# SPECIAL GUEST!! ClickUp's Co-Founder Chris Cunningham 💸 The $1,000 Content Hack Big Brands Miss | Ep. 532

Page: https://stenobird.com/podcast/do-this-not-that-marketing-tips-with-jay-schwedelson-6571740/special-guest-clickup-s-co-founder-chris-cunningham-the-1-000-content-hack-big-brands-miss-ep-532
Text version: https://stenobird.com/podcast/do-this-not-that-marketing-tips-with-jay-schwedelson-6571740/special-guest-clickup-s-co-founder-chris-cunningham-the-1-000-content-hack-big-brands-miss-ep-532.md
Podcast: [Do This, NOT That: Marketing Tips with Jay Schwedelson](https://stenobird.com/podcast/do-this-not-that-marketing-tips-with-jay-schwedelson-6571740)
Published: 2026-07-02T07:00:00+00:00
Episode link: https://jayschwedelson.com/special-guest-clickups-chris-cunningham-the-1-000-content-hack-big-brands-miss-ep-532
Audio file: https://episodes.captivate.fm/episode/33a557c0-8e8b-458c-8fd1-b78b6fbfa815.mp3
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JSON: https://stenobird.com/v1/public/podcasts/do-this-not-that-marketing-tips-with-jay-schwedelson-6571740/episodes/special-guest-clickup-s-co-founder-chris-cunningham-the-1-000-content-hack-big-brands-miss-ep-532
Duration seconds: 1190

## Resource

Partner with Jay: https://www.jayschwedelson.com/contact ㅤ 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 ㅤ Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter ㅤ Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com ㅤ Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com ㅤ 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 ㅤ Leave a comment and follow the show, it really helps us out! ㅤ 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. ㅤ 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. ㅤ 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 act…

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