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…
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Business
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,…
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…
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…
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…
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…
Good riddance to non-competes
I love that the FTC just banned non-competes, as everyone expected they would. Normally, I’m in favor of small government and fewer regulations, but this is one where I think the government has a legitimate interest in setting up guardrails to a free market. We started off at Return Path years ago with a standard and fairly benign non-compete because they were standard. But once California banned them and then we started doing business internationally in countries where they were illegal or not customary, we realized it was unfair to treat some employees different than others, so we got rid of them entirely and reverted to the common denominator. We don’t have them at Bolster. Restricting employees in terms of…