SPECIAL GUEST!! ClickUp's Co-Founder Chris Cunningham 💸 The $1,000 Content Hack Big Brands Miss | Ep. 532
Do This, NOT That: Marketing Tips with Jay Schwedelson · Jul 2, 2026 · 19:50
Do This, NOT That: Marketing Tips with Jay Schwedelson
Do This, NOT That: Marketing Tips with Jay Schwedelson · Jul 2, 2026 · 19:50
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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
Episodes: Do This, NOT That: Marketing Tips with Jay Schwedelson
