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Chris Cunningham
14.6K 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 Edilen47.3K Takipçiler

@thejustinwelsh facts. the more you do, the more surface area you create for luck
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@IamLeoAfonso agree. sometimes the best move is to pause and actually think instead of just continuing the routine
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I delayed the decision for 2 years.
Right after I entered university, I got that relief.
That relief of having made a decision that gives me 3 years to work it out.
And although I was learning on the side.
Time kept passing.
Truth is.
2 years later, and I still had no idea what to focus on.
Last year of university I resolved to settle it out for good.
So I paused.
I stopped the routine that just keeps going.
And sat for a few weeks to work out:
» where should I go next
» what to do to get there
And this goes for anything.
You can achieve things faster if you take more time to sit and solve the problem that is keeping you stuck.
I just kept passing through the days.
Without ever stopping to recalibrate.
You need to interrupt that routine.
| Because most of us are just in a fast car with no brakes, just a steering wheel.
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@EmailCopyJames i’ve seen this too. the moment you sound like yourself things start clicking
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My biggest mistake as an early creator?
I spent 3 months writing like other people.
Same hooks. Same format. Same energy.
I thought if I copied what worked for them it would work for me.
It didn't.
Because people don't follow formats.
They follow humans.
The day I stopped copying and wrote my first post from my real life a stranger commented for the first time.
Your story is the only content nobody else can write.
Use it.
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@ItsAndraz facts. quality of attention > quantity of time every time
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@gbscoach facts. progress isn’t always loud, but it’s still happening
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Your body makes a completely new stomach lining every few days.
If it didn’t, your stomach acid would literally digest your own stomach.
Which means your body is quietly rebuilding and protecting you every single day without asking for applause.
Psychology works like that too.
Most growth is invisible while it’s happening.
You are adapting, recovering, learning, and becoming stronger in ways you probably don’t even notice yet.
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@itstylerrbates taking risks is good. unmanaged risk is where problems start
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In the space of a week I have:
- been on travel to Morocco
- quit my job
- bought a new car
If you’re in your 20s (do this):
- quit that job you hate
- travel to that country you’ve been thinking about for a while
- buy that car (if you can afford it)
Because while I did all those things in a week…
I’ve never felt more alive and excited about the future.
Give it a go!
👉🏼 Follow @itstylerrbates for more!

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@tasornp agree. stability now comes more from adaptability than from any single job title
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The career path our parents taught us is broken.
Good college. Good job. Stay there and collect a good paycheck.
That model worked for their generation.
One stable job could support a family for life.
But AI has turned everything upside down.
Software engineers. Consultants. Lawyers.
The highest paying careers are now being disrupted overnight.
The real safety net isn't tied to any job.
It comes from minimizing your own risk.
Start building something for yourself.
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@MalikHughess agree. validation can quietly control way more decisions than people realize
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@rashiumapathi i like how intentional this is. right place, right tone, right timing
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Reddit gave us 1,200 signups in 7 days.
Here's exactly what we posted (and what got shadow-banned):
First rule of Reddit marketing:
Reddit hates marketers.
Reddit loves builders who share what they learned.
So we never posted as a company. We posted as a person who built something and wanted feedback.
The post that worked:
Title: "I built a tool that does X because I was sick of doing it manually. Here's what I learned after 6 months."
Not: "Check out my new SaaS [link]"
One reads like a founder. One reads like spam.
The subreddits we targeted (in order):
1. r/SaaS - builders who understand the problem
2. r/entrepreneur - people with the pain but not the solution
3. Niche-specific subs - the ones where your ICP actually hangs out
Don't go broad. Go where they're already venting about your problem.
What got us shadow-banned:
- Posting a link in the first comment
- Cross-posting the same post to 5 subs the same day
- Having a username that looked brand new (less than 30 days old)
Build karma first. Then post.
The comment that drove the most signups wasn't even our post.
Someone else asked a question in a thread. We answered it thoroughly. No link.
Then someone replied "do you have a tool for this?"
That's when we linked it. 300 signups from one comment.
The formula:
1. Find the thread where people complain about your problem
2. Write the most helpful reply in that thread
3. Wait for them to ask "how do you do this?"
4. Then mention your product
Patience > promotion.
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@IkeVale007 agree. responsibility feels heavy at first but it’s also where the control comes from
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@benbuaron_ First churn is such a weird milestone cuz it hurts like failure even when it is proof u built something real
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day 45 of building traxy into a $1m biz: we had our first churn. pain.
i knew this was gonna happen. still sucks.
but the craziest part is one $79/month traxy user churning is way more painful than a 5-figure windmill client doing the same.
it's progress. doesn't feel like it at all. but I know it is.
blown away by how generous people are with their feedback.
this customer gave me detailed, specific reasons - stuff i can use. and it's not a fit. he shutdown all outbound - there's no point.
but still very hard. don't care about the MRR - i just want people to be happy.
we closed a new client the day after.
so i don't need to add a minus sign to the growth update.
growth:
active users: 166 (+7)
paid users: 21 (+0)

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@Lilly7862 I rate this hard because consistency still works even when the feedback goes missing and ur brain starts chatting nonsense
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@ConnorGillivan I would add recruitment or talent ops next because every one of those companies probably lives or dies on operator quality
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Buffett has Berkshire. Munger had Wesco. Nathan and I have Hirsch Gillivan.
Meet Hirsch Gillivan: The Hold Co behind my 6 companies (and growing).
For 10+ years, Nathan and I built businesses the hard way.
One at a time. Endless nights. All our focus on a single bet.
Then in 2019, we sold FreeUp at $12M ARR.
And everything changed.
We started studying Buffett and Munger.
Asking different questions:
- What if we owned a portfolio instead of a company?
- What if we weren't the CEOs running daily ops?
- What if we acquired profitable businesses instead of building from zero?
That's how Hirsch Gillivan was born.
Here's what we own today:
1. EcomBalance: monthly bookkeeping for ecommerce brands
2. EcomBalance Tax: tax filing and planning for ecommerce
3. CFO Expertise: fractional CFO services for ecommerce and D2C
4. TrioSEO: SEO content & growth agency for ecom, b2b, & saas
5. HG Media: the media arm running our personal brands
6. Interlace Digital: our newest addition, ads for shopify brands
The mission is simple:
Build the suite of service businesses we WISH we had when we were running our own ecommerce company back in the Portlight days.
Bookkeeping. Taxes. CFO. SEO. Marketing.
All under one roof. All B2B. All cash flow positive.
The goal: 10 companies through acquisition in the next 2-3 years.
Not by grinding 80 hour weeks building from scratch.
But by buying profitable companies, hiring great CEOs, and helping them grow.
---
What would you add to the suite?
Repost if you're building (or thinking about building) a hold co too.
P.S. Follow me for daily updates on growing Hirsch Gillivan from 6 to 10 companies.

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@jimheskel i like this breakdown. simple but it explains why some people convert way easier
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@Dwriteway facts. lessons compound quietly before the money ever does
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@PhilsUpgrades strong point. where your focus goes, your experience usually follows
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@dickiebush show your work is a game changer. publishing early speeds everything up
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I wasted over 1,000 hours reading useless books on writing.
Instead, I could have saved my time and just read these 9 books:
1. The Adweek Copywriting Handbook by Joseph Sugerman
The only copywriting book you'll ever need – full stop.
Learn the art of capturing & keeping attention.
2. The Boron Letters by Gary Halbert
Read this book for 1 reason:
To study Gary Halbert's incredible writing style.
This guy has an incredible way with words – a voice, rhythm, and tone that keeps your eyes glued to the page.
3. Show Your Work by Austin Kleon
The idea of the writer slaving away for months in solitude is no longer true.
The best writers are sharing all of their ideas in public, getting feedback, and iterating.
4. The War of Art by Steven Pressfield
Writing is a daily battle with the Resistance.
But until you're aware of it, the Resistance will dominate you.
This book single-handedly changed my life.
Once you read it, you'll never see creative work the same way.
5. The Sense of Style by Steven Pinker
This is the best book on grammar and style.
It's a modern take on Strunk & White's classic.
6. On Writing Well by William Zinsser
The no-BS guide to writing effective non-fiction.
Filled with examples of classic mistakes that, once you see, you'll never make again.
7. Bird by Bird by Anne Lamott
This is one of the greatest books on the writing process.
It's a comforting, funny, and practical guide to getting words on the page.
8. The Elements of Style by Strunk & White
The most tactical book on this list.
• Active vs. passive voice
• Positive vs. negative form
• Concise vs. verbose writing
• Lists of words to never use again
Keep this one on your desk at all times.
9. The Art of the Pitch by Peter Coughter
Every writer who wants to make money writing online needs to read this.
This book teaches you how to sell your ideas.
After 5+ years as a digital writer, all writing is selling.
This book will show you how to sell your ideas to clients, bosses, and readers.
10. (BONUS) The Art and Business of Online Writing by Nicolas Cole
This book completely broke my brain about what it meant to write online.
• Why you shouldn't start a blog
• Generating an endless amount of ideas
• The "Golden Intersection" of telling personal stories
Truly epic.
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@itsalvinhuang overconsumption feels productive but it rarely moves anything forward
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@bluremark facts. poor sleep quietly destroys performance even if everything else looks dialed in
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