The archive
Every issue.
Every issue of The AI Playbook, newest first. Each one is a single idea you can use at work that week.
Latest issue, No. 31 / November 9, 2026
Are you behind on AI? (stats inside)
Most companies aren't behind on access. They're behind on turning it into repeatable work. Here's how to tell which gap you have.
Read issue 31- No. 30 / October 26, 2026AI Has a Huge Problem: ROI (stats inside)Get your own AI Playbook created in real time
- No. 29 / October 8, 2026AI isn't coming for your jobIt's coming for your tasks. If you run a team, here's the list, and the prompt for every one. Plus what's new on the rebuilt AI Playbook: playbooks, skills, RE+SHAPE and 72 free prompts.
- No. 28 / October 2, 2026Don't just do 'old work' faster (details inside)Most AI advice starts with the technology. A year of asking a different question turned into a framework, and it is now a conversation you can have on the site.
- No. 27 / September 21, 2026700 People Fired! Everyone drew the wrong lesson from Klarna. The AI worked. What broke was the glue between systems — and we answered a context-switching crisis by shipping the 1,201st tab.
- No. 26 / September 8, 2026Is Your Company Behind in the AI Race?65% of CEOs fear they're underinvesting in AI and 80% think their job depends on it. It may all be a LIE!
- No. 25 / August 24, 2026The 95% Problem: Your AI Is Over-EngineeredMIT says 95% of GenAI pilots deliver zero P&L impact. The culprit isn't the models — it's over-engineering. AI should simplify the intelligence layer and be trusted to distill, not generate more things to read.
- No. 24 / July 30, 2026Workflows Are the Key to AI ROIEnterprise AI fails when it demands new behavior. Inject AI into the workflows your teams already run — at the exact bottleneck — and ROI shows up in weeks, not years.
- No. 23 / July 29, 202679% Think They're Winning at AI. Is it true? (Stats Inside)The stats between how well companies think they're doing with AI and how well they're actually doing show an industry-wide delusion. 74% of executives admit they've overstated confidence in their AI strategy. Here's the pattern that separates the 1% from the 79%.
- No. 22 / July 29, 2026The SaaSpocalypse: $234B in Enterprise Software Is About to Get Killed by AgentsGartner just put a number on the knife at the neck of the SaaS industry: $234 billion in enterprise software spending at risk from agentic arbitrage by 2030. Every login-screen product is now optional. Here's what survives.
- No. 21 / July 29, 2026The Botsitting Tax: Your AI Is Costing You 6.4 Hours a WeekThe average knowledge worker spends 6.4 hours a week feeding AI context, checking outputs, and fixing mistakes. Meanwhile 42% save 8 hours a week — a full workday — and 66% have no idea what to do with the time. The real ROI story of enterprise AI in 2026.
- No. 20 / June 30, 2026Distribution is the Hardest Part Now — Not Developing ToolsSoftware used to take days, weeks, months. Now it takes seconds, minutes, hours — which means building isn't the moat anymore. Being seen is.
- No. 19 / June 10, 2026Your Company is officially a start-up. All companies are.Every company is now a startup because the tech stack is obsolete. That makes your executive team a founding team — whether they like it or not. CRMs, BI, BDR and even typing all dead by end of 2026.
- No. 18 / June 5, 2026I Built Dashboards for Sales Teams. AI Killed Them All.Years of building dashboards — pipeline views, leaderboards, attribution boards — now obsolete. Text-to-SQL isn't the answer. The intelligence layer is.
- No. 17 / May 20, 2026The CTO's Line in the SandRemove the entire 'What I'm Building' section (MediaSignals.ai / Essentialist.io / Salesnado.com); flows from 'What I'm Watching' straight to 'The Bottom Line'
- No. 16 / May 12, 2026AI Should be a Painkiller, Not a VitaminAI is a very smart engineer. Its most expensive mistake: optimizing a thing that should not exist. The painkiller list is shorter than you think — and Musk's 5-step Algorithm puts 'Automate' last for a reason.
- No. 13 / May 8, 2026Welcome to the Era of the Vibe HustleEveryone is vibe coding side hustles. Most will fail. But the ones who fail still win — because the real hustle was learning to build.
- No. 14 / May 8, 2026Make A Personal AI Agent with a Brain, Name and EmailHow I built a personal AI agent with its own identity, email, calendar, iMessage, and a persistent Second Brain — and why it changed everything.
- No. 15 / April 30, 2026The Browser Is Dying. Agents Are the New Users.Salesforce just declared software is going headless. 92% of AI searches end without a click. The browser era is ending. Here's what to build instead.
- No. 12 / April 9, 2026Death by a Thousand Subscriptions: The AI Containment Problem78% of employees are bringing their own AI tools to work. Your controller just flagged 75 charges. Here's how to contain the chaos without killing the energy.
- No. 11 / April 6, 2026Who "Owns" AI Inside Your Company?Copilot is the participation trophy of enterprise AI. 3% adoption after two years. Here's who should actually own AI adoption — and the 6 models every company is fumbling through.
- No. 10 / April 4, 2026The Workflow Revolution: When AI Forces You to Throw Out 20 Years of Dev PracticesReal talk on how AI coding isn't just changing what we build—it's forcing teams to completely re-engineer GitHub workflows, deployment cadence, and everything we thought we knew about shipping software.
- No. 9 / March 28, 2026Website. Phone. Email. AI.Zuckerberg says every business will have an AI — just like they have a website, a phone number, and an email. He's not predicting the future. He's describing the present.
- No. 8 / March 25, 202674 Releases in 52 Days. How Is Any CTO Supposed to Keep Up?Anthropic shipped 74 Claude releases in 52 days. Meanwhile, 89% of enterprises are 'learning as we go' and 74% of CIOs regret a vendor decision. Here's a framework for operating in permanent uncertainty.
- No. 7 / March 23, 2026B2A: Your Next Million Users Won't Have FacesY Combinator says 'make something agents want.' AgentMail, Moltbook, and Essentialist.io are already doing it. Welcome to Business-to-Agent — the category that kills per-seat pricing.
- No. 6 / March 19, 2026My Son Shipped an App at Midnight. He's Not a Developer.Two generations, two living rooms, both building software past midnight with AI. Vibe coding isn't a trend — it's the end of gatekeeping in software.
- No. 5 / March 19, 2026Nobody Builds Hero Sections for RobotsMeta bought Moltbook. AgentMail raised $6M. The Nasdaq Cloud Index lost $300B. The visual web is becoming optional — and entire job categories are going with it.
- No. 4 / March 19, 2026Stop Trying to Run OpenClaw on Shared HostingI wasted a weekend fighting Hostinger. OpenClaw on dedicated hardware took 20 minutes. Here's the infrastructure decision that actually matters.