Phil Calçado
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philcalcado.com
Phil Calçado
@philcalcado.com
Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users.
SLOs are a psyop designed by big tech to nerdsnipe smaller companies into arguing about outages, “availability,” and whether a chair is even a chair, instead of shipping anything.
November 13, 2025 at 4:40 PM
when you work in a monolith, need to stack PRs, and that one PR everything else was rebased off is finally reviewed
November 12, 2025 at 6:42 PM
Corporate email inbox these days is either a million irrelevant notifications or that one HR email that, if you miss it, they cancel your health insurance and legally declare you dead.
November 5, 2025 at 5:09 PM
My new favorite way to be passive-aggressive when someone says some stupid shit is to start with: “You are absolutely right!”
November 5, 2025 at 2:27 PM
What phase of the bubble is it when JetBrains is wheatpasting AI ads in a sleepy Carroll Gardens corner. someone’s about to switch IDEs on the walk to get fresh mozzarella from Caputo’s?
November 1, 2025 at 3:13 PM
OH: We send a lot of stuff to Datadog, but mostly money.
October 27, 2025 at 5:22 AM
Every podcast since the pandemic is just people trying to recreate the feeling of happy hour conversations and the hangs we never got back.
October 24, 2025 at 1:47 AM
Love when an AI influencer who sells courses on how to use AI crowdsources the one thing every AI demo swears AI solves.
October 21, 2025 at 12:24 PM
AWS is down, and this coffee shop has turned into an empathy circle. Every five minutes, another pager goes off. We just nod. Just a beautiful shared experience.
October 20, 2025 at 1:40 PM
I really wish ClickHouse had picked different names for “Materialized View” and “ORDER BY.” Spent half my day explaining they don’t mean what everyone thinks they mean.
October 15, 2025 at 5:48 PM
I really wish ClickHouse had picked different names for “Materialized View” and “ORDER BY.” Spent half my day explaining they don’t mean what everyone thinks they mean.
October 15, 2025 at 5:24 PM
lol you guys remember when we laughed at Google Wave for trying to replace email with one unified, structured thing? and now we replaced it with Slack chaos and Google Docs comment soup? Classic us amirite
October 15, 2025 at 12:34 AM
I can’t recommend this video enough for those of us who are trying to get a good idea of what could happen in the next decade. It made me feel like 20 things at once.

And it features Stanford Beer, the OG cybernetics guy!

youtu.be/AYGt_UN0DpM...
October 14, 2025 at 9:56 PM
As a chronic em-dasher, had to disable auto-conversion and use -- instead of — so people don’t think I’m AI-slopping them.
October 14, 2025 at 3:48 PM
2000s: Story points
2020s: CAPEX points

Agile, but make it deductible.
October 13, 2025 at 5:22 PM
Overhearing two random VCs talking at Canal Street’s Think Coffee:

“Once you vibe coded the prototype, taking it to production is very easy. You can have like one DevOps guy part time working for five companies”
October 9, 2025 at 2:54 PM
I step out for a week and OpenAI decides the future of AI agents is… BPEL?
October 8, 2025 at 9:12 PM
Biggest gift ten years of jiujitsu gave me is the experience of training with my older brother…

…who’s a blue belt and I can finally kick his ass as payback for all those years
October 7, 2025 at 2:42 PM
WTF is a AI WAN
October 4, 2025 at 6:40 PM
BREAKING: Startups adopting the Nvidia business model
September 27, 2025 at 12:17 AM
IT support at Hilbert’s Hotel
September 24, 2025 at 5:25 PM
I don’t find Inngest particularly interesting as a durable workflow framework , but it tickles my programming language nerd brain that TypeScript is such an utilitarian language that things like these are idiomatic without much syntactic sugar
September 20, 2025 at 6:07 PM
When Leftpad hit the spotlight, we couldn’t believe anyone imported a lib to save 11 lines of code. Now we burn a million LLM tokens just to indent a file.
September 16, 2025 at 5:51 PM
At too many unicorns “AI” stands for "A lot of Ifs"
September 15, 2025 at 2:46 PM
Phil Calçado’s 10th Rule: Any company claiming to be a “majestic monolith” is surrounded by an ad-hoc, bug-ridden, slow swarm of one-off microservices—including the monolith itself.
September 11, 2025 at 6:56 PM