Benjamin has been writing since his first gig as a fifteen-year-old stringer for the local Suburban & Wayne Times. He was managing editor of The Conestoga Spoke, and contributor to The Syracuse Daily Orange.

Since graduating from Syracuse University with dual degrees in Journalism and Creative Writing (This Boys Life author, Tobias Wolff, led his Senior Workshop), Benjamin has been published in Rolling Stone, Men's Journal, MTV News, Mental Floss, and Swing Magazine on topics ranging from politics to pop culture.

He has interviewed Bono, The Edge, Neil Young, Michael Stipe, Reid Hoffman, Shepard Fairey, Douglas Coupland, Cameron Crowe, Michael Penn, David Gray, Aimee Mann, Ani DiFranco, Matthew Sweet, and Paul Thomas Anderson, amongst others.

Benjamin contributed to the collection, "2 Do Before I Die," and wrote the award-winning PBS documentary, Mister Rogers & Me (2012) and forthcoming Friends & Neighbors (2024).

Benjamin began blogging in 2000, and continues regular weekly updates via his .

He is currently writing a memoir expected in 2024.

Jun 3 2024

A Simple, Radical Act

When my alma mater, Conestoga Senior High School, asked me to speak with students and parents about service and leadership, I figured the small gathering would be a great space to road-test some new ideas. And I decided to go for broke. I would focus my message on parents, lead with the hardest stuff (ie:…
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May 29 2024

A Sort Of Homecoming

In Friends & Neighbors, my father narrates my Iowa origin story thusly: “You were born Saturday morning, September the 4th, and Sunday at two o’clock I left for Maryland.” Mom, Chris, and I followed three weeks later. So when I say I’m from Iowa, it’s factually true. But I was raised in Maryland, Indianapolis, Illinois, Pennsylvania,…
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May 16 2024

Listen to the Friends & Neighbors Premiere Q&A

For a couple of years now, as I’ve been shooting and editing Friends & Neighbors, I imagined the day when the entire cast of helpers would come together to watch the film, and discuss it. That day came last week when we screened Friends & Neighbors for our friends and neighbors at Theater N in…
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