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

Andy Mewborn

Distribute

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Founder & Customer Support

Taplio

Co-Founder

Outreach

Enterprise Sales

Sales Engineering Lead

Scaled the early success team to 14 people.

Manager - Customer Success

Early Employee.
Specialties: Data Sync, API, Onboarding, Platform Integrations, Partner Ecosystem

Product 

Start-Up Chile

Our team was selected for Generation 11 of Start-Up Chile (the YC of South America). We provided solar energy services and installed solar power systems.

Gridlee - Co-founder & Sales

Progress Chef

Sales Development Representative

Muhuru Bay Community Microgrid Project

Designed 3kW off-grid power system
Modeled renewable energy resources at remote site
Implemented system in Kenya
Tested and installed 11-channel GSM telemetry system

Electrical Engineer

Seattle City Light

Power Systems Engineer

Distribute.so

I use to be young & cool. Now I do b2b SaaS. 

Husband. Dad. Ironman. Pilot. Taco lover. 

Founder of Distribute // Co-founder of Taplio (acq. by Lemlist) // Early @ Outreach.io.

Creator

A community of over 4,000+ B2B professionals growing together on Linkedin.

• "Brand30 absolutely did wonders for my business." -Maritha Koortzen

• "Brand30 changed the trajectory of my life...To say it’s opening doors for me is an understatement" - Amanda Stern

• "Brand30 provided the group accountability and expert advice I needed to more than double my LinkedIn engagement in just one month" 

🚀 Start Building An Audience Of Potential Buyers On LinkedIn In 30 Days👇

• https://www.brand30.io/

8 months ago, we had 0 users. Today, Distribute.so has 15,000+ users. I’ve helped build a $250M company before, but this feels different.

Building a startup is glamorized on social media. But the reality is messy. Here are the 7 ugly truths about building fast in 2025 that nobody talks about:

1. Hitting a wall is normal 
I've been stuck at revenue plateaus multiple times. It feels terrible. But you can get moving again if you don't freeze.

2. You will mess up 
I've hired the wrong people. I've built the wrong features. I've spent money on things I didn't need. It's part of the game.

3. People will copy you 
We just beat 4 competitors for a deal. They are going to look at our product and copy it. Let them. By the time they copy us, we will be onto the next thing.

4. Saying "No" is painful 
To close those 18 killer logos, we had to say "no" to hundreds of other ideas. It hurts to say no to customers. But if you try to please everyone, you please no one.

5. Cash flow is everything 
It doesn't matter how cool your idea is. If you run out of money, you die. We watch every dollar.

6. It takes longer than you think 
People overestimate what they can do in a year. And underestimate what they can do in a decade. We are playing the long game.

7. Just start 
Every successful founder started with nothing. No revenue. No customers. No audience. The only difference is they didn't quit.

I’m documenting the whole ride here. The wins. The losses. And the lessons.

Follow along if you want to see how we get to the next level. Just keep building.

Andrew Mewborn

Click my profile, get a free taco 🌮 (also I automate your follow-ups)

7 ugly truths about building fast in 2025

Everyone told me I was crazy. "You can't sell to Enterprise logos without a massive sales team." "You can't be Product-Led and Sales-Led at the same time."

I disagreed. We have 15,000+ users on our self-serve app. But we also just closed 18 massive killer logos in 3 months.

Here is the 7-step playbook we used to move upmarket without losing our soul:

1. We stayed lean intentionally 
Most founders hire 10 reps the moment they get traction. We didn't. We used our own product to handle the volume.

2. We looked at our own backyard 
We didn't buy cold lists. We looked at our 15,000 free users. We found the ones who were using the product every day. Then we asked them: "Who is your boss?"

3. We sold the Result, not the Method killer 
Buyers don't care how your tech works. They care about the problem disappearing. We showed them exactly how Distribute would solve their problem in week 1.

4. We gave before we asked 
We didn't try to trap them in long contracts immediately. We let them use the product. We let them see the value. Trust is built by giving, not taking.

5. We stopped chasing shortcuts 
We didn't use clever tricks. We just focused on making the product 1% better every day. Word of mouth is the only growth strategy that lasts.

6. We kept the team tiny 
We are doing millions in revenue potential with a team that fits in a minivan. This keeps us profitable. And it keeps us hungry.

7. We worked in public 
I shared the wins and the losses on LinkedIn. This built trust with buyers before we ever spoke to them. They felt like they knew us.

TAKEAWAY: You don't need to follow the Silicon Valley rules. You don't need to raise $100M. You don't need a fancy office. You just need a product that people love. And the guts to do it your way.

They said you can't sell Enterprise without a suit.

had our quarterly all-hands today

CEO said we're "laser-focused on execution"

CTO said we're "moving fast and breaking things"

CFO said we have "18 months of runway"

VP Sales said we're "building a repeatable sales motion"

i asked "what does any of that mean?"

got pulled into a 1-on-1 about "culture fit"

turns out "what does that mean?" is not a growth mindset question

i'm now "transitioning to focus on other opportunities"

which means i have 2 weeks to find another company where nobody knows what they're talking about

shouldn't be hard

I helped build Outreach to $250M in revenue. I helped over 4,000 people grow on LinkedIn. Now, I have 15,000+ users on my new company, Distribute.so

I have seen the movie before. And I can tell you that the sequel is very different from the original.

Back in 2015, the playbook was simple: Force the sale. Hire an army of BDRs. Buy a massive list of emails. Send thousands of messages a day. It worked then. It doesn't work now.

Here are the 6 things that have changed in the last 10 years:

1. Buyers ignore the noise 
Email open rates have tanked. Sending more messages doesn't work anymore. You have to earn their attention, not demand it.

2. Don't push, attract 
You can't force a sale anymore. You have to create interest through content and brand. Then you capture that interest when they are ready.

3. Small teams are winning 
We closed 18 killer deals with a tiny team. You don't need 50 reps. You need a few seniors who know what they are doing.

4. Reputation is the new advantage 
Features get copied in a week. But they can't copy who you are. Your personal brand is the most efficient sales channel that exists.

5. Easy beats Powerful 
killer software used to be clunky and expensive. Now, the best tools feel like consumer apps. If it feels like work, they won't use it.

6. Speed over Forecasts 
We don't try to predict every dollar. We try to move fast. We launch, we test, we fix. Speed is the only advantage a startup really has.

TAKEAWAY: If you are still running the 2015 playbook, you are working too hard. The game has changed. You can either complain about it, or you can adapt. We chose to adapt. And it's working.

I helped build Outreach.io to $250M in revenue

I just beat 4 competitors to win a killer contract. We didn't have the most features. We didn't have the biggest sales team. But we have 15,000+ users and just closed our 18th killer logo in 3 months.

How did we do it? We realized that the old way of selling software is broken. Most founders try to build everything for everyone. They add buttons, settings, and complex workflows. They think "more features" equals "more value."

They are wrong. In 2025, buyers are overwhelmed. They don't want another tool they have to learn. They want something that just works.

Here is the 7-step playbook we used to win on Simplicity:

1. Go where the big fish swim 
We didn't wait for them to come to us. We found where they were hanging out and showed up.

2. Prove it, don't pitch it 
Our competitors sent 40-page slide decks. We sent a link to the product. If you have to explain how it works, it's too complicated.

3. The "Zero-Training" Standard 
We built Distribute so a 5th grader could use it. If a user needs a certification to use your tool, you have already lost. Simplicity is the ultimate sophistication.

4. Escape the "Feature Trap" 
Customers will ask for a million things. We said "no" to 90% of them. We only built the things that made the core product faster and easier.

5. Sell it yourself 
I didn't hire a VP of Sales to figure this out. I did it myself. Founders should sell until at least $500K ARR because nobody knows the product like you do.

6. Find the "Aha!" instantly 
We found the one specific thing that made users say "wow." Then we made that experience happen in under 60 seconds.

7. Let the product drive the deal 
When the product is simple, the champion can sell it internally for you. They don't need you to fly in for a demo. They just show their boss, and the boss gets it.

TAKEAWAY: Startups are hard. But in 2025, complex startups are impossible. Stop building more. Start building simpler. That is how you win.

I just beat 4 competitors to win a killer contract

intern: "should I add my phone number to my email signature?"

CEO: "absolutely, we're accessible"

intern: "what about my LinkedIn?"

CEO: "yes, we're modern"

intern: "calendar booking link?"

CEO: "of course, we're efficient"

intern: "headshot?"

CEO: "why not, we're human"

intern sends first email

signature is 47 lines long

includes:

• 3 phone numbers
• 4 social media links
• calendar link
• company tagline
• legal disclaimer
• "Sent from my iPhone"
• sustainability notice about not printing emails
• AI-generated motivational quote

the actual email says "sounds good"

we promoted them to Head of Email Excellence

I spent 3 hours on a crap ton of follow-ups at Outreach while we scaled to $250M. Now our 15,000+ Distribute users do better follow-ups in 30 seconds. After closing 18 deals in the past few months, I learned something most founders miss: complexity kills deals, simplicity closes them.

Here's why the best salespeople are deleting tools, not adding them:

1// YOUR BUYERS DON’T WANT YOUR 55-SLIDE DECK

They want one page with what you discussed, the ROI, and next steps.

We tracked 10,000+ deals.

Average time on slide decks? 47 seconds.

Average time on simple deal pages? 8 minutes.


2// YOUR CHAMPION CAN’T SELL INTERNALLY WITH MEETING NOTES

They need a business case, ROI calculator, and executive summary.

Not a transcript.

When we switched from sending 27 attachments to one link, deal velocity increased MUCHO.


3// EVERY TOOL YOU ADD CREATES ANOTHER PLACE TO LOSE

The average rep uses 10+ tools for follow-ups.

Fathom for notes. Loom for demos. Google Docs for emails. Canva for slides.

The winners? They use one tool that does it all.


4// SIMPLICITY SPREADS FASTER THAN FEATURES

When we made Distribute dead simple, word-of-mouth exploded.

No training needed. No change management.

Just send your follow-up in 30 seconds and move on.


TAKEAWAY:

I watched Outreach grow because it simplified prospecting.

Now I'm watching Distribute grow because it simplifies follow-ups.

The pattern is clear.

Simplicity isn't just a feature.

It's a moat.

We beat 4 competitors  with 90% fewer features

prospect: "tell me about your product"

me: "what if I told you that you could save 20 hours per week?"

prospect: "how?"

me: "great question. let me share my screen. can you see this?"

prospect: "yes"

me: "perfect. so imagine your current workflow..."

**proceeds to spend 40 minutes describing their own job back to them**

me: "...and that's where we come in"

prospect: "what does your product actually do?"

me: "I'm going to send over some case studies and let's reconnect next week"

booked the follow-up

still haven't answered what we do

this is sales

investors rejected our pitch deck last month

they said our projections were "unrealistic"

we were forecasting $100M ARR by year 2 with zero marketing spend

i asked "don't you believe in product-led growth?"

they said "you have 3 customers"

so i updated the deck

changed "customers" to "enterprise partners"

changed "3" to "a curated selection of design partners"

changed "$47 MRR" to "high-intent early revenue signals"

we raised $8M Series A last week

words matter more than numbers

Last week I asked 4,000+ sellers how long they spend on follow-ups. 73% said 2-3 hours. That's 750 hours per year writing emails nobody reads. I helped build Outreach to $250M, and even we were wasting time on follow-ups.

Here's the math that'll make you sick:

Let's say you close 20 deals per year. Each deal takes 5 calls. Each call needs a 3-hour follow-up. That's 300 hours. Or 37.5 work days. You're spending 2 months per year on admin work.

**screams at sky***

While you write follow-ups, your competitors are on their next call.

Here's what actually works in 2025:

1// Stop crafting. Start automating.

AI can write better follow-ups than you.
It remembers everything. Never forgets the ROI discussion.
Includes the right case studies.
Our 15,000 users proved this.

2// Stop sending files. Send experiences.

PDFs get lost.
Attachments get ignored.
But a personalized page? That gets shared with the CFO.
We see 3x higher engagement on deal pages vs traditional follow-ups.

3// Stop hoping. Start tracking.

You need to know when the CFO views pricing. When legal downloads the contract. When your deal goes cold.

Email can't tell you this. 

The sellers crushing quota aren't working harder.

They're working different.

They turned 3-hour follow-ups into 30 seconds.

And their buyers actually engage.

Holy sh*t, right?

You waste 37.5 days per year on follow-ups

I helped scale Outreach to $250M. Then I started my own company and made every mistake I swore I never would. Here are the 6 dumbest things I did building Distribute to 15,000 users:

1// I spent 3 months building features nobody asked for

We had a roadmap. It was beautiful. Customers wanted something else entirely. I should have talked to 50 more people before writing a single line of code.


2// I chased logos instead of problems

Early on, I got excited when big names showed interest. I bent the product to fit them. They churned anyway. The customers who stayed were the ones whose problem we actually solved.


3// I wrote follow-up copy like a robot

I'm embarrassed to show you our early emails. Corporate garbage. The moment I started writing like a human, reply rates doubled.


4// I ignored my own LinkedIn audience for 6 months

I had built a following. I knew how to create content. But I thought "real companies" needed paid ads and SDR teams. Wrong. My posts still drive more pipeline than anything else.


5// I hired before I had a repeatable process

Brought on help too early. They failed. It wasn't their fault. I didn't have a playbook to hand them yet.


6// I thought the product would sell itself

It doesn't. Nothing does. Even great products need someone to explain why they matter.


TAKEAWAY:

Building a startup is just a series of mistakes.

The winners aren't the ones who avoid them.

They're the ones who make them faster and don't repeat them.

I'm still making mistakes every week.

But at least they're new ones.

I made every mistake I swore I never would

spent all morning analyzing our competitors

Competitor A: raised $50M, has 200 employees, beautiful website
Competitor B: raised $30M, has enterprise clients, won industry awards
Competitor C: bootstrapped to $10M ARR, profitable, amazing product

Us: 1 founders, $a couple mil raised, website built on Webflow template, LinkedIn is our entire marketing strategy

but here's the thing...

we respond to customer emails in under 5 minutes

our competitors take 3 business days

we shipped 12 features last month

they shipped a new font

we're not better funded

we're not better positioned

we're just more desperate

and in B2B SaaS, desperation scales

posted "what if we just... listened to customers?" on LinkedIn

38,000 impressions

427 comments saying "this is so true"

16 VCs sent connection requests

got invited to speak at a SaaS conference

my talk is titled "Revolutionary Customer-Centric Strategies for Modern B2B"

it's a 45-minute presentation on literally just talking to people who pay you

they're paying me $5k to speak

i'm writing a book about it called "The Listening Framework"

it's 280 pages explaining how to have conversations

pre-orders are through the roof

disruption is just common sense with better marketing

We just won a deal against 4 established competitors. They had 10X the funding, bigger brands, and fancier demos. But we won all 4 times. After helping 4,000+ people grow on LinkedIn and scaling Outreach to $250M, I knew exactly why: buyers don't want more tools, they want less work.

Here's how we beat everyone:

Competitor 1: 55 features, 3-hour onboarding
Us: 3 features that actually matter, 5-minute setup

Competitor 2: "AI-powered intelligence platform"
Us: "Your follow-up in 30 seconds"

Competitor 3: 47-page implementation guide
Us: Chrome extension. Click. Done.

Competitor 4: $500/month per user
Us: $49/month. Everything included.

**drops mic**

Here's what I learned closing our first big deals:

1// FEATURES ARE A TAX ON YOUR BUYERS

Every feature needs explaining.
Every option needs deciding.
Every setting needs configuring.
We do one thing perfect instead of 50 things okay.

2// COMPLEXITY IS WHERE DEALS GO TO DIE

The moment a buyer says "let me check with IT," you lost.
The moment they need training, you lost.
Make it so simple they can start now.

3// YOUR CHAMPION NEEDS TO LOOK SMART

They don't win by showing a complex tool.
They win by solving a problem fast.
Give them a quick win, not a science project.

We have 15,000+ users not because we're the best.

But because we're the simplest.

And in 2025, simple beats everything.

Every. Single. Time. YALL.

Step by step ↓

Let me tell you what's really going on…

When a prospect says "we don't have budget"…

They're not broke.

They just spent $47 on DoorDash last night. They've got budget for a new CRM. Budget for that conference in Miami.

What they DON'T have?

A reason to fight for YOUR deal.

See… right now, they're sitting in some internal meeting. Your proposal is open on their screen. And their CFO asks:

"Why do we need this?"

And your prospect?

They freeze.

They fumble.

They can't remember what you said. Can't articulate the ROI. Can't justify the spend.

So the deal dies. Not because of "budget." Because you made THEM do the selling.

That's on you.

Here's the fix:

Send them a Deal Summary BEFORE they go dark.

One page. One link. Everything they need to sell this deal internally:

→ The bleeding-neck problem you're solving 
→ The cost of doing NOTHING (this is the killer) 
→ Exactly what you're proposing 
→ What happens next

You do the selling. They just forward the link.

Takes 2 minutes. Saves you from chasing ghosts for 3 weeks.

💬 Comment "TACO"

I'll send you the exact Deal Summary template I use to close deals without begging for follow-ups.

💬 Comment "TACO"

Year 1: "we're pre-product-market fit, iterating rapidly"
Translation: nobody wants this

Year 2: "we're finding early signals of PMF"
Translation: 2 customers didn't churn

Year 3: "we've achieved strong product-market fit"
Translation: we stopped pivoting because we're tired

Year 4: "we're scaling past PMF into market domination"
Translation: we hired a VP of Sales who convinced us we're doing great

Year 5: "we're exploring strategic alternatives"
Translation: acquisition talks because we never actually found PMF

Year 6: got acquired for $8M by a company that will shut us down in 9 months

called it a "successful exit"

changed LinkedIn title to "Founder & CEO (Exited)"

already working on the next one

customer: "can you add dark mode?"
us: "it's on the roadmap"

customer: "can you fix this bug?"
us: "it's on the roadmap"

customer: "can you add SSO?"
us: "it's on the roadmap"

customer: "can we see the roadmap?"
us: "that's on the roadmap"

our roadmap is a Google Doc titled "stuff_we_might_do_idk.doc"

it hasn't been updated since 2023

we closed $2M ARR this year

turns out "it's on the roadmap" is enterprise software for "leave me alone"

Sellers

What’s more dangerous for sales teams: bad managers or bad AI tools?

A) Bad managers – morale killer
B) Bad AI – data chaos
C) Both – one demotivates, the other misleads
D) Neither – blame the process, not the tools

P.S. - My AI handles 90% of my sales process now—prospecting, follow-ups, closing. Set it up in 90 seconds: https://lnkd.in/eNYQ3DeQ

What’s more dangerous for sales teams: bad managers or bad AI tools?

Sellers

What’s the biggest shift in sales since 2020?

A) Buyers research more than sellers
B) Remote selling is the new normal
C) Champions have more power than AEs
D) Product-led growth changed everything

P.S. - Turns out I've been following up like an IDIOT for 5 years. This 90-second quiz showed me my actual follow-up style (and how to fix it): www.distribute.so/quiz

Sellers

Would you take feedback from an AI “sales coach”?

A) Yes – No bias, just data
B) Maybe – Only if it knows context
C) No – You can’t coach without empathy
D) I already do — ChatGPT’s my therapist

P.S. - My AI handles 90% of my sales process now—prospecting, follow-ups, closing. Set it up in 90 seconds: www.distribute.so/quiz

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