Partner with Jay: https://www.jayschwedelson.com/contact

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Pre-order Jay Schwedelson's new book, Stupider People Have Done It (out June 9, 2026).

All net proceeds are donated to The V Foundation for Cancer Research, let's kick cancer's butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206

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Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

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Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

Ask Jay anything: https://www.jayschwedelson.com/ask

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Leave a comment and follow the show, it really helps us out!

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Connect with Chris Cunningham on LinkedIn and on Instagram (@Cunningham), or reach him directly at chris@clickup.com. He's happy to help anyone getting started with content or building on ClickUp.

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Most B2B software gets sold with a webinar and two floating headshots on a LinkedIn promo. Chris Cunningham helped build ClickUp into a $4 billion company by doing the opposite, hiring actors by the day, making genuinely funny videos, and treating a project management tool like a consumer brand. He sat down with Jay Schwedelson to walk through the actual mechanics, from the scrappy month-one tests to mining follower data to land a meeting with McDonald's COO.

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Best Moments:

(02:46) The bet behind the whole strategy, that every company will soon have at least one in-house creator

(04:02) The scrappy growth loop, run tiny tests, prove the signal, then go back for budget

(05:45) The actor day-rate hack that gets you eight to ten videos for under a grand

(08:30) Spotting McDonald's COO in the follower data, then shooting a video just for him

(12:15) Why bloated, slow-shipping software is exactly what gets vibe-coded out of existence

(16:31) Instagram's head says leave the barking dog in, messy video is what's winning reach