steve o’grady
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sogrady.org
steve o’grady
@sogrady.org
helped found redmonk. if you see someone at a tech conference wearing a Red Sox hat, that's probably me. otherwise found in the great state of Maine. wrote the new kingmakers and the software paradox. married to @girltuesday.org. eph.
Pinned
how about 50 pieces of advice?

thisistheway.us
if you know anything about the history of the FBI, this is so spectacularly improbable as to be the equivalent of a pulled fire alarm
The FBI is a rule-bound and tight-lipped institution, but 45 current and former agents spoke to The New York Times Magazine anyway — a sign of the extreme alarm rippling through it. Many said that with the agency under Kash Patel's leadership, the U.S. is less safe. nyti.ms/4qzxs0f
January 22, 2026 at 6:30 PM
to be fair, this is really the only thing you need to know about me
I don't know you well, but I know you well enough to check where you're going before I book a flight
January 22, 2026 at 6:25 PM
ME: hmm, big storm coming this weekend, maybe i should look into flying out of Boston instead of Portland
BOSTON:
January 22, 2026 at 5:54 PM
in case you need some hope today
I came to Minneapolis to report on what's going on, and one of the main questions I showed up with is "just what is the scale of the resistance?" After all, we're all used to the news calling Portland a "war zone" or whatever when it's just some protests in one part of town.
January 22, 2026 at 5:40 PM
these people and their cutesy, evil operation name can get fucked. things are getting very bad here.

the only silver lining in all of this is how hard so many people in this state are working to protect and shield neighbors and community members that don't look like them.
DHS is crudely referring to its newest crackdown in Maine as “Operation Catch of the Day,” preparing to hunt and catch immigrants like lobsters.

Maine’s two biggest cities, Portland and Lewiston, have large Somali populations, and were already on edge. trib.al/OzwC1S7
January 22, 2026 at 3:15 AM
i don't watch football anymore, but this shot really is incredible
This shot from NFL Films is unbelievable
January 19, 2026 at 7:13 PM
so car alarms do have a legitimate use case
People in Minnesota are now using their key fobs to trigger their car alarms from the safety of their homes when they see ICE walking around.
January 18, 2026 at 3:48 AM
the quality of the hotel room i’m given is inversely proportional to the amount of time i’m going to be in them
January 17, 2026 at 2:10 AM
if you’re headed to the denver airport and the light rail is down, i highly recommend not taking the bus instead. the light rail is 40 minutes from downtown.

i’ve been on the bus for an hour and forty minutes and we’re still twenty minutes out.
January 16, 2026 at 6:41 PM
potentially good news for our west coast @monktoberfest.com friends
www.wmtw.com/article/cali...
California dreamin'! New nonstop service coming to Maine airport
The Portland International Jetport will soon offer nonstop flights to two cities in California.
www.wmtw.com
January 16, 2026 at 1:52 PM
that, and the fact that the President hates our Governor because she declined to put up with his bullshit
I was wondering why Maine, but apparently y'all have a group of Somali Americans there :(
January 15, 2026 at 4:39 PM
“i don’t give a shit who you are, where you came from, what color you are. it doesn’t fucking matter. this is wrong.”
January 15, 2026 at 4:34 PM
furious that this is about to happen, proud that the Portland School system still has its principles
January 15, 2026 at 1:37 PM
possibly related: i'm traveling thursday
The first cold wave will reach the East Coast on Thursday, followed by another surge of frigid air this weekend and a third next week, which may be the most severe of the trio.
Temperatures will soon tumble. Here’s how cold it will get.
The first cold wave will reach the East Coast on Thursday, followed by another surge of frigid air this weekend and more next week.
wapo.st
January 14, 2026 at 4:04 PM
TEN YEAR OLD: daddy, i know you're sad about stranger things being over. but don't worry, i made this for you.
January 14, 2026 at 2:11 PM
very cool. well done, anthropic.
pyfound.blogspot.com/2025/12/anth...
Anthropic invests $1.5 million in the Python Software Foundation and open source security
pyfound.blogspot.com
January 13, 2026 at 10:01 PM
that feeling when you have to turn on noise cancellation in the middle of a presentation because your dog is snoring loudly enough to be heard
January 13, 2026 at 6:14 PM
turns out it was breaks of 45 seconds in between alarms for 27 minutes
sitting here outside my daughter’s dance practice listening to one go off for the fifth time in ten minutes, idly wondering if, in their entire history since inception, a car alarm has prevented a single attempted car theft
January 13, 2026 at 12:07 AM
the restaurant would 100% have sushi. that wouldn’t be negotiable.
hmmm... i have to think it would be at least asian-inspired, a cuisine that works great for both beer and wine, and probably either you or James would never tire of?
January 13, 2026 at 12:06 AM
sitting here outside my daughter’s dance practice listening to one go off for the fifth time in ten minutes, idly wondering if, in their entire history since inception, a car alarm has prevented a single attempted car theft
January 12, 2026 at 11:35 PM
we get spam offers of capital all the time, but recently the spammers have become convinced that redmonk is a restaurant which makes me wonder what kind of restaurant we'd be
January 12, 2026 at 10:24 PM
next door neighbor parks and walks into their house: dog goes absolutely bonkers furiously barking at them

door to our mudroom opens as UPS drops a package in there: dog does absolutely nothing and doesn't make a peep
January 11, 2026 at 7:47 PM
preemptively exhausted by the infinite fallout from the sox not signing alex bregman
January 11, 2026 at 3:59 PM
There is No Antimemetics Division is a little bit like Max Berry’s Lexicon crossed with The Magnus Archives
January 10, 2026 at 2:27 AM
i already have people giving me grief about a second edition of new kingmakers, now the software paradox is getting added to that list? 😂
The recent news around Tailwind, to me, is more evidence of @sogrady.org 's thesis in The Software Paradox. Fantastic product, nobody wants to pay for it. The paid product always felt to me like a good passive income idea but not a career. Does The Software Paradox need an LLM update?
January 8, 2026 at 3:46 PM