Matt Gray

Founder OS

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

Founder & CEO

The Matt Gray Show

I help you with proven systems to grow a profitable audience with organic content.

I’ve built 4 profitable companies in the past 10 years, a community of 14 million people, and teams of 50+ people. I now run a portfolio of profitable online businesses doing $13 million revenue a year.

Gray Enterprises

Helping brands drive more customers through technology and our community of 14 million people.

Bitmaker

Grew to largest coding school in Canada. Acquired by General Assembly and subsequently acquired for $410M by Adecco.

Co-Founder & CEO

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://www.founderos.com/newsletter

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

→ GO HERE: https://www.mattgray.xyz/coaching

If you want to join Founder OS Program:

→ GO HERE: https://www.founderos.com/course

Twitter: @matt_gray_
TikTok:@realmattgray
Instagram: @matthgray
YouTube: @realmattgray

I’ve interviewed more millionaires than I can count. 

I always ask them to share their lessons on creating a world-class company culture.

Here's what they told me:

1. Your Values = Your Compass 

Your values are your organization's DNA. They guide decision-making, shape behavior, and create a shared sense of purpose. 

Communicate them clearly and consistently. 

Embrace your values. Eliminate decision fatigue.

2. Build Bulletproof Relationships

• Encourage collaboration and teamwork
• Foster a sense of community and belonging
• Create opportunities for social connection and fun

The strength of the team is each member. The strength of each member is the team.

3. Demonstrate. Don’t Dictate.

As a founder or leader, your actions set the tone. 

• Embody integrity, empathy, and a strong work ethic
• Model the behaviors and attitudes you want to see in your team

As the leader goes, so goes the team.

4. Tap Into the Diverse Talents Within Your Team

Build teams with a wide range of backgrounds, experiences, and perspectives. This drives out-of-the-box thinking. 

Create a culture where everyone feels they can contribute.

The whole is greater than the sum of the parts.

5. Employee Wellbeing Matters

Invest in: 

• A healthy workplace
• Work-life balance
• Mental health support

When you take care of your people, they take care of your business.

6. Engage Your Team on A Deep Level

• Listen actively
• Foster open communication
• Create space for honest feedback
• Give them challenging, meaningful work 
• Provide opportunities for growth and development

Culture is what motivates and retains talented employees.

7. Rinse. Refine. Repeat

Adapt your culture as your company grows and evolves. Stay agile and responsive to your team's needs.

Regularly assess employee engagement and satisfaction. Seek feedback and ideas for improvement.

What gets measured, gets done.

8. Invest In Your Culture. It Will Pay Dividends

A strong, positive culture attracts top talent and boosts performance.

It's your competitive advantage in a world where skilled workers have countless options.

To win in the marketplace, you must first win in the workplace.

Building a great culture isn't rocket science, but it does require intention.

It takes time and effort, but it's worth it. 

Start by defining your values, focusing on engagement, and leading by example.

Culture-building is an ongoing process, not a one-time initiative.

—

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Why is investing in employee wellbeing important for business?

How can I define my organization's values?

How can diverse talents drive out-of-the-box thinking?

I’m obsessed with great leadership. 

But when I was young, I wasted years and opportunities not knowing what great leadership looked like. 

Learn from my mistakes. 

11 clear signals you have a great leader:

1. Integrity Is Their North Star

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

As Bill Campbell, the "Trillion Dollar Coach," once said: "It's not about what you say. It's about what you do."

A great leader walks their talk.

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.

And they know that what gets measured, gets improved.

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.

They know that the ego trip is a journey to nowhere.

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. 

Empathy and understanding are their tools of choice.

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.

Their tenacity is contagious.

They prove that enthusiasm is common, but endurance is rare.

6. Adaptability Is Their Competitive Edge

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

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

As Max McKeown says, “All failure is the failure to adapt; all success is successful adaptation.”

7. Innovation Fuels Them

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

They encourage bold ideas and calculated risks.

Status quo? Not in their vocabulary.

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.

9. They Communicate With Transparency

Delivering the truth courageously is the highest form of respect. 

They believe clear information sharing is power.

Empire building requires clarity of thought and word.

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.

They know that successful people listen more than they talk.

11. They Adopt A ‘Relationships First’ Attitude

They invest time and energy into nurturing authentic connections.

They remember birthdays, ask about family, and genuinely care.

Their single greatest "people skill" is a highly developed and authentic interest in the other person.

—

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What are the key traits of great leadership?

What is the importance of resilience in leadership?

10 YouTube channels that will teach you more in 2024 than a 4-year college degree:

1. Andrew Huberman, Ph.D.

Learn from the Professor of Neurobiology at Stanford.

Lessons:

• How to build physical endurance 
• What are the best supplements and protocols 
• How to enhance my creativity
 
2. Y-Combinator

Learn from the startup accelerator that has created 68 unicorn companies.

Lessons:

• How to get your first customer
• How to assess your co-founder
• The best ways to evaluate startup ideas

3. The Futur 

The Futur teaches millions how to make a living doing what they love. 

Lessons: 

• How to launch a creative business 
• How to present a project / manage your clientele
• How to charge for design with value-based pricing

4. Matt Gray

My channel on how to scale your brand, community, and systems. 

Lessons: 

• How I work 4 hours a day
• 10 rules that'll change your life 
• 7 decisions to stop screwing yourself over

5. Alex Hormozi 

The best place on the internet for business insights, breakdowns, and motivation. 

Lessons: 

• Recession-proof money hacks 
• Getting rich in the AI Revolution 
• How to build a $100M frozen yogurt empire

6. Codie Sanchez 

The go-to place if you want to start building wealth and acquiring boring businesses. 

Lessons: 

• 3 business ideas that never fail
• The underrated 7-figure side hustle 
• How someone makes $12m/year cleaning crime scenes

7. MIT Open CourseWare

1000+ free courses from one of the top universities in the world.

Lessons: 

• How did Chernobyl happen 
• The basics of airplane aerodynamics
• Understanding portfolio management

8. freeCodeCamp

The best online resource to learn how to code for free. 

Lessons:

• Learn web development (HTML + CSS) 
• How to build a Reddit clone 
• Machine Learning for everybody

9. Modern MBA 

In-depth documentaries breaking down how the biggest companies today operate. 

Lessons: 

• Why Airbnb can't disrupt the hotel industry 
• Why Casper & DTC companies failed 
• How Snowflake broke Warren Buffet's lifelong rule

10. Dan Koe 

The journey to building successful one-person businesses and maximizing human potential. 

Lessons: 

• The rise of the value creator 
• How to find profitable niches 
• The roadmap of the one-person business model 

—

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Harsh leadership truth:

Paying a sh*tty salary is the most expensive mistake you can make.

11 other harsh leadership truths that took me 10 years to learn:

1. If you avoid tension, you enable dysfunction  

Have the courage to confront and address issues early before they compound.

Lead conversations with care, compassion, and brutal honesty. 

Burying problems lets cancers grow.

2. All decisions have tradeoffs

Understand deeply what you must give up to move forward.

Make choices wisely by calculating second and third-order consequences, and know that the perfect solution doesn’t exist.  

Don’t try to have it all.

3. The day you stop learning is the day you stop leading

If you think you’ve got it all figured out, I’ve got news for you.

The courage to admit doubts & re-examine assumptions unlocks evolution.

Remaining intellectually humble and teachable is the master skill.

4. You reap what you sow with hiring

If you don’t invest in attracting & developing top talent, mediocrity becomes the norm.

Building a team of A-players is your highest leverage activity as a leader.

5. True character is revealed under pressure  

When stakes are high, leaders either rise up or shrink down. That’s when any facade breaks down. 

How you choose to respond in make-or-break moments defines you.

6. You must give trust to earn trust

Extend good faith to your people. Assume positive intent.  

Trust is the foundation great cultures are built on.

7. If you want A-players, be an A-player

You set the tone. 

Your team mirrors your behaviors, standards, and operating rhythms.  

To attract eagles, you have to soar first.

8. If you lose touch with customers, you’ve lost

Stay connected to changing needs through candid dialogue. Do not get trapped in an ivory tower.  

The market votes with its feet. Listen and watch carefully.

9. Losing emotional control loses respect

As pressure mounts, anchor yourself in stillness. 

Temper and composure inspire followership in storms. 

Losing your cool loses credibility.

10. A loss of self-awareness = a loss of perspective 

Honest self-reflection grounds you in reality and aligns your self-perception to how others experience you.  

Seek critiques. Identify blind spots. Get coaching.

Understand your weaknesses and address them.

11. Talent without systems fosters fragility

Build systems around your unique genius to create replicable systems at scale.

Systemizing the ambiguous separates the good from the great. 

Systemize or die.

—

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10 free websites so helpful they should come installed on every browser:

1. 12ft Ladder

Is there a valuable article locked behind an annoying paywall?

Drop the URL into 12ft Ladder.

All sites have a non-paywall version they send to Google for SEO.

12ft finds this version and serves it to you for free. 

Now you’re in.

2. UnrollMe

Is your Inbox unusable with 60+ spam emails a day?

Use UnrollMe to bulk unsubscribe from useless emails.

Take back control of your inbox. 

3. Darebee

Want workout inspiration but not sure where to go?

Access 1800+ workouts via this database. 

Most of the workouts are body weight and require no equipment.

Never feel uninspired to workout again.

4. PDF24 Tools

PDFs are a nightmare to edit. 

With this tool: 

• Edit PDFs without paying Adobe massive fees
• Easily learn how to use its intuitive tools / features

5. Quillbot

Get inspiration on how to repurpose your content.

• Input text and hit Rephrase
• Get AI inspiration on how to rewrite
• AI checks for plagiarism and credits sources 

6. Remove Bg 

Remove image backgrounds automatically in 5 seconds.

• Upload your image 
• AI removes the background
• Seamlessly add in new backgrounds

7. Jitter Video 

Canva but for motion design. 

Animate your designs to bring them to life: 

• Easy, intuitive UX/UI
• Hundreds of pre-built templates 

8. Render Forest 

The all-in-one branding platform. 

Create high-quality: 

• Videos 
• Logos
• Graphics 
• Mockups 
• Websites 

9. Smart Mockups 

Create free mockups for any device or physical product. 

It's a web app that lets you generate high-quality mock-ups for your: 

• Presentations
• Social media campaigns 
• DTC product

10. Snapdrop 

Airdrop but not exclusively for Mac. 

Don't leave your Android and PC friends behind. 

• Easily transfer files across OS 
• High-speed download / uploads

—

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ChatGPT is a FREE employee. 

But most people don't know how to use it to superpower their marketing. 

Here are 8 ways ChatGPT can save you thousands of marketing hours in 2024:

1. Build an Ideation Machine 

Coming up with content topics can be super hard. 

But ChatGPT can accelerate your ideation process: 

• Ask them to brainstorm a list of ideas around *topic*
• Pick an item in the list to dive into unique insights 

2. Iterate on Hook Formats 

Social media is all about capturing attention: 

• For Twitter threads, your hook delivers 90% of the virality
• For TikToks, your first 3-5 seconds define the total view count 

But how can you use ChatGPT to improve your hooks?

Here's the process: 

• Find the top 5-7 hook formats in your niche 
• Copy and paste them into ChatGPT 
• Ask ChatGPT to spit out other refined hooks you can use to test 

3. Grow Your SEO Skillset 

ChatGPT won't make you an SEO consultant. 

But you can easily accomplish basic tasks (and save $$ on expensive tools): 

• Build keyword lists 
• Quickly reduce research time 
• Summarize articles to create meta-descriptions  

4. Marketing Material Outlines 

The biggest mistake in online writing: 

Starting with a blank page. 

Before, you would endlessly research. 

Now ChatGPT improves that process. 

Type "learn" and paste the URL you want to "research" (blog post, science journal, etc.)

Then, it has the context to generate: 

• Ad copy 
• Blog headlines 
• TikTok scripts 
• Cold email templates 
• Above-the-fold landing page copy 

After that: 

• Pass it to a copywriter 
• Refine it with human touch 
• Make sure the tone is on-brand 

5. Substitute for Google Search 

ChatGPT is not the outright winner in all circumstances. 

But here are some of the pros: 

• Explains complex topics like I'm 5
• Ability to ask targeted follow-ups 
• Better at completing niche asks (i.e. Generate a list of 10 x topics)

6. Think Like a Consumer

Native grew to a $100M company by building for customer needs found in Amazon reviews.

ChatGPT can learn to embody a consumer group and voice their needs.

It's not perfect.

But can provide an accurate gauge of:

• Key pains
• Common outlooks

7. Landing Page Copy 

Constructing a landing page can be daunting. 

These elements are a must: 

• Attention-grabbing headline
• Emotional benefits
• Who it’s for
• CTA 

8. Operationalize Outreach

A tedious but core part of business growth:

Sending cold outreach.

You can have ChatGPT spin up different emails for:

• Different customer groups (i.e. Fintech v. Healthtech founders)
• Different experience levels (i.e. VPs v. associates)

—

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The biggest improvement in my life came when I realized happiness is just a product of good habits.

9 habits I used to unf*ck myself:

1. Say No by Default

Your time's precious: don't give it to people who don't deserve it.

Especially to Energy Vampires who drain your energy.

Conquer FOMO and put yourself first - my rule of thumb is if it's not a f*ck yes, it's a no.

2. Get Addicted to Learning

I put time aside daily before bed to read.

At first, it was tough to stay consistent - but the more I did it, the more its effects compounded.

Your information diet is just like your actual diet: if you eat crap, you'll feel crap.

3. Prioritize Nature

A study of 20,000 people in the UK found that 120 minutes/week in nature improved health and well-being.

It's the planet's greatest healer.

Whenever I’m in a rut, nature’s always the spark that returns color to the gray.

4. Morning Routine

Your routine doesn't need to be 4 hours long or involve a cold plunge - nail the basics:

• No phone first thing
• A small win early (e.g. light exercise)
• Mind primed for deep work (e.g. by journaling)

Your morning is the stretching before the sprint.

5. Embrace Loneliness 

Twice a month, I do something normally "social" alone. 

I'll eat dinner, go to the park, or attend a movie by myself.

Solitude is an essential pillar to truly knowing yourself: it's the secret garden where self-discovery can bloom.

6. Choose Writing Over Complaining

Complaining isn't attractive - it repels ambitious people and fosters a negative mindset.

Write down your thoughts instead: you're forced to think slowly and deeply, so your irrationality loses its edge.

It's the therapy your therapist uses.

7. Pay it Forward

Random acts of kindness boost well-being:

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

The world's a closed system: if you send waves of positivity out, they'll find their way back to you.

8. Maintain Relationships

Human connections are the fabric of life - but you need to be intentional with them amidst life's chaos.

So schedule time weekly for thoughtful texts and calls to those you've neglected.

It's a couple of minutes with an ROI you'll measure in years.

9. Focus on Your Health

I’m convinced most mental health problems are actually physical health problems. Everyone I know who:

• Eats well
• Exercises daily
• Drinks enough water

Has a Teflon mind that repels all negativity.

—

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

Day 1: 

Sleep is Your Superpower by Matt Walker 

• How we can get better sleep
• Why sleep is our life-support system 
• Sleep's impact on learning, memory, and our immune system

Day 2: 

The Power of Vulnerability by Brene Brown 

• How happiness leads to courage 
• Understand the importance of feeling connected

Day 3: 

Inside the Mind of a Master Procrastinator by Tim Urban 

• The conflict between the "instant gratification monkey" and the rational mind 
• Why do we binge YouTube and Netflix to avoid important work

Day 4: 

A Simple Way to Break a Bad Habit by Judson Brewer

• How to rewire your brain
• What is the science behind habits

Day 5: 

Grit: The Power of Passion and Perseverance by Angela Lee Duckworth

• How to develop grit 
• Why your grit correlates with success more than your IQ

Day 6: 

The Happy Secret to Better Work by Shawn Achor

• How to use the "happiness advantage" 
• How to use happiness to inspire you to be more productive

Day 7: 

Your Elusive Creative Genius by Elizabeth Gilbert

• Learn what makes someone a genius
• How to find your own unique, creative genius

Day 8:

The Power of Introverts by Susan Cain

• How to maximize creativity as an introvert 
• Why many transformative leaders were introverts

Day 9: 

What I Learned From 100 Days of Rejection by Jia Jiang

• Rejection is a process
• Asking for what you want can become your superpower

Day 10:

Extreme Ownership by Jocko Willink

• Master the art of discipline
• How independence is vital to living with responsibility

—

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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 a chance 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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I'm 34.

When I was younger, I was obsessed with shit that didn't matter.

You can learn from my fuck ups.

If you're 20-something, read this:

1. Don't Neglect Your Health

If you're rich and sick, you're going to be unhappy.

To be at your best, you need to take care of your mind, body, and soul.

2. Cut Toxic People Fast

You are the product of the 5 people you spend the most time with.

Choose wisely.

3. Experiences > Things

We're all going to die. You can't bring things to your grave.

Travel. Go on road trips. Get lost in nature.

4. Fuck Outcomes

Show up every day and focus on the process.

There are no shortcuts to success.

The key is to fall in love with the journey.

5. Find Your Calling

Don't worry about what everyone else is doing.

Focus on the things that make you happy. Find your reason for being.

6. Experiments > Experts

Put in the reps.

Run as many experiments as you can.

7. Learn Like Your Life Depends on It

Then act.

Read.

Listen to podcasts.

And take massive action. 

Every day.

8. Implement The 5-Second Rule

Don't procrastinate. The illusion is that you have time.

If there is something you should do, do it within 5 seconds.

Get addicted to progress. Build momentum.

Follow these steps and architect the life of your dreams.

Life is too short to give a fuck what others want you to do.

That's a wrap!

—

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