Ryan Osborn (@rozzy) header
Ryan Osborn (@rozzy) profile picture

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

Chicago, IL
Joined April 2007
Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)Photo by Ryan Osborn (@rozzy)
🚨We are on Day 3 of the biggest campaign of our year! Through 12/31, your donation to reliable, responsible local news in the North Shore is DOUBLED‼️ Will you show your support today?: donorbox.org/record-donation…
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Ryan Osborn retweeted
This morning Pope Leo XIV met Bob Dylan 📸: Vatican Media
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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…
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Ryan Osborn retweeted
Everyone who's ever built or made anything needs to read this piece from @dens teapawt.org/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…
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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/…
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Ryan Osborn retweeted
Phoebe Bridgers' Lost Weekend is named Best New Music 🏆 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…
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It's just way more fun to be hopeful. Look up, try new stuff, like more things.
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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.
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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,” & a new archival LP "One Track Mind," the singer is enjoying a revival. Gift link: nytimes.com/2026/07/17/arts/…
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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...
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From early Nirvana to Phish, a Chicago fan’s secret recordings of 10,000 shows are now online. blockclubchi.co/4t6zW7R
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Hear Waxahatchee & Brennan Wedl cover Kathleen Edwards' “Six O’Clock News”, out today: brennanwedl.ffm.to/sixoclock…
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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.
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This entire season defies logic.
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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.
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