The Matt Gray Show

Hosted by Matt Gray

Business Entrepreneurship

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161

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Jun 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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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/brwyRwYour 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/iPJwajAlready 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/dlgCqBWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4vouZrGTwitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 9, 202614 min

how to build a business so magnetic your customers chase you I EP 162

Want to work with me? Go here: https://fos.now/xNUPvDThere are two kinds of businesses, and you can feel the difference the moment you walk into either one.A drained business runs on your grit. Constant fires. Endless meetings. 20+ things on your plate. The second you slow down, everything slows with you.A magnetic business pays you to be you. Small, mighty team. Real leaders running real outcomes. Systems holding the operation. You can leave for a month and come back to something stronger than you left.In this video, I break down what actually separates the two, the founder's scorecard, core velocity meetings, the architect role, and the small set of decisions that turn a draining company into one that magnetizes customers, team, and time.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/iPJwajAlready 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/dlgCqBWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4vouZrGTwitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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/WmWPHzThe 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/dOvxpfAlready 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/FXLylVWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4driwNW Twitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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/HdOZVuIn 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/KTDiCQAlready 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/KqRZNbWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4dpbf14Twitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 26, 202615 min

why your content gets views but makes $0.00 (learn how to fix it) I EP 159

Want to work with me? Go here: https://fos.now/nrLYUWYouTube creators usually measure the wrong thing. Views, likes, engagement, but none of that equals cash.In this video, I show you our actual YouTube performance dashboard that pulls from YouTube Analytics and HubSpot CRM simultaneously. You’ll see the system my team runs every week, tracking twelve variables including cash collected, subscribers, applications, editor performance, and format ROI, so you know with precision what content actually converts.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/mDxJtMAlready 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/yXUYbxWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/498HrmPTwitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 21, 202621 min

how to plan a whole month of content (in 7 steps) I EP 158

Get my Content GPS Alignment Audit here: https://fos.now/vmXqfEDo you want my help systematizing your business? Go here: https://fos.now/utHxKrGet access to Poppy AI here and get a $25 discount on your membership: https://start.getpoppy.ai/mattgrayMost people treat content ideas like a creativity problem. The real problem: the things that should be feeding your content, your sales calls, your analytics, your candid frustrations, have nowhere to go.In this video, I show you the exact workflow I use to run my profitable personal brand and the system we install for founders inside Founder OS when we build their content machine. You'll see the organic sources that generate ideas, the performance signal filter that shows you what to double down on, and the anchor piece strategy that creates months of content in batches.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/UgIGtdAlready 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/ZCZibXWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/492hqp6Twitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray00:00 - Intro 00:05 - Section 1: Organic Sources 06:24 - Section 2: Your Performance Signal Filter 15:26 - Section 3: The Anchor Piece#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 15, 20269 min

how I’m automating 97% of my business with AI I EP 157

Do you want my help systematizing your business? Go here: https://fos.now/vFyCHlIn this video, I walk through my strategy dashboard, the orchestrator system that automates everything from landing pages to email sequences, the weekly actions and Q2 OKRs that keep us aligned, and how we’re making sure AI investment reduces costs or increases profits—not just AI for AI’s sake.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/gHhmiS 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/PArNtJWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4nkzXmo Twitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 14, 202610 min

if you think I have it “figured out”, watch this I EP 156

Do you want my help systematizing your business? Go here: https://fos.now/YflasbIn this video, I talk about being both intense and finding moments of zen, and how I build balance into the business without losing the edge that makes things move forward.When you’re building a business, things get intense. Things get chaotic. My business is no different in terms of this default state of entropy. People quit, fires happen. I want to be real with you: even at twenty years in entrepreneurship, I still struggle with this stuff at times.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/nGKwHgAlready 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/OSkhkUWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4u02dxmTwitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 8, 202613 min

How I'd Start a Media Company (in Just 21 Days) I EP 155

Work with me: https://fos.now/IFxUIsGet The Personal brand Team Evaluation here: https://fos.now/WJmaVqYour content problem isn’t a creativity problem. It’s an org chart problem. You film your own videos, manage the b-roll, manage the analytics, hire the next person, and before you know it, you’re on a content hamster wheel.Here’s what nobody told you when you started building your personal brand: the moment it started generating cash flow, content stopped being about self-expression. It became a business unit. And no one runs a business unit alone.In this video, I show you the exact six-person team behind my personal brand that made it a media company, not for better content, but to build an 8-figure personal brand.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/NYxUuKAlready 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/DBxVihWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4d2CtcpTwitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray00:00 - Intro00:41 - Role #1: CEO of Video02:44 - Role #2 & #3: Distribution & Atribution06:13 - Role #4: Visual Authority07:42 - Role #5: Psychological Messaging09:57 - Role #6: Systems and Leverage#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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 6, 202611 min

how to turn views into clients so fast it feels illegal I EP 154

Work with me: https://fos.now/lFiHeJGet The Content GPS Alignment Audit here: https://fos.now/XCOGcpHere’s what nobody will say out loud: most personal brands posting consistently build a following, get decent views, and are still generating zero predictable pipeline from it. You’ve been told to post more, be consistent, go viral, build an audience. Your revenue from content just keeps staying flat.That’s not a content problem. That’s an architecture problem.In this video, I show you the three beliefs about content that are killing your pipeline, the exact system my team uses to turn content into predictable sales, and the one specific piece of content that proves everything.Want to LEARN proven systems to grow your personal brand? Go here: https://fos.now/GkRswnAlready 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/tpfgMXWant to WORK with a team of A-players? Apply to Founder OS here: https://www.founderos.com/careersConnect with me:Website: https://bit.ly/4umq6inTwitter: https://twitter.com/matt_gray_LinkedIn: https://www.linkedin.com/in/mattgray1TikTok: https://www.tiktok.com/@realmattgrayInstagram: https://instagram.com/matthgray00:00 - Intro00:38 - Part 1: The Reframe - 3 Beliefs Killing Your Pipeline02:49 - Part 2: The System - How to Create Content That Converts08:33 - Part 3: The Moneyball Moment - Optimizing for What Actually Matters#onepersonbusiness #creatoreconomy #entrepreneurshipDisclaimer: 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.