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Phil Calçado

@philcalcado.com
1.1K followers 4.5K following 428 posts

Headed engineering at companies with either billions of users and no revenue, or billions in revenue and no users.

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Phil Calçado @philcalcado.com · 26/09/2026
I feel like every day I find out about another internet comedian I like who lives and/or was raised in Carroll Gardens
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Phil Calçado @philcalcado.com · 24/09/2026
We might have used up all the world’s water, but we finally got DHH to stop writing code. Worth it.
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Phil Calçado @philcalcado.com · 16/09/2026
And I didn’t want to get into this whole thing but the state of evals since late 2024 is kinda sad
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Phil Calçado @philcalcado.com · 16/09/2026
Nobody writes a $3M seed check for a classifier, so at my last startup we called ours something else. What was actually under the hood, and why @typesafeai.bsky.social's launch caught my eye: philcalcado.com/2026/09/15/c...
philcalcado.com
Classification Is (Often) All You Need
I do hope that TypeSafe AI and other companies doing similar work will finally fulfill the 2022 dreams of building AI products instead of merely using AI to build products.
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Phil Calçado @philcalcado.com · 04/09/2026
Email wasn’t replaced by Slack but by four hundred Google Docs on the same topic, all named 'Untitled'. I mean, if we’re writing memos like it’s 1954, we could at least bring back the pneumatic tubes.
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Phil Calçado @philcalcado.com · 24/08/2026
shut up, claude, nobody cares
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Phil Calçado @philcalcado.com · 19/08/2026
The hardest part of being a senior engineering leader is making enough room to do the job philcalcado.com/2026/08/18/t...
philcalcado.com
Treat Escalations as Defects
Every tactical decision that reaches a senior leader only because it has nowhere else to go is a defect—and their volume tells you how much of yourself the organization still needs to function.
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Phil Calçado @philcalcado.com · 18/08/2026
But as I see it the only way this crosses to the type of software I am talking about would be the SaaSpocalypse narrative, which I also think is just the newest iteration of a panic that happens every ten years for one reason or another
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Phil Calçado @philcalcado.com · 18/08/2026
So while I think AI is a potential huge leap in taking foward what these tools have been increasingly allowing power users to do since the 90s, I see just as natural evolution—if it wasn't LLM based AI it would be a future iteration of the lowcode tools
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Phil Calçado @philcalcado.com · 18/08/2026
On the former, I think we had different experiences, because to me, especially as a consultant in large organizations over the 2000s, it wasn't 'shadow IT' because these were supported and the users (accountants, project managers, etc) were expected to know and even have certifications in these
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Phil Calçado @philcalcado.com · 18/08/2026
Yeah, I think we're talking about different things. I'm not talking about eg. Attorneys building software for themselves and their colleagues, I'm thinking about an Attorney writing software that they then offer as a product/service to other organizations
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Phil Calçado @philcalcado.com · 18/08/2026
But isn't it an internal tool? I'm mostly talking about products Still, since I joined the industry in the 2000s there has always been a lot of internal tools built by making Excel talk ODBC with databases, or using VBA, Quickbase, MS Access, etc. I dont think there's really a recent uptick
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Phil Calçado @philcalcado.com · 18/08/2026
That's true, but I have never seen these outside internal tools and systems. Do we have some good examples of these tools being used extensively to build the software product?
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Phil Calçado @philcalcado.com · 12/08/2026
when the coffee shop puts on a bossa nova playlist and you’re the only Brazilian within a five-mile radius
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Phil Calçado @philcalcado.com · 12/08/2026
Being Brazilian in an American coffee shop means everyone else gets pleasant bossa nova ambience while I’m forced to understand that this man has been singing “sun, love, sea, you” on a loop for three minutes
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Phil Calçado @philcalcado.com · 12/08/2026
Being Brazilian in an American coffee shop means everyone else gets pleasant bossa nova ambience while I’m forced to understand that this man has been singing “sun, love, sea, you” on a loop for three minutes
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Phil Calçado @philcalcado.com · 12/08/2026
For ten years I've run the same RFC process for how engineers make technical decisions. In just a few months, AI broke its foundational assumption that a good document meant somebody had done research work So I wrote an update for an AI world—as an RFC, obviously philcalcado.com/2026/07/10/w...
philcalcado.com
Writing AI-Assisted RFCs
The Structured RFC Process was built on the assumption that people hate writing. LLMs inverted it, so the format had to change to protect the one thing still scarce in a review: human attention.
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Phil Calçado @philcalcado.com · 11/08/2026
Captcha-Driven Development
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Phil Calçado @philcalcado.com · 10/08/2026
Commodity code, which is what the majority of SaaS applications are made of, is rarely the hard part indeed. Unfortunately, this often also reflects on the products being commodity... Wrote about this distinction a while ago, and I think it’s even more relevant now: philcalcado.com/2025/02/27/a...
philcalcado.com
AI is not the engineer we wanted, but it might be the one we need
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Phil Calçado @philcalcado.com · 07/08/2026
I've user PagerDuty for, what, at least 15 years? I have no idea what any of the buttons in their terrible UI does except ack and resolve.
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Phil Calçado @philcalcado.com · 07/08/2026
Funny that we’re rediscovering ASD-STE100, as it’s basically how most AIs have talked in fiction, and in the movie Her the whole plot was what happens when they don’t.
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Phil Calçado @philcalcado.com · 30/07/2026
There's a joke I'm not smart enough to make in here somewhere
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Phil Calçado @philcalcado.com · 10/07/2026
If people are this upset about Little Italy(!!), I can't wait to see how these bots go when the new version of the map shows Carroll Gardens as a French enclave
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Reposted by Phil Calçado
Cybertronic Spree @cybertronicspree.bsky.social · 04/07/2026
IMMIGRANT SONG is today's jam.
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Phil Calçado @philcalcado.com · 03/07/2026
I mean, you don't have to tell me that the Anthropic 's Claude Code team doesn't review their AI-written code--it's pretty obvious. Just this week they broke--again--the copy and paste inside the IntelliJ terminal.
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Phil Calçado @philcalcado.com · 02/07/2026
the existence of forward-deployed engineers implies the rest of us are backward-deployed engineers
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Phil Calçado @philcalcado.com · 24/06/2026
hoje tem 🇧🇷
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Phil Calçado @philcalcado.com · 17/06/2026
hot take: Slack is ok for chat and terrible as an email replacement the fragmentation creates more "quick meetings" because eventually the only way to know wtf is going on across channels, threads, and DMs is to summon everyone into a call and no, AI won't solve this
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Phil Calçado @philcalcado.com · 14/06/2026
Anthropic’s whole vibe went from ethos to mythos pretty quick huh
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Phil Calçado @philcalcado.com · 11/06/2026
Having AI do the research and write your tech spec is like keeping a pristine, never-even-opened copy of The Power Broker on your living room bookshelf.
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Phil Calçado @philcalcado.com · 10/06/2026
TTRPG studios and professionals are already under so much hardship, it's incredibly sad what is happening to @paizo.com paizo.com/blog/paizo-r...
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Phil Calçado @philcalcado.com · 08/06/2026
my favorite part of tech keynotes is the AI demo just sitting there like okay what are the SF gang doing today are we planning a trip are we planning a party are we choosing a restaurant are we breaking up with bae where we going AI fam
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Phil Calçado @philcalcado.com · 03/06/2026
Now I want to do it just to title it “Work Sucks (I know)”, but that would require rereading Laszlo Bock’s and that’s no summer read
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Phil Calçado @philcalcado.com · 02/06/2026
I’ve been in this industry for twenty-five years and have seen all sorts of companies and projects. You know what I have never heard? Someone saying, “You know what I really like about working here? Cross-team collaboration.” philcalcado.com/2026/06/01/c...
philcalcado.com
Cross-Team Pragmatics
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Phil Calçado @philcalcado.com · 02/06/2026
OH: Stop trying to square a round pig
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Phil Calçado @philcalcado.com · 01/06/2026
It's disheartening to watch so many companies that were building genuinely useful infrastructure and platform primitives for AI products pivot to AI coding agents.
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Phil Calçado @philcalcado.com · 01/06/2026
* “I slopped it and here’s what I got” means: Take it or leave it. * “I did some research and here’s what I think” means: I researched, formed a view, and used whatever tools helped me get there. Maybe one of those tools was AI. Maybe it wasn’t. From philcalcado.com/2026/05/31/n...
philcalcado.com
Nutrition Labels for AI
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Phil Calçado @philcalcado.com · 01/06/2026
testing bluesky comments
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Phil Calçado @philcalcado.com · 30/05/2026
AWS making S3 strongly consistent in 2020 quietly killed a lot of distributed systems sacred cows. A whole class of designs that used to require databases, queues, or coordination products suddenly became "just a bunch of files in S3." www.opendata.dev/blog/ingesti...
opendata.dev
Ingesting 1Gbps of logs into ClickHouse for $180/month | OpenData
New pipelined producer and consumer clients for OpenData Buffer, plus a ClickHouse integration with batch deduplication, move 1.1 Gbps of logs from an OTel Gateway to ClickHouse via S3 for $180/mo.
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Phil Calçado @philcalcado.com · 30/05/2026
What journalists miss about tokenmaxxing: engineers at big companies have spent their whole careers gaming made-up metrics that map directly to comp. Measuring token usage isnt even close to the silliest thing they’ve been assessed against, and given how easy it is to game, it looked like free money
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Phil Calçado @philcalcado.com · 27/05/2026
So much of so-called AI software engineering is writing docs nobody reads and reading docs nobody wrote
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Phil Calçado @philcalcado.com · 26/05/2026
Fellow immigrants and expats: when you need to count something quickly, do you use your native language or your adopted country’s language? I’ve lived abroad for twenty years, and I still immediately switch to Portuguese when I count cash.
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Phil Calçado @philcalcado.com · 15/05/2026
And with GitHub degrading every day, might as well gear up for the next wave of code hosting while they're at it!
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Phil Calçado @philcalcado.com · 15/05/2026
It's still hard to predict how dev tools will adapt to AI development, but one thing that's already pretty clear is that JetBrains and other tool vendors need to beef up their support for Git worktrees and other ways to coordinate multiple streams of work over the same repository.
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Phil Calçado @philcalcado.com · 12/05/2026
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Phil Calçado @philcalcado.com · 10/05/2026
The greatest trick the devil ever pulled was rebranding consultants and sales engineers as FDEs.
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Phil Calçado @philcalcado.com · 26/04/2026
> The juniors who should be learning right now are either not being hired or developing what a DoD-funded workforce study calls “AI-mediated competence.” They can prompt an AI. They can’t tell you what the AI got wrong. techtrenches.dev/p/the-west-f...
techtrenches.dev
The West Forgot How to Build. Now It's Forgetting Code
The defense industry lost the ability to make weapons when crisis hit. The same pattern is eroding software engineering skills. The timelines are identical.
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Phil Calçado @philcalcado.com · 13/04/2026
I hope this is just the start, and that the next few years in AI are much better than the idiotic last three.
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Phil Calçado @philcalcado.com · 13/04/2026
Its creator and community are humble, kind, and pragmatic. They aren’t contaminated by the zero-sum "ngmi" thinking that curses the current tech industry. They feel more like 2010s tech than 2020s tech.
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