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My favorite podcast on the web. "Productivity, communication, work, barriers, constraints, tools, and more" brought to you by Merlin Mann and Dan Benjamin
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Great commentary on all things Apple by John Gruber (Daring Fireball) and Dan Benjamin. Also, lots of James Bond.
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Marco Arment (creator of the awesome iOS app Instapaper) and Dan Benjamin's show about iOS development...and coffee. Marco turned me on to my prized kitchen gadget, the Aeropress.
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Over a dozen fantastic shows, mostly tech related, created by Dan Benjamin.
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The comedy show featuring Merlin Mann, Scott Simpson, and Adam Lisagor (a.k.a. Lonely Sandwich). "A Journal of Emotional Hygiene"
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The most sensible and consistent menswear blog and podcast around. Hosted by Jesse Thorn (Maximum Fun, The Sound of Young America) and Adam Lisagor (a.k.a. Lonely Sandwich). "A web series about dressing like a grownup"
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The great long-running public radio show by "America's Radio Sweetheart" Jesse Thorn.
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Blogger Andy Traub's interview series with discussions about fear, "the Resistance", shipping, being indispensable, and other subjects and themes of Seth Godin's inspiring book "Linchpin".
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My brother-in-law recently turned me on to this video series available through the NYT iTunes channel. A.O. Scott's short walkthroughs of his favorite films are easy to consume in small or large quantities.
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Interviews with ASC members. Typically as informative and engaging as their print publication.