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.

I’ve hired 90+ high performers in the last 3 years.

Here are 8 rare traits I see in every high performer:

1. Grit

This one’s a non-negotiable. 

What is it?

• Ability to persist through obstacles
• Strength to bounce back from failure
• Tenacity to keep pushing, no matter the challenge

Hard work is common. 

Grit is rare.

2. Relentless Resourcefulness

Some people find a way no matter how “impossible” it seems.

They are innovative problem solvers.

They have the conviction that there's always a solution.

These are the people we want.

They’re like water.

They find a path around any obstacle.

3. Optimism

Entrepreneurship is a roller coaster.

Having optimistic people on your side is a massive mental boost.

Optimistic people don't see roadblocks; they see stepping stones to success.

Their energy is electrifying and infectious. 

A must-have when the going gets tough.

4. Constant Learning

The ROI on constant learners compounds.

In a fast-moving world, learning and adapting is essential.

These hires:

• Seek feedback
• Expand their skills
• Stay curious and hungry

Train them well, and they'll give you an infinite return on your investment.

5. Not Being an Asshole

It might sound simple, but it's vital.

I don’t care how smart, hardworking, or optimistic you are.

If you don’t:

• Show empathy
• Collaborate well
• Treat others with respect

I don’t want you on my team.

Period.

6. Fun to Be Around

I need people that I like spending time with.

Work can be intense. 

Having people who bring: 

• Positive energy
• A sense of humor
• A lightness to the office 

Makes a world of difference.

When we make work feel like play, we're unstoppable.

7. Growth Mindset 

This one is foundational.

I need someone who:

• Embraces challenges as growth opportunities
• Believes abilities and intelligence can be developed

People with a growth mindset get obsessed with the process.

Not fixated on the outcome.

8. Enjoys Responsibility

I need my team to take on responsibility.

I don’t want to chase people down.

If they:

• Take ownership of their work
• Care about doing a good job

We'll perform better.

And I’ll have way more breathing room and feel more at ease.

—

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Matt Gray 

8 Rare Traits I See In Every High Performer

I used to collect quotes like trophies.

Screenshot them. Save them. Share them.

But I never actually lived by them.

Then something shifted.

I stopped collecting and started applying.

These 10 quotes didn't just inspire me.
They became my operating system.

1. Slow Is Smooth And Smooth Is Fast

Rushing creates mistakes.
Patience creates precision.

When you slow down, you speed up in the long run.

2. Small Hinges Swing Big Doors

You don't need massive effort to create massive results.

You need the right leverage points.

Focus on the few things that move everything else.

3. Move Like Everything Is Gonna Work Out, Because It Is

Confidence comes from trusting your ability to figure it out.

Act like success is inevitable.
It becomes more likely.

4. God Has Already Prepared The Way. He's Just Preparing You

The opportunity is already there.

You're just becoming the person who's ready to receive it.

Trust the timing.

5. The Score Takes Care Of Itself

Stop obsessing over results.

Focus on the process.
Do the work.

The outcome will follow.

6. Stop Thinking About It, Do It

Overthinking is just procrastination wearing a disguise.

Action creates clarity.

Start before you're ready.

7. It's You Vs. You

Your only competition is the person you were yesterday.

Compare yourself to others and you'll always lose.
Compare yourself to your past self and you'll always grow.

8. A Single Leap Of Faith Can Change Your Entire Life

The biggest breakthroughs come from the scariest decisions.

One bold move can unlock everything.

9. Not Every Closed Door Is Locked. Push

Most obstacles aren't as solid as they seem.

Test the door before you assume it's closed.

Persistence reveals paths that patience never will.

10. The Magic You're Looking For Is In The Work You're Avoiding

The thing you're resisting is the thing you need to do.

Discomfort is a compass pointing toward growth.

Lean into it.

These aren't just words on a page.

They're operating principles I return to daily.

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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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10 TED Talks in 10 days that will change your life:

Day 1: "How Great Leaders Inspire Action" - Simon Sinek

Start with WHY, not WHAT.

Your purpose drives everything else. 

Sinek breaks down why Apple sells billions while others struggle.

This talk will change how you think about your business, your brand, and your life.

Day 2: "The Power of Vulnerability" - Brené Brown

Vulnerability isn't weakness. It's courage.

Brown shows how embracing imperfection leads to connection, creativity, and change.

Essential for founders who think they need to have it all figured out.

Day 3: "Your Body Language May Shape Who You Are" - Amy Cuddy

Confidence isn't just mental. It's physical.

Cuddy reveals how your posture literally changes your brain chemistry.

Two minutes of power posing before important meetings will transform your presence.

Day 4: "The Puzzle of Motivation" - Dan Pink

Money isn't the best motivator. 

Autonomy, mastery, and purpose are.

Pink destroys traditional thinking about what drives high performance.

This changes how you build teams and design your life.

Day 5: "The Power of Believing That You Can Improve" - Carol Dweck

Fixed mindset vs growth mindset.

Dweck shows how believing in your ability to grow literally rewires your brain for success.

One word change: "I can't do this" becomes "I can't do this yet."

Day 6: "How to Make Stress Your Friend" - Kelly McGonigal

Stress isn't your enemy. 

Your belief about stress is.

McGonigal presents research showing stress can actually improve performance and health.

Changes everything about how you handle pressure.

Day 7: "The Happy Secret to Better Work" - Shawn Achor

Happiness leads to success, not the other way around.

Achor breaks down the neuroscience of positivity and performance.

Simple daily practices that literally rewire your brain for success.

Day 8: "The Skill of Self-Confidence" - Dr. Ivan Joseph

Self-confidence is a skill, not a personality trait.

Joseph shows the exact formula for building unshakeable confidence.

Repetition plus positive self-talk equals an unstoppable mindset.

Day 9: "How to Speak So That People Want to Listen" - Julian Treasure

Your voice is your superpower.

Treasure reveals the vocal techniques that make people lean in.

Essential for founders who need to inspire teams and customers.

Day 10: "The Paradox of Choice" - Barry Schwartz

More options don't make us happier. 

They paralyze us.

Schwartz explains why limiting choices increases satisfaction.

Bonus: After watching all 10, go back and watch your favorite again.

The second viewing hits differently when you have the full context.

That's when the real insights emerge.

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Most people chase opportunities.

I spent years doing the same thing, waiting for the right moment, the perfect break, the big chance.

Then I realized something that changed everything.

The best opportunities don't come to people who chase them. They come to people who are so good they can't be ignored.

Here's how to get so good they can't ignore you:

1. Question Yourself

What do you truly want? What would this look like if it were fun?

Question what you actually enjoy.

Explore your craziest ideas to understand your true north star. 

Make a list of 10-15 items that light you up.

2. Stack Skills

What daily, repeated practice will get you to your goals?

Pick up a new skill every 30 days to accelerate your value.

Each skill compounds. Each one makes you more rare, more valuable, more undeniable.

3. Kill Self-Doubt

What's the worst that can happen to you?

Face your fears. Lean into discomfort.

The gap between where you are and where you want to be is filled with things that scare you. Cross it anyway.

4. Ruthlessly Track Your Time

What does your dream week look like? Which hours are you most productive? What tasks give you the most energy?

Design your ideal week, identify your best hours, and protect them like your life depends on it.

5. Set Anti-Goals

What daily actions will impede your success?

Make an "avoid at all costs" list.

Knowing what to avoid is just as powerful as knowing what to pursue. Sometimes more.

6. Set Specific Goals (And Review Them)

What are your 10-year goals? 3-year goals? 1-year goal? 30-day goals? This week? Today?

Break the future into today. Make the impossible actionable.

Review these relentlessly. Adjust. Iterate. Execute.

The people who become undeniable aren't waiting for permission.

They're building skills. Facing fears. Tracking everything. Avoiding distractions. Setting goals that scare them.

They're getting so good the world has no choice but to pay attention.

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How to get so good they can’t ignore you 

Sales are simple when you understand this secret: 

The moment you start selling, you've lost.

I used to be terrified of sales calls.

Now my team and I close without ever feeling like we're "selling."

Using a proven system I call “Pitch OS”.

I've taught this exact system to founders who went from struggling to book calls to closing 30-50% of their prospects.

Here's the 6-step sales system:

1. Lead With Curiosity

Most salespeople start by talking about themselves. 

Big mistake.

Instead, ask open-ended questions:

• "What are you looking to achieve?"
• "Tell me about your current situation"
• "What made you book this call today?"

Then shut up and listen. 

2. Clarify Their Challenges

You can’t help your prospect if you don’t truly understand their situation.

Some great follow-up questions I use:

• "Tell me more about that"
• "Why is that important to you?"
• "What impact does that have on your life?”

Care about what they say here.

The key is to dig deeper:

• "How long has this been an issue?"
• "What happens if this doesn't get solved?"

Their answers become your roadmap.

3. Co-Create Their Ideal Outcome

Once you understand their challenges, help them paint a picture of what success looks like:

• "What's the ultimate goal here?"
• "What would this allow you to do?"

This creates a vision they're emotionally invested in.

4. Contrast Cost of Inaction vs. Investment

Most people aren't afraid of the cost of your solution.

They're afraid of making a change.

Ask them: "If nothing changes, where will you be in 6 months?"

Help them see what inaction will cost them.

5. Present Your Solution As The Bridge

After successfully going through steps 1-4, I transition into the bridge:

"Based on what you've shared, I think I can help because of my experience in [solving their problem]. Here's how we'd get you to [their ideal outcome]."

I structure my solution around 3-4 clear pillars that directly address their challenges:

"The first thing we'll do is build out what I call [Pillar 1], which will solve [Challenge 1 they mentioned]."

Then, I’d go through each one in detail, following the same format. 

6. No Manipulation

I never use:

• Fake scarcity ("only 2 spots left!")
• False urgency ("price doubles tomorrow!")

Instead, I'm radically honest about what my solution can & cannot do.

Sales don't have to feel gross.

Remember: Trust is built before the call, not during it.

That's why my Content GPS makes sales effortless:

• Monthly workshops with immense value
• Weekly newsletter building a true relationship
• Daily content on social media solving real problems

By the time someone books a call, they're pre-sold on your expertise.

__

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How To Sell Anything To Anyone

My mentor asked me a question that broke my brain:

"What would your life look like if everything was intentional?"

I stared at him blankly.

"Most people live by accident," he continued. 

"They react to whatever shows up. You need to design your life like you design your business."

That night, I grabbed a notebook and sketched out 7 life categories.

Each one got specific, measurable actions.

No fluff. No "someday" goals. Just clear systems.

Here's what happened when I started living by design instead of default:

1. Relationships became rocket fuel 

Instead of random catch-ups, I created adventure schedules. 
 
Weekly parent calls. 
Epic trips every quarter.
Surprise bucket list experiences.

Intentional relationships compound differently than accidental ones.

2. Health became non-negotiable 

Daily movement. 
Time-restricted eating. 
Nature immersion weekly. 

When health is a system, not a mood, energy becomes unlimited.

3. Business operated like a machine 

Monthly filming batches. 

Systematic delegation. 

Deep work blocks carved in stone. 

Consistency at scale beats hustle at chaos.

4. Community became my competitive advantage
 
Instead of networking, I designed belonging. 

Home base finalized. 

Group activities by default. 

Your network becomes your net worth when it's built on intention.

5. Fun became fuel, not escape 

"Whole body yes" decisions only. 

Japan snowboarding trips planned. 

When fun is intentional, it recharges instead of depletes.

6. Spiritual practice became daily wisdom 

Alan Watts before bed. 

Connecting with my 13-year-old self. 

Grounding isn't optional when you're building at scale.

7. Creativity became systematic 

Daily journaling. 
Weekly artist dates. 
Notebooks everywhere. 

Innovation happens when you create space for it.

The shift from accidental living to intentional design?

Game changer.

Most people optimize randomly. 

They fix what's broken instead of building what works.

The magic is having a framework that covers every dimension of life.

When everything is intentional, everything compounds.

—

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The 9 most powerful life hacks i've discovered:

1. Surround Yourself With Optimists

Who you spend time with has a bigger influence on you than you know.

You're the average of the 5 people you spend the most time with.

Each of those 5 should be someone pushing you forward.

I used to tolerate energy vampires.

Then I realized: their mindset was becoming mine.

2. Write Every Day

Writing isn't just for writers.

It's for thinkers.

Writing builds discipline. 
Improves your communication. 
Organizes your thinking.

I write every single day.

Some days it's one sentence. Some days it's ten pages.

What matters is the habit.

3. Build a Personal Board of Advisors

Don't underestimate the power of a mentor.

Epictetus mentored Marcus Aurelius.

Jobs mentored Zuckerberg.

Seeking advice from people 2-3 steps ahead of you gives you access to their lifetime of wisdom in 2-3 years.

4. Sun Exposure Every Morning

Get sunlight in your eyes every morning.

It sounds simple. It is simple.

But it's powerful.

Sunlight sets your circadian rhythm. 
Primes your brain to be alert and focused. 
Enhances your metabolism and immune function.

No phone. No distractions.

Just 10 minutes in the sun.

5. Block Off Time to Read

The most successful people in the world have one thing in common:

They love to read.

I read every day. About things that interest me. And I re-read my favorite books.

An hour a day of reading puts you in the top 0.01% of people.

6. Meditate Daily

"All of man's problems come because he cannot sit by himself in a room for 30 minutes."

Our society is filled with cheap dopamine. 
Constant notifications. 
Screens everywhere.

Meditation is the antidote.

I meditate for 20 minutes every morning.

It's about learning to be present.

7. Set a Bedtime Alarm

Everyone has a morning alarm.

Almost no one has a bedtime alarm.

After this alarm goes off, I allow my mind to relax:

Turn off all devices. 
Take a warm shower or bath. 
Read my favorite fiction book.

Setting yourself up for success the next day starts the night before.

8. Practice Gratitude

Gratitude is a key ingredient for living a fulfilling life.

Gratitude helps people improve their health, feel more positive emotions, and build strong relationships.

I take 5 minutes every day to write down 5 things I'm grateful for.

It rewires your brain to see opportunity instead of obstacles.

9. Invest in Yourself

We spend 8 hours a day working for someone else.

But we won't take 30 minutes to work on ourselves.

I invest in myself through reading, exercising, and learning new skills.

Just 30 minutes a day can change your life.

The best investment you'll ever make is in yourself.

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The 9 Most Powerful Life Hacks I've Discovered

Last year, I wrote down 20 laws that changed how I operate.

Not theories from business school. 

Real principles tested in the trenches.

Here are the 20 laws that transformed my approach:

1. Simplicity Beats Complexity

The founder who can explain their business in one sentence wins.

Strip away everything that doesn't move the needle.

2. Compounding Is The 8th Wonder

Small, consistent actions compound into massive results.

1% better every day = 37x better in a year.

3. Leverage Over Labor

Code, content, and capital scale infinitely.

Build systems that work without you.

4. Taste Is Strategy

Great taste isn't subjective - it's a competitive moat.

Develop your eye for quality in everything you touch.

5. Energy Is Currency

Guard your energy like cash.

You can't pour from an empty cup.

6. Write It Down

Clarity comes from writing, not thinking.

If you can't write it, you don't understand it.

7. Asymmetric Bets Only

Never risk $1 to make $1.

Only take bets where the upside is 10x the downside.

8. Distribution Beats Invention

The best product doesn't win, the best distribution does.

Build your audience before you build your product.

9. Brand Over Product

Products are copied in months.

Brands take years to build and can't be replicated.

10. Constraints Create Breakthroughs

Unlimited resources breed mediocrity.

Constraints force creativity and focus.

11. Ignore The Mob

Public opinion is the slowest form of judgment.

Do what's right, not what's popular.

12. Be A Media Company

Every business is a media company now.

If you're not creating content, you're invisible.

13. Do It Now

Procrastination is a symptom of unclear priorities.

If it's important, do it today.

14. Hire Weapons, Not Helpers

One A-player is worth 10 B-players.

Pay for excellence or pay for mediocrity twice.

15. AI Is Your Second Brain

Leverage AI to amplify your thinking.

It's not replacing you - it's extending you.

16. Profit Is Oxygen

Revenue is vanity.

 Profit is sanity.

Cash in the bank gives you freedom to take risks.

17. Legacy Over Likes

Build something that matters beyond your lifetime.

Social validation is empty calories.

18. Systems Buy Freedom, Hustle Buys A Job

If you're working 80-hour weeks, you don't have a business.

You have an expensive hobby.

19. Founder Brand Is Moat

Your personal brand is your unfair advantage.

People buy from people, not logos.

20. Die With No Regrets

Optimize for joy, not just returns.

The scoreboard resets when you're gone.

When you operate from these principles, you become untouchable, not because you're perfect, but because you're focused.

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Leonardo da Vinci once said:

"Simplicity is the ultimate sophistication."

Here’s how to simplify your life (in 6 months):

Minimal vs Simple

Most people confuse the two. 

Minimalism is about having less. Simplicity is about focusing on what matters.

Your goal isn't to strip everything away. It's to make room for what counts.

When you master this, freedom follows.

The simplest people in history found joy in traditions:

• Simple diets
• Tea ceremonies
• Timeless fashion

Old traditions represent mastery over distraction. 

Here are 3 tips I’ve learned from studying timeless principles:

1. The 80/20 Rule

20% of your habits drive 80% of your health.

20% of your clients drive 80% of your revenue.

20% of your actions drive 80% of your happiness.

Focus on the 20%. Cut everything else.

2. Curate Your Environment

It's not just about a clean desk.

It's about: 

• What media you consume
• What notifications you allow
• Who you surround yourself with

Your environment shapes your behavior.

3. Not-To-Do List

Create a list of non-negotiables: 

• No meeting blocks
• No email before noon
• No social media after 8 PM

Sometimes, the habit you eliminate is more important than the habit you add.

Next, I want to break down 5 insanely simple systems that you can implement today to make you unstoppable:

1. Establish Rules
2. Have A Clear Vision
3. Plan For The Next Day
4. Health > Everything
5. Affirmations

1. Establish Rules

Here are a few I’ve set for myself to maintain a simple life: 

• Batch core meetings
• 3 hours of deep work at dawn
• No morning meetings until 12 PM
• Daily movement is non-negotiable 

Rules + Discipline = Freedom

2. Have A Clear Vision

You must create clear 1 year and 90-day goals for your business. 

When defining them, make sure they follow the S.M.A.R.T. framework:

• Specific
• Realistic
• Achievable 
• Measurable 
• Time-bound 

Without a vision, you will perish.

3. Plan For The Next Day

Write down your 5 priorities for tomorrow every night. 

The Super Bowl is won in preseason. Tomorrow's victory is planned today.

Clarity before bed = Momentum at dawn.

4. Health > Everything

Your most important asset is your body. 

Here’s my (simplified) health protocol: 

Morning: Collagen + H20+ Journaling + Coffee
Afternoon: Apple Cider Vinegar + Lunch + Sunlight 
Evening: Light dinner + 8hrs Sleep

Healthy founders build healthy businesses.

5. Affirmations

These daily reminders become your internal motto. Some of mine include: 

• "I am optimistic" 
• "I recognize less is more" 
• "I am present and loving"

Your words become your reality. Choose them with intention.

—

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How To Simply Your Life (in 6 months)

I can teach you more in 2 minutes than you'll learn in 4 years.

Here are 10 steps to start your own business:

1. Find Your Calling

Don't waste time building a business you hate.

Focus on your purpose by completing your Ikigai.

Ikigai = your reason for being

The thing that gets you up in the morning.

2. Mentors Are Everything

You are the product of the 5 people you are surrounded by.

Reach out to people you respect.

3. Publish Content Daily

Pick platforms where your audience lives.

Share your failures, breakthroughs, and lessons daily.

You're not just building content, you're building proof you can deliver.

Consistency beats perfection.

4. Drive People to Your Email List

Email is your direct line.

No algorithm can take it away.

Give value first, free guides, frameworks, honest lessons.

People join lists for transformation, not pitches.

5. Survey Your Community

Ask people what they want to see from you.

Find something in your calling and mix it with a monetization strategy:

• SaaS
• Course
• Consulting
• Membership
• Paid Newsletter

You got this.

6. Buy a Domain

Perfect is the enemy of launched.

Get a domain, throw up a landing page, start collecting emails.

You'll learn more from 10 real conversations than 100 hours of planning.

7. Be Scrappy

People love hustlers.

Entrepreneurs love to pay it forward.

Get outside the building.

Talk to people.

8. Use No-Code Tools To Build an MVP

Your MVP shouldn't look like Apple's homepage.

Use free tools, hack together solutions, focus on solving one problem perfectly.

Constraints breed creativity. Build fast, learn faster.

9. Business is About Systems

Your business should run without you watching every detail.

Document everything. 
Create playbooks. 
Automate the routine so you can focus on growth.

Systems turn hustle into scale.

10. Get Your Banking Set Up

One business account.

Clean books from day one.

Track every dollar in, every dollar out.

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How to build momentum when you feel stuck:

Step 1: The Minimum Viable Action

When I'm stuck, I find the smallest possible action I can take.

Not the perfect action. Not the big action.

The tiniest step forward.

Make one call.
Share one idea.
Send one email.
Write one sentence.

That's it.

Most people stay stuck because they're waiting for clarity on the whole path.

But you don't need the whole path.

You just need the next step.

Step 2: The Momentum Stack

Here's where it gets interesting.

I layer small actions on top of each other:

• Action 1 creates energy
• Action 2 builds on that energy
• Action 3 multiplies the energy
• Action 4 sustains the energy

Each action makes the next one easier.

This is how momentum compounds.

Step 3: The Friction Elimination

While I'm building momentum, I'm also removing everything that slows me down.

I cut out:

• Unclear goals
• Energy vampires
• Decision fatigue
• Complex processes

Every point of friction you remove doubles your velocity.

Step 4: The Momentum Multipliers

This is the advanced move.

I identify actions that create compound effects:

Systems that create more systems.
Connections that lead to more connections.
Success that enables more success.

These are the leverage points.

One good action creates ten more opportunities.

The Advanced Strategy: Momentum Anchoring

I don't just take action.

I connect that momentum to my identity.

"I am someone who takes action."
"I am someone who follows through."
"I am someone who builds systems."

When momentum becomes part of who you are, it's unstoppable.

Every breakthrough I've ever had followed this pattern:

Stuck → Small action → Slight progress → Increased confidence → Bigger action → Real progress → Sustained momentum

Find the smallest possible action.

Take it. Then take the next one.

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How To Build Momentum When You Feel Stuck

7 mental models that killed my overthinking forever:

1. The Pareto Principle

20% of your efforts produce 80% of your results.

I used to spread myself thin across 30 different tasks. 

Now I ruthlessly identify the critical 20% that actually moves the needle. 

Double down on what matters. Ignore the rest.

Your zone of genius isn't everything; it's the few things only you can do.

2. Occam's Razor

The simplest solution is usually the right one.

I'd overcomplicate every decision with 15-step frameworks and contingency plans. 

Nature doesn't work that way. 

When facing a problem, I now ask: what's the path with the fewest points of failure?

Strip away the complexity. 

The answer is simpler than you think.

3. Regret Minimization Framework

Picture yourself at 80, looking back at this exact moment.

What would you regret more, staying stuck or taking action?

I've never regretted the risks I took. 

Only the ones I didn't. 

4. The Eisenhower Matrix

Urgent vs. Important, most people confuse them.

I used to live in the "urgent" quadrant, constantly firefighting. 

Now I categorize every task: 

Do it now. 
Schedule it. 
Delegate it. 
Eliminate it.

The magic happens when you live in "important but not urgent." That's where you build the future.

5. Inversion Thinking

Instead of asking "what guarantees my success?"

Ask "what guarantees my failure?"

Fear of judgment. 
Analysis paralysis. 
Waiting for perfect timing. 

Once I identified these failure patterns, I could eliminate them systematically.

You can't always control success. 

But you can always avoid failure.

6. Opportunity Cost

Every hour spent overthinking is an hour not spent building.

The real cost isn't the decision itself, it's the life you could have lived while you were stuck deciding. 

I think about this daily: what am I sacrificing by staying paralyzed?

The answer usually terrifies me into action.

7. Parkinson's Law

Work expands to fill the time you give it.

Give yourself a week for a task? It'll take a week. 

Give yourself a day? It'll take a day.

I stopped giving myself endless time to "think things through." 

Tight deadlines force clarity. They eliminate the luxury of overthinking.

Your most valuable asset isn't your ideas. 

It's your time.

Stop thinking. Start doing.

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7 Mental Models To Kill Overthinking

David A. Olson

I make $1.1M per month while taking 4-day weekends. 

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

1. Systems > Hustle

Most founders are stuck working IN their business instead of ON it.

They chase growth through brute force when they should be building systems.

The simple truth:

• You don't need to work harder
• You don't need more hours
• You don't need more motivation

You need systems that run without you.

The difference between a job and a business is whether it works when you don't.

2. The AED Framework

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.

3. The 5 Systems Every Founder Needs

After building multiple 7 and 8-figure businesses, these are non-negotiable:

• Content system (audience growth on autopilot)
• Sales system (predictable revenue generation)
• Delivery system (consistent customer experience)
• Team system (accountable performance)
• Finance system (profitable decision-making)

Build these 5 and you've built your freedom.

4. 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.

5. The Founder Freedom Formula

True freedom requires more than just delegation.
You need:

• Documented processes for everything you do
• Decision frameworks for your team to follow
• Clear metrics to measure performance
• Weekly accountability systems
• Strategic deep work time for yourself

Your business should serve your life, not consume it.

6. The 90-Day Freedom Plan

Want to implement this in your business?

Days 1-30: Document every process you touch 
Days 31-60: Build your team and systems dashboard 
Days 61-90: Transition to 4-hour founder workdays

Most founders never escape the daily grind because they never commit to the systems work.

Be the founder who builds a business, not just another job.

Your systems are your path to freedom.

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Spencer Taylor

I create 247 pieces of content per month.

Time spent? 7 hours.

Most founders stare at blank screens for hours. 

They overthink, delete drafts, and convince themselves they're "not interesting enough."

Here are 6 tips to generate endless content ideas:

1. Stop Waiting for Inspiration

Content isn't about being on camera or feeling creative. 

It's about documenting what you're already doing, thinking, and learning every single day.

2. The Content GPS Framework 

Every week follows five buckets: 

Monday - mistakes I made, Tuesday - systems that work, Wednesday - client transformations, Thursday - contrarian truths, Friday - vision for the future.

3. The 30-in-30 Exercise 

Spend 30 minutes writing: 10 things that frustrate you, 10 lessons you've learned, 10 transformations you've witnessed. 

That's your content calendar.

4. Mine Your Past Self 

Last week at 2am in London, I asked myself one question: "What do I wish I knew 5 years ago?" Wrote 73 ideas in my journal without stopping.

5. Your Struggles Beat Their Quotes 

20-somethings share motivational quotes. Real founders share scars.
 
Your authentic experience will always beat polished perfection.

6. Your Life IS Content 

Every decision you make, every system you build, every mistake you survive, it's all material waiting to be shared with people who need it.

The difference between struggling and thriving with content?

Systems beat motivation every time.

I don't create content because I'm inspired. 

I create it because I have a framework that turns my real experiences into value for others.

That's the power of building in public, transparency becomes your competitive advantage.

Start documenting your journey today. 

Someone needs to hear exactly what you learned yesterday.

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How To Generate Endless Content Ideas

Naval Ravikant once said:

"The most dangerous things are heroin and a monthly salary."

Here’s how to build a 7-figure one-person business (in 90 days):

Most founders are trapped in a business that's running them into the ground. 

Stressed, directionless, unsure how to find peace and grow.

But the future of entrepreneurship is the one-person business model: 

You, your systems, and a remote specialist team helping you scale.

Picture this: running a business you love, with people and customers you adore, living a life of calm and ease.

To turn this 7-figure dream into reality, focus on multiplying four key areas:

• Impact
• Energy
• Output
• Audience

Let's break them down:

1. Multiply Your Audience

The Content Waterfall system is your secret weapon. 

Transform one pillar content piece into 26 across platforms:

• 3 IG reels
• 10 tweets
• 1 newsletter
• 3 YouTube shorts
• And more

Say goodbye to the content hamster wheel forever.

2. Multiply Your Impact

Your story is your north star. Craft an origin story infused with your:

• Mission
• Values
• Vision

Weave this into your content, hiring, sales, every facet of your business. 

Let your story guide you.

3. Multiply Your Energy

As a founder, you are your greatest asset. 

Make your health your #1 priority:

• Quit unhealthy habits
• Find a mentor or coach
• Surround yourself with a supportive founder community

Remember: a business can only be as healthy as its founder.

4. Multiply Your Output

Building an empire is a team sport. 

Hire "weapons" A-players who take ownership of key areas to supercharge your growth.

My game-changing first hires:

• Tech
• Funnels
• Finance
• Copywriting

This gave me the time and energy to create the greatest founder experience possible.

—

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I just turned 36.

I battled to get sober, had my company get raided by the government, traveled the world, started two 8-figure companies and one 7-figure company.

11 lessons for 18-year-old Matt:

1. Prioritize Nature

Nature's been my biggest mentor and therapist.

Getting outside daily, taking my shoes off, and grounding myself have brought infinite stability to my life.

2. Remove Negative People

Negative energy infects your spirit and slowly chips away at your spirit.

If I ever feel drained after meeting someone, they're not meant to be in my life.

3. Learn Aggressively

If you want to fail in life, act like you know it all.

I set aside time to learn something new every day.

Be a lifelong student - read, listen, and learn.

4. Attention is the New Oil

Once you figure out how to get it, your life will take on a new trajectory.

Growing your audience is the fastest way to expand your luck surface area and become a magnet for opportunities.

5. Learn Storytelling Early

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

It's the highest intangible ROI skill you can learn.

The first step:

Study storytelling frameworks and the 7 fundamental human emotions.

6. Rethink Vulnerability

I used to think vulnerability made me weak.

But vulnerability is the birthplace of all meaningful connections.

Be real and open your heart.

7. Embrace Compounding

Aim to get 1% better every day and be 37x better by the end of the year.

It's a simple mindset hack that'll bring you a world of joy down the line.

All you need is consistency.

8. Make your Morning Routine your Competitive Advantage

I plan my day the night before.

Then I'm up at 5:30, go for a walk, and lift weights.

I've won the day before I even start.

I'm not saying follow my morning routine - I'm saying find what works for you and stick with it.

9. Optimize Your Health

In order to be successful, you need to be at peak performance.

Your health is the biggest input.

It's simple:

If you treat your body like shit, you'll feel like shit.

10. Excellence is a Habit

How you do one thing is how you do everything.

And if you slack, you're only letting yourself down.

Aim for excellence in the small things, and the big picture takes care of itself.

11. Fall in Love With The Process

There's no shortcut to success - it's years of showing up every day.

But you can't do it unless you love it.

Enjoy the small stuff: a good day's work, a big email sent, every deal closed.

Success is about stacking tiny wins.

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I used to be stressed out of my mind…

Now, I only work 4 hours a day and travel the world building my dream business. 

10 sentences that helped me 10x my productivity:

1. Your Future Is Built In Invisible Moments

The actions nobody sees today create the freedom everybody will envy. 

Spending 30 minutes daily building systems can save hundreds of hours down the line.

2. Be Consistent Long Enough To Look Talented

Everyone chases breakthroughs, but sustained success comes from showing up daily.

I've posted content daily for 3 years straight, through travel, illness, and burnout.

That consistency (not some magical skill) built my following to 2.8 M.

3. Boredom Is The Doorway To Mastery

Most people think that we should avoid boredom at all costs. 

I disagree. Some of my biggest business breakthroughs have come from: 

• Walking in Joshua Tree
• Biking through the Dolomites 
• Strolling through rice fields in Bali

Doing nothing is sometimes better than doing something.

4. If You're Overwhelmed, You're Doing Too Much Manually

Being busy means you haven't built systems to replace yourself. 

It means you're still trapped in the founder's prison you built.

The moment you feel overwhelmed, it's a signal to automate, delegate, or eliminate, not work harder.

5. Make Your Inputs Louder Than Your Insecurities

Your mind will always find reasons why you can't build the business you want.

Drown those voices with quality inputs: books, conversations with A-players, courses, and masterminds.

6. Execution Speed > Creative Perfection

Ideas are worthless. Execution is everything.

The best entrepreneurs ship FAST. 

Get feedback.

Iterate relentlessly.

I'd rather ship 10 imperfect projects than obsess over one "perfect" one that never sees the light of day.

7. Focus Is A Force Multiplier

Always think about ways of doing less: 

• Less work
• Fewer teams
• Fewer meetings
• Fewer product lines

Fewer things done well beat many things done poorly.

8. Great Brands Are Built On Brutal Clarity

Your messaging should be so clear that someone can explain your offer in one sentence.

If you make people “think” too hard about what you do, they'll move on to someone else.

9. Don’t Escape the Grind, Systematize It 

Your business will eventually ruin you unless you transform it into one that runs itself.

Every repetitive task in my business is documented, templated & assigned to the right person.

I don't need to escape my business because I've built it to run better without me.

10. Rest Is Strategy, Not Reward

Schedule time to completely unplug from your business.

“Distraction is not procrastination. Distraction is a strategy in service of the work.” — Rick Rubin.

Your best ideas often come when you step away.

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7 life lessons people learn too late in life:

1. Never Let Rejection Lead To Self-Rejection

Rejection is a constant experience in life.

It becomes dangerous when rejection instills fear in your heart.

Fear of rejection destroys:

• Risk-taking
• Creativity
• Desire for exploration

Never let fear rule you.

2. Rediscover Your Inner Child

When was the last time you played in the snow?

The goal of life is to discover freedom.

Rediscover your inner child by doing the following:

• Make time for play
• Create space for stillness
• Surround yourself with people that bring you joy

3. Love Yourself

Society has made it popular to seek love from others.

It makes us forget that self-love is more important than:

• Our career
• Other peoples' opinions
• Others' wishes/moods

Love yourself first, and everything else falls in line.

4. The Achievement Will Never Be as Fulfilling as the Journey

It can often feel empty when you are hitting your goals.

The reason we set goals is for the journey they take us on:

• Your 30-day workout streak
• Your first revenue milestone

Life is a journey. Enjoy the trip.

5. Creativity Takes Hard Work

Creativity is:

• Instinctive
• Free-flowing

But it's also:

• Hard-earned
• Improved through practice

Get over the idea that there are "natural creatives."

You are creative.

"Creativity is intelligence having fun." - Einstein

6. Most People Don’t Do What They Love

90% of people work on things they hate.

Don't let others dictate your life.

• Do what is best for you
• Get clarity on your goals and dreams

Do what you love and the necessary opportunities will follow.

7. Own Your Responsibilities, Own Your Future

Never let your present be rooted in your past.

You will never be able to take control of your future.

Past actions are no longer your responsibility.

Only how you attack today matters.

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How to develop influence as a leader:

1. Be the Hardest Worker In the Room

Your business is your baby, & your team is there to help you raise it.

But still, at the end of the day, it’s your baby.

You have to make your own luck.

The responsibility you have as a founder is to set the standard for work at your company.

2. Be Real With Your Team

Many people don’t feel like they can be honest with people who are perceived to be above them.

• Share struggles
• Acknowledge your flaws
• Work to improve

When you’re honest with yourself, your team will be honest with you.

3. Keep Your Eyes On the Prize

This is my preferred method to ensure that my team and I stay aligned on our big-picture vision.

You can’t have a million different projects at once.

No one will get anything done.

Master the spirituality of productivity.

4. Avoid Pointless Meetings

I have policies to make sure that I’m done overwhelming myself and my team with meetings:

• No meetings before noon
• All meetings on Tuesdays
• No agenda, no meeting

These rules are easy in concept but tough in practice, that’s why they work.

5. Learn How to Balance Play and Rest

Leadership is top down and culture is everything.

I aim to be the hardest worker in the room but I have a work-life balance and I want my team to have it too.

A burned-out CEO leads to a company of tired workers.

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Sean Kelly

Founder & Investor. Building companies at the intersection of health, media & founder performance.

Hey there, I’m Sean. I play at the intersection of investing, media and human performance.

I’m a three-time INC 500 founder & entrepreneur with businesses in eCommerce, SaaS, media and B2B services that have collectively generated hundreds of millions of dollars in revenue.

Right now, I serve as a General Partner at The Family Fund and am the CEO of Significant Publications, a B2B digital media holding company.

I'm particularly passionate about our brand FounderIV in support of today's founder-athletes. We help today's top entrepreneurs achieve breakout performance in their personal and professional lives.

I co-founded and led multiple other companies, including SnackNation, a health-centric foodservice and brand discovery platform that served 20,000 businesses across the US. 

Under my leadership, SnackNation was honored as one of the country’s Best Workplaces by Inc. Magazine, recognized for Top Company Culture by Entrepreneur Magazine, and certified as a Great Workplace by Great Place to Work®.

Forbes listed me as one of the top 30 leaders under 30 and one of America’s most promising CEOs under 35. Comparably also ranked me among the country’s top 50 small-to-medium sized business CEOs multiple years in a row. 

Outside of the business world, I’m a two-time national medalist in freestyle snowboarding, hold an advisory role at the growth capital firm, Meaningful Partners, have a degree in Biomedical Engineering from Columbia University and am an avid sports fan of all Michigan sports teams (especially the Wolverines).

I currently live in Venice, CA with my wife and college sweetheart, Shannon, and our goldendoodle, Jameson.

Chairman

Sprouts Farmers Market HQ visit was 🔥

A core tenant of ours at The Family Fund is to create partnerships and collaborations with the most influential people and businesses within the consumer ecosystem.

Those folks who can most move the needle for the founders and companies were fortunate enough to support.

And Sprouts is at the top of this list.

Not sure if any other retailers care as much about helping emerging brands succeed…

And being the first to do so.

When brands partner with Sprouts correctly, king and queen-making can occur.

Thanks to Kim Coffin Scott Romano and Brody Burk for the hospitality, and much more so…

For caring so damn much about the work you do. 

Josh Wand and I loved jamming with you.

Some guys have all the luck.

Just ran into Livio (Italian for “Living Legend”) at Expo West.

He somehow got his hands on a Founderland golden ticket!!

Tried to buy it off of him but he refused.

An early access, VIP ticket to the top B2B consumer health event in Malibu, CA on October 1st!

“Where founders have fun AND deals get done.”

1,000+ of today’s top founders, retailers, strategics and investors…

A B2B festival where value and serendipity reign and transactional behavior is lame.

If any of you know Livio Bisterzo please advise because I am willing to go to incredible lengths to get my hands on of these.

A Founderland.us golden ticket!!!

Shannon Kelly 
Josh Wand  
Seth Gusow

First Founderland Adventure trip in the books.

Yellowstone Club was 🤯

The founder crew we put together was even better.

I don't believe there is a better way create meaningful relationships then getting off of screens, away from the norm and experiencing 3 days of new challenges & outdoor adventure together.

Thanks to our friends and legendary co-hosts:

- Matthew LaCasse Ethan Greaves and Lizzi Ackerman LaCasse from E+PATROL (and our beautiful hosts at YC)

- Kristofer Reddaway, CEPA® from Citizens 

- Gareth Domingo from AppLovin

And to Stephen Ellsworth from poppi for inspiring me to put this ski trip together when we were hanging at Founderland last year.

Pumped (and already planning) the next one... 
 (Have a feeling these adventure trips will be another key way we bring founders together in a differentiated way at The Family Fund & Founder Community)

And thanks to the phenomenal leaders, founders and friends who made this experience OTT:

Josh Wand
Michael Brandt
Jack Savage
Morgan Buehler Zanotti
Adam Goldberg
Tyler Ricks
Josh Deemer
Jeff Mroz
Giancarlo Maniaci
Curtis Christopherson
Wes Van Dyk
Dave Clark

Let’s roll!

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