Sign in

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.

PostsRepliesMedia
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
010
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.
140
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.
130
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.
040
Phil Calçado @philcalcado.com · 24/08/2026
shut up, claude, nobody cares
050
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.
040
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
0171
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
060
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
000
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.
031
Phil Calçado @philcalcado.com · 11/08/2026
Captcha-Driven Development
021
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
130
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.
030
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.
000
Phil Calçado @philcalcado.com · 30/07/2026
There's a joke I'm not smart enough to make in here somewhere
020
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
030
Reposted by Phil Calçado
Cybertronic Spree @cybertronicspree.bsky.social · 04/07/2026
IMMIGRANT SONG is today's jam.
330471
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.
221
Phil Calçado @philcalcado.com · 02/07/2026
the existence of forward-deployed engineers implies the rest of us are backward-deployed engineers
010
Phil Calçado @philcalcado.com · 24/06/2026
hoje tem 🇧🇷
030
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
040
Phil Calçado @philcalcado.com · 14/06/2026
Anthropic’s whole vibe went from ethos to mythos pretty quick huh
030
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.
010
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...
081
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
2133
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
1135
Phil Calçado @philcalcado.com · 02/06/2026
OH: Stop trying to square a round pig
010
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.
130
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
063
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.
040
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
050
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
090
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.
220
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.
110
Phil Calçado @philcalcado.com · 12/05/2026
0131
Phil Calçado @philcalcado.com · 10/05/2026
The greatest trick the devil ever pulled was rebranding consultants and sales engineers as FDEs.
0191
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.
040
Phil Calçado @philcalcado.com · 13/04/2026
Since 2023, I’ve been bothering anyone who would listen with the same idea: AI will only really deliver on its promises once it’s in the hands of builders, not fundraisers or course sellers It’s still early, and things could shift, but Mario Zechner’s Pi feels like validation of that idea. 🧵
151
Phil Calçado @philcalcado.com · 10/04/2026
bad ending: the whole world is scrum master
010
Phil Calçado @philcalcado.com · 04/04/2026
I appreciate what @surf.social is doing and will keep using the app, but I am disappointed that the @flipboard.com team who built a mind-blowing app in 2010 wasn't able to build a better UX here. It's not just about being slow, it's that it's a lot of clicking around to find content--there's no flow
270
Phil Calçado @philcalcado.com · 26/03/2026
This generation’s Y2K starts when subsidies end and everyone tries to save on tokens.
010
Phil Calçado @philcalcado.com · 23/03/2026
Spent the morning sending random people links to the this--such a great episode. Great job @davidpierce.xyz
open.spotify.com
Vocoder: Magic mic
220
Phil Calçado @philcalcado.com · 20/03/2026
Sad to see Clockwise sent off to a Salesforce farm upstate. It saved my ass running large engineering orgs. Ended up rolling it out across DigitalOcean and SeatGeek, and we somehow even became featured customers in their farewell post… which, in hindsight, might explain things. www.getclockwise.com
getclockwise.com
The Clockwise team is joining Salesforce
A new chapter for our team, and an important update for our customers.
000
Phil Calçado @philcalcado.com · 16/03/2026
If anything, the constant pivoting and re-pivoting to build an AI narrative has probably slowed down the delivery of real value while increasing noise and feature churn.
010
Phil Calçado @philcalcado.com · 14/03/2026
The management and incentive thinking I hear from top VCs today sounds like it came straight from an IBM middle manager running a mainframe payroll system in 1987.
030
Phil Calçado @philcalcado.com · 12/03/2026
Wait huge! Need correct. I almost gave wrong. 天天送钱
000
Phil Calçado @philcalcado.com · 10/03/2026
Anthropic: 100% of our code is written by Claude Code Also Anthropic: We've been running Code Review internally for months<...> 84% get findings, averaging 7.5 issues <...> less than 1% of findings are marked incorrect.
020
Phil Calçado @philcalcado.com · 09/03/2026
First WFO (Work From Outside) day of the year
020
Phil Calçado @philcalcado.com · 07/03/2026
I wrote a short thing--it's been a minute > This creates a loop of Brandolini’s law: not only is the original bullshit cheap, but even if you spend a disproportionate amount of time refuting it, generating a new bullshit response to your comments is even cheaper. philcalcado.com/2026/03/06/a...
philcalcado.com
AI and Brandolini’s Hell Loop
151