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…
Category
Leadership
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…
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,…
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 I am Writing About AI (and Why It’s Not Just About My Company)
My marketing team has been asking me to write more about Markup AI — what we do, why it matters, where we’re headed. And I will. I’m the CEO of a company that builds Content Guardian Agents to help enterprises scale AI-generated content smartly and safely. I love what we’re building. I believe in it deeply. And I’ll reference it when it’s relevant. I also love how we’re building things, since we are hardcore practitioners using AI to build our business at decent scale. But if you’ve read this blog over the years — through my two decades at Return Path, my time building Bolster, and three books on startup leadership — you know that’s never been what this space…
Announcing the launch of the Startup CXO mini-books for CFOs, CROs, CMOs, CTOs, and CPOs
I’m thrilled to announce that we created mini-books (about 80 pages long and only $9-10 on Amazon) out of five of the major functional areas covered in Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams, part of our series along with Startup CEO: A Field Guide to Scaling Up Your Business and Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors. I’ve always said that while I love all three books, in some ways Startup CXO is the best because it’s a “book of books.” While I’d still encourage all CEOs and senior executives (CXOs) to read the full manuscript, my friends and co-authors and I are happy to…
Why Executive Searches are So Slow, and What You Can Do About That as a Candidate
It’s been a big break between posts – as many of you probably know, I moved to Board Chair and left the CEO role at Bolster last summer (it’s now in the very capable hands of my friend and co-founder Cathy Hawley), and I’m now CEO of a super cool AI company called Acrolinx. So yes, that means I went through a job search – and I found my ultimate job as a result of an inbound cold email from a headhunter! The rich irony in that as someone who founded an executive search platform is not lost on me. So when a good friend of mine who is also between CEO gigs and looking at several opportunities asked me…
New Podcast – Something Old, Something New, Something Red, White, and Blue
I’ve been uncharacteristically quiet since April (I still hate non-competes and while I respect the right of the Chamber of Commerce to sue the FTC, I hope common sense prevails). Between then and now, we switched things up at Bolster, and my co-founder Cathy Hawley is now the CEO. Things are great there, and if you need any executive search help (Director to C-level or Board/Advisory/Fractional), let me know. I’ve been hard at work on a passion project while I’ve been between things professionally, and I’m excited this week to announce the launch of my new podcast mini-series, Country Over Self: Defining Moments in American History. That link is to the web site where you can see the whole plan…