Sometimes when I’m mentoring an earlier-career founder/CEO, I cover a topic and think “I must have written a blog post about this, or a chapter of Startup CEO or CXO or Boards, in the past…” and then am shocked to discover later on that I haven’t. This topic is one of those topics, which came up in a recent conversation, and since sometimes the top-of-mind answer is the best one, I thought I’d recount it here. Let’s say things aren’t going well in a specific area of your company. Maybe even things have started going worse on a new leader’s watch. How do you know if it’s time to fire the leader? Worse – how do you deal with the…
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Business
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…
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…
Book Short: Incorruptible, right and timely and inspiring and depressing all at the same time
Incorruptible: Why Good Companies Go Bad… and How Great Companies Stay Great by Eric Ries is the rare business book that is the exception which proves that rule that business books should only be 50 pages long – look at the volume of dog-ears in my already-loved copy. I’ve known Eric for years, and he invited me to write a blurb for the inside cover of the book. My blurb was “Every founder eventually faces the board meeting where the mission is on the table. I’ve been in that room. Eric has too – and this book will help you walk out with your soul intact. Incorruptible is as practical as it is inspiring.” That is a good place to…
Fantasy Board: My Second Agent
I wrote my second agent — my Fantasy Board of Directors — inspired by Mike Collins, CEO of Alumni Ventures (I’m on Mike’s board). Mike had been experimenting with building AI personas of famous business leaders as thinking partners, and the concept stuck with me immediately. What if I could build a full board of advisors — people I’d never be able to recruit in real life — and use them to pressure-test my thinking? The idea got some great coverage in Fortune and Business Insider, so clearly it resonated. But what I didn’t share in those pieces was the detailed how — the construction instructions, the prompting approach, and the management discipline required to make it actually useful. Every…
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…
Public markets haven’t figured out how to bake in AI productivity gains
Yes, AI is driving the stock market. But look closely at what’s actually being priced in. Most of the AI-driven market gains are concentrated in companies that are vendors in the AI space — Nvidia, the hyperscalers, the infrastructure layer. The market is pricing in the building of AI. It hasn’t yet figured out how to price in the using of AI. That distinction matters enormously. There’s a line often attributed to Bill Gates, though it actually comes from Roy Amara, the former president of the Institute for the Future: “We tend to overestimate the effect of a technology in the short run and underestimate the effect in the long run.” That’s exactly where we are. The market has overpriced…
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…
AI Shortcut: How to Collaborate on Claude Projects Without a Teams or Enterprise License
I’m increasingly finding Claude useful to tell me how to best use Claude. I’m working on a project right now with a bunch of colleagues, and one of the limitations of Claude, even the Pro version, is that there is no option to invite other Claude users to collaborate on a project. In order to do that, you have to upgrade everyone to a Claude Team or Enterprise license — which may not be feasible for cost or logistical reasons. Our specific use case: a few of my Markup AI colleagues and I are vibe coding an app together in Replit (I can’t wait to tell you about it when it’s further along), and we are doing a bunch of…
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,…