Andrew Henderson

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Andrew Henderson

Self-Determinationthrough entrepreneurship.

Design a business around your life. Not the other way around.

Hi!

I'm Andrew.

Digital creator and Founder of 5-Star Creator

I explore self-governance through content creation and modern entrepreneurship.

Two years ago, I was at the lowest point of my life and professional career. I was depressed and suffering from migraines. I had anxiety about losing my job, and often struggled to get out of bed.

I had a choice to make — look for another job or start building my own online business. I chose to build.

Now, I'm my own man. I decide what's important in my life. I choose who I work with and when. I decide what's worth my time and energy.

We all have passions and talents to share with the world, yet so many of us feel as though we aren't reaching our full potential.

Since I began, I've met countless others with similar stories — people who have chosen lives of authenticity over the status quo.

If you're ready to stop living for the weekend, you've come to the right place.

Learn More

Three waysI can help you.

01

Newsletter

Every Wednesday, I share practical guidance to help you start and scale your internet business.

02

Courses for Entrepreneurs

Learn how to monetize your skills and turn your interests into a scalable online business.

Learn More

03

Socials

Latest Articles

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Scaling & Mastery

What is the Meaning of Life?

We've all asked it. Sometimes in different words. Why am I here? What's the point of all this? Three thinkers helped me find my answer.

· 3 min read
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Breaking Free

Are You the Side Project of Your Own Life?

Most of us are living as secondary characters in our own lives. Here's how it happened.

· 4 min read
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Scaling & Mastery

You're Not Watching the Movie. You're Watching 1987.

Every era has an operating system the people in it can't see. 1987 thought American suburbia was the center of the universe. What does 2025 think? Here's what I learned watching He-Man fight rubber monsters in a New Jersey high school parking lot.

· 6 min read
title

Breaking Free

Do A Students Really Work for C Students?

"A students end up working for C students." It hit close to home. But the more I sat with it, the more I realized it's pointing at something way more interesting than grades.

· 4 min read
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Breaking Free

Michelangelo Never Tasted Tomato Sauce

Most famous Italians from history never tasted tomato sauce. That matters more than you think — especially if you've ever felt guilty for changing careers. In this week's newsletter, I unpack why so much of what feels permanent is actually just... inherited.

· 2 min read
title

Building Momentum

The Healer and the Warrior

Are you the healer or the warrior? The optimist or the critic? What if the answer is both — and the real trap is thinking you have to choose?

· 5 min read
title

Breaking Free

The Ouija Board Called Civilization

A childhood Ouija board taught me something about how the world works. And once you see it, you can't unsee it.

· 5 min read
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Breaking Free

The Comfort of Having an Enemy

Two months into an expensive legal battle, I noticed something uncomfortable: I feel less anxious fighting than I do on a quiet afternoon. This week, I explore why conflict often feels easier than facing ourselves.

· 4 min read
title: When Life Starts “Life-ing”

Scaling & Mastery

Finding the Lesson in the Chaos

When Life Starts “Life-ing”

A few weeks ago, my wife and I had to pack up and leave our home overnight. What followed was weeks of living out of Airbnbs, sorting through chaos, and trying to keep our sanity — and businesses — intact. In the middle of it all, I rediscovered what freedom really means. It’s not about control or comfort. It’s about being equipped to handle whatever life throws your way.

· 2 min read
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Breaking Free

Future Generations Will Wonder: What Were We Thinking?

We built a system that was supposed to make life easier. Instead, it turned luxuries into necessities and trapped us in fear of falling behind. In this article, I break down how everyday problem-solving spiraled into invisible chains — and what it means for anyone trying to reclaim their freedom

· 7 min read
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Latest Videos

title: Niquey Ree

Breaking Free

Trying to Build a Creative Life in an Uncertain World

Niquey Ree

Niquey and I discuss navigating school, work, and creativity in a world that’s changing faster than anyone can plan for.

· 49 min watch
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Building Momentum

How to Start a Personal Brand (3 Steps)

Most creators start defining their brand with inspiration. A big vision. A spark of clarity. But without the right foundation, that “vision” quickly turns into a pile of empty buzzwords — and your content ends up feeling scattered. In this video, I walk you through the 3 steps to building a brand that actually works.

· 5 min watch
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AI Took Our Jobs. Now What?

We convinced generations of people that worth = work. Then we built machines that work better than humans ever could. Now, millions are burning out trying to stay relevant inside systems that no longer need them — and pretending it’ll all be okay.

· 3 min watch
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Breaking Free

Why Gen Z Is Ditching Corporate For Entrepreneurship

Corporate jobs used to be the dream—climb the ladder, collect your paycheck, and retire comfortably. But Gen Z isn’t buying it.

· 6 min watch
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Scaling & Mastery

The Algorithm Shift of 2025: 99% of Creators Don't See This Coming

The rules of the creator economy are about to change dramatically. In this eye-opening analysis, I break down a massive shift happening in the creator economy—one that 99% of creators don’t see coming.

· 4 min watch
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Building Momentum

Why Video Content BEATS AI in 2025 and Beyond?

In a world where AI-generated content is everywhere, video remains the best way to connect with your audience authentically. I share why video is so powerful and why YOU should start filming if you haven’t already. If you’ve been on the fence about creating your own videos, this is your sign to start!

· 90 sec watch
title: My Story + Your Next Steps

Breaking Free

Turn Your Passion Into a Career

My Story + Your Next Steps

Are you ready to turn your passion into a career you love? In this video, I share my journey from feeling stuck in a job I hated to building a business that aligns with my purpose.

· 2 min watch
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Building Momentum

Tips for Using Manual Focus on Solo Shoots

Filming your own content but struggling with focus issues? Auto-focus can often cause your camera to shift focus unexpectedly, ruining your shots. In this video, I share simple tips for setting manual focus so you can keep your footage sharp and worry-free. Perfect for creators filming solo!

· 1 min watch