The Matt Gray Show

Hosted by Matt Gray

Business Entrepreneurship

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167

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Aug 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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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.

July 1, 202618 min

how to build a brand AI can't copy I EP 166

Get The Brand DNA Scorecard here: https://fos.now/Elzdfm Want to work with me? Go here: https://fos.now/VFHYDr In this video, I walk you through the 5 layers that AI can't replicate, starting with the one most founders ignore entirely: aesthetic DNA. You'll see how I use Pinterest as a curation engine, where I pull inspiration from (old Porsche ads, Japanese design, Rick Rubin meets Patagonia), and how that taste shows up in everything from my newsletter to carousels to the motion graphics in our videos. 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/SOyaJS 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/tXdWUY 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/4gutfJ2 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 00:31 - Section 1: Aesthetic DNA 04:57 - Section 2: Idea DNA 07:27 - Section 3: Voice DNA 13:02 - Section 4: Structural DNA 15:58 - Section 5: Vulnerability DNA #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.

June 24, 20269 min

I built a complete operating system for a $4M business (copy this) I EP 165

Get The Leadership Blueprint here: https://fos.now/ezSGPZ Want to work with me? Go here: https://fos.now/OMBVMn Every successful founder eventually becomes the bottleneck of their own company. You went from running the business to being the business. Every decision, every escalation, every senior client relationship — all routing through one person. The reward for building something good turns into 25 hours a week of meetings and a calendar that doesn't belong to you anymore. In this video, I show you the exact 6-part leadership blueprint I built for Lauren Mitchell, a $4M financial consulting founder with 18 team members who was personally answering every question her company asked. You'll see how we redesigned the org chart, installed clear decision authority with a RACI framework, and turned six direct reports into three real leaders who can finally run their own lanes. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/ehdEPS 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/BvLdrn 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/4gku0Ev Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray #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.

June 19, 202617 min

how to build a personal brand so powerful people beg to buy I EP 164

Get My Free Founder Operating System here: https://www.founderos.com/discover/the-founder-operating-system Want to work with me? Go here: https://fos.now/vtuxKX A brand without positioning is just noise with a logo. You can post on every platform, hit publish daily, and still leave people with no clear sense of what you stand for, which means none of them ever buy. In this video, I walk you through the exact brand positioning playbook I use with founders inside Founder OS, built around a real example: a $7.2M growth consultant trying to scale to $20M. You'll see the creative psychology principles, the role of proprietary IP, the Big Why, and how to map a flywheel when your business has multiple arms like consulting, education, and tech. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/XcoaIw 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/CNQLIr 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/444ZdUQ Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray #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.

June 16, 202626 min

I built a social media machine for a $7M roofing founder I EP 163

Want to work with me? Go here: https://fos.now/brwyRw Your business should sit underneath you, not on top of you. Plenty of founders hit this wall around the $5-10M mark. The company they built is paying well, the team is solid, the operation is humming, and somehow they feel more stuck than ever. The business has become their whole identity, and there's no room left to build anything else. In this video, I walk you through the social media machine we're building for a $7M roofing founder in Sydney trying to break out of that exact trap. We're turning his craftsmanship into a founder-led brand, mapping out an education arm, and architecting a flywheel that lets him use the construction business as a launching pad for everything else he wants to build. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/iPJwaj 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/dlgCqB 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/4vouZrG Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray #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.

June 2, 202610 min

if you think like an artist, you will become impossible to ignore I EP 161

Want to work with me? Go here: https://fos.now/WmWPHz The founders I respect most aren't really entrepreneurs. They're artists who built a business so they could keep doing the work they love. In this video, I walk you through how I think about the artist-operator combo: building an autonomous engine around your business so you can spend your days doing the creative work that actually moves the needle, the videos, the funnels, the products, the writing. The kind of work that can change the trajectory of everything in a single shot. Want to GROW your personal brand? Go here: https://fos.now/dOvxpf 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/FXLylV 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/4driwNW Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray #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.

May 29, 202616 min

how I became consistently profitable (the founder OS code) I EP 160

Want to work with me? Go here: https://fos.now/HdOZVu In this video, I walk through the ten principles I live by. These aren’t always easy, but they’re my North Star. You’ll see why moving like it’s gonna work out (because it is) matters, how to stay radically focused on one core thing, why your business should increase your liveliness instead of consuming it, and how to architect freedom instead of running a business that runs you into the ground. Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/KTDiCQ 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/KqRZNb 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/4dpbf14 Twitter: https://twitter.com/matt_gray_ LinkedIn: https://www.linkedin.com/in/mattgray1 TikTok: https://www.tiktok.com/@realmattgray Instagram: https://instagram.com/matthgray #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.