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

One of the oldest laws in markets that everyone forgets:

More capital → more competition → higher entry prices → lower returns.

Abundant capital is great for momentum, but it rarely produces the best long-term outcomes.

The most durable venture returns tend to come from non-obvious places—where fewer checks are being written, expectations are lower, and pricing resets ahead of fundamentals.

You can make money following the herd...

But differentiated returns usually accrue to investors willing to underwrite conviction when capital is scarce.

That’s why we at The Family Fund & Founder Community are bullish on Consumer NOW.

Not despite the pullback in capital—but because of it.

Josh Wand Christine Wang Colleen Kang

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/li-newsletter-14

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.

Life hacks I know at 36, I wish I knew at 19:

1. Learn Storytelling

Storytelling is the highest intangible ROI skill you can learn

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

Start with basic storytelling frameworks (e.g. the Hero's Journey) and the 7 fundamental emotions.

And watch how listeners turn into believers.

2. Rethink Health

Everything changed for me when I came across Symbiotic Success:

Your health directly affects achievement, even if you can't see it.

Now I prioritize meditation, lifting weights and nutrition.

Success is a game of longevity and health is your competitive moat.

3. Work Like a Lion

Society has conditioned us to work like we're cows grazing.

Long hours. 
Low focus. 
Minimal output.

Instead, work less, but work like a hunting lion.

Sprint. Rest. Repeat.

4. Find Your Peak Energy State 

Optimal hours, environment, and work style differ for everyone.

Keep experimenting until you find your most productive state, when you don't have to fight yourself to get stuff done.

Once you find it, energy flows where your focus will be.

5. Learn to Communicate Concisely

Most people's emails and messages are full of fluff:

'Hope you're well!'
'I just wanted to ask...'
'Could we circle back on...'

Stop. 

Be concise and get to the point, your value increases with the effort your readers save.

6. Be Happy for Other People's Successes 

It's a positive-sum world out there; there are 22 million millionaires in the US alone. 

Recognize that one person's success isn't your failure and offer genuine congratulations.

Joy for others manifests future accolades for you.

7. Be Boring 

A lot of success comes from just saying no to cheap dopamine. 

And instead, focusing on the mundane:

• Maximizing sleep
• Guarding time for workouts
• Not eating out in favor of your nutritious diet

Boring's the secret the successful don’t want you to know.

__

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Michael Delisle

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

Steve Jobs once said:

"The most powerful person in the world is the storyteller."

But most people don’t know how to tell a good story.

10 storytelling techniques to make you unstoppable in business and life:

1. Highlight The Problem

Jobs highlighted user frustrations with existing tech.

Identify your audience's pain points. 

Address them directly to build excitement for your solution. 

Make your audience nod along, thinking "Yes, that's exactly my issue!"

2. Build Anticipation

Jobs teased "3 revolutionary products" before revealing they were all one device, the iPhone. 

Create suspense. Make your audience crave what comes next. 

Don't give everything away at once. 

Leave them wanting more.

3. Show Don’t Tell

Jobs didn't just describe iPhone features. He demoed them live. 

Use visuals, demos, and storytelling to make concepts tangible. 

Let your audience experience your solution. 

Bring your ideas to life.

4. Use Strategic Repetition

"An iPod, a phone, and an internet communicator" - Jobs repeated this to drive home the iPhone's 3-in-1 value.

Repeat your key message creatively, not robotically.

Make it stick. Make it memorable.

5. Connect To A Larger Vision

Jobs tied the iPhone to Apple's history of revolutionary products, changing its name from "Apple Computer" to "Apple."

Your offer should serve a bigger vision and mission that you share with your customers.

Show them the forest, not just the trees.

6. Make It Personal

"I didn't sleep a wink last night, I was so excited," Jobs shared. 

Vulnerability creates connection. Let your audience see the human behind the product.

Your authenticity is your secret sales weapon.

7. Close With Inspiration

Jobs ended with Wayne Gretzky's quote:

"I skate to where the puck is going to be, not where it has been." 

Leave your audience inspired and motivated to take action. 

Give them a vision of the future they can't resist being part of.

8. Practice Relentlessly

Jobs rehearsed for hours, perfecting every detail.

Great storytelling looks effortless, but it's the result of deliberate practice.

Treat your presentations like an athlete treats training. 

Repetition breeds excellence.

9. Simplify Complex Ideas

Jobs made revolutionary tech accessible to everyone.

Your audience shouldn't need a PhD to understand your value proposition.

If you can’t explain your idea to a 5-year-old, simplify it until you can.

10. Create An Experience

Jobs didn't just launch a product. 

He crafted an unforgettable moment.

Turn your pitch into an immersive experience. 

Engage all senses.

Make your audience feel like they're part of something special.

__

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10 habits that will make you happier than 98% of people:

1. Take Care of Your Health

You only get one mind and one body.

Both must last you a lifetime.

Habits formed in your 20s and 30s will determine how you live in your 60s and 70s.

Take your health seriously.

Without it, you have nothing.

2. Give Sincere Appreciation

Practice gratitude daily.

It helps you keep things in perspective.

If you’re reading this, you probably have access to:

• Food
• Water
• Shelter
• Tech
• Internet

Appreciate it, then plan to seize the day.

3. Pay it Forward

Studies show random acts of kindness improve well-being.

You can practice paying it forward by:

• Holding the door for someone
• Picking up trash outside
• Giving a compliment

One simple action can alter the trajectory of your day.

4. Choose Optimism

Optimists encourage you to live out your dreams.

Pessimists tell you to stay as you are, never changing.

Pessimists often sound smart.

But in the long run, optimists are the ones who live a life they’re proud of.

5. Reduce Your Wants

It is not the man who has too little that is poor.

It is the man who craves more.

Happiness is not the result of external objects.

It is instead an internal sense of fulfillment.

Find your minimal lifestyle.

6. Don't Compare Yourself to Others

Comparison is the thief of joy.

There will always be someone:

• Who is healthier
• Who has more money
• Who's "living" a better life

Compare yourself to who you were yesterday.

If you are 1% better today, you’re winning.

7. Ignore the Nonessential

Shiny object syndrome kills motivation and growth.

It's commonplace today.

There is always a new opportunity or distraction available.

But in the long run, it will be those who can stay focused on what’s most important who will be most successful.

8. Constantly Read

A reader lives a thousand lives before he dies.

Anyone who doesn’t only lives one.

Books give you access to the:

• Thoughts
• Stories
• Philosophies

of those who came before you.

Don't navigate life without pre-existing playbooks.

9. Prioritize Growth

If you’re not growing, you’re dying.

There is no such thing as stagnant.

A 1% improvement in a day is a 3,700% improvement in a year.

Every morning ask yourself, “how can I improve today?”

10. Write Daily

Putting your thoughts on paper forces you to organize them.

If you lack understanding, it will expose gaps in your thinking.

This is valuable information, as you can now fill in these gaps.

Use writing to sharpen your thinking and increase your brainspace.

__

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Good habits are the new antidepressants.

If you're in a bad spot in your life, read this:

1. Remove Negative People

Negative energy is contagious.

It infects and saps your spirit.

I have a simple test, after meeting someone, do I:

Feel full of energy?
Feel drained?

To escape the darkness, cut out those who embody it.

2. Be Vulnerable

I used to think vulnerability made me weak, but vulnerability sparks all meaningful connections.

Be real and open your heart.

And diminish your stresses into collaborative problems to solve with your loved ones.

3. Grow Your Network

If you're in a conversation you find boring, the problem's not the other person; it's you.

Everyone has valuable expertise on something.

You just need to extract it.

Genuine interest is the catalyst to your circle expanding on autopilot.

4. Embrace Solitude

Loneliness ≠ solitude.

Solitude is an essential pillar to knowing yourself.

Cultivate it by doing something normally "social" alone, eat dinner, go to the park, or attend a movie.

It's your secret garden where self-discovery blooms.

5. Life Doesn't Owe You Anything

Nothing's free in life, you have to go out and win it.

Expecting something from the world is just plain ignorance.

And it's how you set yourself up for disappointment.

Life’s ledger balances action with reward, not wishes with handouts.

6. Never Feel Sorry for Yourself

Considering yourself a victim saps your sovereignty.

You've left your destiny down to the world's whims - vs grasping it yourself.

It's simple: if you've chosen the wrong road, go back and find the right one.

7. Don't Worry About What Others Think

Never seek others' approval.

Only your own.

Because, besides, no one cares as much as you think anyway - that's the beauty of the Spotlight Effect.

Focus on self-respect: it's the most rewarding respect of all.

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I wasted my 20s building other people's dreams.

At 35, I finally built mine.

If you're reading this in your 30s or 40s thinking you're behind, this message could change everything.

The world celebrates 22-year-old founders, but here's what they don't tell you about starting "late."

8 advantages older founders have:

1. Self-Knowledge 

You don't need to "find yourself" - you know exactly who you are and what you want.

2. Battle-Tested Wisdom 

You know what doesn't work because you've tried it. 

That's worth 10 years of trial and error.

3. Real Resources 

Credit. 
Savings. 
Network. 
Reputation. 

While they're raising pre-seed, you're bootstrapping to profitability.

4. Content with Depth 

20-somethings share quotes. 

30+ founders share scars. 

Authenticity trumps energy every time.

5. Purpose-Driven Decisions 

You're building for legacy, not lifestyle. 

For your family and future. 

This depth of purpose drives better decisions.

6. Competitive Focus 

Your competition is still figuring out who they are. 

You're figuring out how to dominate.

7. Urgency as Fuel 

Time pressure creates decisive action. 

You can't waste 5 years "figuring it out." 

This urgency is your superpower.

8. Systems Thinking 

You know who you are, what you want, and you just need systems to get there.

The best founders start "late."

Vera Wang was 40. 

Colonel Sanders was 50. 

Ray Kroc founded McDonald's at 52.

Your time is now, not then.

__

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I'm 35. If You're in Your 30's Or 40's, Read This

The most powerful life hacks I've discovered:

1. Go Outside for 15 Minutes Every Morning

Get sunlight in your eyes every morning.

It helps you:

• Set your circadian rhythm
• Primes your brain to be alert and focused
• Enhances metabolism and immune functionality

Watch this transform your overall mood and well-being.

2. Meditate Daily

All of man’s problems stem from the fact that he cannot sit alone in a room for 30 minutes.

Our society is filled with:

• Cheap dopamine
• Constant notifications
• Screens everywhere we look

Take time to slow down and be present.

3. Surround Yourself With Optimists

Who you surround yourself 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.

Choose wisely with whom you spend your time.

4. Practice Gratitude

Gratitude is a key ingredient for living a fulfilling life.

Gratitude helps people:

• Feel more positive emotions
• Build strong relationships
• Improve their health

Take 5 minutes/day to write down 5 things you're grateful for.

5. Build a Personal Board of Advisors

Don’t underestimate the power of a mentor.

Epictetus mentored Marcus Aurelius.
Jobs mentored Zuckerberg.
Buffett mentored Gates.

Seek advice from people 2-3 steps ahead of you.

You can access their lifetime of wisdom in 2-3 years

6. Write Every Day

Writing is essential in unleashing your creative potential.

Writing every day:

• Builds discipline
• Allows you to organize your thinking
• Improves your vocabulary and communication skills

Mastering this skill will lead to success in the modern economy.

7. Invest in Yourself

We spend 8 hours a day working for someone else, but won’t take 30 minutes to work on ourselves.

Invest in yourself through:

• Reading
• Exercising
• Learning a new skill

Just 30 minutes a day can change your life.

8. Block Off Time to Read

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

They love to read.

• Read about things that interest you
• Re-read your favorite books
• Read every day

An hour a day of reading puts you in the top .01% of people.

9. Take a Cold Shower

A 3-minute cold shower will provide you with benefits that last the rest of the day.

Taking a cold shower:

• Increases dopamine
• Boosts metabolism
• Burns brown fat

Anything else you have to do afterward will seem easy.

10. Set a Bedtime Alarm

After this alarm goes off, allow your mind to relax:

• Turn off all your devices
• Take a warm shower or bath
• Read your favorite fiction book

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

__

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Most successful people aren't more intelligent than you. 

They're just more disciplined. 

7 other harsh truths to change your life:

1. Confidence Pays Off More Often Than Talent

Confidence ensures you take 100% of the shots you see. 

• Unlocks exponential upside
• Increases your surface area for luck 
• Enhances your resilience for when you are inevitably rejected 
 
1 yes is more powerful than 100 nos.

2. Finding Your Niche is Hard AF 

Ikigai exercises are useful, but the process of finding your niche is hard. 

You have to accept that it's a mix of: 

• Relentless iteration 
• Constant self-reflection 
• Rapid content generation 

Keep going.

3. You Have Few True Friends 

True Friends are the ones that: 

• Show you respect when you need it most 
• Show you loyalty when the deck is stacked against you 
• Show their support when you have nothing to offer them 

Learn to identify them and protect those relationships.

4. Consistency > Hard Work

How do you get great? By being good. Repeatedly. 

The best people understand life is a marathon, not a sprint. 

It's about showing up every day and delivering consistent results and upside.

5. Most People Suck at Setting Goals 

Setting lofty goals is often useless. 

It's good to have a vision, but oftentimes after setting a goal we realize it's not the right one. 

Instead, set anti-goals. 

Setting guardrails for what NOT to happen steers us on the right path.

6. Most Hacks are Created In Retrospect 

A heavy bag of luck is involved in success.

Successful people always form hacks in retrospect to attribute their success.

The only true hack is: an unrelenting work ethic and a constant expansion of your surface area of luck.

7. Happiness is Related to Who Not What 

Early on, material goods are our proxy for happiness. 

In the long-term, who we become is the solution for long-term happiness. 

• How you are working 
• What you are working on
• Who you spend time with 

It's most important.

—

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Why Smart People Get Stuck

You're not depressed.

You're just stuck in a sh*t situation.

And here's the brutal truth nobody wants to tell you:

Your brain chemistry isn't the problem. Your life circumstances are.

I spent years thinking something was fundamentally wrong with me. 

Tried everything. 
Read all the books. 
Nothing changed.

Then I realized: I wasn't clinically depressed. 

I was just living a life that would make anyone miserable.

Here's what actually pulled me out:

1. Found My Ikigai

That intersection of what you love, what you're good at, what the world needs, and what pays you.

Without purpose, your brain will create depression for you.

2. Dopamine Detox

I deleted the apps. 
Ditched instant gratification. 
Spent Saturdays barefoot in nature instead of scrolling.

Your brain needs to remember what real pleasure feels like.

3. Cut The Alcohol

Every single benefit I chased through drinking? Sobriety gave me in spades.

Better sleep. 
Stable mood. 
Improved gut health.

Alcohol isn't relaxation; it's a mask for problems you're avoiding.

4. Seeing Health as a Priority

Eat Well. Meditate. Lift Weights.

Basic? Yes.

Effective? Absolutely.

No one does these three things consistently and stays depressed. 

Your mind lives in your body. Treat it accordingly.

5. Time In Nature

Nature is nice, sure, but it's also clinical therapy.

Getting outside daily, grounding myself, taking my shoes off. 

It brings stability that nothing else can.

6. Remove Toxic People

If you feel drained after seeing someone, they don't belong in your life.

Negativity spreads like a disease. 

Protect your energy ruthlessly.

7. Never Skip 2 Days

With any habit you're building, miss one day maximum.

Two days in a row? You've killed momentum. 

The habit must stay alive in your mind.

Stop waiting for motivation. 
Stop thinking you need fixing.

You just need better circumstances, and you're the only one who can create them.

__

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Hoe To Get Unstuck and Make Progress Fast

Plenty of founders are using AI wrong.

They're treating it like a tool when it's actually a force multiplier.

I've spent the last year rebuilding my entire operation around AI.

Here are the 6 skills you need to dominate in the AI era:

1. Workflow Design

This is the foundation.

I built AI projects for every part of my business.

One for YouTube scripts. 
One for email sequences. 
One for sales frameworks.

My team gets 5X output because I designed the workflows that AI executes.

Most people ask AI random questions and wonder why they get random results.

Elite founders design repeatable workflows that AI amplifies.

2. Voice-to-Text

I save hundreds of hours a month by speaking my thoughts instead of typing them.

I voice-dump ideas for new offers.

I expand on YouTube scripts by talking through frameworks.

I capture way more detail than I ever could typing.

Voice-to-text isn't just faster. 

It's richer.

Your spoken thoughts contain nuance that typing never captures.

3. AI-Assisted Content Creation

My secret weapon: 

200+ documentation files loaded into my AI project.

My social team references them to conceptualize assets.

AI suggests the idea and copy.

The team designs the final product.

Result: 

7 posts a week. 
Zero AI-looking content. 
100% on brand.

AI handles the heavy lifting. Humans add the polish.

4. Loom AI SOPs

Record once. Never explain again.

I Loom my process. AI generates the transcript plus action items.

My team has the SOP forever.

90% of "Can you show me how to..." questions disappear overnight.

5. Sales Call Analysis

AI listens to my best sales calls.

It pulls the exact phrases that make people buy.

It tells me the top 5 objections and how I handled them.

I use that language everywhere: emails, scripts, landing pages.

40% conversion increase.

This is the closest thing to reading your customer's mind.

6. Data Dashboard

Every morning, 10 minutes.

AI shows me my biggest bottleneck.

It's like having a COO in my pocket.

I don't need to dig through spreadsheets or guess where the problem is.

The data tells me exactly where to focus.

Here's what most people miss:

AI doesn't replace your thinking.

It amplifies it.

You bring the strategy, the ideas, the stories, the voice.

AI brings the execution, the formatting, the multiplication.

Master these 6 skills and you'll operate at a level most founders can't touch.

The future doesn't belong to people who use AI.

It belongs to people who design systems that AI executes flawlessly.

—

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I built an AI clone trained on 16 years of my knowledge that handles 80% of my daily decisions.

Now I'm showing you exactly how to build your own.

Get the free 9-day Founder Clone email course here:  https://lnkd.in/eKuYDxtE

6 Skills For The New AI Era

Hard skills get you the job.

Soft skills get you the promotion.

Here are 7 rare soft skills you need to accelerate your career:

1. Emotional Intelligence (EQ)

The best type of intelligence.

Hone it by:

• Practicing empathy
• Being highly self-aware
• Controlling emotions (vs them controlling you)

Intelligence is knowledge. Emotional intelligence is wisdom.

2. Visionary Thinking

The ability to:

• Think unreasonably big
• Imagine possibilities that others don't see
• Believe in visions long enough to make them reality

Is a common trait among billionaires.

They’re almost always called crazy - until they’re right.

3. Resilience

Most people give up at the first sign of failure.

You’ll be in the top 1% if you simply keep going.

Iterate, pivot, change strategy, sure. But never give up.

You can’t lose if you never stop playing the game.

4. Influencing and Persuasive Skills

Influencing isn’t forcefully changing the other person’s point of view.

It’s about:

• Listening 
• Empathizing
• Making someone feel heard

And gently guiding their thoughts to your point of view.

As if they came to it all on their own.

5. Decisiveness

You’ll never have 100% info when making decisions.

Fill in the gaps with frameworks.

My favorite?

One-way/two-way doors:

Can this decision be reversed (two-way) or not (one-way)?

Two-way: be decisive, fast.

One-way: slow down, make sure the choice is obvious.
6. Leadership

A person isn’t born a leader; he chooses to be one.

Leadership mantras I live by:

• How you do anything is how you do everything
• Extreme ownership (never act like a victim)
• Always flatten the hierarchy

Leadership is not a rank; it’s a habit of mind.

7. Learning Agility

Learning how to learn is a superpower.

And the best way to learn is:

1. By doing
2. With a purpose

E.g. Don’t just learn to code. Have a project in mind you want to build.

The more you learn, the quicker you learn.

Constant learning compounds.

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Mark Twain once said: 

"The two most important days in your life are the day you are born and the day you find out why."

Here’s how to find your ‘why’:

The catalyst for finding your why is a concept called Ikigai.

It’s a Japanese word that translates to "reason for being."

I came across it years ago when I was completely lost and didn’t know where to go.

This simple exercise transformed my life. 

Ikigai is the intersection of four crucial elements:

1. What you love
2. What you're good at
3. What the world needs
4. What you can be paid for

Finding this sweet spot is like unlocking your personal cheat code for success and happiness.

Here’s what mine looks like:

At the end of this exercise, you will find a few topics in the center of the diagram. 

This becomes your compass that guides you towards work that aligns with your values.

Follow this path and you will never have to work a day in your life. 

You’ll live "Every Day Retirement."

I speak from experience here. 

After discovering my Ikigai and aligning my business with it, everything changed. 

My audience exploded: 

• Twitter grew to 350K
• LinkedIn grew to 700K
• Newsletter subscribers grew to 137K 

Never underestimate the power of clarity.

After finding your purpose, internalize these 5 golden rules of Ikigai:

• Give thanks
• Follow your ikigai
• Reconnect with Nature
• Take it slow, enjoy the journey
• Surround yourself with positivity

Master these to live a calm and fulfilled life.

1. Take It Slow, Enjoy The Journey

Solutions come when we stop forcing them. 

Sooner or later, you realize you don’t need to be in such a rush.

The goal isn't just to get there. It's to have fun along the way.

You’re not in a race; you’re in a marathon.

2. Surround Yourself With Positivity

People are everything.

Recruit A-players who believe in your mission and learn from mentors 10 steps ahead of you. 

“You’re the average of the 5 people you spend the most time with” - Jim Rohn

Surround yourself with people who inspire you.

3. Reconnect With Nature

Take regular breaks in nature.

It resets your mind and provides fresh perspectives.

"Nature does not hurry, yet everything is accomplished." - Lao Tzu

Embrace the fact that nature is your greatest mentor.

4. Give Thanks

Gratitude will show you that true fulfillment doesn't come from external sources but from self-awareness.

When I'm in a slump, being grateful always pulls me out of it by putting my problems in perspective.

It turns what I have into enough.

5. Follow Your Ikigai

You have just discovered what sets your soul on fire. 

When you align your business with your purpose, your energy becomes electric. 

Without it, I wouldn’t have reached my full potential. 

—

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I’m 36.

When I was younger, I battled to get sober, had my company raided by the government, traveled the world, and started multiple 8-figure companies.

11 lessons for 21-year-old Matt:

1. Prioritize Nature

Nature's been my biggest mentor and therapist.

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

2. Never Stop Building Your Network

Over the years, I've created a personal Board of Advisors.

Some of my closest friends are killers across sales, writing, YouTube, community building, and strategy.

I know world-class advice is just a phone call away.

3. Never Compromise Your Ethics

In tough decisions where blurring the lines is an option, choose moral.

NEVER compromise your ethics.

It'll affect you in subconscious ways you never imagined.

4. Be Boring 

A lot of success comes from just saying no to cheap dopamine.

And instead, focusing on the mundane:

• Maximizing sleep
• Guarding time for workouts
• Not eating out in favor of your nutritious diet

Boring's not a bad word when you're on the up.

5. Become a Self-Starter

The fastest way to grow your career: 

Find your bosses' pain points and solve them without being asked.

You put yourself on the radar - and train your entrepreneurial muscle for when you need it.

6. 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.

7. Be Humble

However hard it is on your ego, you need to swallow your pride every damn day.

It's how you'll take criticism better, know when to ask for help, and know when to cut your losses.

Grasping onto an image of who you are only limiting what you might become.

8. Never Skip 2 Days

With whatever habit you're forming, only skip a maximum of one day.

Once you skip two in a row, you've lost momentum.

I've found this rule much more practical than 'never miss a day'.

9. Find Your Peak Energy State 

Keep trying new work environments.

Experiment with working at different times.

Until you find when you're most energetic, at ease, and productive.

That's your competitive advantage.

10. Embrace Compounding

Aim to get 1% better everyday - 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.

11. Never Feel Sorry for Yourself 

Embrace the suck and use it as fuel to level up.

You're not a victim - don't get in the habit of thinking you are one.

That's a surefire way to never achieve anything.

It's simple: if you've chosen the wrong road, go back and find the right one.

—

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Harsh truth I wish I knew at 18:

Getting a degree is a complete waste of time. 

I've built different businesses without ever needing mine.

Skip the degree and learn these 27 sentences instead:

1. A confused mind always says no. Clarity in your offer is non-negotiable.

2. The goal of marketing isn't to be clever; it's to be clear.

3. Your offer should be a painkiller, not a vitamin.

4. The riches are in the niches. Own your category. 

5. The most powerful marketing tactic? Word of mouth. 

6. Provide value with 0 expectations of anything in return.

7. Build your product after talking to customers, not before. 

8. People buy with emotion, then justify with logic.

9. Your customer's story is more powerful than yours.

10. Your brand is a promise. Your customer experience is the fulfillment of that promise.

11. Your business is a reflection of you. Evolve yourself to evolve your business.

12. Systems beat goals every time. Build a business that runs without you.

13. Sell the transformation, not the product.

14. Automate, delegate, or eliminate to buy back your time. 

15. Perfectionism is an illusion. Done is better than perfect.

16. Attention is the new oil, and your personal brand is the pipeline.

17. No agenda, no meeting. Eliminate pointless gatherings.

18. Implement the 80/20 rule to everything. Focus on what truly moves the needle.

19. Focus on being irreplaceable, not just profitable.

20. Build a business that serves you, not the other way around.

21. Embrace experimentation over perfectionism. Test, learn, iterate.

22. Listen more than you talk. 

23. Know your customers better than they know themselves. 

24. Make something people want.

25. Do things that are obvious. 

26. Fall in love with the problem, not your solution.

27. Love the customer. Don’t build a business around people you hate.

—

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Leadership is a superpower.

Learn it and you can achieve just about anything.

8 ideas to level up your leadership in the next 5 minutes:

1. Simon Sinek's Golden Circle:

• Why - Your purpose (Ikigai)
• How - Your process or way of doing things
• What - Your product

Most leaders communicate from the outside in (what – how – why).

Great leaders communicate from the inside out (why – how – what).

2. Feedback

Feedback is one of the most important skills for a leader.

It’s also one of the most difficult.

Here's a simple system:

• Describe the specific situation
• Explain the impact of that behavior
• Offer suggestions for improvement

Feedback is a gift.

3. Delegation

Delegation is not about giving tasks.

It's about empowering others.

• Choose the right person
• Specify desired outcome
• Provide resources/support
• Set deadlines
• Give feedback

Delegation is an investment in your team and yourself.

4. Emotional Intelligence

IQ is how smart you are.

EQ is how well you understand and manage emotions.

SQ is how well you navigate social situations.

All are important for leaders, but EQ reigns supreme.

5. Leadership Styles

There's no one-size-fits-all approach to leadership.

Here are the 6 most common leadership styles:

• Visionary
• Coaching
• Affiliative
• Democratic
• Pacesetting
• Commanding

Find the right one for you and you will thrive.

6. 7 Laws of Honorable Leadership

Leadership is a privilege, not a right.

• Serve others
• Lead with courage
• Embody your values
• Pursue excellence
• Take accountability
• Foster inclusion
• Leave a legacy

To earn respect, you must lead with honor and integrity.

7. The 80/20 Rule

The Pareto Principle states that 80% of your results come from 20% of your efforts. 

Your job is to identify and focus on the 20% that really moves the needle.

Here's how:

• Prioritize ruthlessly
• Automate, eliminate, or delegate
• Batch tasks
• Take breaks

8. Building a World-Class Team

Use this success sheet to improve your team:

• Psychological Safety
• Dependability
• Structure & Clarity
• Meaning
• Impact
• Growth Mindset

Great teams are only as strong as their leaders.

—

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I’m convinced the biggest reason I was able to build 4 multi-million dollar businesses was through self-confidence.

How to build bulletproof self-confidence:

You’ll never be confident if you care what other people think.

But let me tell you a secret:

1. Most people aren’t thinking about you
2. Those who are, aren’t worth impressing

So stop worrying and start doing. Your time is limited.

1. Realize Everyone is Winging It

I used to think everybody had it all figured it out.

The reality? They were winging it just as much as I was.

Once you realize this, you’ll lose all impostor syndrome and start taking swings.

It’s you vs yourself, not you vs others.

2. Accept Your Weaknesses

The most confident people in the world don’t try to do everything.

They find what they’re good at and love doing and triple down on it.

They become the best at what they do.

You don’t win by being good at many things. You win by being great at one thing.

3. Take Action and Get Good

You often don’t lack confidence when you’re the best at what you do.

How do you get there? By doing the boring basics every day for longer than anyone else is willing to do.

Impostor syndrome = lack of competence.

Talk less. Do more.

4. Measure Success on Your Terms

Don't let others dictate what success means for you.

Life’s too short to spend it pleasing others, doing things you don’t want to do.

Find YOUR definition of success based on YOUR values and dreams.

The only competition is your past self, not others.

5. Build a Community of Weapons

Surround yourself with people who believe in you more than you believe in yourself.

Find a community of smart, hard-working, positive weapons.

You don’t get points for playing alone.

Find your tribe and win.

6. Have the Courage to Say No 

Saying no is anything but selfish.

It means you truly value your time and pick things that align with your purpose.

You weren’t put on this planet to be a people pleaser.

Save your yeses for what matters most.

7. View Challenges as Opportunities

This is my favorite Stoic teaching, reframing every single obstacle as an opportunity to grow. When you do this, everything becomes a good thing.

You relish challenges. You wake up motivated. You attack the day.

Strong storms make tough trees.

8. Be Fatalistic About Your Situation

The only thing ever in your control is your reaction to the things that happen to you.

Once you know this, you’ll move with a peace that exuberates confidence.

Let go. Stop resisting. And let life surprise you with the gifts it has in store.

__

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Great leaders have 10 clear signs that set them apart:

1. Integrity Is Their North Star

They do what's right, even when no one's watching.

They make the hard call when it would be easier to cut corners.

Their word is their bond. And that consistency builds trust at every level.

2. They Measure Output, Not Input

They care about outcomes achieved, not FaceTime.

They know that results are the currency of business, not promises and hours spent.

If you hit your numbers, they don't care if you did it in 20 hours or 60.

3. They Wear Humility Like A Badge

They're not afraid to admit when they're wrong or don't know something.

They're always eager to learn from others, regardless of their position.

Ego doesn't cloud their judgment. Growth does.

4. Emotional Intelligence Is Their Sixth Sense

They have an uncanny ability to read people and situations.

They navigate complex emotions and interpersonal dynamics with flair.

They know when to push, when to listen, and when to step back.

5. Resilience Runs In Their Blood

They view setbacks as stepping stones, not roadblocks.

When knocked down, they dust themselves off and keep pushing forward.

Failure doesn't define them. 

How they respond to it does.

6. Adaptability Is Their Competitive Edge

They adapt themselves to circumstances, as water moulds itself to the glass.

They don't just embrace change, they champion it.

When the market shifts, they shift faster.

7. Innovation Fuels Them

They foster a culture of creativity and outside-the-box thinking.

They encourage bold ideas and calculated risks.

They know that playing it safe is the riskiest move of all.

8. They Don't Wear Masks Or Play Politics

What you see is what you get: 

Real. Raw. Relatable.

They create depth. 

And depth creates authenticity.

No hidden agendas. 
No corporate theater. 
Just truth.

9. They Communicate With Transparency

Delivering the truth courageously is the highest form of respect.

They believe clear information sharing is power.

They don't sugarcoat. 
They don't hide. 
They tell it straight.

10. Active Listening Is Their Nature

They don't just hear, they listen to understand.

They give their undivided attention and make others feel truly understood and heard.

This is how they earn loyalty that money can't buy.

If you want to build a great company, start by becoming a great leader.

Your team will follow your example, not your instructions.

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10 Clear Signs You Have a Great Leader

13 steps to build a $15k/month side hustle:

1. Ask Yourself: "What Topics Can I Help People Get Massive Clarity On?"

Start with what you already know.

Ask your friends and co-workers what you're an expert in.

You don't need to be the world's best. 

You just need to be ahead of your audience.

2. Distill Your Value

By helping someone achieve massive clarity, what are they able to achieve?

This is your value proposition.

If you can't articulate the transformation, neither can your customers.

3. Pick A Platform. Where Do The People That Need Your Help Reside?

LinkedIn is perfect for professionals looking for growth.

Fast algorithm. 
High intent audience.

Go where your customers already are.

4. Create Daily Content That Talks About The Clarity You Can Provide

Document what you know.

Share insights. 
Answer questions. 
Provide value daily.

Consistency beats perfection.

5. DM Every Account That Interacts With Your Content

Ask them what they do and what their goals are.

This isn't selling. It's connecting.

Build relationships before you need them.

6. If You Can Help Them With Their Goals, Ask Them If They'd Want To Jump On A 1:1 Call

Offer value first. Always.

Most people will say yes to a free consultation if you've already provided value.

7. Run A Consultation On Zoom

Afterward, reflect on:

• What exercises worked? 
• What were their major blockers? 
• What resources could I create to increase the value? 

Every consultation is market research.

8. Do 20 More Consultations To Understand

Pattern recognition beats guessing.

• What outcomes can I promise? (Better sales systems)
• Who is my target demographic? (Early stage leaders)

9. After Every Consultation, Add Each Member To A Group Chat 

Community is your moat.

Give people a place to connect with each other, not just you.

10. Start Creating Longer-Form Content

Show your work and build authority.

• Case studies of consultations
• Breakdowns of what processes you are teaching

11. Give Them The Option To Opt Into A Paid Community

• Weekly Q&A
• Daily standup
• Monthly goal check-ins

Free gets them in. 

Value keeps them paying.

12. Redirect Traffic From Your Content

Your content → New website → Stripe checkout → Calendly 1:1 link

Make it frictionless to buy.

13. As The Community Grows, Invest To Make It Stronger

• Coaches
• AI 1:1 match-making
• Community managers

Scale by adding leverage, not hours.

__

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Money without meaning is prison.

You have roughly 4,000 weeks if you're lucky.

You've already used a bunch of them working on things that don't matter.

Here's how to build a life you don't need to escape from in 2026:

Your Ikigai sits at the intersection of 4 things:

What you love. 
What you're great at. 
What the world needs. 
What you can be paid for.

Find that center, and every decision runs through it.

1. What You Love

What could you do for free?
What makes you lose track of time?
What would you build even if no one paid you?

That's your fuel.

Without it, you're just trading time for money.

And that's how you build a business that feels like a job.

2. What You're Great At

What comes easy to you that's hard for others?
What do people ask you for help with?

This is your unfair advantage.

It's not just what you can do. 

It's what you can do better than anyone else without even trying.

3. What The World Needs

What problems are you obsessed with solving?
What keeps your ideal client up at night?
What transformation do they desperately need?

If you can't answer this clearly, you don't have a business.

You have a hobby.

4. What You Can Be Paid For

What would someone invest $10K to learn from you?

If you can't answer that, you're not ready yet.

The center of these four circles is your North Star.

Every decision runs through this.

Should I take this client? Does it align with my Ikigai?

Should I launch this product? Does it serve my North Star?

Should I spend my time on this? Does it move me closer to the center?

When you're operating from your Ikigai, work doesn't feel like work.

You're not chasing someone else's definition of success.

You're not building a business that feels like a job.

You're building a life you actually want to live.

Here's the brutal truth:

You only get 4,000 weeks.

You've already spent a bunch of them chasing the wrong things.

Climbing ladders leaned against the wrong walls.

Building businesses that trapped you instead of freeing you.

Your Ikigai is how you make sure you don't stay trapped in a business that owns you.

2026 is the year you stop escaping your life and start building one you never want to leave.

Find your Ikigai. 
Let it guide every decision. 
Build from the center.

__

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Build A Life You Don't Need To Escape From

I used to be depressed, broke, and anxious. 

Now, I only work 4 hours per day and travel the world. 

10 habits that transformed my life:

1. Daily Deep Work

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

No phone, no social media, no distractions.

This is when your mind is freshest and most creative.

Protect this time at all costs.

2. The AED System

Automate, Eliminate, Delegate

Ruthlessly apply this system to every task.

• Automate repetitive tasks
• Eliminate unnecessary ones
• Delegate what does not require your unique skills

Your time is gold; start acting like it.

3. Quarterly Resets

Every quarter, take a step back, take a break, and reassess your goals, strategies, and habits.

What's working? What's not? Make adjustments.

Regular resets ensure that I stay aligned with my long-term vision and core values.

4. Focus on the 4 W of Work

Optimize the Who, What, Where, and When of your work:

• Who: Surround yourself with high-performers
• What: Focus on high-impact tasks
• Where: Create an optimal environment
• When: Leverage your natural energy

Small tweaks yield huge gains.

5. Sobriety

Eliminating alcohol was a game-changer for my productivity and clarity.

No hangovers, brain fog, or wasted time.

Sobriety allows you to operate at your peak consistently.

You need to be sober to change your life for the better.

6. No Agenda, No Meeting

With my team, if a meeting doesn't have a clear agenda and desired outcome, it doesn't happen.

Period.

This simple rule eliminates countless hours of pointless meetings.

Work matters, but most of your meetings don’t.

7. No Meetings in the Morning

Mornings are for deep work, not meetings.

Protect your peak creative hours.

Schedule meetings in the afternoon when your energy naturally dips.

Systemize your life.

8. Hell Yes or No

This is an extension of AED.

If an opportunity or request isn't a "Hell Yes!", it's a no.

Ruthlessly guard your time and attention.

Saying no to the mediocre allows you to say yes to the exceptional.

9. Personal Time/Energy Audit

Track how you spend your time for a week.

Categorize activities as energizing or draining.

Then, systematically eliminate or minimize the draining activities.

The time audit raises your hourly rate by thousands of dollars.

10. Daily Exercise

Those who prioritize fitness enjoy a life expectancy up to 7 years longer.

Your quality and duration of life is determined by your fitness habits.

Exercise is key to unlocking your full potential.

I don’t care if it sounds corny: health is wealth.

—

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Matt Gray

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