I write about AI strategy, leadership, and technology.
Most companies are running two AI strategies. The official one lives in slide decks, steering committees, and enterprise agreements. The real AI strategy runs in the tabs that get minimized when the boss walks by. After letting teams run wild with expensive tools, Microsoft started canceling most Claude Code licenses across a major division and Uber burned through its entire 2026 AI budget in four…
In 2025, 42% of companies abandoned most of their AI initiatives - up from just 17% the year before. The culprit wasn’t bad implementation or insufficient data. It was math: a 99% accurate AI agent performing 50 sequential steps succeeds only 60% of the time, and most enterprise workflows require far more than 50 decisions. The industry has been optimizing the wrong variable. Executives…
Anthropic’s AI agent was the most prolific code contributor to Bun’s GitHub repository, submitting more merged pull requests than any human developer . Then Anthropic paid millions to acquire the human team anyway. The code was MIT-licensed; they could have forked it for free. Instead, they bought the people. Everyone’s heard the line: “AI will write all the code ;…
Palantir didn’t have a working product for the first several years. What they had were brilliant engineers building custom solutions on customer sites. Somehow that “broken” model made them worth nearly $500 billion. The company that couldn’t ship software became one of the most valuable enterprise platforms of the decade by doing the one thing every engineering VP tries to…
During a summer blackout when I was a kid, a neighbor ran an orange extension cord across the street so our freezer wouldn’t thaw. It looked absurd: this thin line humming with borrowed power, keeping the lasagna alive. But it worked. In a pinch, you build your own grid. OpenAI is doing the grown-up version. Not with cords, but contracts. They’re stringing a private power grid across…
When I was eight, my save button was a pencil. Not the controller. A pencil. And a scrap of paper. You’d finish a stage in Mega Man 2 and the game would show you a grid. Five rows of dots, each one either empty or filled. You’d copy it down dot by dot, turn off the NES, and come back days later. Enter that same pattern and your world reappeared. All eight robot masters. Every E-tank.…
Remember when Neo downloaded kung fu directly into his brain? “I know kung fu,” he said, eyes snapping open after seconds of upload. That scene from The Matrix doesn’t feel like science fiction anymore. It’s basically Tuesday for any junior analyst with ChatGPT. Generative AI has become an experience accelerator that compresses decades of pattern recognition into an…
A reputation can be erased with three permissions most companies don’t control. Think of it like Thanos’s gauntlet, but the stones are Reddit Mod, SERP (Search Engine Result Page), and LLM (like ChatGPT). Slip that glove on and reality bends. Not because the truth changed, but because the places people trust to find the truth did. The Bootcamp That Got Slowly Strangled Lars Lofgren documented a…
There's a specific kind of technology leader who has become endangered: the one who builds things. Not the kind who orchestrates vendors. Not the kind who manages integration roadmaps between Salesforce, HubSpot, and whatever AI wrapper launched last week. I'm talking about the CTO who looks at a problem and thinks, "We should own this." David Heinemeier Hansson (DHH to most) is one of these…
A team installs AI coding assistants. Engineers report feeling 40% faster. Ship dates don't move. A lab buys pipetting robots. Throughput jumps 3x per station. Projects still run late. A finance team automates their models. Analysts save hours daily. Deal flow stays flat. The pattern is so consistent it's almost boring: tools create capacity, but capacity without workflows dissipates. The energy…
Watch someone use ChatGPT to research. They type, wait, skim, and act. No scrolling endless search results. Just a verdict, a decision, and a click. That behavior is why Answer Engine Optimization (AEO) exists - the craft of showing up in the synthesis, not ranked on a page. Google trained us to climb to number one on a page of blue links. Now the “page” is a paragraph stitched from everywhere.…
The most expensive real estate in the world isn’t oceanfront - it’s the default button. Google reportedly paid Apple $18–$20 billion to be the default search on Safari - not the best search, the one that shows up without a thought. That price isn’t about features. It’s about gravity: the path everything takes when no one is pushing. This matters because most teams still try to win by arguing,…
In every great kitchen, speed and consistency don't come from more gadgets. They come from mise en place — the small, disciplined set of knives, pans, and staples laid out the same way, every time. I learned this watching a chef glide through a Friday dinner rush with the grace of a violinist. Her secret wasn't molecular gastronomy equipment; it was a ruthless commitment to the few tools she…
A few months ago, a product lead at a mid-market SaaS company told me about her team’s long, expensive slog to launch an “AI-powered” dashboard. They spent months wrangling data, tuning models, and building a feature that would predict churn and surface insights. The result? A widget that looked impressive in demos, but rarely changed what users actually did. Meanwhile, her backlog ballooned.…
Last week, I spoke with a CTO running technology for a $500M distribution company. He's a sharp executive with two decades of experience, overseeing custom-built systems moving twice as fast as the industry standard. They'd already deployed ChatGPT licenses, engaged an AI automation vendor on a six-figure deal, and achieved such productivity with developers using AI that they were moving faster…
In 1927, Henry Ford made a revolutionary decision to transition his workforce to a five-day workweek. The reason wasn't just altruism - he discovered that productivity actually increased when people had more personal time. Nearly a century later, we're facing a similar inflection point with artificial intelligence. The most compelling AI solutions don't replace humans. They free us to be more…
Not too long ago, if you wanted to picture a technology that made decisions on its own, you might think of Tony Stark chatting with J.A.R.V.I.S. - that all-knowing AI butler from the Iron Man movies. J.A.R.V.I.S. wasn’t just an assistant; it was an active partner, anticipating needs, solving problems, and pushing Tony forward. Once, that kind of autonomy seemed squarely in the realm of Hollywood…
We romanticize beginnings. January 1st becomes a sanctuary for our procrastination, a mirage of the perfect time to start. But here's the harsh truth: big projects don't wait on calendar dates. They require momentum, and momentum starts now. Waiting for January feels safe. It gives us a cushion, a grace period to "prepare." But our cushion quickly turns into quicksand. The first weeks of the new…
In 1985, Warren Buffett wisely said, "The first rule of investment is don't lose. And the second rule of investment is don't forget the first rule, and that's all the rules there are." Similarly, the first rule of AI investment is to focus on the customer first . And the second rule of AI investment is don't forget the first rule. In the four decades since Buffett's quote, investors around the…
CIOs have the hardest job in the C-Suite in 2024. The pace of change is eating your lunch, while the constant pressure to innovate within shrinking budgets makes the role particularly challenging. This pain radiates at every level of the organization. I love Stranger Things , the era, the mystery, and the ability to watch reality break down in real time, right in front of our eyes. One day, you…