
Hi, I’m Joshua.
I was Chief of Staff at a fast-growing AI company, where you’d expect the team to be experts in using AI. Instead, I saw so much AI slop from my coworkers that I felt closer to Claude than to them.
While I was ahead of most of my coworkers, our CEO was miles ahead of me. Watching him work was inspiring. It showed me just how much faster and better I could become. But even though I worked with him more closely than anyone else, I couldn’t ask him for advice. It wasn’t that he would have minded. His focus was the most valuable thing in the company, and protecting it was literally my job. I was working remotely too, so there was no one at the next desk to lean on either.
Meanwhile I was under the same pressure as everyone else to produce more and move faster. To keep up, I built an automation to send the executive team their action items after every meeting. One day it ran without my supervision, something that was never supposed to happen, and sent out action items from a meeting that were plain wrong.
The AI doesn’t get in trouble when it’s wrong; the person who trusted it does.
A couple of weeks later, I was laid off. I’ll never know the exact reason, but that mistake certainly didn’t help.
That experience didn’t make me want to use AI less. When it works, it really works. I can accomplish in an afternoon what used to take me a week. But when it fails, it’s confidently, absurdly wrong, which stings even more because “intelligence” is in the name. The real issue wasn’t the tool. I had no guardrails around it, no habit of double-checking, and no one to ask whether the setup would hold. So I went and got properly good at this, and changed the way I work.
Ahead is exactly what I needed back then. Someone who’s already done what you’re trying to do, who keeps up as the tools change, and whose whole job is you.
