The operating system behind 7 to 9-figure founder brands. Founder & CEO, Founder OS
Brooklyn, New York, United States
924K followers
500+ connections
About
Over the last decade, I’ve built 4 successful companies and a community of over 14 million people.
My mission is to inspire 100 million founders to live their dreams through proven systems.
I help entrepreneurs remove themselves from operations, grow on autopilot with content and an engaged audience, and automate core systems.
I’m the founder of Founder OS, Gray Enterprises, and Bitmaker (acq. General Assembly).
My portfolio:
→ I'm the founder & CEO of Founder OS, a community of 650 entrepreneurs
→ I’m the founder & CEO of Gray Enterprises with a community of over 14 million people
→ I teach the Founder OS Program to help entrepreneurs scale their online businesses to $1M+ revenue
→ I coach entrepreneurs that need help with marketing, sales, systems, community, and growth
→ I advise early-stage companies in AI, Education, Creator Economy, and SaaS verticals
My results:
→ 14M+ people community
→ 2.5M+ people following Founder OS
→ 2B content impressions annually
→ 0 advertisements
→ 80%+ margins
If you want to learn more about how I built this, you can join my newsletter:
→ GO HERE: https://fos.now/OdJnIQ
If you want to explore 1:1 coaching or consulting visit my personal site:
→ GO HERE: https://fos.now/li-book-now
If you want to join Founder OS Program:
→ GO HERE: https://fos.now/li-course
Twitter: https://fos.now/li-twitter
TikTok: https://fos.now/li-tiktok
Instagram: https://fos.now/li-instagram
YouTube: https://fos.now/li-youtube
Articles by Matt
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924K followers
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Matt Gray shared thisI'm writing this from the Dolomites. Mountains in every direction, phone somewhere I can't reach it, business running fine without me. None of this costs a dollar, and it's worth more than any deal I closed this year. I built my whole business around 5 rules. They live on a card in my journal and I read them every morning. Steal any that serve you. If it costs peace, it's too expensive. The revenue looks great on the invoice. The client is a fire drill. That's not a client, that's a tax. Peace is the currency you spend every time you say yes to the wrong thing. What I touch has to compound without me. If the thing only pays while I'm standing next to it, it isn't an asset. It's an expensive job. I protect mornings like my most valuable asset. Because they are. The first 4 hours own the day. The day owns the week. The week owns the year. I remove myself before I optimize. You can't optimize what you're still holding. Delegate first, systemize second, optimize third. Most founders run that order backwards and wonder why nothing scales. I trust slow, inevitable wins over loud ones. The loud win looks like a home run in the moment. Six months later it usually costs more than it made. The slow win looks boring. Then one random Tuesday it quietly hits, and you realize you've been rich for a while. Every week, make one Architect Move. One action that removes a future decision. One delegation that sticks. One simplification. Over 90 days, that's 36 compounding subtractions in a single quarter. That's not incremental. That's how you go from a 60-hour week to a 20-hour week without touching your profit. You subtract. Weekly. Ruthlessly. For as long as it takes. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. These 5 rules turned into a working operating system are what I teach at my Dolomites mastermind, October 9th to 13th. If you want the whole thing built with you, come find us: founderos.com/apply
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Matt Gray shared thisFor years, I tried to live every decade like it was my 20s. Grind harder. Push faster. Stay up later. Squeeze more out of every hour. Then I burned out at 32 and learned something that changed everything: Life has seasons. And the founders who win long-term are the ones who stop fighting the season they're actually in. Here's the rhythm I wish someone had taught me earlier: 1. Your 20s Are for Grinding This is the decade nobody can do for you. You're not building wealth yet. You're building yourself. Use it to: • Learn every skill you can • Make every mistake cheaply • Say yes to rooms you don't belong in • Get rejected so much it stops stinging The grind isn't punishment. It's tuition. Pay it now or pay it later with interest. 2. Your 30s Are for Building This is where the foundation gets poured. You stop chasing every shiny thing and start building one thing that compounds. The shift: • From wide to deep • From hustle to systems • From opinions to convictions • From "what works" to "what's mine to build" Your 30s are when you finally stop performing and start producing. The work feels heavier. The reward starts becoming real. 3. Your 40s Are for Compounding This is where the math gets beautiful. Everything you planted in your 20s and 30s starts paying you back. Your relationships compound. Your reputation compounds. Your skills compound. Your assets compound. Most people quit one decade too early. They build for 15 years, see the curve flatten, and walk away right before it bends sharply upward. Compounding feels boring until it doesn't. Stay in the chair. 4. Your 50s Are for Owning This is the decade you stop renting your life. You own: • Your time • Your calendar • Your decisions • Your standards • Your relationships • Your version of success You stop optimizing for the opinions of people you wouldn't trade lives with. This is where most founders finally exhale. Not because the work is done. Because the noise is. 5. Your 60s Are for Enjoying This is what the grind was for. Not the yacht. Not the title. Not the trophy on the shelf. The enjoyment is in the quiet things: • A body that still moves • A mind that's still curious • Time with people you love • Mornings without urgency • Work you choose, not work you owe If you skip the seasons, you don't earn this decade. You arrive at it tired, wealthy, and wondering what it was all for. The mistake most founders make isn't working too hard. It's living every decade like it's the same decade. Grind when it's time to grind. Build when it's time to build. Compound when it's time to compound. And when the season changes, change with it. That's the real wealth. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Want to find out exactly how much your personal brand is really worth right now? Get the complete framework here: https://fos.now/ANOpPX
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Matt Gray shared thisIn 2015 I had a panic attack. From the outside the business looked great. Team, revenue, press. And every morning I woke up with a knot in my chest, because the whole thing depended on me being switched on. I'd built a beautiful prison and locked myself inside it. So I sold it, packed two suitcases, and went traveling. In a quiet villa in Thailand, one simple truth landed: The founders who create the most freedom aren't the best operators. They're the best architects. That's the whole game. Now every decision I make passes one test. Does this reinforce the Architect, or pull me back into Operator mode? Architect is thinking, designing, writing, allocating. Operator is managing, fixing, approving, reacting. If it's Operator work, it gets delegated or redesigned. It never lands on me. There's one line I've repeated for a year that changed everything: If something requires my constant presence, it's broken. If it needs you standing next to it every day, you don't have a system. You have a job wearing a business costume. Here's something you can hand your team this week. Before anyone escalates a decision to you, they answer 5 questions: 1. Is there a clear owner for this? 2. Is it already written down somewhere? 3. Does this actually need my judgment, or can they make the call? 4. Have they made a recommendation? 5. If I were offline for 30 days, how would they handle it? If they can't answer all 5, they don't escalate. They resolve it themselves. Post it on your team wiki. Enforce it for 30 days. Watch your life get quiet. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. The full operating system behind this, the filters, the checklists, the delegation maps, is what I install with a small group of founders at my Dolomites mastermind this October 9th to 13th. If 2026 is the year you run the company differently, come see it: founderos.com/apply
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Matt Gray shared thisEvery Friday at 4pm, I sit alone for 60 minutes with a notebook and a pen. Phone in another room. Laptop off. It's the single most valuable hour on my calendar. Nothing else is close. I call it my Weekly Board Meeting. Here's exactly what happens in it. First 15 minutes. I answer 4 questions by hand: 1. What gave me energy this week? 2. What drained my energy this week? 3. What can I remove or redesign? 4. What decision have I been avoiding? If you can't answer those honestly on a Friday afternoon, you're on autopilot. And the plane is heading somewhere you didn't choose. Next 15 minutes. I make three moves. No more, no less. One action that removes a future decision. One delegation that actually sticks. One simplification. Last 30 minutes. I walk with no phone, no music, no podcast. Just walking. When I skip it, the next week is worse. When I do it, the next week is calmer and sharper. That part isn't optional. One thing you can steal this week: hunt your paper cuts. Every drained-energy moment from question 2 is a paper cut. The meeting nobody needs. The client who costs 3x the attention for 1x the money. The tool your team keeps complaining about. Write down 5 of them this Friday. Fix 3 next week. Do that for 12 weeks and the whole thing runs smooth. Not because you scaled. Because you subtracted. The founders who look the calmest aren't the ones with the biggest teams. They're the ones who quietly fixed 3 paper cuts a week for a decade. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. I'm running this exact system, and the rest of my operating system, with a small group of founders at my mastermind in the Dolomites this October 9th to 13th. If building a business that runs without you is the goal for the rest of 2026, come architect it with us: founderos.com/apply
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Matt Gray shared thisA thought that makes me care a lot less about what people think: — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Your life gets lighter when you stop performing for an audience. Get the complete framework here: https://fos.now/ANOpPX
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Matt Gray shared thisI stopped trying to “make content” a long time ago. It was exhausting. Every platform felt like another job. LinkedIn needed a post. YouTube needed a video. Instagram needed a carousel. Email needed a newsletter. The breakthrough was realizing they were all the same job. Have one idea worth sharing. Now I can talk through an idea once and let the system multiply it across every platform. That changed content from something I had to constantly produce into an asset that compounds. The best content strategy isn’t creating more. It’s making your best ideas travel further. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. The habits you repeat become the life you build. Get the complete framework here: https://fos.now/ANOpPX
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Matt Gray shared this33 habits that drastically changed my life forever: — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. The habits you repeat become the life you build. Get the complete framework here: https://fos.now/ANOpPX
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Matt Gray shared thisYou can be busy for years and barely move. I learned this the expensive way. The work that feels exciting gives you an immediate hit: New ideas. New projects. New strategies. But almost everything meaningful I’ve built came from doing the opposite. Writing when nobody was reading. Publishing when nothing went viral. Building systems before I desperately needed them. Having the same weekly meetings. Improving the same offer. Doing the same few things long enough for compounding to finally become obvious. That’s the frustrating part about progress: For a long time, it looks like nothing is happening. And right around that point, most people go looking for something new. Stay boring long enough. That’s usually where the magic is. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. The work that compounds rarely feels exciting while you’re doing it. Get the complete framework here: https://fos.now/ANOpPX
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Matt Gray shared thisThe best personal brands don’t feel like they’re selling. You follow someone for 6 months. You start using their language. Their ideas change how you see a problem. So when they finally make an offer, buying feels obvious. That’s the game. Clear positioning gets you remembered. A distinct voice makes people care. The right niche gives you somewhere to build for years. And a system turns all of that attention into something that compounds. Most people focus on the sale. I’d rather build the conditions that make the sale inevitable. — Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Become the brand people trust before they ever need what you sell. Get the complete framework here: fos.now framework
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Matt Gray liked thisMatt Gray liked thisThe harsh truth is, running a company is simply a game of prioritizing problems. Here’s how to become the Chief Problem Solver in your business: Want to know Elon Musk's secret to running Tesla, SpaceX, and 3+ other billion-dollar companies? According to Marc Andreessen, it's simple. He shows up every week, identifies the biggest problem, fixes it, and does that 52 weeks in a row. Most companies hide from problems. - They reframe them as challenges - They create layers of abstraction - They delegate them into oblivion But problems aren't biohazards. They're your biggest opportunities. Bigger the problem? Bigger the potential. There’s a reason SpaceX is able to send a 400-foot skyscraper into the sky knowing it might explode. Because they want to know exactly what breaks, when, and why. Every failure incapacitates dozens of future problems. This approach works because running a company is simply prioritizing problems. Your earnings directly reflect what you solve, and big problems pay better. Another great example of this is Brad Jacobs. He built 7 billion-dollar companies in logistics, waste, and warehousing. Industries most people find boring until they see his bank account. Here’s how he evaluates risk vs reward on different deal sizes: - Small, low-risk deals: exist but limited reward - Small, high-risk deals: limited reward with high risk (avoid) - Big, low-risk deals: unicorns (don't exist) - Big, high-risk deals with solvable problems: the bingo quadrant One of my favorite lines from his book is, "If you want to win, you have to rearrange your brain to lean into those big, hairy problems and figure out how to cut off the hair and de-risk." This is exactly what your job is as a CEO. Hire the smartest people in the world... and solve the problems they can't figure out. That's it. Not avoiding problems, but identifying and selecting the right ones to solve. Becoming a Chief Problem Solver requires you to create your own weekly problem-solving loop: - Identify your single biggest constraint - Focus all resources on solving it - Measure the result - Repeat next week 1 problem. 1 solution. 52 weeks in a row. The best entrepreneurs don't just think differently about problems. They actively build muscles for problem identification and execution. Then they do it again and again. Fair warning though, this isn't glamorous work. It means: - Living inside friction - Facing uncomfortable truths - Fixing things no one else wants to touch Not pretty, but it's where all the leverage is. If your business is stuck, your unlock is often solving ONE big problem. Maybe you know exactly what it is, but don't know how to solve it. Or maybe you're not sure what the problem is yet... So if you want to see how we think about solving these problems for our own businesses, you might want to check out this free masterclass: https://lnkd.in/e45s3vub
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Matt Gray liked thisMatt Gray liked thisWhat's AI actually doing to the job market in 2026? And how should job seekers be responding? Let's dive in 👇 MSCI's midyear research offers some insight into this. The big takeaway is this: AI isn't lifting the entire market; it's causing a split. Here's what the research found: 1. Semiconductor stocks returned +55% in the first half of 2026. The global benchmark returned +11%. Software and services fell 18%, the worst of any industry. A lot of people miss that last line. 2. Just two industry groups explain 86% of the global equity gain. 3. Software is falling because investors worry AI agents will break the per-seat pricing model most software companies depend on. 4. Private markets show the same split. Buyout funds' U.S. software holdings lost 7.9% in Q1, while AI-native startups commanded premium valuations. 5. There isn't much cushion. The extra return investors expect for holding stocks is 0.41%, against a long-run average of 4.39%. It was last this thin in the dot-com era. The report is about investing, not hiring. But hiring follows capital, so here's how I'd read it as a job seeker: - A rising index doesn't mean broad hiring. When two industry groups drive most of the gains, most employers aren't feeling a boom. If your search feels harder than the headlines suggest, it's not you. - Follow the $$$. AI infrastructure (chips, DCs, power, hardware) needs more than engineers. There are lots of opportunities here. - Interview software employers about their AI plan. If a company charges per seat, ask how its pricing and product are changing. A vague answer tells you something about how stable the role is. - The pressure on per-seat software applies to careers too: value is shifting from how many people do the work to what gets done. Show results, and show how you use AI to get them. Job Seekers: Don't mistake a "hot sector" for a safe job. One poor earnings season can turn hiring plans into freezes. Do your due diligence. From the coaching side, I'm seeing job growth in firms and industries that are touching Energy, Data Hardware, Processing Hardware, Electrical Grid Tech, and many more. PS - Are these 'info' posts helpful for job seekers?
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Matt Gray liked thisMatt Gray liked thisNobody hands you an invitation to lead. You show up well before the title. The biggest leadership lie? You'll start leading once they promote you. Respect comes from character, not credentials. Influence comes from ability, not authority. None of this takes natural talent. Just the right mindset paired with the right actions. Here are 9 skills that make you a leader worth following: 1. Be Easy to Work With ↳ Own your mistakes fast. ↳ Leave people better than you found them. 2. Lift the Energy in the Room ↳ Open with wins before problems. ↳ Ask questions that get people talking. 3. Keep Your Commitments ↳ Write down every promise you make. ↳ If plans change, say so early. 4. Find the Courage to Say No ↳ Protect what matters most. ↳ Offer an alternative, not just a refusal. 5. Be Relentlessly Resourceful ↳ Find the way around the obstacle. ↳ Build your network before you need it. 6. Communicate Clearly ↳ Make your point in one sentence. ↳ Synthesize. Don't just summarize. 7. Sell Your Solutions ↳ Tie every fix to a shared goal. ↳ Show you understand the real problem first. 8. Continuous Learning ↳ Turn every mistake into a playbook. ↳ Go learn outside your comfort zone. 9. Lead Before the Title ↳ Take on real problems nobody assigned you. ↳ Bring others along with you. Titles are given. Respect is earned. Want help building these skills? The MGMT Accelerator turns them into systems, with direct coaching, in 8 live modules over 4 weeks. Our last cohort of 2026 starts Oct 6: https://lnkd.in/e5jW-PZa
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Emmie Chang
A YC launch is no longer the amplification, it's just credibility. Here’s how I think about leveraging a launch—based on studying 500+ launches and announcement videos. The ones that went viral. And the ones that just did 'ok'. Yesterday, two of my friends announced their fundraises via the Y Combinator launch post on LinkedIn. Text + Photo only. No video. Their companies are doing AMAZING things — beautiful products, strong visuals, real mass appeal. The response was great. Strong signal. Tons of congrats. But reach for both companies was less than a recent product launch of an older, not as sexy company. We all know $X Million Fundraising Announcements > Product Launches So what happened? They amplified it with video. Founder on camera. Clear story. Native video attached to the moment. Strong Visual Hook That post traveled way further than it “should have.” Here’s the mistake most companies make: They think the launch post is the amplification. It’s not. Text activates your social graph — followers, investors, peers. Video activates the content graph — discovery, reach, velocity. The algorithm doesn’t amplify importance. It amplifies engagement signals: watch time, replays, presence. And yes — that product launch? They used Yuzu Labs’ software and video setup to do it. Not an agency. Not a one-off shoot. They used the platform to: - Create the launch video (fully non AI) - Tell the story clearly - Keep amplifying it after day one - Use all the assets to continuously create product updates A launch is a short window. Momentum only compounds if you attach the right format to the moment. YC opens the door. Video decides how far it goes. So how far do you want to go? Comment Demo if you want to try our product or get a launch video!
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Elias Benjelloun
What's the biggest opportunity for entrepreneurs to use tech to grow their business today? And why is now such a special time for innovators? The ability to "vibecode" an idea into a Minimum Viable Product (MVP) is leveling the playing field. Historically, Black and Brown founders have been held back by funding gaps. Now, you can quickly build something, test it, and refine your customer base. Don't wait for perfection. Build it, put it out there, and learn. Your competition won't wait for you. #Entrepreneurship #TechInnovation #MVP #BlackFounders #BrownFounders #Startups
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Rohit Bhargava
AI can automate a lot. But it can’t replace the kind of people who bring judgment, leadership, and ownership...and those people are harder than ever to attract. Over the last few year, I’ve spoken to hundreds of founders through The Komo Club, The Startup Playbook Podcast and Playbook Ventures and despite AI transforming how teams operate, one thing keeps coming up: “The biggest barrier to our growth is finding the right people.” People who move fast. People who can think independently. People who raise the standard for everyone around them. AI is replacing tasks, but it’s not replacing leaders, problem-solvers, or culture carriers. Which is why the founders who are scaling fastest right now are the ones building gravity, a pull strong enough that great people want to work with them, even before the brand is big. Tomorrow at 2pm AEDT (11am SGT), we’re running a live session on exactly this: How Great Founders Attract Great People (in the age of AI and leaner teams). We’ve brought together an exceptional panel: Matt Loop - VP & Head of Asia @ Rippling Hassanah Rudd - ex-Global Head of Workforce Planning @ Canva Colin Kleine 🚀 - Co-founder @ SCALERR Hosted by: Olivia Dewi Cinta H. We’ll cover: – How AI is changing what top talent looks for – Why great people follow certain leaders (not logos) – How companies like Canva & Rippling build hiring gravity – What’s universal across APAC vs. what’s different – How founders can attract A-players even without big budgets If you’re thinking about your next 5–10 hires, or how to build a team that can truly scale, this will be a useful hour. 📅 Tomorrow (Tuesday) 18th November ⏰ 2pm AEDT | 11am SGT 🔗 Register here: https://luma.com/dwlj7s9s Hope to see you there.
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Laurel Carpenter
Confession: I help clients clarify their brand positioning. But my own was vague. When anyone asked who I work with, I said "purpose-led founders" for years. It felt true, but as one coach pointed out to me: what does that even mean? I've been on a quest to answer that question — and in my recent conversation with Kate Lewis on her podcast The Resilient Entrepreneur, I talked about where that quest has taken me. We covered: 🌟 How I landed on the "Quiet Activist" as my ideal client profile — and why a LinkedIn post about it got more engagement than anything I'd written in five years of posting 🌟 The lesson I learned from a client project that fell apart (hint: it involved two consultants with competing agendas and a client caught in the middle) 🌟 Why "swim upstream and target startups" is advice that sounds good, but doesn't work if you don't have the connections to back it up 🌟 How surviving the pandemic required a pivot that I'm still proud of As someone who often interviews other people's clients as part of my process, it's a little strange to be the one answering the questions for once. But it was probably good for me. P.S. If you consider yourself a quiet activist — someone who left corporate or nonprofit life to build something better — I'd love to hear from you. I'm doing market research and would love to hear your thoughts. Also, many thanks to Kate for such a fun, engaging and real conversation. If you haven't found The Resilient Entrepreneur yet, check it out.👇
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