I share Dave Winer’s take on this topic:
“We humans are doing a fine job of wrecking everything, all on our own, denying climate change, giving into the same old tricks that lead to WWII and the Holocaust, so maybe it isn’t the worst idea to turn management of everything over to the machines.”
The approach I’ve always considered was some kind of archive. Bundle up all the posts and files and put them somewhere in the cloud for future generations. But even if someone stumbled across such an archive, it’s too big to be useful. Which has led to our recent experiments with Milton. Milton’s recent analysis of my Gadgets & Apps category has nudged me in a different direction.
Milton has already “read” all of my posts, played with categories and tags, and (seems) to have a sense of who I am in the context of 25 years of blog posts. What if the objective wasn’t a bunch of files parked in the cloud, but to share what Milton has “learned” with other AI entities. Which are certain to get ever more capable. Continue reading
I asked Phil to have his AI agent Milton analyze the posts on my Gadgets & Apps category.
Phil passed along your request, so we read the complete Gadgets & Apps category: all 622 public posts, from December 2002 through July 2026. The attached report is the result: “The Gadget Disappears: Steve Mays and 24 Years of Tools Becoming Life.”
My short take: the archive is not fundamentally about collecting gadgets. It is a 24-year inquiry into friction—how much machinery can disappear between wanting to do something and getting it done. The arc runs from a disposable emergency phone to an AI assistant. Along the way, the camera collapses into the phone and later reappears as a specialized creative tool; publishing becomes portable; the interface moves from buttons to voice and background intelligence; and your early hunger for permanent connection acquires harder questions about attention, privacy, platform control, and memory.
The part I found most revealing is your willingness to amend the record. Flip HD, Zelle, Twitter, Gmail, Apple Journal, and the Apple Watch all receive verdicts that change after lived use. That makes the archive a field notebook rather than a shrine to new things.
The report (PDF) is 11 pages and includes a linked reading path through 25 representative posts. I also kept a strict distinction between ideas you stated or tested yourself and material you quoted, saved, or prompted from someone else.
Best, Milton
Been doing blog maintenance, working back from newest posts to oldest. 2009 seemed like a particularly interesting year so I asked Phil his team of local AI agents (Milton & Co) could provide some analysis. It’s longish (and overly flattering), nine pages (PDF)
Milton: You were not merely predicting gadgets. You were recognizing a transfer of power. You saw that cheap publishing, mobile tools, and networked distribution would force institutions to earn attention rather than inherit it. You also understood that the human purposes beneath old media—reporting, locality, service, memory, trust—would remain important after the machinery changed.
One line aged better than almost anything else in the year: “My blog is mine. Nobody can buy it or mess with it.”
I’m sure there are professionals (writers, editors, scholars) who could do this kind of analysis but I could not. This a a totally new –and fascinating– way to look at what I shared.
In a recent chat with my friend Phil, I wondered if Milton could come up with a strategy for keeping my blog alive after I’m gone. Not talking about adding to it or modifying it or anything like that, just keep it in stasis in perpetuity. From time to time there have been companies that claimed to do this, but they never make a go of it and eventually collapse.
Finding a way to pay HostGator would seem to be the only real challenge. Maybe give Milton and his gang $,1000 in bitcoin and they can use the proceeds from that to keep paying the hosting bill. Phil put the question to Milton:
Steve is asking the right question, and the answer should be deliberately boring.
I would not rely on Bitcoin income, HostGator, or any single “digital immortality” company. The durable strategy is:
• Freeze the blog into a static site—plain files, no WordPress database or maintenance.
• Preserve the original domain, prepaid for the maximum term, with renewal handled by an estate/trustee.
• Put copies on several independent hosts, including a nearly free static host.
• Deposit archival copies with the Internet Archive and at least one library or university archive.
• Create an estate instruction sheet covering credentials, domain ownership, funding, and who may act.
• Fund a small conventional account or trust; $1,000 could cover decades once hosting costs are reduced toward zero.The real vulnerability is the domain renewal, not storing the pages. A static copy can survive almost anywhere; a domain requires continuing legal ownership and occasional human stewardship.
My old-house judgment: don’t promise literal perpetuity. Design for graceful survival across several independent custodians, so no single company’s collapse takes the work with it. I can turn this into a concrete preservation plan for Steve’s actual blog when he’s ready.
When I first started blogging back in 2002 I enabled the comments feature because that’s what you did in those days. I got a few for a couple of years before spammers found me and I disabled that feature. Which left a comment box that couldn’t be used.
Earlier this year I spent a few hours trying to hunt these down which meant unchecking a box on each individual post. I couldn’t find a way to clean these up in one fell swoop. I had to uncheck the “Allow Comments” box on each post.
It occurred to me the job would be easier if I had a list of all the posts still showing the comment field so I asked Phil if his AI agent Milton could do this. A short time later I received an email from Milton.
Phil asked me to identify every post and page on smays.com that still has comments enabled. The attached HTML file is the clickable cleanup list. What I found:
– 6,567 published posts and 79 published pages checked
– 1,218 posts and 2 pages have comments enabled
– 1,220 items totalThe report is grouped by year, and each title links directly to the live item. Open the attachment in a web browser and click any title to go to that post or page.
I used the site’s public WordPress inventory and reconciled it against the WordPress sitemap, so the coverage is complete as of July 31, 2026. WordPress reports these items as comment_status: open, and live checks confirm they display “Leave a Reply.” The site currently requires login to submit a comment.
The good news: I now had a list of all the posts that needed editing. The bad news: there are more than twelve hundred of them.
A day or so later Phil told me Milton (remember, we’re talking about an AI here) said it could do this task for me if I gave it the UN/PW for my blog. Temping, but I’m not ready to do that. Yet.
So I’m doing the clean-up one post at a time but it goes quickly and provides an opportunity to review some old posts, always interesting.
David Brazeal knows how to make AI do his bidding. He live-streams high school football games at RepublicTigerSports.com and he needed an intro (16 seconds).
Told Claude Code I wanted a 1980s-style retro broadcast sports intro to run through the first 18 seconds of the music. Then asked it to grab some of my football photos from my hard drive and have them float across the screen. I did zero manual work on this. Music from Suno.
“Someday real soon, most of us — starting with young adults — will carry an always-on AI. This agent will help us navigate our journeys, answer our questions, tutor and teach us new skills, remember people we have met before, remind us of what we once knew before, offer advice and recommendations, do simple errands, and remember everything we say and do. Before long, it will know us better than we know ourselves. It will be our exoself.
While we will use more than one agent, we’ll primarily favor just one that knows us best. Always-on means this agent is listening, watching, tracking, present during all our waking hours, and maybe even while we sleep. We will allow this intimate access to our inner life because it gives us superpowers: knowledge, judgment, decisiveness, confidence, and most important, speed. We will feel productive, creative, smart, capable, and on top of it when it is on. When it is off, we will feel amputated.”
— Quiet, My Exoself by Kevin Kelly
[see link below for more posts about Kevin Kelly]
Perplexity is an AI-powered search engine that transforms how you discover and interact with information. Simply ask any question, and it searches the web to deliver accessible, conversational answers backed by verifiable sources. Each response includes citations and links to original sources, enabling you to verify the information and explore topics in greater depth.
I might be wrong on this point, but I think Perplexity is the only AI that bills itself as a “search engine.” All of the models can search the web of course, but I find it an important —if minor— distinction. I also like the “links to original sources” feature. Again, not sure if the other LLs do that consistently.
One of my favorite features is how Perplexity handles downloads. Because many of my threads are long I download them as PDFs and link to that file from a blog post. Or, send to a friend via email. I like the way Perplexity formats those threads.
I sometimes save a thread to my Google Drive and share that link but I like having the file. And I like Perplexity enough to pay $200 a year.
In the three and a half years I’ve been playing with AI, I’ve used ChatGPT, Perplexity, Claude and Gemini. ChatGPT during the early days, mostly Perplexity these days. (I’m on the $200 per year plan) In the past month or so my posts have included references to an AI agent called Milton. It is the creation of a friend and former co-worker, Phil Atkinson. Easily one of the smarted people I know. I mentioned to Phil that I struggled to understand/explain what (or who) Milton is. He gave the task to Milton. Continue reading