There’s a fundamental truth about AI that most people don’t think about enough: the transformer architecture — the engine underneath ChatGPT, Claude, Gemini, all of them — is predictive by nature. It analyzes the most likely next word and generates it. That’s extraordinary and powerful, but it also means AI isn’t thinking. It’s pattern-matching at superhuman speed. And here’s the other thing: AI models are typically trained at a point in time. They’re not updated in real time as the world changes around us. Not yet, anyway (although some are designed and some are getting better at incorporating real-time search results). What does that mean for people using AI to help them write things? Or for people building agents to…
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Current Affairs
Curated Reading on AI, Part II
In Part I, I curated a lot of big picture articles about AI and society. Today’s post will be more practical and tactical about the business of AI. First from Thomas Tunguz at Theory Ventures – The AI Problem Matrix, which does a great job of laying out a framework for where and how humans (and also AI/Software) will be able to create value in the new world and where it will be capped. Next, two interesting articles about where pricing is headed or not headed in the world of AI where everyone is waxing philosophic about “outcome based pricing,” but no one has quite figured out what that means yet for the vast majority of use cases. We certainly…
July 4, 2026, Post III: Launching Bedrock.guide, a new civic identity and action platform for independent-minded citizens
Yesterday I published a five-thousand-word roadmap for fixing America’s broken political system (the Small). Thirty-odd structural reforms, fifteen years in the making. Nonpartisan redistricting. SCOTUS term limits. Killing the debt ceiling as a weapon. The whole plumbing. And the day before that, I relaunched the Country Over Self podcast – the Medium. Consider this the finale of a three-day civic bender to celebrate the 250th anniversary of America’s founding this long weekend. Here’s the uncomfortable thing about that roadmap: I can’t do a single item on it. I’m not in Congress. I’m not on the Court. I can’t summon an independent redistricting commission into being from my desk. The roadmap is what should happen. It is not, by itself, something…
July 4, 2026, Post II: A Roadmap to Fix America’s Political System…15 Years Later
As part of my three blog posts to celebrate the 250th anniversary of America’s founding this long weekend, this is the Medium (yesterday’s was the Small). I’ve written about two intersecting topics on this blog over the years. In 2011, I wrote what I called “the beginnings of a roadmap” to fix America’s badly broken political system — a short list of structural reforms framed, as I noted at the time, as “a typical entrepreneur’s approach.” And in 2021 and 2023, I wrote twice about whether CEOs should wade into politics — moving gradually from “only when it directly affects your business” to “also when it indirectly affects your business, including the health of democracy itself.” Fifteen years later, I…
July 4, 2026, Post I: Country Over Self redux
I’m going to write three blog posts to celebrate the 250th anniversary of America’s founding this long weekend, one per day. They fall into Small, Medium, and Large t-shirt sizing. Today, the Small. I launched a limited edition podcast series called Country Over Self: Defining Moments in American History in October 2024 – at the time, I blogged about it here. The series had 13 episodes in which I interviewed prominent historians about individual presidencies and critical moments to analyze the premise of presidents choosing country over party or country over self (or not). My hope was that, in some small way, telling some of our shared stories and highlighting some of our shared values as a country might plan…
Chatting with my DNA – a fascinating personal use case and a deep rabbit hole
This one has nothing to do with running a company. But it’s one of the most fascinating things I’ve done with AI, and I fell down such a deep rabbit hole that I have to share it. My friend Chad Dickerson — former CEO of Etsy, now an executive coach — mentioned that he’d uploaded his raw DNA file to an AI and started asking it questions. My reaction was something like: wait, you can do that? You can. Here’s how. If you’ve done 23andMe (or Ancestry.com — the process is similar), you can download your raw DNA data file. It’s just a text file full of SNPs — single nucleotide polymorphisms, the genetic markers that make you you. Upload…
Don’t Start a Forest Fire to Roast a Marshmallow (literally or figuratively with AI)
My friend Andrew Winston has spent the second leg of his career the last two decades working on corporate sustainability, advising some of the largest companies in the world on how good business practices drive good business outcomes, and writing some amazing books. I posted about his first three here and here and here many years ago and oddly didn’t post about his most prominent book with Unilever CEO Paul Polman more recently. Andrew was recently named the #1 Management Thinker in the World by Thinkers50, which I didn’t even know was a thing, but now I get to tease him that he’s Public Intellectual #1. Andrew had a great idea recently for a small but powerful browser extension that…
AI Isn’t Hard. You Just Need a Cheat Sheet.
Running Markup AI — a content governance platform built on top of large language models — means I spend a lot of time talking to executives about AI, as well as friends and family who aren’t involved in the tech sector for a living. And I’ve watched the same scene play out over and over: a smart leader sits through a vendor demo, someone drops “context window” or “RAG pipeline,” and they nod along confidently while having absolutely no idea what was just said. I’ve been that person. You probably have too. Here’s the thing — the concepts aren’t complicated. The inventors just gave simple ideas intimidating names. Here’s your cheat sheet. Large Language Model (LLM) or Foundational Model or…
Claude and Henry Kissinger, aka, Is This Your Best Work?
I was recently reminded of the great story about Henry Kissinger and work product quality. I can’t figure out if it’s true or apocryphal, but it doesn’t really matter. Here’s the version I found online, commonly attributed to Winston Lord, who served as Kissinger’s Special Assistant and later as Ambassador to China. Lord works for days on a report and submits it to Kissinger. Kissinger returns it with one question: “Is this the best you can do?” Lord takes it back, reworks it, resubmits. Kissinger returns it again. Same question. “Is this the best you can do?” This goes on — six, eight, maybe ten rounds. Finally, Lord brings back a draft and declares: “Damn it, yes, it’s the best…
SaaS Is In Even More Trouble Than The Hype Would Have You Believe
The current debate about whether “SaaS is dead” has two camps. Camp one: SaaS is in serious trouble at the hands of AI. Camp two: SaaS is just fine, nothing to see here, folks. Both camps are wrong. The truth is more interesting — and more concerning for incumbent SaaS companies — than either side admits. The Stock Market Is Sending a Signal Start with what the public markets are telling us. Salesforce is down over 40% from its highs, and the slide has been relentless — dropping 20% in 2025 and another 10%+ to start 2026 as AI monetization concerns shake the software sector. Adobe is in even worse shape —down 34% in the past year, hitting a seven-year…
Curated Reading on AI
One of the hardest things about being a CEO in the AI era isn’t the technology itself — it’s the firehose of information about the technology. There’s so much being written about AI right now that it’s almost impossible to separate the signal from the noise. Hot takes, doomsday predictions, breathless hype, vendor pitches dressed up as thought leadership — it’s exhausting. So I thought I’d do something useful and share periodically a curated basket of the most interesting reading I’ve done. Think of it as the reading list I’d hand to a fellow CEO who said, “I know I need to get smarter about AI — where do I start?” This first batch is a bit of a catch-up,…