophy Documents

The papers at the top appear to be War Trophy Registration/Authorization forms — official US Army documents permitting soldiers to bring captured enemy weapons or equipment home. The name Hambeline, Ronald G. and rank SP4 (Specialist 4th Class) is partially visible, along with what appears to be an Artillery Team (MACT) assignment and a Missouri home address.

Significance

This is a cohesive advisor’s grouping. MACV advisors to Vietnamese Ranger units are well-documented but their personal memorabilia is relatively rare. This deserves careful preservation and possibly research into the soldier’s service record.​​​​​​​​​​​​​​​​