Do This, NOT That: Marketing Tips with Jay Schwedelson

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

July 2, 2026

AI Summary

5 min read

Chris Cunningham, co-founder of ClickUp, built a $4 billion SaaS company's organic marketing strategy by borrowing playbooks from B2C and treating content like a TV show rather than a lead generation funnel. His approach—hiring actors on day rates, testing small before scaling, and mining social followers for sales pipeline—offers a concrete alternative to the AI-generated "slop" he says is flooding feeds. The episode is a tactical walkthrough of how to break through a crowded category without a massive budget, and why human imperfection still beats AI in content.

The B2C Playbook for B2B

Cunningham's core insight is that B2B marketers should stop acting like they're in B2B. He came from Celsius and fashion, where he ran influencer campaigns, and brought that mindset to ClickUp. "I watch B2C. That's been my playbook the whole time," he says. He pitched his board on hiring a single creator to make funny videos—two grown men dancing and acting out office scenarios—rather than producing polished product demos. The board was skeptical, but he asked for minimal budget to prove the concept.

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What you'll learn

1 (00:00) **Introduction & Guest Welcome** - Jay introduces Chris Cunningham, founding team member of ClickUp, a $4B+ AI-driven project management platform.
2 (01:56) **The Organic Breakthrough: Pitching "Crazy" to the Board** - Chris explains how he convinced ClickUp's board to let him experiment with B2C-style organic content.
3 (03:24) **The Scrappy Test-and-Learn Method** - First month: modest results (20-30K views). Second month: a few million-view videos. Third month: 25 million impressions.
4 (04:10) **The $1,000 Content Hack for Small Marketers** - Chris breaks down how any company can replicate his approach without a big budget.
5 (06:43) **Turning Viral Views into Pipeline & Demos** - How ClickUp converts organic attention into real business outcomes.
6 (09:48) **The Missed Opportunity: Intentional Follow-Up** - Most marketers ignore the high-value people already engaging with their content.
7 (10:22) **AI's Impact on SaaS: Chris's Unfiltered Take** - Chris shares his opinionated, positive view on AI and software.

+ Full timestamped outline available in the app

Show Notes

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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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Connect with Chris Cunningham on LinkedIn and on Instagram (@Cunningham), or reach him directly at [email protected]. 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