The Matt Gray Show

Matt Gray

I create content to help you grow your audience, brand, and community through proven systems. I’ve built 3 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 internet businesses. I am obsessed with helping founders build leverage through content and community - my newsletter, blog, and products will bring you clarity and massive momentum.

  1. Sep 19

    I Sold My Business for 8 Figures. Here’s What I’d Build First: I EP 172

    Get The Profitable Personal Brand Playbook here: https://fos.now/xxvzfi Want to work with me? Go here: https://fos.now/wpiaho I sold my first business for eight figures. Looking back, the most valuable asset I've built is my personal brand and the audience around it. In this video, I walk you through the full story: growing up in Canada, building and selling Bitmaker, scaling Herb, and finding my way to Founder OS. I share the government raid that nearly shut us down, the acquisition offers I turned down, and what it took to rebuild my health and find work I wanted to do. You'll see how building an audience opened doors across my businesses, why it means I never have to start from zero, and what I'd prioritise if I were starting again. Chapters: 00:00 - The story behind my businesses 00:52 - Growing up in small-town Canada 02:37 - Leaving corporate life and starting Bitmaker 04:38 - The government raid that nearly shut us down 09:34 - Selling Bitmaker and what came next 10:45 - Finding my next business: Herb 13:39 - Raising investment for Herb 15:20 - Turning down the $50 million offers 16:19 - Layoffs, regret and burnout 20:28 - Getting sober and finding my direction 21:38 - Building my personal brand and Founder OS 26:36 - The most valuable asset I've built 30:31 - Three lessons I'd pass on Want to LEARN proven systems to grow your personal brand? Go here: fos.now/NUzpEe Already doing $30K+/month? Come to my next free workshop and I'll show you how to systemize your business and get your time back → fos.now/XtIMBY Want to WORK with a team of A-players? Apply to Founder OS here: founderos.com/careers Connect with me: Website: bit.ly/45fJanM Twitter: twitter.com/matt_gray_ LinkedIn: linkedin.com/in/mattgray1 TikTok: tiktok.com/@realmattgray Instagram: instagram.com/matthgray #personalbranding #entrepreneurship #founderstory Disclaimer: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. This video shares my personal experience and growth building businesses over 15+ years of consistent effort. Your results will vary depending on your own actions, strategies, and circumstances.

    I Sold My Business for 8 Figures. Here’s What I’d Build First: I EP 172
  2. Sep 12

    The 7 Laws of a Personal Brand Everyone Loves I EP 171

    Get the Profitable Personal Brand Playbook here: https://fos.now/JaWoip Do you want my help systematizing your business? Go here: https://fos.now/CZGkMS Six behaviors make people watch you. One makes them love you. Every personal brand with real loyalty runs the same seven laws. Six earn attention: radical proximity, weaponized weirdness, polarization, insane generosity, subtraction, and treating business like play. All learnable. Most founders run two. The seventh is the one nobody wants to do. Point the spotlight at everyone but yourself. In this video, I break down all seven with the founders who built billion-dollar brands off each one, plus the three moves to apply this in your business tomorrow. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/FMlxQK Already doing $30K+/month? Come to my next free workshop and I'll show you how to systemize your business and get your time back → https://fos.now/eUVtfx Want to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careers Connect with me: Website: https://bit.ly/4g265Z0 Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray 00:00 - Intro 00:48 - Law 1: Radical Proximity 01:52 - Law 2: Your Weirdness Is Your Weapon 03:16 - Law 3: The Polarization Principle 04:35 - Law 4: Insane Generosity 05:50 - Law 5: The Power of Subtraction 07:24 - Law 6: Business as Play 08:45 - Law 7: Make Others the Hero #personalbrand #ceopsychology #entrepreneurship #7laws Disclaimer: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. This video shares my personal experience and growth building businesses over 15+ years of consistent effort. Your results will vary depending on your own actions, strategies, and circumstances.

    The 7 Laws of a Personal Brand Everyone Loves I EP 171
  3. Sep 6

    Personal Branding Is Hard Until You Build Systems Like This I EP 170

    Get Profitable Personal Brand Playbook here: https://fos.now/GVtwUi Do you want my help systematizing your business? Go here: https://fos.now/YmLiWZ You take one week off and the whole thing stalls. If your reach dies the second you stop posting, you don't own a personal brand. You own a shift, and you're the only employee working it. The founders with real leverage stopped treating content like a performance and started running it like a system. Inputs, process, outputs, ownership. The same way you'd run any part of the business you actually trust. In this video, I hand you the 5 systems mine runs on: the one-word test, the archive mine, the generosity algorithm (giving away my best playbooks returned 6x more than anything I gated), the Slack test (the only metric that predicts revenue), and the 3-question client survey. Plus the final exam question that tells you in ten seconds whether you've built a brand or an expensive job. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/BVCKgW Already doing $30K+/month? Come to my next free workshop and I'll show you how to systemize your business and get your time back → https://fos.now/Ircagp Want to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careers Connect with me: Website: bit.ly/4bq7k2p Twitter: twitter.com/matt_gray_ LinkedIn: linkedin.com/in/mattgray1 TikTok: tiktok.com/@realmattgray Instagram: instagram.com/matthgray 00:00 - Intro 00:38 - System 1: One-Word Moat 02:04 - System 2: Five Year Mirror 03:55 - System 3: Generosity Algorithm 05:15 - System 4: Slack Test 07:06 - System 5: Disappearing Act #personalbrandstrategy #contentsystems #brandbuilding #foundercontent Disclaimer: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. This video shares my personal experience and growth building businesses over 15+ years of consistent effort. Your results will vary depending on your own actions, strategies, and circumstances.

    Personal Branding Is Hard Until You Build Systems Like This I EP 170
  4. Aug 20

    Why grinding harder won't build you wealth I EP 169

    Get The Psychology of Building Wealth Doc here: fos.now/kDEXwn Want to work with me? Go here: fos.now/IYpAmD In this video, I walk you through the 4-part mental model I use to build wealth as a founder: why you are the biggest asset on your balance sheet, why boring diversified investing beats every clever strategy, why investing in the architect (coaches, breathwork, health budgets, empty calendars) isn't optional, and why you're a free agent who gets to choose the environment that designs you. Want to LEARN proven systems to grow your personal brand? Go here: fos.now/TIIAsM Already doing $30K+/month? Come to my next free workshop and I'll show you how to systemize your business and get your time back → fos.now/MoKCZN Want to WORK with a team of A-players? Apply to Founder OS here: founderos.com/careers Connect with me: Website: bit.ly/4bq7k2p Twitter: twitter.com/matt_gray_ LinkedIn: linkedin.com/in/mattgray1 TikTok: tiktok.com/@realmattgray Instagram: instagram.com/matthgray 00:00 - Intro 00:35 - You Are The Asset 03:27 - Boring Investing Wins 08:23 - Invest In The Architect 10:39 - You Are a Free Agent #personalbrand #contentsystems #entrepreneurship Disclaimer: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. This video shares my personal experience and growth building businesses over 15+ years of consistent effort. Your results will vary depending on your own actions, strategies, and circumstances.

    Why grinding harder won't build you wealth I EP 169
  5. Aug 19

    your goals keep failing until you run this meeting I EP 168

    Get My Personal Board Meeting Template here: fos.now/QYGUUW Get My Velocity Weekly Meeting Template here: fos.now/fYWLfg Want to work with me? Go here: fos.now/ifXRtR In this video, I run the July 2026 edition of my personal board meeting live on camera. You'll see how I set my monthly financial target, map the highest-leverage priorities to hit it, review my 30-day themes, sync everything to the 10-year vision, and use my inner circle of advisors, human and AI, to pressure-test every decision before it costs me a month. Want to LEARN proven systems to grow your personal brand? Go here: fos.now/BmznQY Already doing $30K+/month? Come to my next free workshop and I'll show you how to systemize your business and get your time back → fos.now/BospxP Want to WORK with a team of A-players? Apply to Founder OS here: founderos.com/careers Connect with me: Website: bit.ly/4p4YQDH Twitter: twitter.com/matt_gray_ LinkedIn: linkedin.com/in/mattgray1 TikTok: tiktok.com/@realmattgray Instagram: instagram.com/matthgray #personalbrand #contentsystems #entrepreneurship Disclaimer: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. This video shares my personal experience and growth building businesses over 15+ years of consistent effort. Your results will vary depending on your own actions, strategies, and circumstances.

    your goals keep failing until you run this meeting I EP 168
4.8
out of 5
12 Ratings

About

I create content to help you grow your audience, brand, and community through proven systems. I’ve built 3 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 internet businesses. I am obsessed with helping founders build leverage through content and community - my newsletter, blog, and products will bring you clarity and massive momentum.

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