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…
Category
Entrepreneurship
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…
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…
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…
AI won’t necessarily take your job, but someone who uses it will
AI is going to destroy a lot of jobs. Let’s just start there. White collar jobs. Desk jobs. The kind of jobs where your primary output is information, analysis, or words on a screen. This isn’t speculation — it’s already happening. But here’s the thing: the world has survived every major technological disruption in history. When the power loom arrived in the early 1800s, hand weavers rioted — literally smashed the machines — because they were certain it was the end of work. It wasn’t the end of work. It was the end of that work. New work emerged that no one could have predicted, like, oh say, the commercial mass-produced clothing industry, which had even more jobs on the…
MattBot: My First Agent
In May 2023, Fred Wilson wrote a post about being approached by a company that had trained a large language model on all 9,059 of his AVC blog posts. They wanted to offer a chatbot called “Ask Fred.” He said no thanks. His reasoning was sharp. He’s fine with anyone using his content to train AI. He put a Creative Commons license on his blog from the start. But he didn’t want a bot pretending to be him. The whole point of his blog is the humanity — the daily conversation, the thinking out loud, the relationship with readers. A chatbot that mimics Fred Wilson isn’t Fred Wilson. It’s a parlor trick. I read that post and agreed with Fred…
Meet Chatgipity: a Unified AI Platform for Our Company
A little over a year ago, my friend Dan Shapiro, CEO of Glowforge, showed me what his team had built internally with AI tools. Not one-off ChatGPT experiments. Not an AI pilot program. A real, unified infrastructure where the whole company was using AI through a common platform with shared agents, shared memory, and shared integrations. I walked away from that conversation knowing we needed to do the same thing. A few weeks later, our VP of Technical Operations, Martin Hempstock, stood up an instance of LibreChat — an open-source AI platform that brings together all the major LLMs into a single, customizable interface. Martin had it provisioned under a new subdomain within days. It’s changed the way we work….
Why AI Content Needs a Guardian: Introducing Markup AI
(I realize I’ve been relatively quiet since I started my new job in January…this is what I’ve been up to. It may be the most interesting job I’ve ever had…but more to come on that over time.) I was at a recent Gartner CEO conference on AI in New York City, and one phrase keeps rattling around in my brain: “There is such a rapid pace of development that we are regularly seeing ‘obsolescence before maturity.’” In other words, by the time AI products reach early adoption in the market, they’re already obsolete. But here’s the thing – while everyone’s racing to build the next AI breakthrough, they’re missing a massive problem hiding in plain sight. AI has fundamentally changed…