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Chris Cunningham
13.9K posts

Chris Cunningham
@ChrisClickUp
Founding Member @clickup. Scaling Clickup in public and sharing how I'm securing raving fans via influencer marketing, community, and brand strategy.
Miami Fl Katılım Kasım 2010
1.8K Takip Edilen47.5K Takipçiler

@Codie_Sanchez this is how you build real relationships, not just transactions
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If you want to make more money, the ROI on “unscalable” work is about to go through the roof.
Magic Moments:
- Handwritten thank-you notes
- Sending flowers (to clients and friends alike)
- Calling (not texting) when you need something
- Showing up in person when an email would've been fine
Costs almost nothing. In a world where every interaction is getting sanded down into a frictionless automated nothing... humanity hits like a defibrillator.
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@CoachDanGo mindset matters, but you still have to face what’s actually happening head on
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@david_meszaros_ facts. without self compassion it turns into a cycle of pressure instead of progress
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@noahkagan Airbnb Hype Sold Everyone A Dream
But Predictable Income Builds Predictable Lives
Stability Scales Sanity
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The older I get the less money I want to make.
And it's more I want less BS to deal with in my life.
My old house was on AirBnB - took it off and put it up for long-term rental.
Weekly complaints, city taxes, annoying my neighbors, etc...oy vey.
Just rented it out for long-term today. And as it turns out long-term rental makes more money! Go figure.
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@davidmotta simple systems repeated > new ideas every week. that shift changes everything
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@jonbrosio I Stopped Chasing Confidence And Started Chasing Consistency
Funny How Results Suddenly Started Respecting Me
Discipline Attracts Momentum
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@Tim_Denning I Agree Business Thinking Changes Ur Brain Chemistry
Once U See Revenue As Creation Not Survival
Everything Starts Feeling Like A Game
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@SahilBloom Yes Social Proof Is Not Ego It Is Risk Reduction
Decision Makers Buy Confidence Before They Buy Services
Signal Matters More Than Style
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A few cold emails changed my life.
Here are some tips if you're trying to send one:
1. Short and simple gets read (long and complex gets deleted). Stop with the long cold emails. They make eyes glaze over and get deleted. 4-5 lines, space them out with hard enters (makes them appear more optically pleasing and digestible).
2. Simple direct subject line. Stop with the shock factor cold emails. They may get an open, but the person won't take you seriously (sorry). Just be direct.
3. Personalize it (and don't use AI). Make sure it's clear it's not a mass email. Just do the unscalable thing. Learn something about the person you're sending it to and include that detail.
4. Embed a bit of social proof on why the person should take you seriously. What have you done? What makes you different or interesting? If you have nothing, focus on building some skills first. Your skills are networking magnets.
5. Create some value for the person. Don't "gate it" behind a follow-up call or email, just share it. If you're pitching a service, create a mock-up of what you'd do for the person and include a screenshot in the email. If you're trying to get an interview, include a doc breaking down your observations about the company and opportunities.
6. End with a clear call-to-action. Ideally a single line, short sentence, and bolded or clearly standing out from the email.
Hope this helps someone out there. I know it would have helped me.
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@DeanBuilds22 I Love Watching Products Grow Up In Public
Transparency Builds Trust Faster Than Perfect Messaging
Keep Showing The Messy Middle
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Day 30 - 2 days until launch
Just hit 150 companies on the waitlist.
What started as "AI that knows when to call for help" is now a full platform:
• Multi-bot support
• Live agent dashboard
• Analytics
• Integrations
• API access
• Team management
Tomorrow is the final prep day. Thursday we launch.
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@RetentionAdam Exactly
Culture Is Not Created In Bars
It Is Built In Clear Direction
And Respectful Monday Morning Energy
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3 decisions I made as a founder that I'll never, ever do again:
1. I had 38 people coming to my apartment every day.
5,000 square foot loft, and I turned it into a sales floor. Two bathrooms for 38 people. I put a stool next to the laundry room sink to handle overflow…dudes pissing in the sink was my solution!!!
There was no separation between my work and my life. I never left because work never left me.
It was absolutely horrible. Now I won't have an employee in the same city I live in. That's how far the pendulum swung.
2. I bootstrapped my first company with a family member as a financial partner.
What I'll say is that bootstrapping is already hard - it takes longer than you think, costs more than you plan, and the stress is constant. When things are good they are great, but when they are bad, adding a family relationship to that equation makes every difficult moment harder because of this added dynamic.
3. Every Friday, I'd take my team out, and we'd get hammered.
I wasn't building culture, but just getting drunk with my team. That's just not how I'd choose to bond with a team now.
All 3 of these felt like founder instincts at the time.
> Hustle
> Loyalty
> Camaraderie
Looking back, they were just defaults I never examined that were holding me back in some capacity - and changing them helped me AND my businesses to grow beyond any ceiling I’d hit before.
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@ChrisWillx Yes Everyone Obsesses Over Being Correct
Few Focus On Staying Consistent Long Enough
Visibility Compounds Even When Belief Doesn’t
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Chris Cunningham retweetledi

Here is: "Vaporwave kanban board for coding agents"
Figma is down 8%
Barrier to entry for design tools is plummeting. This will exist as a feature in horizontal platforms like @clickup whiteboards etc. soon
Immense value to integrating this with other platform primitives



Stitch by Google@stitchbygoogle
Meet the new Stitch, your vibe design partner. Here are 5 major upgrades to help you create, iterate and collaborate: 🎨 AI-Native Canvas 🧠 Smarter Design Agent 🎙️ Voice ⚡️ Instant Prototypes 📐 Design Systems and DESIGN.md Rolling out now. Details and product walkthrough video in 🧵
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@Dwriteway Keep it clear
Keep it tight
Make buying feel obvious
That is how money moves
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@PhilsUpgrades The best part is you are not framing healing like a hustle plan
That alone makes this land harder
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@Jayyanginspires I have seen brilliant people stay stuck for years cuz being right felt safer than being seen
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@dickiebush i like how you owned the mistakes too. makes it way easier to trust the process when you see what didn’t work as well.
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@Nicolascole77 Prompt writing gets way better once u stop treating tasks like one lump and start breaking the mess into movable parts
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@NathanHirsch99 Everyone obsesses over growth
Very few obsess over preventable stupidity
That second one keeps the lights on
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10 management fails that bankrupt companies.
(WeWork ignored #1).
Bankruptcy rarely happens overnight.
It follows predictable leadership mistakes.
Avoid these or face collapse.
Save your business now.
Spot them early → save your company:

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@itsalvinhuang agree. growth problems are rarely solved by more activity, they’re solved by better alignment between product, message, and audience.
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@ChrisClickUp Just stumbled across your profile. Is there a way to discuss managing an account directly with you? No AI shotgun stuff.
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Google's new AI Max now handles your ad targeting, bidding, AND creative automatically.
So what exactly does the media buyer do now?
Serious question.
If the platform decides who sees it, how much you pay, and what the ad looks like, you're not running ads. You're watching ads run themselves.
The last defensible skill in paid media is knowing when to turn it off.
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