Husband. Dad. Maybe we don't see ourselves the way we really are.

Chicago, IL
Joined April 2007
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/technolog…
4
13
1
38
15,549
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/som…
3
4
54
4,255
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/…
43
151
35
897
332,395
Ryan Osborn retweeted
Phoebe Bridgers' Lost Weekend is named Best New Music šŸ† 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/albums…
9
69
38
911
69,734
Ryan Osborn retweeted
It's just way more fun to be hopeful. Look up, try new stuff, like more things.
37
64
11
645
144,653
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 — 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.
9
7
3
45
56,888
Ryan Osborn retweeted
My latest for The New York Times on the life, death, & resurrection of Gary Stewart. Spurred by the publication of Jimmy McDonough’s 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/…
2
4
13
964
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...
14
78
27
898
170,249
From early Nirvana to Phish, a Chicago fan’s secret recordings of 10,000 shows are now online. blockclubchi.co/4t6zW7R
259
5,121
799
23,890
6,834,614
Ryan Osborn retweeted
Hear Waxahatchee & Brennan Wedl cover Kathleen Edwards' ā€œSix O’Clock Newsā€, out today: brennanwedl.ffm.to/sixoclock…
1
2
3
734
Ryan Osborn retweeted
An objectively wild career move and one I couldn’t 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, I’ll be a much better reporter for this experience.
I was wondering why this guy disappeared from politics Twitter. Voluntarily going from NBC political reporter to editor of a regional newspaper covering a population of roughly 150k people seems like a wild career move, but if it makes you and your loved ones happy, go for it.
157
658
52
10,926
802,448
Ryan Osborn retweeted
This entire season defies logic.
5
9
317
10,450
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.
192
264
88
3,745
428,042
This Tedx Talk by @kataiyeroĀ has it all, from journalism's "Terminator moment" to the opportunity we have to turn it around — and make it better than ever. Grateful for her spotlighting @BlockClubCHI's story alongside our friends @TheRecordNS. youtube.com/watch?v=NEzMQD4j…
2
602