Chris Cunningham

Founding Member @clickup. Scaling Clickup in public and sharing how I'm securing raving fans via influencer marketing, community, and brand strategy.

[Chris Cunningham @ChrisClickUp]

Kids are making $25K/month with digital products.

But most people don't know how.

So I built 170+ Digital Product ChatGPT prompts to help you make money too.

Normally $39, but next 24 hrs, it's FREE!

To get it:

1. Follow me (so I can DM you)
2. RT this tweet
3. Reply "SEND"

[Jake Fleshner @JakeFleshner]

Having the best time @ Reserve

NY Tech Week

@ChrisClickUp @MichaelAxman

[Chris Cunningham @ChrisClickUp]

@testingcatalog 🔥

[🚨 AI News | TestingCatalog @testingcatalog]

ClickUp is working on a Cowork feature 👀

> Cowork can help users build, edit, and take action alongside them, and other agents at the same time

> Sessions are persistent, so context carries across the entire workday

> Multiple users can collaborate in the same Brain session simultaneously

Brain Cowork can proactively work in the channel just like a human teammate, drafting docs and setting reminders in the same thread where the team is actively working.

[ClickUp @clickup]

When corporate jargon gets taken a little too literally.

[Chris Cunningham @ChrisClickUp]

@moneyries @DJ_CURFEW @alex @jack @moneyries I'd love to talk to you and see how we can improve. We have a new release coming soon that fully addresses what you're speaking about.

Sending you a dm now!

[Chris Cunningham @ChrisClickUp]

@its_joeyp @0xMarcB @DJ_CURFEW Keep me posted @its_joeyp - happy to help you ensure to get this working!

[Robert Katai @katairobi]

Brands like GaryVee, @stanforcreators, and @clickup (@ChrisClickUp ) show how:

[🚨 AI News | TestingCatalog @testingcatalog]

ClickUp's AI Brain will soon be able to build fully interactive apps from a single prompt, with live data integrations.

Some examples 👀

> Sprint tracker - to reshape your team operations into an analytics dashboard for stakeholders.

> CRM tool - to have a custom dashboard with customizable controls on top of your existing data.

> Live OKR dashboard - to have a dynamic view that can pull the latest updates automatically

[Justin "Results" French 🥷🚀 @JustinRFrench]

Can your business run without you?

If the answer is no, you don't have a business. You have a high-paying prison.

🧵 Here's the systems audit every operator needs to run this weekend:

1/ The Content Revenue System

One Space. One transcript. 14 pieces of content. Buffer queue.

I've run it every weekday since October. It compounds.

If your content stops the second you stop showing up — that's a gap. I personally use @clickup to help my team & I stay organized + it is now integrated with @claudeai (video coming soon....)

2/ The 5-Minute Rule

Inbound DM hits → respond within 5 minutes → est. 80% higher close rate.

Most operators have notifications off and check messages "when they get to it."

That's how warm leads die.

3/ The 97/3 Rule

Only 3% of your audience is ready to buy right now.

Your job is to find them. Scour LinkedIn. Scour X. Search for "looking for a fractional CMO" — they're publicly telling you.

Stop spraying. Start hunting.

4/ Every business has gaps. Even Hormozi's.

Two reps from https://t.co/RZa662cEYn called me months apart with zero CRM continuity. No notes. No context. Restart from zero.

8-figure operation. Still leaks.

Audit. Yours. Weekly.

5/ The Freedom Machine (Hat tip @JudasPhiGates8 )

Build a system that delivers value, social impact, AND high-quality inbound — without your hands on every lever.

Not no humans. Smarter humans + smarter systems.

That's the path.

⚔️ DISCIPLINE → daily systems
📊 DATA → tracked signals
🎯 RESULTS → predictable revenue

What's the ONE manual task you're killing this week?

At the end of our lives, we will ask ourselves 4 simple questions: Did I live? Did I love? Did I matter? Did I make a difference? Keep making a difference. Build that mind. Build that body. Build that business. Build that bank account. But most importantly — build that legacy. Stay healthy. Stay hungry. Stay humble. We'll see you at the top!

🥷 The Revenue Ronin / ⚔️ Discipline. 📊 Data. 🎯 Results. / https://t.co/RGBMNtGCLi

Thank you again to @clickup @ClickUpCrew @ChrisClickUp for sponsoring the space! 🫡🥷

[Chris Cunningham @ChrisClickUp]

@testingcatalog Game Changer

[🚨 AI News | TestingCatalog @testingcatalog]

ClickUp is reshaping its Brain platform UI based on which model you pick.

> With Claude Opus 4.7, the interface reads "Tell Claude what to do next."

> With Gemini 3.1 Pro, it becomes "Let's ask Gemini."

> With GPT 5.5, it says, “Let's ask ChatGPT.”

The confirmed models are Claude Opus 4.6, Claude Opus 4.7, GPT-5.4, GPT-5.5, and Gemini 3.1 Pro, all selectable from a single dropdown on both desktop and mobile.

[Chris Cunningham @ChrisClickUp]

@benln @clickup Brain2 makes this happen!

[Chris Cunningham @ChrisClickUp]

@clickup @wesbrummette Lets go!

[Chris Cunningham @ChrisClickUp]

@iamjasonlevin Absolutely

[ClickUp @clickup]

ClickUp Hackathon Day 1

[Chris Cunningham @ChrisClickUp]

@ItsWillHenry damn should I come back to SF

[Chris Cunningham @ChrisClickUp]

@cute_n_clocky @clickup SOON!

[ClickUp @clickup]

Founders from all over Miami gathered for an afternoon of competition, conversation, and tons of talk about AI.

We teamed up with our good friends at Nucleus Network to bring founders together so they could swap stories about what they're building and play padel, all with the Miami skyline in the background.

Sometimes the best connections happen between sets.

Thanks to everyone who came out. What networking event should we throw next?

[Chris Cunningham @ChrisClickUp]

@FracSlap @clickup has both and context on your work. (As well as can create tasks and more for you directly after your call)

Happy to hook you up if you want to check it out