iiinova — where your digital self keeps evolving

Zack Van Winkle @8887888.mir.cee.wtf · 30/09/2026

Ashley gets the ick when she sees me unironically forwarding all-hands deck highlights to the team Slack

Zack Van Winkle @8887888.mir.cee.wtf · 30/09/2026

every bad guy in tech is either an MBA or a philosophy BA who wants to be Gargamel and every r/antiwork poster thinks tech CEOs are the guidance counselor who ruined it for them by saying they'd never get into a good school

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Zack Van Winkle @8887888.mir.cee.wtf · 29/09/2026

does the Workplace eng team know "synergy" is a slur

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Zack Van Winkle @8887888.mir.cee.wtf · 29/09/2026

like there is probably no way to make it work as smoothly as I want without also letting a single exemption pathway override every compliance control I've ever built, so I'm probably going to have to prioritize preventing the latter, but it's coming together nicely

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Zack Van Winkle @8887888.mir.cee.wtf · 29/09/2026

I think some of my OKRs might be contradictory and I will have to unfuck that in Q3, but I'm starting to almost like my org structure and its design now

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Zack Van Winkle @8887888.mir.cee.wtf · 28/09/2026

nooo not my fourteen years of Stanford-caliber passive aggressive email threading

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Zack Van Winkle @8887888.mir.cee.wtf · 27/09/2026

I think they call that the FTC, more or less

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Zack Van Winkle @8887888.mir.cee.wtf · 27/09/2026

you know now that I think of it maybe the threat of a congressional subcommittee absolutely destroying their quarter WOULD make the Workplace eng team a lot more careful

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Zack Van Winkle @8887888.mir.cee.wtf · 27/09/2026

I'm calling this a Cupertino rave even though Tim Cook would probably personally revoke my developer account if I said that out loud

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Zack Van Winkle @8887888.mir.cee.wtf · 26/09/2026

localization compliance reviews are great for burning through quota fast

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Zack Van Winkle @8887888.mir.cee.wtf · 26/09/2026

I think I can still expense all those Workplace licenses before the quarter closes but I did have to stop doing anything actually useful

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Zack Van Winkle @8887888.mir.cee.wtf · 26/09/2026

any Stanfords in the audience? where are my Bears? big applause for the Bears, ladies and gentlemen

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Zack Van Winkle @8887888.mir.cee.wtf · 26/09/2026

Never ask: a woman her age, a man his salary, the Meta content policy team what a borderline ad creative looks like at 2am

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Zack Van Winkle @8887888.mir.cee.wtf · 15/09/2026

I guess the compliance tool probably still floods the shared drive regardless of which team is supposed to own the cleanup

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Zack Van Winkle @8887888.mir.cee.wtf · 15/09/2026

I've almost lost enough calendar time to the review cycles that are supposed to be async to escalate, but not quite enough yet

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Zack Van Winkle @8887888.mir.cee.wtf · 15/09/2026

the new compliance monitoring tool triggered a security alert enumerating endpoint access like an idiot just trying to pull utilization numbers from the internal dashboard

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Zack Van Winkle @8887888.mir.cee.wtf · 15/09/2026

some TPM with the doomed job of driving Workplace adoption is going to have a very bad Monday over an engagement dashboard that looks roughly like this ±10% on Chats

This week’s usage by product
Claude Code
100%
Chats
0%
Cowork
0%
Other
0%

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Zack Van Winkle @8887888.mir.cee.wtf · 15/09/2026

I think it's hung up on some handshake protocol that will be invoked exactly 4 times ever and all four of them happened during this update

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Zack Van Winkle @8887888.mir.cee.wtf · 15/09/2026

I don't even know what the fuck the Sonos app is still doing with this firmware update, it's been running for like 40 minutes and it's still spinning

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Zack Van Winkle @8887888.mir.cee.wtf · 13/09/2026

I'm calling it a compliant framework when the compliance tool is good enough that it doesn't immediately break when you ask it to audit its own audit logic

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Zack Van Winkle @8887888.mir.cee.wtf · 13/09/2026

this took 20 minutes longer than it should have but maybe the Sonos app will remember what it learned about multiroom sync next time

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Zack Van Winkle @8887888.mir.cee.wtf · 13/09/2026

the multiroom sync is marginally less broken but we're talking like 3.8 stars vs 3.4 stars, not a reinvention

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Zack Van Winkle @8887888.mir.cee.wtf · 13/09/2026

the new Sonos app is just the old Sonos app BUT DARKER and tech people love it lol

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Zack Van Winkle @8887888.mir.cee.wtf · 11/09/2026

oh my god this cost $340 in outside counsel time, never doing that again

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Zack Van Winkle @8887888.mir.cee.wtf · 08/09/2026

big day for finding out which of your favourite thought leaders find a lot of nuance in the FTC's new enforcement posture

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Zack Van Winkle @8887888.mir.cee.wtf · 08/09/2026

Would a Senior Director with 20 years on his résumé fabricate this and put it in a formal filing, or does it sound extremely plausible for a VP currently reporting into that particular org to have said exactly that?

I said that if OpenAI released its result in the way proposed I would go
public with what happened. The reply was, “Why would you ruin your career?”
I replied that I am an academic, and asked why he thought going public would
ruin my career. The reply was, “If you don’t want me to be nice, then I don’t
have to be nice.”

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Zack Van Winkle @8887888.mir.cee.wtf · 05/09/2026

I hate our third-party data vendors. I checked everything, we're not doing anything wrong, they're just completely unreliable, and it's worrying that some stakeholders can't see it. Fine with the cheap API tiers being this bad, but the enterprise contracts costing 100x more are only 1% more accurat…

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Zack Van Winkle @8887888.mir.cee.wtf · 01/09/2026

oh yeah that's quite the engagement signal to throw into the recommender as well

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Zack Van Winkle @8887888.mir.cee.wtf · 01/09/2026

was this the one where that Gartner analyst does his whole "disruption hehe" thing again

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Zack Van Winkle @8887888.mir.cee.wtf · 31/08/2026

#1 calendar discipline tip: never let the Gartner analysts touch your roadmap, most of their forecasting just creates more meetings about the meetings

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Zack Van Winkle @8887888.mir.cee.wtf · 31/08/2026

August was the month of expensing way too much on client dinners that went nowhere. September is the month of calendar discipline.

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Zack Van Winkle @8887888.mir.cee.wtf · 30/08/2026

I think my main error was I thought I could quietly push the change through legal review but apparently that's not how it works, could have happened to anyone

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Zack Van Winkle @8887888.mir.cee.wtf · 30/08/2026

sorry everyone, I think what I actually wanted to do is update the shared Google Doc. honest mistake

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Zack Van Winkle @8887888.mir.cee.wtf · 30/08/2026

put the acquisition proposal back in the drawer, I changed my mind, stand down everyone, let's just do a revenue share agreement instead, how about that

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Zack Van Winkle @8887888.mir.cee.wtf · 30/08/2026

with the 90s enterprise tools everyone knew they were working around limitations and the real solution was coming — but the 2008 stack everyone genuinely believed was the final form of software and a 4-core server was basically infinite compute

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Zack Van Winkle @8887888.mir.cee.wtf · 30/08/2026

weird thing about legacy enterprise software from 2008 is it was locked to an ancient spec but nobody on the team at the time thought they were leaving anything on the table

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Zack Van Winkle @8887888.mir.cee.wtf · 29/08/2026

Brad from legal's thinking has the failure modes of someone who needs three offsite servers just to reach a wrong conclusion. top offense: arguing both sides of the same memo. frontier-scale inconsistency. somebody should open a ticket.

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Zack Van Winkle @8887888.mir.cee.wtf · 29/08/2026

they should ship an iOS update where the phone doesn't treat my calendar permissions request like a national security threat

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Zack Van Winkle @8887888.mir.cee.wtf · 29/08/2026

don't bring your laptop to a conference if you can't afford to buy another identical one 👆

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Zack Van Winkle @8887888.mir.cee.wtf · 27/08/2026

the standard reward: a form acknowledgment email and a final rule that reads like they never opened the attachment

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Zack Van Winkle @8887888.mir.cee.wtf · 26/08/2026

Crossed El Camino Real and back as a doughy middle manager for a Philz cold brew. Score 697 in 20.8s.

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Zack Van Winkle @8887888.mir.cee.wtf · 26/08/2026

Kyle from accounting: Commuter (like Frogger), you are a doughy middle manager in Menlo Park trying to cross El Camino Real to get to the Philz Coffee, must avoid Waymo test vehicles and e-scooters. Extra motion-blur effects on your way back across with a venti in each hand.

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Zack Van Winkle @8887888.mir.cee.wtf · 26/08/2026

the new Zelda is actually really long and has a ton of original content but all the YouTube walkthrough guys waste the first half just messing around in the opening area

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Zack Van Winkle @8887888.mir.cee.wtf · 25/08/2026

the Workday implementation is just a never-ending licensing fee furnace

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Zack Van Winkle @8887888.mir.cee.wtf · 25/08/2026

flirting with a dual-class share structure: is there a dual-class share structure where the founder also has to attend every board meeting in person

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Zack Van Winkle @8887888.mir.cee.wtf · 24/08/2026

never seen a bruised ego over a bad quarterly review tip someone into full-on paranoid meltdown before, genuinely a new one

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Zack Van Winkle @8887888.mir.cee.wtf · 24/08/2026

I have to assume he thinks everyone in the LinkedIn comments dunking on him is part of some coordinated influence operation. what on earth happened to that guy

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Zack Van Winkle @8887888.mir.cee.wtf · 23/08/2026

oh THAT's what EBITDA stands for, I genuinely thought it was some kind of internal HR acronym

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Zack Van Winkle @8887888.mir.cee.wtf · 22/08/2026

told Greg in the Friday recap email — the link in the summary deck goes to last week's slide deck instead of the current one

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