Matt Gray

Founder & CEO, Founder OS | Proven systems to grow a profitable audience with organic content.

Over the last decade, I’ve built 4 successful companies and a community of over 14 million people.

My mission is to inspire 100 million founders to live their dreams through proven systems.

I help entrepreneurs remove themselves from operations, grow on autopilot with content and an engaged audience, and automate core systems.

I’m the founder of Founder OS, Gray Enterprises, and Bitmaker (acq. General Assembly).

My portfolio:

→ I'm the founder & CEO of Founder OS, a community of 650 entrepreneurs
→ I’m the founder & CEO of Gray Enterprises with a community of over 14 million people
→ I teach the Founder OS Program to help entrepreneurs scale their online businesses to $1M+ revenue
→ I coach entrepreneurs that need help with marketing, sales, systems, community, and growth
→ I advise early-stage companies in AI, Education, Creator Economy, and SaaS verticals

My results:

→ 14M+ people community
→ 2.5M+ people following Founder OS
→ 2B content impressions annually 
→ 0 advertisements
→ 80%+ margins

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Founder & CEO

Founder OS helps you build a predictable lead engine with organic content & make $1M+ online.

33 habits that (quietly) changed my life forever: 

1. Protect The First 4 Hours Of The Day

Your morning hours are sacred. Guard them like your life depends on it.

2. Write Before The World Wakes

Clarity comes in silence. Write first, react later.

3. Break A Sweat Daily, Energy Is Everything

Movement isn't optional. It's the foundation of everything.

4. Watch The Sunrise Often

Nature resets your nervous system better than any app.

5. Say "No" With Love

Protect your time without burning bridges.

6. Ask: "What's The One Domino That Knocks The Rest?"

Focus beats volume every single time.

7. Operate From Systems, Not Moods

Systems eliminate the need for motivation.

8. Journal My Fears Until They Dissolve

Writing exposes irrational thoughts.

9. Automate One Task Every Week

Compound small automations to leverage.

10. Build Once, Distribute Forever

Create assets that work while you sleep.

11. Re-Read My 10 Year Vision Weekly

Clarity fades without repetition.

12. Ask "Who Not How" Every Day

Delegation beats doing it yourself.

13. Leave One Day Plan-Free

Spontaneity feeds creativity.

14. Call My Parents Unprompted

Connection matters more than productivity.

15. Give Credit Publicly, Often

Generosity compounds faster than hoarding.

16. Build A Brand I Actually Admire

Don't build what you think will work. Build what you respect.

17. Return To Nature Every Week

Disconnect to reconnect.

18. Practice: Slow Is Smooth And Smooth Is Fast

Rush kills quality. Patience wins.

19. End Showers Cold

Discomfort training builds mental resilience.

20. Carry A Pocket Notebook Everywhere

Ideas don't wait for you.

21. Sketch Ideas Instead Of Typing Them

Visual thinking unlocks solutions.

22. Meditate On Impermanence

Everything ends. That makes today matter more.

23. Leave My Phone Outside The Bedroom

You before notifications.

24. Let Go Of One Grudge

Carrying resentment only punishes you.

25. Sing Alone In The Car, Loudly

Joy doesn't require an audience.

26. End The Day With Gratitude

What you focus on expands.

27. Eat Until I'm 80% Full

Discipline at the table creates discipline.

28. Eat The Same Lunch Every Day

Decision fatigue is real. Eliminate unnecessary choices.

29. Invest Automatically Monthly

Wealth is built through systems, not impulses.

30. Edit My Possessions Every 90 Days

Clutter in your space creates clutter in your mind.

31. Block One Full Week Per Quarter Fully Off-Grid

Deep rest creates deep work.

32. Sleep Without An Alarm

Your body knows what it needs.

33. Replace "I Have To" With "I Get To."

Language shapes reality. Choose empowering words.

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Matt Gray 

How to set a company strategy you'll actually use:

PURPOSE (Start Here)

1. Our One Sentence Mission

Strip it down until a 10-year-old could repeat it.

If you need a paragraph to explain your mission, you don't understand it yet.

2. Why The World Needs Us

This isn't about you, it's about the problem you're solving.

If the world wouldn't notice you disappeared, dig deeper.

3. What Would Break If We Disappeared

The answer reveals your true purpose.

UNIQUE ADVANTAGE (Your Moat)

4. The "Secret" We Believe That Others Don't

Every successful company operates on a contrarian belief.

5. What Makes Us Hard To Copy

Real competitive advantages take years to build.

If a competitor can replicate it in 90 days, it's not your moat.

6. Core Moat

Is it your brand? Your tech? Your network? Your execution speed?

Name it specifically. Own it completely.

7. Where We're Already Winning Disproportionately

Double down on what's already working before you chase what's not.

8. 10X Better Than Status Quo

Being 10% better doesn't change behavior.

You need to be dramatically superior to make people switch.

THE MARKET (Who You Serve)

9. Who Our Dream Customer Is

"Everyone" is not a strategy.

10. Their Biggest Pain / Unmet Job

What problem would they pay anything to solve?

11. Market We Dominate First

Win a niche beachhead before you try to conquer the world.

STRATEGIC CHOICES (Your Discipline)

12. What We Will ALWAYS Do

These are your non-negotiables.

The principles you'll protect even when it hurts.

13. What We Will NEVER Do

This is harder than it sounds.

Saying no defines your strategy more than saying yes.

14. Our #1 Priority This Year

Not three priorities. Not five. One.

Everything else is secondary or shouldn't exist.

15. Our Constraint / Bottleneck Right Now

What's actually holding you back?

Name it specifically or you'll never fix it.

16. How We'll Remove That Bottleneck

Talk is cheap. What's the actual plan?

EXECUTION SYSTEM (Making It Real)

17. Quarterly Targets (3 Max)

Pick three metrics that matter most.

Everything else is noise.

18. Monthly Milestones

Break quarters into months so you can adjust faster.

19. Who Owns Each Metric

One owner per metric. No committees.

STRATEGIC STORY (Your Narrative)

20. The Narrative We Want Team / Customers To Repeat

What do you want people saying about you when you're not around?

That's your strategic story.

21. Sticky Phrase For This Strategy

Mine is "We win because ______"

If you can't fill in that blank in five words, you're not clear yet.

The best strategy isn't the most sophisticated one.

It's the one your team can remember and execute on Monday morning.

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Notebooks are the new operating systems.

I know that sounds surprising, but hear me out.

Most founders have 17 half-filled notebooks scattered across their desk, car, and backpack.

Each one started with good intentions. Each one abandoned by week two.

Last year, I threw out every productivity app and went back to paper.

I built what I call "The Daily OS" a one-page framework that actually works.

Here's how to organize a notebook you'll actually use:

1. Theme Of The Day 

Start every day by naming what it's about.

Not a to-do list. An intention.

"Today is about deep creative work."
"Today is about strategic planning."
"Today is about connecting with my team."

This single sentence filters every decision you make.

2. Top 7 Priorities

Not 20 tasks. 
Not 50 emails. 
Seven priorities.

If you can't pick seven, you don't have clarity yet.

List them by impact, not urgency.

3. Meetings / Leverage Calls 

Here's the filter: Does this meeting create leverage or consume time?

If it doesn't compound, decline it or delegate it.

Only write down the calls that actually move needles.

4. Notes / Insights

Throughout the day, capture insights immediately.

Don't trust your memory. 

Write it down in the moment.

This section becomes your second brain.

5. The Scoreboard

Track three metrics daily:

• Gratitude (1 thing you're grateful for)
• Energy (1-10 scale, where 10 = you feel unbelievable)
• Revenue (1-10 scale, where 10 = you made significant progress)

Numbers don't lie. 

This scoreboard reveals patterns you'd otherwise miss.

6. End Of Day Reflection

Ask yourself 3 questions every evening:

What worked?
What didn't?
What will I accomplish tomorrow?

This 2-minute practice compounds into massive clarity over time.

The entire system fits on one page.

No apps. 
No syncing. 
No notifications.

Just a notebook and a pen.

Why does this work when digital tools fail?

• Because writing activates your brain differently than typing
• Because paper doesn't have notifications competing for your attention
• Because you can't optimize what you don't track, and this forces you to track what matters

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I'm finishing 2025 with less.

Not more goals. 
Not more hustle. 
Not more complexity.

Less.

Founders usually enter a new year by adding more projects, more meetings, more commitments.

Then they wonder why they're overwhelmed by March.

I spent the last week doing the opposite.

Deleting everything that doesn't move the needle.

Here's what I'm ruthlessly removing before 2026:

1. Instagram Before 9am

Your brain's sharpest in the morning, don't waste it scrolling.

I used to grab my phone before my feet hit the floor. 

Now I protect those first hours like they're sacred. 

Because they are.

2. Meetings That Don't Move The Needle

If it doesn't produce revenue, a decision, or a deliverable, cancel it.

I audited my calendar last week. 

Half my meetings existed just to "stay connected." Those are gone.

3. Software You're Not Actually Using

Check your subscriptions, cancel anything you haven't opened in 30 days.

I found $847/month in tools I forgot I was paying for. That's over $10,000 a year on digital clutter.

4. Your Lowest-Paying Client

They take 60% of your time for 10% of your revenue.

You know exactly who I'm talking about. 

Fire them. 

Your business will thank you.

5. Slack Notifications After 6pm

Your team will survive; you need to recharge.

I turned off after-hours notifications six months ago. 

Not a single emergency. 

Plenty of sanity gained.

6. The Project You Haven't Touched In 3 Months

It's not "on hold", it's dead.

Archive it. Stop pretending you'll get back to it. 

That mental weight is costing you more than you realize.

7. Coffee Meetings With No Agenda

"Pick your brain" equals wasting your time.

If someone can't send a clear agenda beforehand, they don't respect your calendar enough to deserve a spot on it.

8. Your 47-Item To-Do List

Write down 3 things that actually matter, do those.

Long to-do lists are productivity theater. 

They make you feel busy while keeping you from what's important.

9. The Need For Perfection

Ship the draft you've been sitting on for 2 weeks.

Done beats perfect every single time. 

Perfectionism isn't excellence, it's fear wearing a fancy mask.

10. Saying "Let Me Think About It"

You already know, decide now.

Indecision is a decision to stay stuck. 

Trust your gut and move forward.

Every "yes" to something meaningless is a "no" to something that could transform your business.

I'm entering 2026 lighter.

Fewer commitments. 
Fewer distractions. 
Fewer things competing for my attention.

More focus. 
More energy. 
More impact.

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10 Things To Delete Before 2026

10 phrases every founder should read:

1. "Revenue is vanity. Profit is sanity. Cash is reality."

2. "Your business should work without you, or it's not a business—it's a job."

3. "Systems run the business. People run the systems."

4. "Charge what you're worth, then double it."

5. "Problems are just undiscovered profit centers."

6. "You don't get what you deserve. You get what you negotiate."

7. "Focus is saying no to 1,000 good ideas."

8. "Your network is your net worth, but only if you give before you receive."

9. "Perfectionism is procrastination in disguise."

10. "The market doesn't care about your feelings."

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10 Phrases Every Founder Should Read

I read 112 books in a year, here's which ones you should read:

1. Deep Work By Cal Newport

In a world of constant distractions, focus is a priceless asset.

Newport teaches you:

• The value of deep vs shallow work
• How to avoid the trap of 'busyness' 
• How to create rituals and routines for focus

Conquer distractions with this book.

2. Zero To One By Peter Thiel And Blake Masters

This book redefines the startup landscape.

You'll learn to:

• Challenge conventional business thinking
• Grasp the philosophy of true innovation
• Learn how to build a monopoly 

Don't iterate.

Innovate.

3. Scaling Up By Verne Harnish

Grow your business smartly with Harnish's insights.

He talks about:

• Recognizing the barriers to scaling up
• Mastering the four major decisions in business
• Implementing actionable tools and techniques 

Scale with strategy, not just size.

4. The Power Of Now By Eckhart Tolle

Awaken your mind to the present moment.

Tolle guides you through:

• Achieving personal liberation 
• The profound concept of the 'Present Moment'
• Recognizing patterns of self-created suffering

Live now. 

Everything else is a dream.

5. Shoe Dog By Phil Knight

Learn about Nike's extraordinary journey.

Knight shares:

• The evolution of a global brand 
• The raw hustle of entrepreneurship
• The risks and rewards of his venture

Every empire starts with a single step.

This book makes this clear.

6. Built To Last By Jim Collins And Jerry I. Porras

Discover what makes visionary companies thrive.

Collins and Porras reveal:

• Timeless management principles
• The habits of successful companies
• The 'Preserve the Core/Stimulate Progress' concept

7. Rework By Jason Fried And David Heinemeier Hansson

Redefine the way you perceive business.

Fried and Hansson advocate:

• Challenging the norms of the corporate world
• Embracing a simpler way of working
• Less is more

Revamp your strategy. 

Less fuss, more clarity.

8. The Lean Machine By Dantar Oosterwal

Embark on a journey of streamlined processes.

Oosterwal presents:

• Harley-Davidson's remarkable transformation 
• How operational excellence can fuel success 
• The guiding principles of lean thinking 

Efficiency is precision.

9. The CEO Within 

Recognize and unleash the inner leader in you.

Dive into:

• Building trust and fostering team unity 
• Harnessing innate leadership qualities 
• Navigating corporate politics with finesse 

You can be the leader you've been looking for.

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How to monetize your expertise (without selling your soul):

Most experts are broke.

They have incredible knowledge but no system to monetize it.

Knowledge without systems is just expensive hobbies.

1. My Expertise Transformation Story

2017: Built my first system, hit $5,000/month

2021: Systemized everything, reached $150,000/month 

2024: Founder OS generates $464,000/month

Same expertise. Different systems.

2. The $100K/Month Math

$100,000 per month breaks down to:

• $3,333 per day
• 28 customers at $3,571 each
• 10 customers at $10,000 each
• 5 customers at $20,000 each

The higher your price, the fewer customers you need.

3. The Attract → Nurture → Monetize Formula

Most experts skip straight to monetization.

Big mistake.

My 3-step system:

• Attract strangers with valuable content
• Nurture them into believers
• Monetize believers into customers

Each step must be systematic, not random.

Step 1: The Expertise Amplification System

Your expertise is worthless if nobody knows about it.

My content strategy:

• Tell case studies (proof of expertise)
• Give contrarian takes (attention grabbers)
• Break down processes (step-by-step value)
• Share frameworks (your intellectual property)

Goal: Position yourself as THE authority in your niche.

Step 2: The Trust Acceleration Engine

Most experts think content is enough.

It's not.

You need a systematic nurture process:

Week 1: Welcome + immediate value delivery 
Week 2: Personal story + credibility building
Week 3: Case study + social proof 
Week 4: Soft introduction to your offers

Trust before transactions. Always.

Step 3: The High-Value Monetization Model

Here's where most experts mess up:

They sell their time, not their systems.

Wrong: $200/hour consulting 

Right: $20,000 systematic transformation

Scale your expertise, not your hours.

4. The Expertise Authority Stack

Layer 1: Valuable free content (builds awareness) 

Layer 2: Lead magnets (captures emails) 

Layer 3: Email sequences (builds trust)

Layer 4: Case studies (proves results) 

Layer 5: Premium offers (monetizes expertise)

Each layer feeds the next.

5. The Expertise Scaling System

Month 1-3: Document your methodology 

Month 4-6: Test with 5 pilot customers

Month 7-9: Systematize delivery process

Month 10-12: Build content machine 

Year 2: Scale to $100K/month

Systems first. Scale second.

Remember, your expertise is worth millions.

But only if you systematize it.

Most experts die with their knowledge.

Smart experts build systems that scale their impact.

Don't take your expertise to the grave.

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Founders are terrified AI will replace them.

I had the opposite realization.

I built an AI team that works while I sleep.

Here's how I built my AI team:

Step 1: Upload Your Universe

Feed it everything that makes you, you.

PDFs, books, posts, transcripts, brand guidelines, every piece of content that represents your voice and vision.

This becomes its knowledge base.

The more context you give it, the better it thinks like you.

Step 2: Train On Your Tone

Teach it to write like you. Think like you.

Upload examples of your best writing and tell it: "This is how I communicate."

The AI learns your patterns, your voice, your style.

Now it can draft emails that sound exactly like you wrote them.

Step 3: Connect Your Stack

Integrate it with the tools you already use:

• Slack → Daily syncs
• Notion → Task boards
• Figma → Visual output
• Google Drive → Summaries

Your AI team now lives inside your workflow, not outside it.

Step 4: Assign Roles

I created four distinct AI assistants:

• Writer GPT - drafts content in my voice
• Designer GPT - creates visual assets
• Analyst GPT - pulls insights from data
• Chief of Staff GPT - manages my calendar and priorities

Each one has a specific job. 

Each one operates independently.

Step 5: Chain Them Together

Here's where it gets powerful:

These AI assistants update dashboards, draft reports, and sync information without me.

They work while I sleep.

They hand off tasks to each other like a real team.

Step 6: Test + Tune

Feedback loops = faster learning.

The more you correct and refine, the smarter the system gets.

I spend 30 minutes per week tuning my AI team.

They save me 20+ hours per week in return.

You now run a company with 4 AI employees.

Founders are still treating AI like a search engine.

They ask it one-off questions and wonder why it's not useful.

But AI becomes transformative when you treat it like a team member.

Assign it roles. 
Give it context. 
Connect it to your systems.

That's when magic happens.

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I spent 3 years working 16-hour days and almost broke myself.

Now I have built successful companies while maintaining work-life balance.

The difference isn't more effort. 

It's systems.

Your hustle got you to $20K per month, but it won't get you to $100K. 

I learned this lesson the hard way so you don't have to.

Here's what transformed everything for me:

1. Content Creation Systems

The right systems turn strangers into buyers automatically. 

Not through endless hustling, but through systematized content that works while you sleep.

2. Team Operating Systems

Most founders stay trapped because they can't remove themselves from operations. 

Systems let you build teams that operate beautifully without your constant involvement.

3. Offer Scaling Systems

Breaking free from the 1:1 model requires systematic approaches to scale what you offer. 

This is how you create exponential rather than linear growth.

4. Consistency Over Hustle

Money loves systems, but wealth loves consistency. 

The entrepreneurs who build real wealth aren't working 80-hour weeks – they're consistently applying systems that compound over time.

5. Freedom Through Design

Poverty loves hustle. It keeps you spinning your wheels. 

True freedom comes through intentionally designed systems that eliminate the need for constant grinding.

Stop building your business like it's 1995. 

The old approach of outworking everyone else is the slowest path to growth.

Your freedom is literally one system away.

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Your Hustle Got You To 20K Per Month

I analyzed 10,000 sales calls and discovered something shocking.

The highest-converting calls had zero pitching.

Just stories.

Here's the systemized approach I use to sell without selling:

1. The Discovery

Stories activate mirror neurons in your brain. 

When I tell you about my transformation, you don't just hear it, you experience it. 

They literally feel your results.

2. The 4-Part Story Architecture

Every conversion story needs these elements:

Catalyst → (what changed)
Contrast → (before vs after)
Conflict → (what you overcame)
Conquest → (where you are now)

Example: "I was working 80-hour weeks, burned out and barely profitable. 

Then I discovered that 97% of success is systems. 

This insight changed everything, but I had to systematize every aspect of my business first. 

Now I work 4 hours per day while helping 14 million founders achieve freedom."

The gap between before and after = their desired transformation.

3. The Advanced Technique

Start story A, interrupt with story B, finish story B, then complete story A.

This creates hypnotic attention because the brain craves closure.

4. The Psychology Loop

Stories create emotion.

Emotion creates logic.

Logic creates action.

When you master this, you're not selling products - you're selling transformations.

The founder experience is everything. 

When founders hear your story, they see their future.

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How I Use My Story To Sell

Steve Jobs once said:

"Deciding what not to do is as important as deciding what to do."

11 more golden nuggets on decision-making from the founder of the first trillion-dollar company:

1. Efficiency

Jobs believed in making decisions fast, valuing efficiency over collaboration.

“When you innovate, you make mistakes. It's best to admit them quickly and get on with improving other innovations.”

2. Clear priorities

Knowing what matters most to you makes all decision-making far easier. 

“Being the richest man in the cemetery doesn’t matter to me. Going to bed at night saying we’ve done something wonderful, that’s what matters to me.”

3. Trusting intuition

Don't fear the unknown.

"You can't connect dots looking forward; you can only connect them looking backward. 
 
You have to trust that the dots will somehow connect in your future. 

4. Cutting corners

Jobs knew excellence was a habit.

"When you're a carpenter making a chest of drawers, you're not going to use plywood on the back, even though nobody will see it. 

5. Get rid of your ego

We often cling to a viewpoint in fear of admitting we were wrong. But shedding your ego leads to the most growth.

“I’ll admit that I’m wrong a lot. It doesn’t really matter to me. What matters to me is that we do the right thing.”

6. First principles

Never blindly accept anything you're told. Always ask why.

The answer you invariably get is ‘That’s just the way it’s done.’ 

Nobody knows why they do what they do. Nobody thinks about things very deeply in business. 

7. The shortness of life

Whenever you're scared to take a big leap, recall death.

"Remembering that you're going to die is the best way to avoid the trap of thinking you have something to lose. 

8. Simplicity

In a world of noise and distractions, the ability to concentrate on a few things that truly matter is a huge advantage.

One of my mantras is focus and simplicity. "Simple can be harder than complex; you have to work hard to get your thinking clean to make it simple."

9. The power of collaboration

Interdependence, not independence, is key to success.

My business model is The Beatles: They were four guys who kept each other’s negative tendencies in check; they balanced each other. 

And the total was greater than the sum of the parts.

10. Just do you

It's easy for your dreams to be muted by the armchair criticism of others. 

Your time is limited, so don't waste it living someone else's life and don't let the noise of others' opinions drown out your inner voice.

11. The Genius Effect

Sometimes, if you have unwavering conviction and no one's on your side, persist. You might just change the world.

While some see them as the crazy ones, we see genius. 

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Most people are stuck in the same place they were 5 years ago.

Same habits. 
Same routines. 
Same results.

Then they wonder why nothing changes.

I used to be one of them.

So here's how to get ahead of 99% of people:

1. Lifestyle: Morning Routine

Your morning makes or breaks your entire day.

Take control by shutting out inputs, no emails, texts, or social media first thing. Kickstart your body with exercise before your mind gets cluttered. 

Schedule deep work when your energy peaks, not when meetings demand it.

Your morning isn't negotiable. Protect it like your business depends on it, because it does.

2. Lifestyle: Evening Routine

A supercharged morning starts the night before.

Write down your 5 needle-moving tasks for tomorrow so you wake up with clarity, not confusion. 

Ease into sleep with reading or meditation instead of scrolling.

Sleep is the ultimate performance enhancer. Treat it that way.

3. Upskilling: Storytelling

Sales, hiring, marketing, it's all storytelling.

There's no soft skill that'll benefit you more.  

Master these and you'll close more deals, attract better talent, and build stronger brands.

Facts tell, but stories sell.

4. Upskilling: Negotiation

The crux of negotiation is empathy and understanding.

By learning negotiation, you become a better listener, communicator, and persuader. 

Everything is a negotiation. Learn the game.

5. Upskilling: Learning to Learn

To succeed at something fast, you'll have to constantly pick up skills.

That's why you need a robust system for learning: learn by doing, with a purpose, and with accountability. 

Speed of learning determines speed of earning.

6. Monetization: Passion

To find what'll make you wealthy without sacrificing your sanity, you need to introspect.

What are you good at? 
What do you love to do? 
What does the world need? 

Passion without profit is a hobby. Profit without passion is prison.

7. Monetization: Sales

Sales is 20% selling and 80% prospecting.

Get good at finding and feeding the starving crowd, and you'll never worry about revenue again.

8. Monetization: Offer

If sales are full of friction, you're doing it wrong.

Great offers sell themselves. List out perceived roadblocks, identify an outcome, then package solutions to roadblocks into an offer. 

Don't sell a product, sell a transformation that eliminates their pain and delivers their dream.

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How To Get Ahead Of 99% Of People

I stopped treating Monday like the hardest day and started treating it like my competitive advantage.

While everyone else is dragging through Monday morning fog, I'm three steps ahead.

Not because I'm more disciplined, but because I have a system.

I call it the "Weekly Reboot Template".

So here's how to make Monday the best day of your week:

1. Reset Your Energy

Morning Rule: Sunlight + Silence + Sweat before phone.

No exceptions.

Get outside for 10 minutes. 

Sit in silence for 5. 

Move your body before you check a single notification.

This one habit sets the tone for your entire week.

2. Set The Intention

Answer two questions:

• This week I want to feel...
• My single word for the week...

Not goals. 
Not tasks. 
Feelings and focus.

"This week I want to feel productive and present."

"My word is 'clarity.'"

Everything you do filters through this lens.

3. Top 3 Priorities (In Order)

Not 10 priorities. Not 20 tasks. Three.

Write them in order of impact.

If you only accomplish these three things this week, would you consider it successful?

If no, rewrite them.

4. Delete What Doesn't Matter

Two questions:

• I'm saying "no" to...
• I'll automate or delegate...

Subtraction creates space for what actually moves needles.

Name what you're eliminating before you start adding.

5. Schedule Your Power Blocks

Block your calendar in three categories:

• Meetings
• Deep work
• Creative play

Don't hope you'll find time. 

Design time.

Protect your deep work blocks like they're investor meetings.

6. Design Your Environment

Two questions:

Where will I work from today?
What can I remove from my space?

Environment shapes behavior.

A cluttered space creates a cluttered mind.

Remove distractions before you need willpower to resist them.

7. End With Gratitude

Close your Monday with two reflections:

• One thing I'm proud of...
• One way I'll reward myself tonight...

Gratitude compounds momentum.

Celebrate the win before chasing the next one.

This entire template takes 15 minutes on Monday morning.

But it saves you 10+ hours of wasted time, scattered focus, and decision fatigue throughout the week.

Monday isn't the problem.

Starting Monday without a system is the problem.

I've used this exact template for the past year.

Every single Monday.

And Mondays went from my most dreaded day to my most productive day.

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Most founders are addicted to being needed.

The traditional business playbook says "hustle harder" and "be indispensable."

But I built a successful business while prioritizing time freedom.

Here's how to build a business that runs without you:

1. AED Implementation 

This is the exact system I use to remove myself from operations:

• AUTOMATE what's repetitive
• ELIMINATE what's unnecessary
• DELEGATE what's not in your zone of genius

When something lands on your plate, run it through this filter immediately.

Your most valuable resource isn't money, it's your attention.

2. Document Everything 

If you do it twice, write it down.

Write down:

• Screenshots or videos
• Tips and best practices
• Step-by-step instructions
• Common mistakes to avoid

Thousands of hours can be saved with a single document.

3. Your Team = Your Leverage

Most founders hire too late, too cheap, and without systems.

Here's your first three game-changing hires:

• Executive Assistant (buys back 20+ hours weekly)
• Content Manager (builds your audience while you sleep)
• Operations Manager (runs your systems when you're gone)

Hire for systems, not tasks.

The ROI on great people with great systems is infinite.

4. Freedom Architecture 

Design businesses around your ideal lifestyle rather than sacrificing life for business growth. 

• Control WHEN you work (time autonomy)
• Choose WHERE you live (location freedom)
• Decide WHO you serve (customer selection)
• Own WHAT you create (intellectual property)

Each "W" you surrender costs you.

This isn't just a business. It's about owning your life.

5. Strategic Deep Work 

Dedicate the first few hours of your day to deep, focused work on your needle-moving work.

No phone, no social media, no distractions.

This is when your mind is freshest and most creative.

Protect this time at all costs.

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Here's How To Build A Business 

My business was growing, but I was falling apart.

Then I realized the problem wasn't my circumstances.

It was my daily operating system.

Most founders optimize their business systems but ignore the system running their life.

9 habits I used to unf*ck myself: 

1. Say No by Default

Your time is the most precious asset you'll ever own.

Stop giving it to people who don't deserve it, especially energy vampires who drain you dry. 

My rule: if it's not a hell yes, it's a no. 

Conquer FOMO and put yourself first.

2. Get Addicted to Learning

I put time aside daily before bed to read.

At first, staying consistent was brutal, but the more I did it, the more the effects compounded. 

Your information diet is just like your actual diet: if you eat crap, you'll feel like crap.

3. Prioritize Nature

A study of 20,000 people in the UK found that just 120 minutes per week in nature improved health and well-being.

It's the planet's greatest healer. 

Whenever I'm in a rut, nature's always the spark that returns color to the gray.

4. Morning Routine

Your routine doesn't need to be 4 hours long or involve a cold plunge.

Just nail the basics: no phone first thing, a small win early like light exercise, and prime your mind for deep work through journaling. 

Your morning is the stretching before the sprint.

5. Embrace Loneliness

Twice a month, I do something normally "social" alone.

I'll eat dinner, go to the park, or attend a movie by myself. 

Solitude is an essential pillar to truly knowing yourself; it's the secret garden where self-discovery can bloom.

6. Choose Writing Over Complaining

Complaining isn't attractive; it repels ambitious people and fosters a negative mindset.

Write down your thoughts instead: you're forced to think slowly and deeply so your irrationality loses its edge. 

It's the therapy your therapist uses.

7. Pay it Forward

Random acts of kindness boost well-being in ways most people don't realize.

Hold the door for someone. Pick up trash outside. Give a compliment. 

The world's a closed system: if you send waves of positivity out, they'll find their way back to you.

8. Maintain Relationships

Human connections are the fabric of life, but you need to be intentional with them amidst life's chaos.

Schedule time weekly for thoughtful texts and calls to those you've neglected. 

It's a couple of minutes with an ROI you'll measure in years.

9. Focus on Your Health

I'm convinced most mental health problems are actually physical health problems.

Everyone I know who eats well, exercises daily, and drinks enough water has a Teflon mind that repels all negativity. 

Your body and mind aren't separate; they're the same system.

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(99+) Post | LinkedIn

9 Habits I Used To Unf*ck Myself

Kaci M.

9 ways to rewire your brain (based on science):

1. Cold Therapy  

Exposure to cold increases norepinephrine levels by up to 500%.

Norepinephrine enables brain plasticity and cell metabolism.

It can help you enhance:

• Mood
• Focus
• Attention
• Vigilance

A 3-minute cold shower provides huge returns.

2. Practice Breathwork 

Go through guided exercise on: 

• Diaphragmatic breathing 
• Coherent breathing 
• 4-7-8 breathing 

Find the techniques that help you: 

• Reduce stress 
• Improve mood 
• Battle anxiety

3. HIIT Workouts 

Exercise supports the brain on multiple levels.

• Increases gray matter
• Improves blood flow to the brain
• Regulates neurotransmitter levels
• Activates molecules that drive cellular adaptation

HIIT exercises maximize value/time.

4. Improve Your Sleep 

Sleep is essential for learning and memory.

Invest in your sleep by: 

• Using mouth tape 
• Buying blackout curtains 
• Getting a thermoregulated mattress
• Getting 0 screen time 2 hours before bed

5. Meditation 

Chronic stress reduces brain activity.

Use meditation to combat stress: 

• Maintain focus 
• Build emotional control 
• Center yourself during hectic times 

Building a consistent meditation practice will do wonders for your brain.

6. Learn Something New

The action of learning is plasticity.

When you learn something new, your brain physically changes.

• Pick up a new instrument 
• Study a foreign language 
• Learn a new skill

Learning something new every day keeps different parts of your brain active.

7. Eat Clean

A diet high in saturated fats and refined sugars:

• Impairs memory
• Raises stress levels
• Reduces learning capacity

But a diet with complex carbs and healthy fats:

• Improves mood
• Enhances memory
• Supports brain functioning

8. Ditch Positive Affirmations 

Affirmations do nothing to change our brains.

But asking ourselves questions does. 

• Who do I want to be? 
• What do I need to achieve to be that person? 

The process of searching for answers rewires our brain to think in a "can-do" manner.

9. Build Positive Habits 

40% of our daily actions are unconscious habits.

Employ the Habit Loop to build positive habits and cut negative ones. 

• Identify your cues 
• Control your cravings 
• Tailor your responses 
• Maximize your rewards

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Most founders burn out by Sunday night.

I used to be one of them.

I'd work all week, then fill my weekends with more work and by Monday morning, I felt more exhausted than I did on Friday.

Here's how to plan your weekend effectively:

1. Theme

What do I want to feel?

Start here, not with a to-do list.

Peace? 
Aliveness? 
Connection? 

Name the feeling first. Everything else follows from this.

2. Intention

This weekend is about...

Fill in the blank with one sentence.

"This weekend is about deep rest."
"This weekend is about creative exploration."
"This weekend is about quality time with family."

One intention. That's it.

3. Energy Reset

What will recharge me the most?

Not what you think you should do, what actually fills your tank.

For me, it's nature, movement, and solitude.

For you, it might be completely different.

4. One Domino

The one thing that makes everything easier.

What's the single action that would make the rest of your weekend flow?

Meal prep? 
A tough conversation? 
Organizing your workspace?

Do this first. 

Everything else becomes unnecessary or easier.

5. No-List

What will I do not do this weekend?

This is more important than your to-do list.

No email. 
No social media before noon. 
No saying yes to obligations that drain you.

Protect your weekend like you protect your bank account.

6. Adventure

One New Experience.

Create a story worth telling on Monday.

It doesn't have to be grand. 

Just something that breaks the pattern.

7. Connection

Who do I want deep time with?

Not surface-level hangouts. Deep, quality time.

Name the person. Schedule it. Protect it.

8. Creation 

One small act of art.

Journal. 
Sketch. 
Cook something new. 
Build something with your hands.

Creation is medicine for the soul.

9. Body

How will I move my body?

Hike, lift, swim, stretch, your body needs movement to process the week.

10. Mind

What am I reading or listening to?

Feed your mind something nourishing, not just entertaining.

11. Systems Reset

What do I want organized by Monday?

Clean workspace. 
Meal prep done. 
Calendar reviewed.

Set yourself up to win the week.

12. Sunday Reset

Three Questions:

What worked last week?
What drained me last week?
What is my intention this week?

The difference between founders who scale and founders who burn out?

They design their weekends intentionally instead of letting them happen accidentally.

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How to remove yourself from operations (and scale 10x faster):

1. Track Your Time on 15-Minute Intervals 

Free up time to focus on high-impact work. 

To track your tasks: 

• Use a timer 
• Review the list 
• Identify tasks to outsource 

2. Mark Tasks That Can Be Delegated

Delegating frees up time and boosts productivity.

Ask yourself:

• Do I like doing this?
• Is it repeatable?
• Can it be delegated?

3. Value Your Time at $2k/Hour

Setting a high hourly rate will make it easier to filter tasks to outsource.

Delegate tasks that are valued lower than this hourly rate.

4. Hire a VA to Scale Your Workflow

Delegate tasks to VAs who can do them 80% as well as you.

They won't have: 

• Efficiency
• Full context
• Years of experience

And they don't need to.

5. The Quality VA Criteria

During your search, filter for: 

• $10k+ earned
• High approval rating
• Native English speaker
• Great training services

Your VA must meet these requirements to be a solid hire.

6. Onboard Your VA

Effective communication = smooth operations.

Onboard your VA to discuss:

• How often you meet
• How you communicate (Slack, Asana etc...)
• How they should track and update you on completed tasks

Set expectations early to minimize unexpected challenges.

7. Create Systems for Each Task

Your VA won't know the full context of what they're working on and why.

Create documents and videos for each step:

• Create how-to's
• Draft best practices
• Record Loom videos

Clear and concise systems will 10x your VAs output quality.

8. Review Systems and Performance Weekly

With your VA, learn to track unexpected challenges that you're not prepared for.

• Create a new process
• Create new templates
• Change an existing process

Build these with your VA to optimize your working relationship with your VA.

9. Spend Quality 1-1 Time

Working together 1-1 for up to a month to help them learn the ropes.

• Meet often
• Give detailed and direct feedback
• Listen to their suggestions

Experienced VAs can 10x the efficiency of your processes.

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How To Remove Yourself From Operations

Tony Robbins once said:

"Clarity is power. The more clear you are about exactly what it is you want, the more your brain knows how to get there."

Here’s how to cut the noise and find your true clarity:

1. Clarity Helps You Understand What Truly Matters To You

Without clarity, you may spend years pursuing goals that don't matter to you, leading to unfulfillment.

But how do you find clarity in a world full of distractions?

The answer lies in the concept of Ikigai.

2. Ikigai Is A Japanese Word That Translates To "Reason For Being"

It's the intersection of four elements:

• What you love
• What you're good at
• What the world needs
• What you can be paid for

It's a powerful framework for discovering your reason for being, your "why."

3. Ikigai Is The First Step On The Journey To Clarity

It's the compass that guides you towards work that aligns with your values.

When you have a clear Ikigai, you can make better decisions and take action toward creating the life you want.

4. Finding Your Ikigai:

• Identify the four elements of Ikigai
• Journal daily about your passion and your 10-year vision
• Reflect on what gets you out of bed in the morning and fills you with energy and excitement

Discovering your Ikigai is a process of self-exploration.

5. Implement These 5 Golden Rules Of Ikigai

• Give thanks
• Follow your Ikigai
• Reconnect with nature
• Surround yourself with positivity
• Take it slow and enjoy the journey

6. Align Your Life & Work With It

This is where the real magic happens.

When you pursue what brings you joy and aligns with your values, your energy becomes electric.

Clarity fuels you to take massive action towards your goals.

When I aligned my life and work with my Ikigai, everything changed.

My content resonated deeply with my audience, and my reach exploded:

• Twitter grew to 214K
• LinkedIn grew to 266K
• Newsletter subscribers grew to 68K 

Clarity is the rocket fuel that propels you.

7. Use Your Ikigai As A Roadmap For Designing A Life You Love

• Build a team that shares your values
• Craft a business that supports your dreams
• Create content that lights you up and inspires others

With clarity as your guide, you can architect a life that truly serves you.

Clarity is not a one-time destination but a lifelong journey of growth & self-discovery.

Don't buy into the myth that success requires sacrificing your health and happiness.

You can have it all: a wildly profitable business and a deeply fulfilling life. 

Unlock your potential, and master the art of working when, where, and how you choose.

Clarity is the key.

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The best habit you can develop is building systems.

 Systems are your clone.

They encode your decisions. 
They scale your expertise. 
They multiply your time.

These 3 systems transformed my business from needing me to running without me:

1. Decision Systems = Your Brain in a Doc

When this happens, do that.

If client asks X, respond with Y. 

Your judgment becomes their execution.

I documented every decision pattern I was making repeatedly. 

Client onboarding. 
Pricing negotiations. 
Scope changes. 
Refund requests.

Now my team acts like me - even when I'm not there.

2. Content Systems = Your Voice on Repeat

Bank 60 ideas in advance. 
Batch create in a few hours. 
Post 7 days without thinking.

I stopped creating content daily and started creating content strategically.

One focused session gives me weeks of consistent output. 

My brand grows while I sleep.

3. Delivery Systems = Excellence on Autopilot

Client onboarding? Templated. 
Weekly check-ins? Scheduled. 
Results delivery? Systematized.

Every touchpoint in my client experience runs on rails. Consistency without chaos. Quality without constant oversight.

I installed these systems over 6 months.

Now my business runs while I travel 47 countries. 

Same revenue. 
Zero daily fires.

It feels slow at first.

Documenting processes takes time. 
Creating templates requires thought. 

Building SOPs feels like busy work when you could be "doing the real work."

But that's exactly backwards.

The "real work" is building the machine that does the work.

Everything else is just trading hours for dollars with a fancy title.

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The Best Habit You can Develop

Scot Chisholm & Co. 

Every week I tackle management, operations & startup topics that are helping 100,000+ people become better leaders.

Scot’s Newsletter

Highland

Highland is a “school” & community for founders. If you're a founder/CEO, we should talk!

Founder & Chief Professor

Tall Timbers Holding Co.

A family office and holding company with wholly owned businesses, private investments, and property holdings.

Managing Director & Founder

GoFundMe

After the merger of Classy and GoFundMe, I’ve taken on a strategic advisory role to the CEO & executive team, mainly focused on longer-range product strategy and M&A

Strategic Advisor, GoFundMe & Classy

Classy

Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Founder & Chairman

Classy is a SaaS giving platform that powers the fundraising of over 10,000 nonprofit organizations. Classy is a certified B-Corp, has a team of 300+ people and has raised over $5 billion for social good since 2011.

CEO & Founder

In Classy’s earliest days, we hosted large scale fundraising events with the goal of connecting millennials with local nonprofits in the San Diego area.

CEO & Founder (pre tech company)

Haskill Creek

Haskill Creek is a new type of self-care store. Imagine a healthier & more holistic version of a Walgreens or CVS. Family owned business.

Co-Founder

ALBION SC

Albion Soccer Club is one of the top youth soccer franchises in the United States with over 10,000 players and hundreds of teams across the country.

Co-Owner

Save Farmland

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

Abundant Montana

Board Member

AERO Montana

Abundant Montana (a program of Aero), makes it easy for anyone to find and choose local food in Montana.

Advisory Board

CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Multi-time founder but operator at heart. 

Industrial engineer and lean six sigma nerd by training. 

Now I write about management, operations & startup topics that are helping 200,000+ people become better leaders.

scotchisholm.com/newsletter


MY BACKGROUND ————— 

🚀 Founder of Classy, a SaaS platform for 10k+ nonprofits raising billions per year. 

🎗️Acquired by GoFundMe in ‘22 to create the largest giving platform in the world. Together we’ve raised over $30 billion for individual & nonprofit causes. 

🏔️ Founder of Highland, a private community & leadership “school” for high-potential founders. 

🏡 Co-founder of Haskill Creek, a much healthier version of a Walgreens or CVS. 

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland. 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation 


👇 WAYS TO CONNECT —————

→ Podcast / speaking oppty? email: partner@scotchisholm.com

→ Join my free newsletter: https://scotchisholm.com/newsletter-linkedin-profile

→ Check out my private community for founders: www.joinhighland.com

Scot Chisholm

Sh*tty managers ruin lives. 
Great managers change them. 

I’ve managed hundreds of people over the last 20 years. 

One of my biggest takeaways is the massive difference between an average manager and a truly great one. 

But, here’s the truth:

No one starts out as a great manager (literally no one). 

And, becoming a great manager can be learned by anyone. 

Just focus on these 12 habits:

1/ Provide business context
2/ Set high standards
3/ Take full ownership
4/ Focus (then focus again)
5/ Create operating cohesion 
6/ Lead with data
7/ But be decisive 
8/ Let your team make decisions
9/ Don’t give sh*tty feedback
10/ Take feedback like an adult
11/ Listen more than you talk
12/ Always be learning

The gap in quality managers is large, but the right behaviors are simple. 

Focus on these 12 habits daily and you’ll be ahead of 99%. 

What habits resonated most?
Let me know in the comments 👇

⁂

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Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

12 insanely simple habits to become a high performing mana

Leadership is misunderstood.

Building Classy taught me that the best leaders aren't necessarily the ones with the biggest titles, or the ones who can charm a room.

Some of the best leaders in our 300+ person company were individual contributors at the very bottom of the org chart. Young managers. First-time team leads.

Over the years I started noticing what made these unlikely leaders so effective. They had traits that, quite honestly, my executives lacked at times. Including me.

Over time I boiled them down to 10 core traits that our best leaders always exhibited. It’s no surprise they rose fast within the company. Many are still there today, 15 years later.  

The very best leaders: 

• Clarify - Never assume everyone understands
• Believe - Push forward when everyone doubts
• Adapt - Evolve rapidly without ego
• Anticipate - Solve problems before they explode
• Persist - Get kicked in the teeth, get up anyway
• Empower - Create leaders, not followers
• Own - Own failures without excuses
• Hold the line - When quality dips and others compromise
• Always Learn - Learn and grow faster than the company
• Lead by Example - Live values when no one's watching

Most leaders start off strong in a few, but not all of these traits. You must intentionally develop them over time. It's a lifelong thing. 

But many executives forget this. Maybe they were great once. But they start slipping. They stop learning. They get cocky. I've seen this too many times. 

I don't care where you’re at in your career. Keep these traits in mind. And never stop developing them. 

⁂

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Top 10 traits of the very best leaders:

Every high performance culture starts with this… 

I recently asked a founder about his culture. And he started talking about free lunches and other perks. 

This is not culture. 

He was a coaching client of mine, so I nicely explained… 

Here's what real culture looks like: 
→ A shared purpose. Everyone understands and resonates with the 'Why'.

→ Excitement about the future. The vision is clear to all and it creates an almost kid-like excitement about the future.

→ Strong empathy and trust. Great orgs know if you neglect empathy, trust evaporates.

→ The correct level of accountability. People know you're building a championship team.

→ Mutual respect and encouragement. High performers have admiration for each other.

→ Hunger to learn and improve. Without being asked. That's the diet of champions.

→ Aligned financial incentives. Compensation that's aligned to the organization's top goals.

→ Career mobility. Lots of opportunity, with clear expectations around advancement.

→ Work-life balance. Clear boundaries that are enforced across the org.

→ Pride in the work. Numbers one through nine create an amazing sense of pride. You'll find yourself bragging about work to complete strangers.


When you get the culture right, people are excited to show up, employees self-manage, and retention is extremely high. 

And great business results naturally follow.

 ⁂

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10 signs of great culture.

Most people waste their leadership meetings. 

Do this instead: 

When I was building Classy I got this meeting wrong for years. We’d talk about everything BUT the important stuff. Too much time wasted on low-level “issues”. Too many tangents and distractions. Everyone left feeling:

• Confused
• Misaligned 
• Unaccountable

I talked to advisors and scoured the internet for help. But it took loads of trial and error to land on a meeting structure that actually worked. We stuck with it for nearly ten years. 

One of the major improvements was focus. Teams spend months setting goals only to let them collect dust. Your leadership meeting should be your #1 checkpoint for progress. 

Once we got “tight at the top” as a leadership team, everything started to change. More results, less talk. It became the tip of the spear of our entire operating rhythm.

To this day, I call it your most important meeting. If I only had one, it’d be the leadership meeting. 

The entire leadership team meeting structure is in the carousel. Copy it for your own company and let me know what you think. 

⁂

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How to nail your  leadership meeting every time:

Most people think goals fail because the team screwed up. 

They’re wrong. 

99% of goals fail because of poor leadership.

It doesn’t matter what framework you use…

→ OKRs
→ Rocks
→ SMART

If you’re sloppy with your approach, the company won’t hit its goals. 

That’s on you. 

I learned this the hard way, running a company with hundreds of people. 

Now I see it working with nearly 100 CEOs across all industries. 

Here are 7 non-negotiable rules that will make your goal-setting 10x better…

(regardless of your framework) 

⁂

Rule 1 –  
Focus (then focus again):

• Maximum three goals, period
• Goals aren't task lists
• Everything priority = nothing priority

Rule 2 – 
Always be measurable: 

• Three metrics maximum per goal
• Measure outcomes, not tasks
• "$1M ARR" beats "update deck"

Rule 3 – 
Challenging but realistic: 

• Impossible goals kill momentum
• Stretch without delusion
• No sandbagging, mutual accountability

Rule 4 – 
Never forget the ‘why’: 

• No context leaves team guessing
• Each goal deserves a 'why'
• 1-3 sentence rationale

Rule 5 – 
Track consistently:

• Break annual into monthly
• Weekly red/yellow/green updates
• Never leave dashboards stale

Rule 6 – 
Create accountability:

• Use leadership meeting
• Address every yellow or red
• 20% status, 80% solving

Rule 7 – 
Align incentives:

• Pay goals to comp
• Ignore the OKR purists
• Bonus plan is perfect for this

Does this resonate? 
What rules would you add?
Let me know in the comments 👇

 ⁂

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How to actually achieve your company goals in 2026

If there's one thing you do on Linkedin today... 

I'd be forever grateful if you'd consider applying, or sharing this role with someone you really respect. 

Christopher Himes & I started dreaming up this company about a year ago.  Now the dream has turned to reality. 

With a fresh round, a tiny team of insane talent, and a massive opportunity in front of us... 

We. are. ready. to. go!

Who wants to join us? 

p.s. We're not listing this company as "stealth" because that's dumb. But you'll learn way more about the market, opportunity and product when you apply. Trust me its badass. 

🔥

taplio

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taplio

The Battle

Matt Gray

Scot Chisholm

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Matt Gray's LinkedIn Performance

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