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Phil Calcado

@pcalcado@mastodon.social
  • Open on mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users.

Coding, Brazilian Jiu-Jitsu, and D&D

Brooklyn

0 Followers
0 Following
16 Posts
Joined December 12, 2022
Content:
https://philcalcado.com
Work:
https://outropy.ai

Posts

Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · May 15, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

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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pcalcado
Phil Calcado @pcalcado@mastodon.social · May 12, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social
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pcalcado
Phil Calcado @pcalcado@mastodon.social · May 10, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

The greatest trick the devil ever pulled was rebranding consultants and sales engineers as FDEs.

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Apr 26, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

> we’ll need senior engineers. People who understand systems end to end, who can debug distributed failures at 2 AM, who carry institutional knowledge that exists nowhere in the codebase. Those engineers don’t exist yet because we’re not creating them. 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.

https://techtrenches.dev/p/the-west-forgot-how-to-make-things?triedRedirect=true

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Apr 13, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

🧵

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Apr 10, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

bad ending: the whole world is scrum master

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Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · Apr 04, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

I appreciate what @surf@flipboard.social doing and will keep using the app, but I am disappointed that the @flipboard@threads.net 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

flipboard.social

Surf (@surf@flipboard.social) - Flipboard

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 26, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

This generation’s Y2K starts when subsidies end and everyone tries to save on tokens.

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Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 20, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

Sad to see Clockwise get sent off to a Salesforce farm upstate.
Was always a big fan; 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. https://www.getclockwise.com/

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 16, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 14, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

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Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 12, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

Wait huge!
Need correct.
I almost gave wrong.
天天送钱

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Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 10, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

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Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 09, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

First WFO (Work From Outside) day of the year

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Open post
pcalcado
Phil Calcado @pcalcado@mastodon.social · Mar 07, 2026
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

https://philcalcado.com/2026/03/06/ai_and_brandolinis_hell_loop.html

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pcalcado
Phil Calcado @pcalcado@mastodon.social · Sep 16, 2025
Phil Calcado
@pcalcado@mastodon.social

Headed engineering for companies w/ either millions of users but no revenue or millions in revenue but no users. Coding, Brazilian Jiu-Jitsu, and D&D Brooklyn

mastodon.social

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.

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