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The Executive Dropout Podcast

The Executive Dropout Podcast

By: Jacob Sager
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About this listen

 The Executive Dropout is what happens when you quit the script but keep the curiosity. Part discussion, part monologue, part research rabbit hole, part untested theory blurted out before it’s ready. We wander through McLuhanism, media environments, technological change, the liberal arts, and automation — not to tie them up neatly, but to see what frays. Some episodes feel like lectures that forgot to end. Others are conversations that won’t sit still. There will be probes. There will be tangents. There will be moments of clarity you immediately doubt. Fun and frustrating in equal measure, this is a podcast for anyone who suspects that the medium isn’t just the message — it’s the air, the water, and the itch you can’t quite scratch.© 2025 Art Economics
Episodes
  • Talking with Tom Cooper

    Talking with Tom Cooper
    Aug 15 2025

    In this conversation with scholar and author Tom Cooper, we trace the overlapping currents of McLuhan and Innis — how McLuhan’s Catholicism quietly shaped his media theory, and how geography steered Innis’ thinking. Tom shares stories from his time as McLuhan’s teaching assistant, giving us a rare, inside look at the man behind the aphorisms.

    We also dig into his new book, a fresh lens on the Toronto School’s history and influence, and how those ideas keep mutating in today’s media environment. It’s a blend of personal memory, intellectual history, and a little bit of myth-busting.

    Chapters
    • (00:00:01) - The Executive Dropout Podcast
    • (00:00:12) - Sunny weather for Hawaii
    • (00:00:56) - Talking to Marshall McLuhan and Harold Innes
    • (00:02:16) - McLuhan and Innes: The Story Within a Story
    • (00:07:28) - Innes and McLuhan: The Relationship
    • (00:16:14) - McLuhan and Ennis Day
    • (00:17:39) - Toronto's intellectual scene in the 60s
    • (00:22:35) - On Marshall McLuhan's Controversy
    • (00:30:17) - McLuhan on His Assistants
    • (00:35:50) - The Media Ecology Moment
    • (00:46:02) - Marshall on His Use of Analogies
    • (00:47:34) - The Essential McLuhan: A PhD Dissertation (2018)
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    51 mins
  • Shmooze with Paul Levinson

    Shmooze with Paul Levinson
    Aug 15 2025

    We kick off The Executive Dropout with media theorist, author, and all-around McLuhan troublemaker Paul Levinson. In this hour we dismantle the tired “AI = Terminator” storyline, detour into the true story behind McLuhan’s cameo in Annie Hall (spoiler: he made up his own punchline), and wrestle with how the Tetrad can morph into a chiasmus — yes, it’s worth the listen.

    Paul also traces his evolution from author to publisher back in the age of compact discs, and we talk about his latest venture, ConnectED Editions, which is bringing out Tom Cooper’s new book on McLuhan and Innis.

    It’s part theory jam session, part media history deep-dive, part shmooze — exactly how we like it.

    Chapters
    • (00:00:01) - Paul Levinson on ChatGPT and the Future of AI
    • (00:03:21) - An Index to Marshall McLuhan's The World of Technology
    • (00:08:55) - McLuhan: In the Age of Social Media
    • (00:11:16) - The Kindle and Creativity
    • (00:20:27) - Marshall McLuhan on Writing Fiction
    • (00:22:51) - In the Elevator With Marshall McLuhan
    • (00:30:58) - Marshall McLuhan on His Books
    • (00:34:08) - The Bookmark: Understanding Media, Take Today
    • (00:36:19) - McLuhan: The Gutenberg Galaxy in an Age of Social
    • (00:41:39) - McLuhan on Taking Today
    • (00:43:52) - Understanding Media: Marshall McLuhan's Contributions
    • (00:50:47) - Marshall McLuhan's The Tetrad
    • (00:56:59) - Marshall McLuhan on Woody Allen's "
    • (01:02:45) - The Tetrad and the Chiasmus
    • (01:03:37) - Tetrad Wheels of Revolution
    • (01:06:59) - Paul Evanson: On the Publishing of His Work
    • (01:17:52) - Paul Levinson on The Wisdom Weavers
    • (01:19:25) - Marshall McLuhan: The Mechanical Bride
    • (01:22:15) - A Chat With Paul Levinson
    • (01:24:23) - The Executive Dropout Podcast
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    1 hr and 25 mins
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