Raising, Mentoring, and Learning at the Same Time
Building with AI feels like parenting a kid, running an internship, and taking a masterclass, all in the same afternoon.
Hi All!, reall John here, I am going to write a few articles over this holiday weekend. This is the first one. I went to a conference this week (Ship!NYC a Vercel event). It was amazing. I spent the day with a v0 expert and a Vercel Solutions architect. Not because I’m special, but because they wanted to see how their projects worked in the wild. It did not go well originally, and then the next day it all clicked for me. It is almost 12:30am (and for those who know me this is exceptionally late) and I’m a morning person. But I’m excited… I’m building stuff for work and loving my job. Anyway, was playig with Fable again, the new sonnet, switching to Codex, and figuring out how to work with AI not repetitively but in a fun way that is efficient. 9 of diamonds. if you know you know. Ok, life is fun and exciting, and sometimes I think I’m getting bored and not sure what else to do… and then… a week like this happens and I have new problems, new tools, and new ideas. Anyway, I’ll write a bit more this weekend and some of it won’t be coherent, it will truly be a stream of consciencness writing… you know a brain dump. I may do a live stream but definitely play some street fighter. Have a great weekend.
Let’s get into the newsletter…
I caught myself doing something strange last week. I was three hours into a session with Claude Code, and I switched voices without even noticing. One minute I was setting boundaries, telling it exactly what NOT to touch, the way you’d tell a toddler not to run into the street. Ten minutes later I was reviewing its output like a manager grading an intern’s first pull request, generous but specific. Then it explained a pattern back to me that I hadn’t considered, and I was the student, taking notes from a professor who happened to be running on my laptop.
Three roles, one session, no script for any of it.
That’s the part nobody prepared me for. Everyone talks about AI coding tools like they’re a single relationship. Prompt in, code out. But if you’ve actually built something real with these tools, you know it’s not one relationship. It’s three, shifting under you depending on the moment, and the builders who get the most out of AI are the ones who know which role they’re playing at any given second.
The Parent Moment
Early in a project, you’re the parent. You set the rules before the kid can break anything expensive. This is your CLAUDE.md file, your project conventions, your “don’t touch the payment logic without asking.” Skip this step and you’ll spend your evening cleaning up a mess a two-year-old made with a permanent marker on your architecture.
I learned this the expensive way building Cash Critters. Early sessions without clear boundaries meant I’d come back to files touched that had nothing to do with what I asked for. Once I started treating context the way you’d childproof a house, before letting the kid loose, not after, the chaos dropped fast.
The Manager Moment
Once the guardrails exist, you shift into managing an intern. A sharp one. Fast, tireless, occasionally overconfident. You review the output. You ask clarifying questions. You don’t just accept the first draft because it compiled. Managing an intern well isn’t about micromanaging every keystroke, it’s about knowing when to trust the output and when to say “walk me through your reasoning here.”
This is where model selection actually matters, and it’s not a minor detail, it’s the whole management decision. Handing your intern the wrong tool for the job is on you, not them. There’s real research right now on context engineering, the discipline of curating exactly what an agent sees instead of dumping your whole codebase at it and hoping for the best. The teams treating this seriously are seeing real gains. The ones skipping it are getting confident, wrong answers delivered with a straight face, which is worse than an intern who says “I don’t know.”
The Student Moment
Then, without warning, the roles flip. The tool explains something I didn’t fully understand, a pattern, a tradeoff, an edge case I hadn’t thought through. Suddenly I’m not managing anything. I’m learning. That’s the moment most builders miss because they walked in expecting a vending machine, not a professor. If you never let yourself be the student in this relationship, you’re leaving half the value on the table.
What Actually Works
Here’s the practical version, because I promised you something you can use, not just a metaphor to nod along with:
Set the boundaries before you need them. Write your context files, your conventions, your “don’t touch this” list, before the session starts, not after the damage is done.
Match the tool to the task, deliberately. A UI generator is not a debugging specialist. Know which model or tool you’re reaching for and why, the same way a good manager doesn’t hand every task to the same person regardless of their strengths.
Review the output like you’d review a junior dev’s PR. Ask why, not just what. Confidence from an AI is not the same as correctness.
Let yourself learn. When the tool surfaces something you didn’t know, sit with it. That’s not the tool showing off, that’s the actual upside of working this way.
The builders who are winning right now aren’t the ones with the fanciest prompt. They’re the ones who know which relationship they’re in at any given moment, parent, manager, or student, and who switch between them without ego getting in the way.
That’s the whole game. Set the boundaries, manage the output, stay humble enough to learn something.
Go build something amazing.
John Mann is the founder of Startups and Code LLC, a software engineering executive, and the guy who built Cash Critters for $50/month because constraints are a feature, not a bug. Subscribe for weekly takes on AI, startups, and building things that matter.