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

Chicago, IL
Joined April 2007
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/technolog…
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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…
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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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Almost 20 years after EveryBlock … is the time now? I believe that if any city can do it, it’s Chicago.
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Ryan Osborn retweeted
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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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,” & 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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Transforming TV news is a seductive siren. It’s exciting to launch things, it’s really hard to build things that last. I’m always rooting for new ideas and reinvention but have seen a lot of smart, ambitious people humbled by this process.
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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...
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“you never tell the singer no"
Lovely interview with the author of a new biography about Justin Townes Earle, someone who's music I've gotten really obsessed with in the last few years. dontrocktheinbox.com/what-do…
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Hacky sack is back!
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What a musical obit. Can all agree this tune will live forever. youtu.be/iMph7ygbBfk
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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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