AI is brilliant for automating things you already know how to do, or to create things based on content you’ve already mastered. But there’s an inherent risk in it. Human brains learn things by reading, processing, and doing, and outsourcing critical components of that process to AI is a disaster in the making, not by being great at writing prompts and distributing their downstream output. Let’s take an obvious somewhat extreme example. A clever sixth grader with a vague interest in American history could create a somewhat sophisticated analysis of a thorny constitutional law question – let’s say, an analysis of the Presidential immunity decision by the Supreme Court a couple years ago against the background of our own Constitution…
Category
Management
Garbage In, Garbage Out
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…
Where The Pundits Are Getting It Wrong – We Still Need Talented Software Engineers
There’s a narrative gaining steam in the AI discourse that goes something like this: coding assistants are getting so good that we won’t need software engineers anymore. Some version of “AI writes code now, so why would you hire humans to do it?” This take is wrong. Not slightly wrong — fundamentally wrong. And it’s wrong because it confuses three very different things. Writing Code, Building Products, and Building Companies Coding assistants write code. That’s a real and valuable capability. They can generate functions, debug errors, scaffold entire applications, and produce boilerplate at superhuman speed. No argument. But writing code is not the same as building a software product. And building a software product is not the same as building…
When is it time to fire an executive?
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…
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…
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…
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…
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….