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:

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Founder & CEO

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

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

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

1. Grit

This one’s a non-negotiable. 

What is it?

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

Hard work is common. 

Grit is rare.

2. Relentless Resourcefulness

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

They are innovative problem solvers.

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

These are the people we want.

They’re like water.

They find a path around any obstacle.

3. Optimism

Entrepreneurship is a roller coaster.

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

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

Their energy is electrifying and infectious. 

A must-have when the going gets tough.

4. Constant Learning

The ROI on constant learners compounds.

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

These hires:

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

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

5. Not Being an Asshole

It might sound simple, but it's vital.

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

If you don’t:

• Show empathy
• Collaborate well
• Treat others with respect

I don’t want you on my team.

Period.

6. Fun to Be Around

I need people that I like spending time with.

Work can be intense. 

Having people who bring: 

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

Makes a world of difference.

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

7. Growth Mindset 

This one is foundational.

I need someone who:

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

People with a growth mindset get obsessed with the process.

Not fixated on the outcome.

8. Enjoys Responsibility

I need my team to take on responsibility.

I don’t want to chase people down.

If they:

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

We'll perform better.

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

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Matt Gray 

How to design your dream life in 2026.

Take these steps:

“Luxury is feeling unrushed. It is designing a life that allows you to do what you want with high leverage, with many options, all while feeling unrushed.” 

- Tim Ferriss 

The power of lifestyle design: 

• Intentional action
• Unlocking your time 
• Finding what you enjoy

Step 1: Build a Habit of Reflection 

Learn to become keenly in tune with how your body feels. 

What words describe your feelings right now? 

• Flowing?
• At ease?
• Confused? 
• Exhausted? 

Begin to track how you feel and analyze why you might feel that way.

This builds a habit of constant reflection. 

You begin to understand: 

• What makes me feel good? bad? 
• What are the nuances of my good moods? my bad ones? 

When I started, I learned I was in a negative mood 70% of the time! 

That completely shocked me.

Step 2: Assume Control 

Repeat this message: 

"I am the root cause of my feelings." 

You are the one in control of your actions. You're never powerless to change how you feel. 

Sounds easy, but it's the most difficult step. 

We hate assuming responsibility for how we feel.

Hate your job? Who's forcing you to stay in the current one?

Feel frustrated with friends? Who's stopping you from communicating?

It may seem impossible. 

But taking small steps creates instant relief.

You reassume control and learn that you can fix any problems that come up.

Step 3: Create Your Ideal Future

Write answers to these prompts: 

• Do you prefer spontaneity or routine? 
• What kind of diet is important to you? 
• What does your ideal 24-hour-day look like? 
• Where do friends and family play a role in your ideal life?

More: 

• Are you pursuing FIRE? 
• Where is your dream location?
• Can you combine hobbies with work? 
• Do you want more hobbies/less? Which do you actually love? 
• Do you want to experiment with philosophies like downshifting, slow living or minimalism? 

Get to a granular level: 

• What does working out feel like? 
• What does working my job feel like?
• What does waking up feel like on an ideal day? 

Step 4: Take Action 

Synthesize all your answers to the past prompts. 

Instead of setting a written goal, create an image of your ideal future in your head. 

Whenever you need motivation, bring up that image to fill you with an unstoppable drive.

Then begin to reverse-engineer your better lifestyle. 
 
• Create a group of regular gym-goers 
• Set up a budget to help you hit FIRE 
• Make the purchases to improve your sleep stack
• Begin to incorporate mindfulness practices weekly, then daily 

Small steps, big goals.

—

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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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How to build a plan for 2026 you'll actually use:

1. Start With One Word

Not a paragraph. 

Not a mission statement.

One word that defines your year.

Mine for 2024 was "simplify."

Every decision ran through that filter.

Should I take this meeting? 
Does it simplify or complicate?

Should I launch this product? 
Does it align and simplify?

One word creates instant clarity.

2. Write Your Dream Outcome

People usully set goals.

I write the headline I want written about me on December 31st.

What do you want to have accomplished?
How do you want to feel?

This is your North Star.

3. Identify Your Top 3 Goals

One business growth goal.

One team goal.

One health goal.

More than three and you're lying to yourself about what matters.

4. Find Your One Metric

You need proof you're winning.

Choose one number that shows undeniable progress.

So you can track it.

For me, it's active community members.

5. Build Your Systems First

Here's where most plans die:

People focus on what they'll do.

I focus on what I'll build to make it automatic.

What will I delegate?
What will I automate?
What habit must I lock in?
What system must I create?

Systems beat willpower every single time.

6. Name Your People

Success isn't a solo sport.

Who's going to help you get there?

I write down specific names and roles:

• One mentor I'll lean on for guidance
• One teammate I'll empower to level up
• One accountability partner who'll call me out

Vague support systems fail. 

Specific people show up.

7. Define Your Non-Negotiables

What will you always do?
What will you never do?

What's your number one priority when everything's on fire?

These are your laws from now on.

For me: 

I will always protect my morning deep work. 
I will never compromise on team culture. 
My priority is solving our biggest constraint first.

8. Map Your Constraint

Most people try to do everything at once.

I identify the one bottleneck holding everything back.

Then I solve one constraint per month for the entire year.

January: Fix hiring process.

One focused constraint. 
One month. 
Then move to the next.

9. Schedule Quarterly Reviews

A plan without checkpoints is just hope.

Every 90 days, I ask three questions:

What worked?
What didn't?
What did I learn?

Then I adjust. 

The plan evolves because I do.

Build a plan for the person you actually are.

Make it so simple you can't ignore it.

Make it so focused you can't fail.

__

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How To Build A Plan For 2026:

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

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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Here's how to scale (without selling your soul):

1. The Faster You Grow, The More You Must Slow Down

Speed without systems creates chaos.

Slow down to speed up.

2. Scaling Chaos Doesn't Create Freedom, It Multiplies Pain

Fix the foundation before you scale the building.

3. What Got You Here Is Hustle, What Gets You There Is Harmony

Different stages require different strategies.

4. Build Systems, Not Stress

Systems eliminate the need for heroics.

5. If It Drains You, It Doesn't Scale

Energy is your currency. 

Spend it wisely.

6. Your Nervous System Is Your Operating System

If your body is in fight-or-flight, you can't think strategically.

7. Freedom Is The Ultimate KPI

Revenue is vanity. 

Freedom is the metric that matters.

8. Complexity Is Ego Wearing A Productivity Costume

Simple systems beat sophisticated chaos every time.

9. Simplicity Compounds Faster Than Speed

Elegant solutions outlast complicated hacks.

10. Don't Chase More. Design Less, But Better

More isn't the answer. 

Better is.

11. The Founder Who Can Relax Under Pressure Wins

Calm is a competitive advantage.

12. Stillness Is A Strategy, Not A Vacation

Your best ideas come in silence, not chaos.

13. You Don't Need More Time, You Need Fewer Decisions

Decision fatigue kills more companies than lack of effort.

14. Every System Is Designed To Protect Your Energy

Design your business around your wellbeing, not against it.

15. Energy Creates Clarity. Clarity Creates Systems. Systems Create Freedom

It all starts with managing your energy.

16. Work Should Feel Like A Creative Ritual, Not A Survival Drill

If you dread Mondays, something is broken.

17. Profit Means Nothing If Peace Is Missing

What's the point of wealth if you're too stressed to enjoy it?

18. The Goal Isn't To Escape Work, It's To Enjoy Building Again

Fall back in love with the process.

19. Burnout Is What Happens When Your Calendar Owns You

Take back control of your time.

20. True Leverage Is A Peaceful Mind Directing Powerful Systems

Calm + systems = unstoppable.

21. Automate The Repetitive. Delegate The Rest. Keep The Art

Your genius work can't be delegated. 

Everything else can.

22. Build In A Way Your Future Self Will Thank You For

Short-term wins that destroy long-term health aren't wins.

23. Don't Scale To Escape Your Life. Scale To Express Your Soul

Build something that reflects who you actually are.

24. The Real Exit Is Daily Freedom

 Founders are scaling the wrong things.

They're scaling revenue while sacrificing health.

But what if you could build a company that grows without consuming you?

That's what scaling without selling your soul looks like.

__

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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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11 habits that will transform your life in 3 months:

1. Get Morning Sunlight

This is essential to get your body in great health.

It’s proven to:

• Release cortisol, priming your brain for focus
• Improve overall mood and emotional regulation
• Set a circadian rhythm, which will help you fall asleep at night

2. Hide Your Phone

Our attention is constantly pulled in a million directions.

Notifications from our phones are the most powerful distraction.

Turn on airplane mode, set aside 4 hours, and focus on deep work.

Your output will dramatically increase.

3. Take a Cold Shower

There’s no better way to feel alert and awake than a cold shower.

Forcing yourself to get in makes the rest of your day easier.

You’ll also get:

• A boost in metabolism
• An increase in dopamine
• Enhanced muscle recovery

4. Make Your Bed

Start your day with a win.

Use this momentum for the rest of the day.

A 1-minute practice sets the tone for the next 12 hours.

One small action serves as the trigger for a great day.

5. Review Your Goals

Set process goals over end goals.

Reading 10 pages a day is less intimidating than reading a 1000-page novel.

Running for 10 minutes is less intimidating than running a marathon.

Once you commit to strong daily habits, the end goal will take care of itself.

6. Upgrade Your Sleep

Your sleep defines your productivity:

• No screen 1 hour before bed 
• Stop drinking caffeine after noon
• Cut out naps and late-night snacks

7. Upgrade Your Nutrition

You are what you eat.

If you eat like shit, you’ll feel like shit.

• Cut out sugars 
• Cut out processed foods
• Eat easily-digestible foods (0 bloating)

8. Walk Without Technology

Our brain needs time away from constant stimulation.

Our mind needs time to:

• Rest
• Recharge
• Recalibrate ideas

Letting your mind wander is key in the idea-generation process.

9. Have To-Do’s Ready For When You Wake Up

Plan out your morning the night before.

Having a plan:

• Reduces anxiety 
• Promotes great sleep
• Gets you productive immediately the next day

Prevents distractions from disturbing your deep work periods.

10. Walk After Meals

Walking after eating is essential to keep your performance high throughout the day.

It is proven to:

• Aid in digestion
• Boost your metabolism
• Keep energy levels high

Just a 10-minute walk after every meal will kickstart these benefits.

11. Send a Nice Text

Human connections are the most valuable in life.

Nice texts make someone’s day.

But they also:

• Make you feel good
• Give you a reason to reconnect
• Allows you to disconnect from work

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Sid R

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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If you want to give yourself a personal MBA, read these 10 books:

1. Zero to One 
by Peter Thiel 

Subject: Strategy and Positioning 

Lessons: 

• Last can be first 
• Rivalry causes us to copy the past 
• Progress comes from monopoly, not competition

2. Expert Secrets 
by Russel Brunson 

Subject: Marketing 

Lessons: 

• Maintain absolute certainty 
• The riches are in the niches 
• Convince with emotion first, then logic

3.$100M Offers 
by Alex Hormozi 

Subject: Sales 

Lessons: 

• Create grand slam offers 
• Find the starving crowd 
• The fundamental equation of value

4. Deep Work 
by Cal Newport 

Subject: Productivity 

Lessons: 

• Embrace boredom
• Create daily rituals 
• Find your work-style 
• Treat work like a craft

5. The War of Art 
by Steven Pressfield 

Subject: Unlocking Creativity 

Lessons: 

• Live your unlived life 
• Embrace and expect fears 
• Recognize resistance and love misery

6. Get Together 
by Bailey Richardson, Kevin Huynh, and Kai Elmer Sotto

Subject: Community

Lessons: 

• Attracting authentic community members 
• Developing community leaders

7. Hustle Harder, Hustle Smarter 
by 50 Cent

(Highly recommend the audiobook - he narrates himself) 

Subject: Hustle 

Lessons: 
• Finding fearlessness
• Constructing your crew 
• The power of perception

8. Obviously Awesome 
by April Dunford 

Subject: Positioning 

Lessons: 
• Layering on trends 
• The 6 components of positioning 
• Mapping attributes and features to "value themes"

9. The Minimalist Entrepreneur 
by Sahil Lavingia 

Subject: Entrepreneurship 

Lessons: 
• Market by being you
• Build as little as possible 
• Sell to your first hundred customers

10. The Ride of a Lifetime 
by Robert Iger 

Subject: Leadership 

Lessons: 
• Pursue perfection 
• Learn to love exertion
• Lead with calm while encouraging risk

—

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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.

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6 Skills For The New AI Era

If I could go back and tell 20-year-old Matt what actually matters, here's what I'd say:

1. Your Energy Is The True Currency

 Money compounds when your energy does

You can't build wealth if you're exhausted.

Protect your energy like your bank account depends on it. 

2. Discomfort Is The Tuition For Growth

Every time you feel resistance, you're at the edge of growth.

Lean into it.

3. Focus Is A Spiritual Act 

Every distraction is a prayer to mediocrity

What you give attention to grows.

Choose carefully.

4. Rest Is A Weapon, Not A Weakness

Recovery isn't optional. It's strategic.

The best performers rest intentionally.

5. The Version Of You That Got You Here Can't Take You There

Who you were yesterday won't build tomorrow.

Evolve or repeat.

6. Comparison Kills Creativity

Your only competition is the person you were yesterday.

Stay in your lane.

7. The Hardest Part Of Leadership Is Letting Go

Control is comfortable. Delegation is freedom.

Learn to trust your team.

8. The More You Chase, The Further They Run

Desperation repels. Confidence attracts.

Build yourself first.

9. You Don't Rise To Your Goals, You Fall To Your Systems

Goals are wishes. Systems are results.

Build better systems.

10. Wealth Is What Happens When Purpose Becomes Procedural

Money follows systems, not motivation.

Automate your path to wealth.

11. Clarity Is Violent

Real clarity requires cutting away everything that doesn't matter.

It's painful. It's necessary.

12. Repetition Isn't Boring, It's The Rhythm Of Mastery

Excellence is boring to build and exciting to witness.

Embrace the grind.

13. Your Content Is Your Consciousness Made Public

What you share reveals who you are.

Make it count.

14. If It Isn't Measured, It Isn't Mastered

You can't improve what you don't track.

Measure everything that matters.

15. You Can't Copy Conviction

Authenticity can't be faked or replicated.

Your uniqueness is your moat.

16. You Don't Find Purpose, You Design It

Purpose isn't discovered in a cave. It's built through action.

Start building.

17. The Future Belongs To Founders Who Can Write, Automate, And Hire Top Talent

These three skills create infinite leverage.

Master them.

18. You Can't Scale Chaos

Fix the foundation before you scale the building.

Systems beat hustle.

19. Every Environment Either Amplifies Or Destroys You

Your environment shapes you more than your willpower.

Design it intentionally.

20. Simplicity Is Genius

Complexity is ego. Simplicity is mastery.

The best solutions are the simplest ones.

__

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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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How to build a 4-person team that creates 200+ pieces of content per month:

Most founders try to do content alone.

They burn out, get inconsistent, and give up.

Here's how I built a media machine:

1. The Solo Creator Problem

Doing content alone means:

• Tracking all metrics
• Managing all platforms
• Handling all distribution
• Creating every piece yourself

This doesn't scale.

2. The Media Team Framework

I don't create content. 

I design content systems.

Role 1: Content Strategist (Me)

• 4 hours per month
• Set overall direction
• Provide strategic input
• Create flagship content

Role 2: Content Editor

• Full-time role
• Maintain brand voice
• Ensure quality standards
• Transform raw ideas into polished content

Role 3: Visual Designer

• Part-time role
• Design video thumbnails
• Build presentation slides
• Create scroll-stopping graphics

Role 4: Distribution Manager

• Part-time role
• Manage content calendar
• Handle all platform posting
• Track performance metrics

3. The Content Multiplication System

I create 1 piece of flagship content per week.

My team transforms it into:

• 3 blog posts
• 1 newsletter
• 1 YouTube video
• 1 podcast episode
• 5 short-form videos
• 7 social media posts
• 10 micro-content pieces

Total: 28 pieces from 1 original.

3. The Hiring Strategy

Don't hire content creators. 

Hire content operators.

Content creators think in pieces. 

Content operators think in systems.

The Onboarding Process

Week 1: Voice Training

• Learn our frameworks
• Study my best content
• Practice writing in my style
• Get feedback on early attempts

Week 2: System Training

• Learn our workflows
• Understand our tools
• Practice content creation
• Get comfortable with processes

Week 3: Quality Control

• Refine approach
• Prove capability
• Create test content
• Receive detailed feedback

Week 4: Full Integration

• Hit production targets
• Maintain quality standards
• Take on full responsibilities
• Create content independently

The Results

Before (just me):

• Limited reach
• Constant stress
• 5 posts per week
• Inconsistent quality

After (team of 4):

• 10x reach
• Consistent quality
• Systemized process
• 200+ pieces per month

The Investment

Total team cost: $22,000/month 

Content revenue generated: $264,000/month 

ROI: 1,200%

—

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How To Scale With A Small Team

Dino Depasquale

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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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

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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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

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

Founder dinners, step aside.

Founder adventures have arrived.

My stoke meter is fully pegged thanks to the launch of the Founderland Adventure Series…

Kicking off with a fully Montana winter experience, more specifically:

“The Most Epic Founder Ski & Snowboard Trip Ever”

From Feb 9th to 12th of 2026 we’ll be experiencing:

- Full access to the ultra-exclusive, members-only Yellowstone Club in Big Sky, MT

- 3 nights lodging at the 5-star Lone Mountain Ranch resort

- Sleigh ride dinners, private saloon take-overs and other wild winter adventures

All with a group of 15 of the top founders on the planet.

Calling phenomenal founders that enjoy attacking the slopes just as hard as they attack every day biz.

Comment below if you know someone who fits.

Massive shout out to Kristofer Reddaway, CEPA® from Citizens and Gareth Domingo from AppLovin and Axon for partnering with us at The Family Fund & Founder Community for making this epic experience possible.

Buckle up and/or strap in!

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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

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