The Matt Gray Show

Hosted by Matt Gray

Business Entrepreneurship

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173

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Nov 2026

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About the show

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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November 9, 202625 min

How To Get Everything You Know Into Everything You Publish: I EP 176

Get the Profitable Personal Brand Playbook here: https://fos.now/ExfNth Work directly with me here: https://fos.now/SzrVmF Mark makes $300K a month coaching fitness founders. And he's building a brand he doesn't quite believe in anymore. In this video, I run a live whiteboard session with Mark on rebuilding the brand from the inside out. We map the two layers every real brand needs: foundation, the values only he can speak from, and leverage, using Claude to turn those values into every piece of content he ships. By the end he has a creative sparring partner that thinks like him, writes like him, and stops him from defaulting back to the safe version. Your business shouldn't get bigger while you get smaller. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/oQODqm 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/ xdCCBn 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/4xLYbu1 Twitter: matt_gray_ LinkedIn: mattgray1 TikTok: realmattgray Instagram: matthgray

November 2, 202631 min

How To Turn Your Passion Into a High Ticket Offer: I EP 175

Get Profitable Personal Brand Playbook here: https://fos.now/kVFxgT Do you want my help systematizing your business? Go here: https://fos.now/Ubjevt Amy came in doing $4K a month with 8 different offers, 3 platforms, and one exhausted human running all of it. Same trap almost every first-time high-ticket founder falls into. More tiers looks like more flexibility. To the client it just means more decisions, more risk, more reasons to say "let me think about it." In this video, I coach her live through the cut. We rebuild her offer architecture around one high-ticket and one lead-gen. I hand her the 20-20-20 sales call structure I use to close $25K clients cleanly. And we get into why cold ads are a hamster wheel and why YouTube drives me 4x more leads than every other platform combined. The most addicting drug on earth is momentum. It never comes from adding. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/WNQqEq Already doing $30K+/month? Come to my next free workshop AUG 25 @ 5pm NY time and I'll show you how to post once and get paid forever → https://fos.now/sABtmZ Want to WORK with a team of A-players? Apply to Founder OS here: https://bit.ly/4xLYbu1 Connect with me: Website: https://bit.ly/4xLYbu1 Twitter: / matt_gray_ LinkedIn: / www.linkedin.com/in/mattgray1 TikTok: / realmattgray Instagram: / matthgray

October 28, 202612 min

If I Wanted to Build a Personal Brand, I'd Do This: I EP 174

Get The Profitable Personal Brand here: https://fos.now/bHVXnw Want to work with me? Go here: https://fos.now/toUUFp In this video, I break down the exact 7-step operating system that runs my $15M company, including the Claude Al skills that now do about half the work: nailing your message with my content ritual, turning one idea into 30+ pieces of content with the content waterfall system, growing an email list you actually own through contextual lead magnets, and building trust through workshops instead of salesy content. I'll also tell you the number of hours a week I actually spend running this brand. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/fbxriJ 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/ruWahZ 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/4wxmMT9 Twitter: matt_gray_ LinkedIn: mattgray1 TikTok: realmattgray Instagram: matthgray

October 19, 202615 min

If You Only Watch One Personal Brand Video, Make It This: I EP 173

Get The Profitable Personal Brand Playbook here: fos.now/uVnJLb Want to work with me? Go here: fos.now/aEJthq In this video, I break down the 5 levels every founder moves through when building a personal brand: The Dreamer (stuck on limiting beliefs and an undefined message), The Tinkerer (posting inconsistently and mistaking activity for progress), The Beautiful Prison (growing revenue but trapped inside your own brand), The Media Company CEO (building systems and a team around your content), and The Iconic Founder-Led Brand (the level that actually compounds). I'll show you exactly which level you're at, the one shift that moves you to the next, and the single question at Level 5 that tells you whether you've actually made it. 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 camaraalmattara

September 19, 202631 min

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.

September 12, 202611 min

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.

September 6, 202610 min

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.

August 20, 2026Episode 16913 min

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 1 0:39 - 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.

August 19, 2026Episode 16812 min

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.

July 7, 202614 min

I built a content machine that runs itself with Claude Code I EP 167

Get The Tasteful AI Content Playbook here: https://fos.now/mnyLKZ Want to work with me? Go here: https://fos.now/GZTvap AI is making most content worse, not better. Taste is the biggest competitive advantage any founder has right now, and most people pipe it straight down the drain the moment they open ChatGPT. The result is a wave of content that looks like everyone else, sounds like everyone else, and gets scrolled past like everyone else. In this video, I break down the exact 4-tool AI stack I use to make content that still sounds like a real human being: Fathom to capture every call in my company, Clip Engine to turn long-form into short-form, Poppy AI for structured ideation, and Claude Code for the deeper research and writing work. You'll see how I turn one high-value founder call into a full newsletter on the psychology of wealth, and how I build voice-of-customer documents from transcripts of my highest-paying clients. Sign up for Poppy AI from here using the code “MATTGRAY” to get $25 off and my content template for free: https://start.getpoppy.ai/mattgray Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/mHYTFI 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/BPRIpK 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/4eHVT8n Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray 00:17 - Tool #1: Fathom 04:51 - Tool #2: Clip Engine 07:32 - Tool #3: Poppy AI 10:06 - Tool #4: Claude Code #onepersonbusiness #creatoreconomy #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.