_{February in review!}

Five weeks ago I started this newsletter barely knowing if I'd have anything to say. I had Claude, a newsletter account, and 51 people who were kind enough to humor me. Ten posts later, something has clicked that I didn't explicitly plan: every piece I've written comes back to the same idea that has been rattling around inside me for a year.

AI doesn't replace you. It reveals you. This newsletter explores what that means for transit, and how to get started.

So here's the best of month one — and where to start if you're just joining us.

Is Your AI Policy Setting You Back? has struck a nerve. Everyone is grappling with this right now, and most agencies are getting it exactly backwards — mandating a single tool when the tools change every few months. I make the case for two guardrails and a green light. If you're writing (or rewriting) your AI policy, start here.

The Operator We Almost Lost is the piece I'm most proud of. It's about a bus operator — one of the best you'd ever want representing your agency — who's about to fail his CDL test for the third time. Not because he doesn't know the material, but because a 150-page PDF in his second language doesn't match how his brain learns. It's also about me, and the guilt I've carried since I was a co-op student about how my own brain works. AI didn't fix either of us. It met us where we are — and that changes everything.

These are the pieces where I've been working out what this moment really means for how we lead, hire, plan, and serve communities.

Why You Should Love Walmart makes the case that AI is the biggest paradigm shift since the personal computer — and most agencies are responding to it the way Walmart's competitors did. The real story isn't about adopting a tool. It's about rebuilding your operation around the reality that analysis is now instant. I point to a dashboard that a former NYC Transit SVP built in two hours that would have taken 24 months in 2021. Let that sink in.

AI Has a Trust Problem was born from a question I keep hearing: "Can I trust this?" When AI compresses three weeks of work into three hours, we lose time-spent as our proxy for thoroughness. I lay out three skills — intuition, judgment, and influence — that your entire team needs to develop to turn AI-assisted velocity into outcomes people actually believe in.

I'm Not Betting on AI. I'm Betting on Humanity. is the philosophical stake underneath all of this. When AI handles the research, analysis, and synthesis, the scarcest resource becomes our humanity — empathy, lived experience, the wisdom that only comes from being wrong. If you're thinking about AI training for your team, don't start with the tools. Start with the humans.

Is Paying for AI Really Worth It? is the question I get asked more than any other. Short answer: yes. The free models are Zoolander — gorgeous, confident, not a lot going on upstairs. The paid "thinking" models are where the real magic lives, and I break down exactly why with a side-by-side comparison that'll make you laugh and then immediately open your wallet. Twenty dollars a month. The ROI is absurd.

"Why Does This Suck?" is the single most useful habit I've built. Once you have a draft of anything, ask your AI why it would fail. Not to rewrite it — to poke holes so you can think better. I've thrown out entire polished drafts because of this question, and the replacements were always stronger.

Also worth your time: Spit It Out Already — the best way to get started with AI is to stop typing carefully and just talk (you've been doing it since you were two). Follow Your Energy — how connected AI lets you capture good thinking from anywhere, even lying in bed at 9pm. And Welcome to Transit Intelligence — the origin story of how Claude smashed my piñata and got me writing.

This month I'm going deeper. I'll be exploring why urgency matters right now and why waiting to adopt AI isn't the safe bet it feels like. I'm diving into the art of transit leadership itself — what it actually looks like to lead through a paradigm shift. And I'm getting into the practical magic of tools like Deep Research and Claude Cowork that are dramatically changing what a single person at a small agency can accomplish.

Stay tuned.

I started this with 51 people. We're now at nearly 100. I don't have an ad budget or a marketing team — this grows when you forward it to someone who needs it and they subscribe. If one piece above made you think of a colleague, send it to them. We’re bootstrapping change in the industry together.

One person. 🙂

TransitGPT is where I share practical AI insights for transit leaders. Subscribe if this resonates or forward to a colleague who needs it. And hit reply — I read everything.

Go shatter your glass ceiling.