I love Matt’s advice and systems because they’re based on his experience actually doing this stuff. This isn’t some fluffy course. If I woke up with no audience and no customers, Matt is the first person I’d call to help me build it back up.

Austin Belcak

Founder, Cultivated Culture
Followed by 1.4M+

Matt is more than a successful entrepreneur. He is a next-level systems thinker who is giving an entire generation of entrepreneurs the tools to succeed in business and life. He doesn't accept that good business and good life should be mutually exclusive.

Alex Lieberman

Co-Founder, Morning Brew
Sold Morning Brew $75M to Business Insider

The proof is in the pudding. Matt's approach has helped grow Herb into a major media company with a massive community, and his personal brand continues to grow impressively.

Sahil Bloom

Investor | Entrepreneur | CreatorFollowed By 850k+

*IMPORTANT: Earnings and income disclaimer

While all testimonials on this page are from real clients, the results you see on this page are not typical. Their experiences do not guarantee similar results for you. Your results may vary based on your skills, experience, motivation, as well as other unforeseen factors. Founder OS has yet to perform studies of the results of its typical clients.

Founder OS is a marketing education and training company. We do not sell a business opportunity, “get rich quick” program, or money-making system. We believe, with education, individuals can be better prepared to make decisions, but we do not guarantee success in our training. We do not make earnings claims, efforts claims, or claims that our training will make you any money. All material is intellectual property and protected by copyright.

In this strategy session, you’ll discover:

My structure for compelling content.

Little-known ways to capture the attention of your ideal audience.

Battle-tested strategies for building an irresistible offer.

How to escape the “hustle mode” that traps so many founders.

How you can build trust and make sales WITHOUT having to be “pushy".

The real reason many founders never achieve true freedom, and how you can prevent it.

And much, much more…

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Founders,

We begin with a realization: the conventional path isn't working.

Like you, I once walked the expected route. The business degree. The startup launch. The relentless hustle that society celebrates but that slowly erodes everything else that matters.

What I discovered in that journey was sobering – anxiety, isolation, and a successful business that somehow left me both financially and spiritually unfulfilled.

The freedom I sought seemed further away with each new achievement.

Perhaps you've felt this disconnect too.

That moment of clarity became my turning point. I made a sacred promise to myself: I would never again be captive to my own creation. Instead, I would build a life defined by true freedom – the ability to work where I want, on what I want, with whom I want, whenever I want.

The path wasn't immediate or without challenges, but through patient experimentation and systematic thinking, I discovered something extraordinary – a methodology that has transformed not just my business, but my entire relationship with work and life.

At the heart of this transformation sits what I call The Content GPS – a system that has helped hundreds of founders automate their growth and reclaim their freedom.

On May 22nd, I'm setting aside time to share this framework with you. Not as a quick-fix solution, but as a fundamental reimagining of how a business can serve its founder rather than consume them.

We'll explore:

  • The structural flaws in conventional business building
  • How to design systems that grow your company while you're away
  • Creating content that resonates deeply and converts reliably
  • Building frameworks that generate freedom rather than dependency

This workshop isn't about incremental improvements. It's about a fundamental shift in how you approach your business – one that aligns growth with the life you actually want to live.

The attendance is capped, and as I'll be sharing this invitation with my community of over 2,200,000 followers, I encourage you to reserve your spot now if this vision of founder freedom resonates with you.

With appreciation for your entrepreneurial journey,

-Matt

From the desk of Matt Gray

New York City

05/05/2025

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Hey, I'm Matt.

For over 14 years, I've built companies guided by one essential truth: business should create freedom, not consume it. I built Herb to reach over 12 million people, successfully exited my first company, and now guide a portfolio of businesses that generate revenue while respecting my boundaries.

I believe in creating systems that bring the founder journey into harmony with a life well-lived. My passion is helping others escape the hustle trap and build businesses that serve their vision of freedom.

Trusted by the world’s most ambitious entrepreneurs.

*IMPORTANT: Earnings and income disclaimer

While all testimonials on this page are from real clients, the results you see on this page are not typical. Their experiences do not guarantee similar results for you. Your results may vary based on your skills, experience, motivation, as well as other unforeseen factors. Founder OS has yet to perform studies of the results of its typical clients.

Founder OS is a marketing education and training company. We do not sell a business opportunity, “get rich quick” program, or money-making system. We believe, with education, individuals can be better prepared to make decisions, but we do not guarantee success in our training. We do not make earnings claims, efforts claims, or claims that our training will make you any money. All material is intellectual property and protected by copyright.

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