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.

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Too may legends too little time.

Such is life at Expo West.

Loved seeing each one of you.

I continue to be inspired by the better-for-you consumer ecosystem.

Most importantly the founders that are battling each and every day to solve problems that they deeply care about.

We are in the golden age of CPG.

AI ain’t removing our need for atoms and physical goods.

And with the OpEx reduction automation will allow us to experience…

Better margins…

Higher enterprise valuations…

And entrepreneurship will continue to explode.

Love where we’re at!

Will Nitze 
Stephen Ellsworth 
Michael Brandt 
Josh Wand 
Morgan Buehler Zanotti 
Jack Savage 
Gulrez Arora 
James Boyd 
Taylor Griffin 
Steve Young 
Colleen Kang

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!

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

If you want to learn more about how I built this, you can join my newsletter:

→ GO HERE: https://fos.now/OdJnIQ

If you want to explore 1:1 coaching or consulting visit my personal site:

→ GO HERE: https://fos.now/li-book-now

If you want to join Founder OS Program:

→ GO HERE: https://fos.now/li-course

Twitter: https://fos.now/li-twitter
TikTok: https://fos.now/li-tiktok
Instagram: https://fos.now/li-instagram
YouTube: https://fos.now/li-youtube

Founder & CEO

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

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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Matt Gray 

3 years of progress in 90 days.

That's not hype. 

That's what happens when you build a plan you'll actually use.

A great 90-day plan isn't about doing more; it's about doing what matters with absolute clarity.

This framework changed how I operate:

1. Start With Foundation

Before you set a single goal, get crystal clear on four things:

One word for the next 90 days. 

Your dream outcome (where you want to be on December 31st). 

Why it matters emotionally (not just financially). 
The success headline you want written about you.

This takes 30 minutes and saves you 90 days of confusion.

2. Then Set Real Goals

Not 10 goals. 
Not 20 goals. 
Three.

One team goal. 
One health goal.
One business growth goal. 

Plus one metric that proves you won.

That's it.

3. Build The Systems

Goals without systems are just wishes.

Identify:

• The one habit you must lock in
• The one system you must build
• What you'll automate or delegate
• What you'll stop doing completely
• Your weekly ritual to stay on track

Systems create the compound effect.

4. Get The Right People

You can't do this alone.

Define exactly:

• One mentor you'll lean on
• One accountability partner
• One teammate you'll empower
• Who can help you (name + role)

5. Execution

Break your 90 days into 12 weekly themes.

Week 1 might be foundation. Week 8 might be scale.

This prevents you from trying to boil the ocean in week one.

The magic isn't in the planning.

It's in having a plan simple enough to remember and specific enough to execute.

I've compressed years of progress into quarters using this exact framework.

Not because I work harder, but because I work clearly.

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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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Kim E. Andrews, PCC, BCC, CDCS, CGC

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

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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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

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)

7 steps to design the life you want:

1. Prioritize Your Health

Your mind lives in your body.

Express gratitude every morning. 
Get 8 hours of sleep. 
Lift weights. 
Meditate. 
Seek morning sun. 
Cut out energy vampires. 

Without a strong foundation, nothing else matters.

2. Take Control Of Your Future

Stop waiting for perfect conditions.

When you're unfocused, run. 
Burnt out, seek nature.
Tired, go for a walk.
Uninspired, read. 
Upset, breathe. 
 
You have simple tools to shift your state. Use them.

3. Be Consistent

Get 1% better every day and you're 37.7x better by year's end.

The greatest returns in life come from compounding over the long-term.
 
Small daily improvements create extraordinary results. 

Consistency beats intensity every single time.

4. Quit Procrastinating

Build systems. 
Stop doomscrolling. 
Turn off your phone. 
Create your own story.

Stop the false hope that somehow tomorrow is gonna be better. 

Tomorrow never comes. 

The only moment you have is right now.

5. Craft A Compelling Vision

What is your mission? 
Your purpose? 
Your vocation? 
Your passion?

Answer these questions down to your 90-day goals. Break your 10-year vision into 3-year milestones, then 1-year targets, then this week's priorities. 

Clarity creates momentum.

6. Take Massive Action

Do hard things and embrace discomfort. 

When in doubt, execute.

Take extreme ownership over your life and surround yourself with A-players. 

Don't be paralyzed by analysis paralysis. 

Focus on decision velocity.

7. Choose Play And Adventure

Most men die at 27, we just bury them at 72.

Life's too short to spend it behind a desk doing work that drains you. 

Build a life with space for exploration, for nature, for the things that make you feel alive.

The life you want isn't something you find.

It's something you design.

One intentional decision at a time.

Start today.

__

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7 Steps To Design The Life You Want

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

I just spent two weeks in Japan.

Tokyo to Niseko. Snowboarding, editing my book, conversations with founders.

Japan always reminds me of what matters when you're building something that lasts.

Here are 6 principles about building a brand that matters:

1. Sweat the Details

Met a 60-year-old retired founder on a chairlift.

Built multiple successful companies over 40 years.

Asked him his biggest lesson.

He said: sweat the details.

Every pixel. 
Every word. 
Every design choice.

That's what separates good from legendary.

Most founders skip this part.

They rush to launch. 
They settle for good enough.

Then they wonder why their brand feels forgettable.

The details are everything.

2. Mastery Takes Devotion

The Japanese way: obsession around quality, devotion to craft.

Not rushing it. 
Not settling.

I'm deep in editing my book right now.

Been working on it for three years.

This place reminds me to keep going.

To craft something transformative, not just good enough.

Mastery isn't about speed.

It's about devotion.

3. Customer Service is Care

Japanese customer service is next level.

Everyone's so friendly. 
They genuinely care. 
They want to make sure you're treated well.

That level of care, love, devotion.

That's what I want to bring to every founder we work with at Founder OS.

Most companies treat customer service as a checkbox.

In Japan, it's an art form.

4. Rest is Creative Work + Nature

Four or five hours snowboarding in nature every day.

Onsen every other day.

Still writing. 

Still moving tasks along.

That mix? That's rest.

Not doing nothing.

Doing what makes you feel alive.

Founders usually think rest means stopping completely.

But real rest is active. 
It's being present.

5. Sensory Overload Sparks Creativity

Tokyo is museums, art galleries, architecture, design everywhere.

It gets your creative juices flowing.

Sometimes you need to put yourself in environments that overwhelm you in the best way possible.

When I'm back home, I get stuck in routines.

Here, every corner sparks something new.

Creativity needs fuel.

6. The Mission's Different

When I'm on the mountain, I'm not thinking about business.

Just listening to music. 
Enjoying the flow. 
Feeling like a kid.

Taking in the beauty. 
Trying to find fresh powder.

That sense of wonder.

That's what I'm building for.

Not money. Not status.

Wonder.

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6 Principles For Building a Brand That Matters

Most founders waste their 90-day plans.

They set ambitious goals, then wonder why nothing sticks.

I just mapped out my next 90 days using a framework that compresses 3 years of progress into a single quarter.

Here's the exact system I'm using:

1. Foundation First

Before you touch tactics, get crystal clear on four things:

• Why it matters emotionally
• Your one word for the next 90 days
• The success headline you want written about you
• Your dream outcome (where you want to be December 31)

Clarity drives execution. 

Confusion kills it.

2. The Rule of Three

Pick your top 3 goals only:

• #1 Team goal
• #1 Health goal
• #1 Business growth goal

Then identify one metric that proves you won.

More goals don't equal more success. 

They equal more distraction.

3. Systems Over Willpower

Map out the exact systems you need:

• Habit you must lock in
• System(s) you must build
• Weekly ritual to stay on track
• What you'll automate or delegate
• What you'll stop doing (subtraction)

Your habits determine your results. 

Design them intentionally.

4. People Make It Possible

Identify your support team:

• One accountability partner
• One teammate you'll empower
• Who can help you (name + role)
• One mentor/advisor you'll lean on

You can't do this alone. 

Stop trying.

5. Weekly Execution Blocks

Break your 90 days into 12 weekly focus areas.

Each week gets ONE priority.

Week 1, Week 2, Week 3... all mapped out with surgical precision.

This isn't just planning.

It's building a system that turns your vision into reality.

I'm sharing this framework publicly because transparency creates momentum.

When you declare your plan, you commit to the work.

The difference between dreamers and builders? 

Builders have systems.

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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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Success is stupidly simple.

Here are the 6 fundamentals that actually matter:

1. Work Hard

Not hustle porn. Not burnout culture. 

Real, focused work on things that move the needle.

Most people overestimate tactics and underestimate raw effort.

2. Hire Great People

Your network isn't just who you know. 

It's who you surround yourself with daily.

One world-class hire changes everything.

3. Have A Big Vision

Small goals create small actions. 

When your vision is massive, you make different decisions.

You think in decades, not quarters.

4. Do The Necessary Things Daily

Success isn't built in moments of inspiration. 

It's built in the boring repetition of fundamentals.

The daily grind nobody sees becomes the overnight success everyone celebrates.

5. Invest In Yourself

Your business can only grow as much as you do. 

Books, mentors, courses, therapy, fitness.

Every dollar invested in yourself returns 10x in your business.

6. Play The Long Game

Compound interest isn't just for money. 

Small improvements daily become massive advantages yearly.

What looks like overnight success is usually 10 years in the making.

We overcomplicate this game because complexity feels sophisticated.

But the founders who win? They master the basics while everyone else chases shortcuts.

Stop looking for the secret. There isn't one.

Just fundamentals executed relentlessly for years.

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Success is Simple

Being surrounded by the right people is the best hack for ultimate growth.

Your circle determines your ceiling.

Everything shifted when I found mentors who were 10x my level.

Their "normal" became my new baseline.
Their problems became my new targets.
Their thinking became my new standard.

Environment is stronger than willpower.

Here are 6 ways to upgrade your circle today:

1. Join Communities of High-Performers

Seek environments where excellence is the minimum standard, not the exception.

I've found that when you're the least accomplished person in the room, your growth accelerates exponentially.

High-performance communities create natural accountability that no app or system can replicate.

2. Attend Events Where Your Heroes Gather

The magic rarely happens during the presentations, it's in the lobby conversations, the dinners after, the unexpected connections.

I met one of my most influential mentors not during his keynote, but while waiting for coffee at an event I almost didn't attend.

Proximity creates possibility.

3. Create Value Before Asking

The moment you shift from "what can I get?" to "what can I give?" everything changes.

I spent six months helping others in my industry before ever asking for anything in return.

This approach built a reservoir of goodwill that continues to overflow years later.

4. Share Your Work Publicly

Building in public isn't just about transparency, it's about signaling.

When you openly share your journey, values, and systems, you naturally attract aligned people while filtering out those who don't resonate.

My most valuable relationships began when someone reached out after seeing something I'd shared.

5. Be Genuinely Curious

Curiosity is the hidden superpower in relationship-building.

I've found that asking thoughtful questions and truly listening creates deeper connections than any amount of impressive talking.

People remember the person who made them feel understood, not the one who tried to sound intelligent.

6. Invest in Relationships

The relationships that transformed my business weren't built over a single coffee meeting, they developed through consistent investment over time.

I block time every week specifically for relationship nurturing, treating it with the same importance as any business-critical activity.

I've seen this play out over and over with founders in our community. When they upgrade their circle, their business transforms almost automatically.

Your network isn't just your net worth. It's your thinking, your standards, your opportunities, your energy, and ultimately, your future.

Who are you surrounding yourself with?

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Your Circle Determines Your Ceiling

The bottleneck in your business isn't strategy.

It's execution hygiene.

I see founders obsessing over the wrong things. New frameworks. 

Growth hacks. 

The latest tactics from some guru. 

But when I ask them basic questions about their business, they go silent.

"What's your cash runway?" Silence.
"What's your team's one metric?" Crickets.
"How does your culture operate when you're offline?" Blank stare.

You're not running your business. You're reacting to it.

Here are the 3 things I obsess over every single week:

1. Numbers

When you miss tracking cash runway, you're gambling. 

When someone on your team doesn't know their one metric, they're guessing. 

When your culture only exists in your head, it disappears the moment you're not in the room.

I know my cash position, bottlenecks, and who owns what metrics without looking them up. 

If I can't answer these in under 10 seconds, I'm babysitting my business, not leading it.

2. People

If my team doesn't have clear outcomes and KPIs, they can't win without me. 

That's not a team. That's expensive chaos.

My team operates with clarity, not consensus. 

Everyone knows their one number. Everyone owns their domain. 

When decisions happen in Slack instead of documented systems, you're building on quicksand.

3. Culture

If culture isn't documented and enforced, it's just vibes. 

The founders who scale cleanly don't have more talent. They have more rigor.

Their culture runs the business when they're offline. 

Mine does too. 

Not because I'm in every meeting, but because the systems are so clear that the business operates without me.

The gap between where you are and where you want to be isn't another framework.

It's discipline in the small things that compound into systems.

Stop guessing. Start building rigor into these three areas.

That's how you scale complexity into freedom.

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Business Owners Should Obsess Over 3 Things

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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Things I'm doing at 36 to avoid regret when I'm 86:

1. Sip, Don't Gulp

Gently reminding myself that life is a marathon, not a sprint.

Patience in my 30s will help me avoid rash decisions and ensure I am optimizing for the life I want.

2. Investing in Personal Relationships

Building relationships with incredible people gives me energy, ambition, and happiness.

3. Prioritize Personal Health

I want to make sure I will have the energy and ability at 85 to keep pursuing my interests and passions.

4. Be Aware That I'm Breathing

Too often we never appreciate just living and what that truly means.

5. Read And Write Daily

They are the most nourishing forms of meditation and enable me to maintain a habit of continuous learning and curiosity.

6. Embrace The Journey

I want to build a lifestyle that enables me to value each step I take and build memories that I can look back on.

7. Never Conform to The Norm. 

I want to make decisions built to optimize my family in the future (city selection, homeschooling kids, etc.)

8. Dispel Hate

Hate is a pointless emotion that spreads rapidly.

9. Don't Fall Into The Trap of Constant Aimlessness

I don't want to watch TV aimlessly. 

This doesn't mean to value TV less. 

Value it more by being selective when you watch it and why.

10. Be Near Nature

I want to build on a plot of land. 

I want to plant trees, be near trees and fall in love with nature.

11. Stop Overworrying

I want to get rid of my habit of letting unrealistic scenarios dominate my brain.

12. Practice Yoga and Mindfulness

I want to have control over my mind and body in an era where technology's goal is to disrupt that.

13. Be Transparent With Myself

I want to let my thoughts flow and have a true conversation with my inner mind.

14. Build an Understanding of Philosophy

I want to understand fundamental human behaviour and broaden my perspective

15. Attain Economic Freedom

I want to build generational wealth and retire my parents. 

I want 3 generations of Gray's to have the freedom of time together.

16. Be Brave. 

I want to build a habit of believing in myself more, so by the time I am 85, I won't have missed anything I regret.

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I failed at business until I understood this: 
You’ll always be the bottleneck until you make yourself unnecessary. 

I used to work 16 hour days. 

It was ruining my health. My business plateaued, and I even lost friends.

Until a mentor helped install one simple system that changed my mindset and gave me 20+ hours / week back. 

I used to think more time working = more success. 

But this new system showed me the real formula for growth: 

Right work + Right Team = Freedom

Here’s the system I used to implement that formula and remove myself from operations in just 90 days. 

It seems overly simple, and almost no one does it. 
But if you follow these steps you’ll cut your work hours in half. 

#1 - Audit your time. 

The reason I couldn’t scale was because I didn’t know where my time was truly going. 

Bookkeeping, chasing payments, writing proposals – all things I THOUGHT I had to do myself. 

But you can’t fix what you can’t see. 
Getting clarity on where I was actually spending my time was the first step.

Break your day into 15-minute blocks. 
Track EVERYTHING. 

Do this for 2 months. Be relentless with it. 

When I did this it revealed that I spent 40% of my week on work that drained me. 

Even crazier - these were tasks that others could do at least 80% as well as I could. 

That’s where I started removing myself first.

#2 - Eliminate the unessential

This step gave me 15% of my time back instantaneously. 

If it doesn’t drive revenue or give you more energy → cut it. 

Low value meetings. 
Prospects who never convert. 
Tasks that don’t move the needle. 

Be ruthless. 

If you’re not sure what is essential – try unplugging everything from the wall and see what breaks. 

#3 - Automate anything that repeats

We live in a time where you can automate most things with the right tool. 

If you can imagine it – it probably already exists. 

Here’s the tools I use for posting, email followup, lead research, etc.:
- Hyperfury for X
- Chat GPT for strategy
- TextExpander for typing
- Claude for content ideas 

My team runs operations. I run the future. 

#3 - Delegate what drains you 

Anything you’re doing, someone else can do at least 80% as well. 
But they need the right systems to succeed. 

Give your team a single source of truth for how everything works in your business. 

Include loom videos that show your thinking process. Teach your team how your brain works. 

Yes, it will take time at first. But it will save you months of confusion and errors. 

Those 3 steps took me from 16-hour days, to a calm company that runs without me. 

This system works. I’ve used it for years. 

Try it for yourself and let’s win together. 

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How To Remove Yourself From Operations:

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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