95% of AI pilots never make it to production. If you’re reading this, yours probably didn’t either. Most people blame technology. Wrong model, wrong vendor, wrong implementation. Brett Schklar has spent two years working with 1,800 CEOs and business owners, tracking AI adoption across every department and industry vertical. His data tells a different story. […]
When Models Lie and You’re Still Paying for the Tokens
The $200 Lesson in AI Reliability Your AI just confidently walked you through a solution that made your problem worse. And you’re still paying for those tokens. This exact scenario happened to my podcast co-host Eli last week. His bike’s electronic drivetrain stopped working properly, a system so reliable he’d never learned to adjust it […]
Why Your AI Productivity Wins Are Making Your Best People Miserable
Your top AI performers are burning out, and the productivity metrics you’re celebrating might be hiding a human infrastructure crisis that threatens everything you’ve built. I had three different conversations last week with leaders running “AI-first” teams. Each was bragging about 10x, 50x, even 100x productivity gains. But when I dug deeper, the same pattern […]
The Implementation Reality Nobody Talks About
Aaron Wilt should be winning at AI. He’s technically sophisticated, runs a 40-person company, understands the technology deeply, and has given his team access to every major AI platform. Six months after his initial rollout, they were still doing most things manually. This isn’t a story about companies that don’t “get” AI. This is about […]
The Microsoft-Claude Connection That Actually Transforms Productivity
The Integration Most Companies Are Missing I’ve been a Microsoft skeptic for years. Word and Excel always felt like digital relics compared to Google’s cloud-native approach. But something fundamental shifted in the productivity landscape that caught me completely off guard. It wasn’t Microsoft Copilot, that’s still an expensive Clippy with better graphics. The breakthrough came […]
Most Organizations Are on Level One. Here’s What the Map Actually Looks Like.
When I ask audiences what they’re using AI for, the honest answer, the one that cuts through the excitement and the strategy decks and the pilot program announcements, is that most people are still opening a chatbot, typing a question, and closing the tab. That’s not a failure. It’s a starting point. But it’s worth […]
Token Maxing Is Burning AI Budgets. Here’s What Your Company Actually Needs
A Stockholm engineer recently told The New York Times he spends more on Claude than he earns in salary. Uber engineers reportedly burned through their entire 2020 AI budget before Q1 ended. Jensen Huang declared that $500,000-a-year engineers should consume $250,000 worth of tokens annually, or he’d be “deeply alarmed.” Welcome to the token maxing […]
Why Your Chief of Staff Dreams About You (And How the Monothread Format Changes Everything)
Your company spent six figures on AI tools last year. Your team is still switching between twelve different apps to get anything done. If this sounds familiar, you’re not alone. I see this pattern constantly: organizations buying AI solutions that solve the wrong problem entirely. They want better writing, faster analysis, smarter automation. What they […]
The Day My Entire AI Operation Went Dark (And What It Taught Me About Vendor Risk)
At 6:15 AM on tax day, I learned an expensive lesson about AI dependency that most organizations haven’t considered yet. I was excited to use the early morning hours productively. Pacific time zone advantage, quiet house, perfect conditions to build the automation I’d been planning. Then Claude went offline, and 22 different business tools stopped […]
The End of Fiddliness: How One Conversation Replaced Seventeen Apps
I haven’t opened ClickUp in six days. Not because I stopped using it. Not because I found a better project management tool. Because I realized something that changes everything about how we work: most productivity problems aren’t tool problems. They’re interface problems. Here’s what happened when I decided to eliminate what I call “administrative fiddliness” […]










