E7: Building ClickUp from a $0 Budget to a $4B Valuation with Chris Cunningham

In this power-packed episode of our Happy Hour series, I sit down with Chris Cunningham, co-founder of ClickUp, the $4 billion AI-powered project management platform. Chris takes us behind the scenes of ClickUp’s explosive growth and shares his no-nonsense strategies for scaling, networking, and leveraging AI to build massive business impact. From grassroots marketing to raising over $500M in funding, this conversation is loaded with entrepreneurial gold.

 

We talk about what it means to lead with value, how Chris overcame a debilitating fear of public speaking, and why he believes in showing up and shipping—even if things aren’t perfect. Whether you’re building a startup, scaling an agency, or just trying to keep your business organized, Chris delivers both inspiration and practical advice to help you move faster and smarter.

Episode Highlights

[0:00] - Introduction

[1:10] - Meet Chris Cunningham, ClickUp co-founder and master connector

[2:07] - Joe’s automation genius: Why he’s the best ClickUp + Zapier trainer

[3:28] - Why AI is opportunity, not threat—if you’re willing to learn

[5:04] - What makes ClickUp the all-in-one productivity tool

[6:12] - Competing with giants: How ClickUp disrupted a saturated market

[8:05] - Raising $535M: ClickUp’s unique edge that won over investors

[9:10] - Funny + bold: How ClickUp’s marketing crushed the SaaS playbook

[11:10] - The scrappy moves that gave ClickUp early traction

[12:33] - The AppGator tool that turned bad reviews into sales leads

[13:27] - What it really takes to push through fear and doubt as an entrepreneur

[15:15] - Why resilience, not perfection, is the true key to success

[16:07] - The power of giving first and building real relationships

[18:09] - The single most overlooked way to get your ideas noticed

[20:18] - How Chris turned public speaking from fear into a superpower

[22:03] - Tips on building an irresistible brand personality in your content

[24:40] - Using short-form content to build long-term business relationships

[27:55] - Why most people fail to get their ideas seen—and how to fix it

[30:14] - Chris’s thoughts on ClickUp’s biggest missed opportunities

[33:02] - The long-term play of community and audience building

[36:18] - What Chris is excited about in the AI space right now

[38:47] - Behind-the-scenes of running an AI-first business

[41:10] - Chris’s playbook for startup founders in today’s tech landscape

[44:55] - The one behavior shift Chris recommends to every entrepreneur

[47:20] - Why the “ship fast, iterate faster” mentality still wins

[49:45] - How to keep your energy and optimism high—even in chaos

 

5 Key Takeaways

 

1. Be Scrappy and Ship Fast: ClickUp’s early growth came from prioritizing action over perfection. They pushed updates weekly and welcomed feedback—even when the product had bugs.

2. Leverage AI with Intentionality: Embrace AI as a partner in productivity. Chris urges us to learn the tools rather than fear them—especially when platforms like ClickUp are integrating it daily.

3. Build to Serve, Not to Take: Chris credits his success to focusing on adding value to others before asking for anything in return. That mindset built a powerful, loyal network.

4. Content is Leverage: Whether you’re creating videos that get 200 views or speaking on a stage, consistent visibility in communities can open massive doors.

5. Overcome Fear by Outworking It: From stuttering in childhood to commanding rooms of thousands, Chris proves that fear is beatable—with enough time, practice, and grit.

 

Links & Resources

 

• ClickUp: https://clickup.com/

• Connect with Chris: [e-mail]

 

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