Hey there.

So I did the thing where you spin up a brand new site, pick a name you're excited about, and then almost immediately realize it's not quite right. stackandsignal.com had a very short life. The newsletter name stays, but everything else now lives at jimmypiraino.com. Blog posts, projects, the little weird stuff I build on weekends -- all under one roof, all under my actual name. The reason is simple: I wanted a single place that was just mine, not a brand I'd have to explain or justify.

Ethan Marcotte wrote a piece a few years back called Let a website be a worry stone, and that idea has been bouncing around my head ever since. A personal site as something you return to, tinker with, sand down the edges of. Not because anyone's watching, but because the tinkering itself is the point. That's what jimmypiraino.com is for me now. It'll probably never be done, and that's the whole idea. Tune in next month for its next massive redesign.

Recent Posts

Tech Debt Has a Shared Login I found a rogue email platform hiding inside a previous org. Shared login, manually imported lists, segment names that only made sense to the three people who built them. The kind of scrappy setup that made perfect sense five years ago and is now a compliance, security, and deliverability risk. A post about empathy, nostalgia, and the unsexy work of actually fixing these things.

The Internet Made Me Who I Am (And Now I Don't Know What to Do With It) A personal essay about growing up online, building my first computer as a kid, falling down rabbit holes on the early web, and now trying to figure out what kind of relationship I want with technology as a parent. The internet I grew up with isn't the one that exists now, and I'm still working out where the good corners are.

Vendor Red Flags I've Learned to Spot A decade of evaluating martech has taught me what to watch for on vendor calls. The suspiciously perfect demo, the "our API can do anything" deflection, pricing that requires a call, changelogs that haven't been updated in 18 months. Practical questions to ask instead of taking the pitch at face value.

Am I Overengineering This? (A Quiz for People Who Already Know the Answer) I built an interactive quiz to help you admit what you already suspect: you're making this too complicated. Includes a confession about a Marketo lead scoring model I built with 40+ triggers that eventually got replaced with "did they fill out the demo form?" Ship it.

Links I'm Into

The reporter who tried to replace herself with a bot — Platformer's Ella Markianos spent 20 hours building a Claude-based agent to do her job, then put it to work alongside her. The results are funnier, more nuanced, and more unsettling than you'd expect from the headline.

Local-first software: You own your data, in spite of the cloud — Ink & Switch's essay on building software where your data lives on your device first, with collaboration layered on top rather than the other way around. If you care about owning your stuff and not renting your digital life from someone else, this is essential reading.

AGI is here (and I feel fine) — Robin Sloan's opening edition of his pop-up newsletter Winter Garden makes a sincere (and strategic) case that we should just go ahead and call it: AGI arrived. Not because nothing is left to build, but because endlessly debating the threshold is less interesting than asking what comes next.