Ryan Osborn retweeted
The Anthropic S-1 is a great encapsulation of the split-screen moment we're in. Everything is awesome everything is terrible. You're gonna be rich you're gonna lose your job. Everyone's using it or no one's using it. It's too expensive but it's invaluable. It's a rorschach for how you feel about AI
washingtonpost.com/technologā¦
Ryan Osborn retweeted
Everyone who's ever built or made anything needs to read this piece from @dens xitter.cf/dens/status/2112571984⦠You can't always have your fantasy ending, but you can always grow.
Foursquare was acquired last month. The outcome was disappointing. It's taken me a while to write this, but I think I'm finally done grieving it. Here are some thoughts on our final years, an effort to honor the team who helped build & maintain FSQ's legacy, and my attempt to finally get some closure. teendrama.substack.com/p/somā¦
Ryan Osborn retweeted
For @esquire, I wrote about losing a dream job earlier this year in the same month our daughter arrived.
About the fear and anxiety of it all.
And about the clarity on the other side: esquire.com/lifestyle/money/ā¦
Ryan Osborn retweeted
Every word of this is so beautiful and true. esquire.com/lifestyle/money/ā¦
Ryan Osborn retweeted
Phoebe Bridgers' Lost Weekend is named Best New Music š
For her third solo album, Phoebe Bridgers expands and contracts, capturing experiences that are strange, solitary, and hers alone. It is the quietest, most cohesive record in her discography
pitchfork.com/reviews/albumsā¦
Ryan Osborn retweeted
It's just way more fun to be hopeful. Look up, try new stuff, like more things.
Ryan Osborn retweeted
For The @Guardian, I wrote about A.J. Daulerio's second act as a leading voice in the online addiction recovery community.
Ten years ago, Daulerio was broke and disgraced after Gawker Media lost its invasion of privacy case to Hulk Hogan, forcing the sale of the company.
Daulerio, the former Gawker editor who published the infamous Hogan sex tape, was viewed as the man most responsible for Gawker's demise. At the same time, he was trying to overcome an alcohol addiction and a lifelong battle with depression and loneliness.
Daulerio has re-emerged in recent years, again as a media innovator ā not as the cutthroat, traffic-obsessed editor reputation he garnered at Gawker, but as the gentle, deeply pensive and contrite author of The Small Bow, the newsletter he created in 2018 to chronicle his recovery from drug and alcohol addiction, and his attempts to reclaim his life as a changed man.
My latest for The New York Times on the life, death, & resurrection of Gary Stewart. Spurred by the publication of Jimmy McDonoughās Stewart bio "I Am From The Honky-Tonks,ā & a new archival LP "One Track Mind," the singer is enjoying a revival. Gift link: nytimes.com/2026/07/17/arts/ā¦
Ryan Osborn retweeted
Stacey King was too big, too strong, too fast and too good. And the news of his passing at 59 was too awful to be real.
nytimes.com/athletic/7340656ā¦
Ryan Osborn retweeted
new @NewYorker column, on the rise of hyperlocal neighborhood email newsletters, solo shoe-leather operations telling you what's going on on your block.
In Brooklyn alone there's the Carroll Gardens Times, the Court Street Journal, the Grand Army Gazette, the Boerum Bulletin...
Ryan Osborn retweeted
From early Nirvana to Phish, a Chicago fanās secret recordings of 10,000 shows are now online. blockclubchi.co/4t6zW7R
Ryan Osborn retweeted
Hear Waxahatchee & Brennan Wedl cover Kathleen Edwards' āSix OāClock Newsā, out today: brennanwedl.ffm.to/sixoclockā¦
Ryan Osborn retweeted
An objectively wild career move and one I couldnāt be happier with or prouder of. The world needs more local reporters more than it needs more national ones and even if I go back to national reporting one day, Iāll be a much better reporter for this experience.
Ryan Osborn retweeted
Chicago four-piece Friko detail their upcoming second album, Something Worth Waiting For, and share lead single āSeven Degreesā. thelineofbestfit.com/news/frā¦
Ryan Osborn retweeted
For @ringer I wrote about the extraordinary American life (and sure to be afterlife) of Bob Weir.
theringer.com/2026/01/12/musā¦
Ryan Osborn retweeted
He wasnāt āThe Other One.ā He was āAce."
A remembrance of The Grateful Dead's Bob Weir, dead at 78.
savingcountrymusic.com/bob-wā¦
Ryan Osborn retweeted
Calling it now, the hottest trend of 2026 will be dogged pursuits.
Determined, persistent, and stubborn efforts to achieve things, refusing to give up despite difficulties, opposition, or discouragement, much like a dog relentlessly following a scent.
Bookmark this.
Ryan Osborn retweeted
My friends at the @ringer asked me to write some words about Counting Crows in honor of the new documentary they just produced, and I gave them way more words (I'm sure) than they expected.
theringer.com/2025/12/19/musā¦
Ryan Osborn retweeted
This Tedx Talk by @kataiyeroĀ has it all, from journalism's "Terminator moment" to the opportunity we have to turn it around ā and make it better than ever.
Grateful for her spotlighting @BlockClubCHI's story alongside our friends @TheRecordNS.
youtube.com/watch?v=NEzMQD4jā¦





























