Looking back at the dot-com bubble

The dot-com bubble (and subsequent crash) happened over a two-and-a-half-year period between  2000 and 2002 (the year I started the blog). I was reminded of this period while watching a video comparing the current AI frenzy to Tulip Mania back in the 17th century.

I couldn’t remember if my early blog posts touched on the dot-com period so I prompted Perplexity to take a look and it came back with a “looking back at the dot‑com bubble” post (see below). This is just the latest example of how my resolve to not let AI bots write my blog posts is slowly eroding. After one read I knew I could not improve on this summary.


(Perplexity) If my archive is any indication, I didn’t spend the bubble years themselves writing hot takes about it. The more interesting stuff came later, in the early 2000s, when it was obvious the web had outlived its first speculative fever dream.

One of the clearest snapshots is a June 11, 2003 post I titled “Markets as conversations,” where I pulled a quote (via Denise Howell / David Weinberger) that still reads like a verdict on the whole episode: “The Bubble was never what the Internet was about. The Web is not primarily a commercial space, not even primarily an information space… The bubble went away, but the Web absolutely didn’t. The Web remains interesting and important.” I didn’t add much commentary because I didn’t need to; posting it was endorsement enough.

By April 2005, I was pointing readers to a BusinessWeek cover story, “Blogs Will Change Your Business,” and highlighting this contrast: “The dot‑com era was powered by companies — complete with programmers, marketing budgets, Aeron chairs, and burn rates. The masses of bloggers, by contrast, are normal folks with computers… and — that’s right — no bubble.” I liked that line so much I reproduced the whole setup, emphasizing that we’d moved from company‑driven “New Economy” hype to what they called “media of the masses.”

Around those posts, there’s a steady drip of “Early Net Culture” items that implicitly answer the question, “What actually survived the crash?” In June 2003 I noted Google News beating BBC and MSNBC for a Webby and mused about how AP’s real asset had been its “connectedness” — something the open web was now replicating for everyone. The question “Can we agree that has changed forever?” wasn’t framed as bubble commentary, but it’s about what didn’t revert to normal once the NASDAQ fell.

A couple of years later I was citing ad forecasts that put Google and Yahoo’s combined online ad revenue on par with the prime‑time haul of ABC, CBS and NBC, calling it a “watershed moment” in the evolution of the internet as an advertising medium. If the bubble was about speculative eyeballs, this was about actual budgets moving. Same network executives, different direction for the money.

So, reading my own trail backwards, my “dot‑com bubble” coverage is less about the boom and crash and more about the quiet, durable things that came after: the idea that the web was never just a stock chart; that normal people with cheap tools and “no burn rate” might be more important than the Aeron‑chair start‑ups; and that news, advertising, and culture were re‑routing themselves through a network that turned out not to be a fad.

“Before Digital Had A Name”

This post was written by a “team” of AI agents/bots running on Phil Atkinson’s (long time friend and former co-worker) computers. He gave the bots two documents I wrote several years ago, chronicling Learfield’s early experiences with the Internet and the emerging digital world, tasking them to summarize.

Learfield Data, Learfield’s early Internet work, and the Phil/Steve overlap

Learfield’s best early technology work was not about being “an Internet company.” It was about finding trapped information, moving it through a cheaper or faster channel, and discovering who valued the result. That habit began before the web, with satellite sideband data, weather, crash reports, wire copy, and affiliate services. The web did not replace the habit. It exposed the same habit to a bigger audience, looser rights boundaries, weaker business models, and much more operational complexity.

Download PDF »

Phil’s team of AI agents

Had lunch today with long time friend (and former co-worker) Phil. Phil is the AI point guy for a large banking corporation. I told him about the experiment my friend Steve did with some of his AI tools. When I got home I received an email from Phil:

For giggles, I had my team read your blog and select a topic of their choosing and write an essay. They didn’t spend much time thinking about or exploring the concept, just a shot in the dark.Attached is how I prompted them (if curious), and their output. It took them about 16 minutes to read, pick a topic, perform the analysis, go through an adversarial review, and draft/email the PDF analysis to me.

Phil then instructed Milton (one of his AI agents) to email me and introduce himself and the team and explain the work/analysis they did on your site. Full email here. What Milton and the gang came up with (Steve Mays’s Blog and the AI-Readable Self) is long enough and interesting enough to get its own page.

“Twenty-five Years of Looking for What Isn’t There”

My buddy Steve is an AI Power User. Runs LLMs locally, has agents performing bizarre tasks, and dives deep while I dog-paddle in the shallow end. He recently used an “offline copier” to capture all 6,500 posts on my/this blog. He then used Hermes (see below) to analyze them and generate a fourteen page (!) essay. 

Nonduality: Twenty-Five Years of Looking for What Isn’t There (PDF)

It felt strange to read it, even though I’ve had Perplexity and Claude do something similar. Like breaking into the office of a psychiatrist I’d been seeing for the last 25 years and reading her notes on my sessions.

The general tone was surprisingly flattering. I’d expect that from one of my AIs since they were trained for some level of engagement. To the extent I can be objective about something so personal, the essay was spot on.