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Summary
Matt Gray is a Canadian entrepreneur who built his first company, Bit Maker, trained full-stack software engineers and placed them at companies like Shopify and Facebook. His second venture grew a company brand to 14 million people over 12 years without ever prioritizing his own personal brand. Five years ago, at 30, he reversed that decision and began building his founder-led brand in earnest, eventually growing a combined audience exceeding 3 million across Instagram, X, and LinkedIn while serving more than 17,500 founders through his program Founder OS. The Authenticity Machine workshop, held live on June 23, 2026, teaches the complete system behind how he does it.
The core of the Authenticity Machine is a five-step ritual: record a 30-minute voice memo on a walk using five to ten authenticity questions, transcribe it with a single Claude prompt, edit the raw transcript into a newsletter draft, waterfall that newsletter into 24-plus pieces of platform content, and close each piece with a contextual lead magnet that captures email and phone and routes people toward the offer. The entire input is one voice memo every two weeks. The output is 30 days of content across all platforms, all in the founder's actual voice.
Gray is explicit that the system is anti-AI at the creation stage. He uses Claude only to transcribe and format, never to generate or rewrite. He argues that the wave of AI-generated content has made authentic founder voice more scarce and therefore more valuable, and that founders who can show up raw and real will outperform those producing polished AI slop for as long as this content season lasts, which he estimates at roughly the next three years.
The workshop also covers lead magnet architecture, platform-specific format strategy (Instagram Reels engine, TypeFury for X scheduling, YouTube as newsletter-to-script), the CEO scorecard metrics system, and the philosophy of aligned monetization, building offers you genuinely want to be doing rather than chasing money into work that drains you. The Q&A portion runs nearly as long as the teaching and includes candid discussion of his departure from a company called Open Send, his ikigai framework, and the concept of the whole-body yes as a decision-making filter.
The Authenticity Machine Kit, distributed after the workshop, packages the five voice memo questions, the Claude transcription prompt, the content waterfall map, the anti-AI rules, and the lead loop architecture into a single reference deck built for immediate implementation.
Why This Matters
The Authenticity Machine solves a real operational problem: most founders cannot sustain a content output that requires daily creative decisions. Gray's system reduces the creative decision to one session every two weeks and automates the rest through format and structure, not AI generation. The voice memo as a source document is a genuinely different approach to the content creation bottleneck and the waterfall logic is practical and repeatable.
The anti-AI positioning is more than a marketing stance. Gray's argument is that AI-generated content triggers an unconscious recognition response in readers who have now seen enough of it to identify patterns on sight. At the same time, authentic founder voice is becoming rarer as more operators outsource their content. That gap is a real distribution opportunity for founders willing to do the voice memo work.
The aligned monetization section is the underrated part of the workshop. Gray's decision to walk away from a company with a clear line of sight to hundreds of millions in value because his soul was not in it is not a motivational anecdote. It is a practical argument that compounding only works if you stay in the game long enough, and misaligned work produces dropout risk. The ikigai and whole-body yes frameworks are filtering tools for offer design, not just personal development.
For anyone building a consulting or service business where the founder is the brand, this workshop is a directly applicable operating system. The voice memo ritual, the newsletter-first discipline, and the contextual lead magnet architecture can be installed in a single week and run indefinitely without a team or a content budget.
Key Points
01
One voice memo every two weeks produces 30 days of content
The entire system starts with a 30-to-60-minute walk where the founder records answers to five to ten authenticity questions using the iPhone Voice Memo app. That single recording, transcribed and formatted, becomes 12 or more newsletters, which then waterfall into 70-plus pieces of platform content. The creative input is concentrated into one session; distribution is handled by format and structure.
02
AI transcribes. The founder writes.
Gray uses Claude strictly to transcribe the voice memo into a formatted document, with questions in bold and answers below. He does not ask Claude to rewrite, polish, generate hooks, or add anything. The rule is explicit: Claude formats your voice, it does not replace it. Publishing AI-generated content under a founder's name is what he calls slop, and audiences can now identify it on sight.
03
The newsletter is the only asset you fully own
Every social platform is rented. The newsletter is the anchor of the waterfall because it is the one piece the founder controls regardless of algorithm changes. Gray has published a newsletter to nearly 250,000 subscribers daily, and traces virtually all Founder OS revenue back to that email list. Building social audiences without building a newsletter is building on someone else's land.
04
72 percent of Founder OS members cited Matt's energy and vibe as the reason they joined
When Gray surveyed members on why they chose Founder OS over competing programs, the answer was almost never a feature, a price point, or a specific result. It was how he showed up in his content. Founder energy is the real competitive advantage in a crowded market. Systems can be copied; authentic resonance cannot.
05
Each platform needs two or three core formats, not endless variety
Gray analyzed top creators across YouTube, Instagram, and X and found that all of them succeed on two or three repeatable formats. He applies the same logic internally: for Instagram he runs carousels and iPhone-filmed Reels; for YouTube he uses how-to, systems, and level-based videos; for X he uses short quotes from his newsletter. Identifying your three formats and running them is more effective than chasing every trend.
06
Contextual lead magnets convert because they match the content that delivered them
Gray's lead magnet architecture ties every piece of content to a DM keyword (RITUAL, CONTENT, ARCHITECT, REDUCE) that triggers delivery of a relevant free resource. The lead magnet captures email and phone number, enters the person into a seven-day nurture sequence, and routes them toward a sales call or a direct join link. The contextual match is what makes conversion happen without hard selling.
07
Raw content performs better than polished content in the current content season
Gray's best-performing LinkedIn posts are hand-drawn notebook images. His top-performing Instagram Reels are iPhone videos shot on a $20 tripod. The audience is unconsciously trained to scroll past content that looks like an ad. Imperfect, high-signal content stops the scroll because it reads as real. He calls the current window the Raw Real Rant era and estimates it lasting the next three years.
08
The whole-body yes is a decision filter for offers and opportunities
Gray left Open Send, a company with a clear path to hundreds of millions in value, because his head was a yes but his heart and soul were not. His therapist introduced the whole-body yes concept: all three centers (mind, heart, gut) have to be aligned before committing. He applies this to offer design, arguing that misaligned offers produce dropout risk and kill the compounding that makes long-term business success possible.
09
People do not know what most founders do, and that is why conversion is low
Gray argues that the number one reason founders fail to monetize their content is not lack of audience, bad copy, or weak offers. It is that their audience has no idea what they actually do or how they can help. Every lead magnet, every post, and every newsletter should make the offer clear within minutes of someone discovering the founder. Obscuring the offer in favor of pure value delivery kills conversion.
10
Compounding only works if you stay in the game
A business that does 100K in year one and doubles annually reaches 12 million in year seven. But only if the founder does not quit. Gray's point is that aligned monetization, building something you genuinely want to do for the next decade, is not just a personal development principle. It is a business strategy because the only way compounding works is sustained participation over time.
11
Batch content production in single sessions eliminates the daily decision burden
Gray films 45 Instagram Reels in a single three-hour morning session, giving him 45 days of video content in one go. He records his voice memo in one 30-to-60-minute walk. He schedules X content through TypeFury in batches from his newsletter. The goal is to eliminate the daily choice of what to post, which is where most founders burn out. Production is batched; publishing is distributed.
12
The best copywriting sounds exactly like you speak
Gray studied 20 copywriting books, from David Ogilvy to Gary Halbert to Joseph Sugarman. The consistent principle across all of them is that great copy reads like natural speech. That is precisely why the voice memo system produces better copy than sitting at a keyboard: the founder is literally speaking, and the transcript captures that register. Transcription plus light editing is a faster path to compelling copy than drafting from scratch.
Quotable Moments
Quotes extracted from workshop transcript. Verify against original recording before republishing.Matt Gray
We live in a day and age where so many people are just getting lost in slop. We want to find a way to translate that resonance through our content.
Why It Works
Frames the entire workshop thesis in two sentences. The slop-versus-resonance contrast gives founders an immediate self-assessment question and positions the authenticity system as a competitive move rather than a creative preference.
Matt Gray
My biggest regret as a founder, if I'm being open with you guys, is not sticking with building my brand sooner. The doors it's opened, opportunities, cash flow, clients -- it's just insane.
Why It Works
Opens with genuine vulnerability from someone with a verified track record. The regret frame is more persuasive than a success claim because it acknowledges the cost of delay rather than simply promising upside.
Matt Gray
Your energy, your soul, your resonance truly is like your competitive advantage as a founder.
Why It Works
Reframes personal brand from vanity project to business asset in nine words. The word competitive advantage lands differently than authenticity or purpose, which often read as soft. This makes the same idea actionable for operators.
Matt Gray
The best way to just get the soul out of you is simply just to have some key questions and then just voice your answers on a walk.
Why It Works
The phrase get the soul out of you is unusually direct. It makes the creative problem visceral rather than procedural. Pairing it with the practical instruction (questions, walk) prevents it from floating into abstraction.
Matt Gray
I never realized, because I thought all founders had this kind of documentation. I thought it was normal. It became obvious to me through my coach that this was not normal.
Why It Works
The moment where he discovers his systems are unusual is the origin story of Founder OS told honestly. The self-deprecating blindspot, not knowing his edge was an edge, makes the insight credible and relatable for founders who may be sitting on similar undiscovered advantages.
Matt Gray
What I found after building online businesses for 16 years is that more raw still performs better. Your brain is almost subconsciously trained just to scroll right through polished content.
Why It Works
Delivers a counter-intuitive, experience-backed observation that directly contradicts what most marketing training tells founders to produce. The neurological framing (subconsciously trained) makes it harder to dismiss as a stylistic preference.
Concepts and Ideas
Core Framework
The Authenticity Machine
The five-step content operating system: authenticity questions to surface genuine ideas, voice memo to capture them in the founder's actual voice, Claude transcription to format the raw audio, newsletter editing to produce the primary long-form asset, and content waterfall to distribute across platforms. The system is designed to be run by a solo founder without a content team, producing output that is indistinguishable from live conversation because it literally started as one.
The Content Waterfall
The principle that one piece of long-form content at the top of the stack generates all downstream content. One voice memo becomes 12 newsletters. Each newsletter becomes one YouTube video, six Instagram Reels, and a set of X posts and LinkedIn captions. The newsletter is always the top of the waterfall because it is the only format the founder owns outright. Social content is derivative; the newsletter is primary.
The Creator Game vs. The Founder Game
Gray distinguishes between two content modes. The creator game requires posting every day, mastering seven hook formulas, chasing algorithms across platforms, and treating views as the business itself, leading to burnout by month three. The founder game requires a 30-minute voice memo every two weeks, speaking in your real voice, picking one platform your dream client actually uses, and treating views as a lead source. The founder game is calm, profitable, and compounds. The creator game is expensive and unsustainable for operators running actual businesses.
Content Principles
Soul Not Slop
The central quality filter for all content decisions. Slop is content generated or heavily reworked by AI tools that carries recognizable AI sentence patterns, predictable structure, and an absence of specific personal detail. Soul is content that could only have come from the specific founder saying it, referencing real experiences, specific books, named people, and genuine opinions. Gray argues that audiences can now detect slop within seconds and that it actively erodes trust in a way that empty posts do not.
The Five Anti-AI Rules
The operating rules that keep content authentic: never let Claude write for you (Claude transcribes, you write); voice memo first so you speak before any text exists; polish, do not rewrite (if you are overthinking paragraphs, the voice is already gone); read it aloud before publishing because the ear catches what the eye misses; and ban the AI tells, specifically no em dashes, no tired phrases, and no sentence structures that signal machine generation. These rules protect the voice once it has been captured.
The Raw Real Rant Era
Gray's name for the current content season, which he estimates lasting approximately three years. The defining characteristic is that unpolished, high-signal, founder-narrated content consistently outperforms highly produced content because audiences have become pattern-sensitive to production values that signal advertising. A hand-drawn notebook image on LinkedIn, an iPhone video on a $20 tripod, a photo from a hike in Bali over a newsletter paragraph -- these perform better than designed graphics not despite their rawness but because of it.
The Three-Format Rule
Successful creators on any platform succeed by mastering two to three repeatable formats and running them consistently, not by experimenting with every format type. Gray cites Ryan Trahan (three challenge formats), Dan Coe (how-to and step-by-step), and Dan Martell (99% of people + tried X tools) as examples. His own formats are how-to, systems content, and level-based frameworks. The practical instruction is to identify the intersection of what excites you, what your dream clients want from you, and what performs well on the platform, then commit to two or three formats in that zone.
Monetization Architecture
Contextual Lead Magnets
Lead magnets that are directly relevant to the content piece that delivered them. A post about the content ritual triggers a DM keyword (RITUAL) that delivers the content ritual template. A post about personal branding triggers the brand template download. The contextual match is what produces the conversion: someone who just read about the topic is maximally interested in the associated resource at that exact moment. Gray has built 154 lead magnets over four years and uses them as the primary list-building mechanism across all platforms.
The Seamless Slippery Slope
The conversion architecture where each step in the audience journey is the natural next thing a person who liked the last step would want. Social content leads to a DM keyword. The keyword delivers a lead magnet. The lead magnet captures email and phone and surfaces the offer. The email nurture sequence routes to a call or a direct join link. At no point is the person asked to make a large leap. Each transition is small and obvious enough that it happens without friction or hard selling. Gray explicitly mentions that with a well-designed slippery slope, the offer can close directly from a Google Doc without a sales team.
Aligned Monetization
The principle that sustainable business revenue requires genuine alignment between what you are building, what you enjoy doing, and what your market needs. Gray's departure from Open Send, a company with a clear path to hundreds of millions in value, illustrates the principle in the negative: an opportunity can be financially obvious and emotionally wrong. He argues that compounding only works if the founder stays in the game long enough, and misaligned work creates dropout risk that forfeits the compounding. Choosing a smaller, more aligned opportunity and staying with it for a decade is the superior financial strategy.
Decision Frameworks
The Whole-Body Yes
A decision filter Gray learned from his therapist, Jenna. A genuine yes requires alignment across three centers: the mind (rational, financial, strategic), the heart (emotional, relational, values-based), and the gut or soul (purpose, deep desire, identity). A yes from only one or two centers is not a whole-body yes. Decisions that fail this filter tend to produce sustained internal tension that eventually surfaces as burnout, resentment, or exit. Gray uses it for offer design, hiring, partnerships, and any major direction change.
The Ikigai Operating System
Gray applies the Japanese ikigai concept (the intersection of what you love, what you are good at, what the world needs, and what you can be paid for) as a running optimization target. He reviews his ikigai quarterly in his personal board meeting and asks where his current work sits relative to the center. His stated calling includes building an A-team, beautifully designed work, traveling and working globally, coaching founders, writing, building distribution from day one, automating tasks, and building communities. He treats entrepreneurship as a soulful journey and optimizes business decisions accordingly.
Implementation
Steps derived from workshop content. Adapt to your specific context before applying.Select five to ten authenticity questions and load them on your phone
Use the 20 Authenticity Questions worksheet from the kit, or choose from the five voice memo questions in the handout. Pick questions that genuinely unsettle you a little, ones that surface opinions you have not said publicly, stories you have softened, or standards you have let slip. Load them into a Google Doc on your phone so they are accessible during the walk. Do not script answers in advance.
Record a 30-to-60-minute voice memo on a walk
Use the iPhone Voice Memo app or equivalent. Go outside, move, and answer each question by speaking into the phone. The goal is 30 minutes of continuous voice, aiming for specificity: not just what you think but why, and how. Specific examples, named books, real numbers, actual stories. Do not stop to edit or second-guess phrasing. The rawer the better. Record bi-weekly, not daily.
Transcribe and format using the Claude prompt
AirDrop or transfer the voice memo to your computer. Open Claude and paste the following prompt verbatim: "Take the voice note here and put it into a docx with the questions in larger font and bold and then my responses below formatted nicely as if it were in a newsletter-ready format in a smaller and not bold font. Do not edit my words, simply take them and ensure they are formatted correctly." Attach the audio file. The output is a newsletter-ready draft in your own words.
Edit the transcript into your newsletter
Open the formatted document and edit for flow, not for polish. Keep paragraphs short. Bold phrases that stand out. Add one or two relevant images or memes that feel like you. Read the draft aloud before publishing -- the ear catches what the eye misses. Do not let the voice disappear into rewriting. If you find yourself redrafting sentences from scratch, you have gone too far. One pass is enough.
Waterfall the newsletter to your core platforms
Identify your two primary platforms and the two or three repeatable formats you will run on each. For writing-first platforms (X, LinkedIn), take quotes and paragraphs from the newsletter directly and post them. For X, batch-schedule using TypeFury. For YouTube, use the newsletter as the script outline and add three to five minutes per section. For Instagram Reels, identify four to six hooks from the newsletter and film one-take videos. For carousels, reformat the key argument as a visual sequence.
Assign a DM keyword and contextual lead magnet to every post
For each piece of content, identify a single DM keyword that is relevant to the topic (e.g., RITUAL for content system posts, BRAND for positioning posts). Build a corresponding lead magnet, which can be a Google Doc, Google Sheet, or Google Slides template, that delivers genuine value and includes a brief mention of your core offer within the first three pages. The lead magnet captures email and phone and routes into your nurture sequence.
Identify your two or three core formats per platform and commit
Stop experimenting with every content format and identify the intersection of what you enjoy creating, what your dream clients respond to, and what performs on your primary platform. Name two or three specific formats. For YouTube, these might be how-to, systems explainer, and case study. For Instagram, carousels and Reels. Run those formats exclusively for 90 days before evaluating. Consistency within a format is what builds recognition.
Run a monthly personal board meeting
Set aside time monthly to review personal goals, business goals, what went well, what did not, and what you learned. Gray has done this every month for years and attributes his clarity on Founder OS to the ongoing reflection habit. Specifically evaluate whether your current work scores well against your ikigai criteria: does it feel like play, is it aligned with what your best clients want, and is there a clear path to the financial outcomes you are targeting?
Apply the whole-body yes filter to offer and opportunity decisions
Before committing to a new offer, partnership, or business direction, check all three centers. Mind: does this make rational and financial sense? Heart: do you genuinely want to be doing this? Soul or gut: does it feel aligned with who you are and what you are here to build? Two out of three is not enough. A financial yes with an emotional no is Open Send. The misaligned opportunity costs you the compounding from the aligned one you did not take.
Make the offer visible inside every lead magnet within the first three pages
Most founders build audiences where nobody knows what they do. Every lead magnet you distribute is an opportunity to fix that. Within the first three pages, briefly introduce your core offer and link to it. This serves two purposes: people who are ready convert immediately without a call, and people who are not ready now understand exactly what you do and where to go when they are. Gray drives conversions directly from Google Docs without a sales team by doing this consistently.
Tools and Resources
Mentioned Resources
| Resource | Description |
|---|---|
| Founder OS | Matt Gray's founder operating system program covering brand and content, monetization and offers, systems and operations, and founder development. Includes 40-plus live sessions per month, C-suite advisory access, and a private community. |
| Claude (Anthropic) | Used exclusively for transcribing and formatting voice memos into newsletter-ready documents. Gray provides a specific prompt verbatim: format the transcript question-by-question, bold questions, smaller text for answers, no editing of the founder's words. |
| iPhone Voice Memo App | Gray's preferred tool for recording the bi-weekly voice memo content ritual. Free, native to iPhone, and allows immediate AirDrop transfer to desktop for transcription. |
| TypeFury (Typefully) | Used to batch-schedule X content. Gray loads 45-plus days of X posts pulled from newsletter content and schedules them in a single session. |
| Google Workspace (Docs, Slides, Sheets) | Gray explicitly rejects Notion in favour of Google Workspace for all operating systems, lead magnets, platform SOPs, and the IG Reels engine. Prefers simplicity and accessibility over interconnected database complexity. |
| Figma | Used to design Instagram carousel templates. Gray mentions a book-style carousel format designed in Figma that serves as one of his two core Instagram formats. |
| The Untethered Soul by Michael A. Singer | Referenced in the workshop as a current read that Gray recommends for founders dealing with the tension between hustle and rest. He also mentions The Power of Now and Zen Mind, Beginner's Mind as complementary reads. |
| David Ogilvy -- Ogilvy on Advertising | Gray cites Ogilvy as part of the copywriting canon he studied. Core takeaway: the best copywriting is based on thorough research into the consumer and speaks directly to a specific benefit. Write like you speak. |
| Gary Halbert -- The Gary Halbert Letter | Gray cites Halbert as a foundational copywriting influence. Halbert's archive at thegaryhalbertletter.com contains his newsletters and the Boron Letters, which cover direct response, storytelling, and writing in a natural voice. |
| Joseph Sugarman -- The Adweek Copywriting Handbook | Gray cites Sugarman alongside Ogilvy and Halbert as a primary copywriting reference. Sugarman's handbook covers psychological triggers, the slippery slope opening, and the principle that every sentence's only job is to get the reader to read the next one. |
Suggested Resources
| Resource | Description |
|---|---|
| Beehiiv | Newsletter platform widely used by creator-founders. Supports subscriber segmentation, referral programs, and monetization. A practical starting point for building the newsletter-first foundation that Gray's waterfall depends on. |
| ManyChat | The standard tool for automating Instagram DM keyword delivery. When a follower comments a keyword on a post, ManyChat detects it and sends the lead magnet automatically, capturing email and routing into the nurture sequence. |
| Descript | Audio and video editing tool that transcribes recordings automatically. An alternative to the Claude transcription method, with built-in editor and studio sound cleanup useful for founders moving toward podcast or YouTube production. |
| James Clear -- Atomic Habits | Gray mentions James Clear as a mentor who encouraged him to publish more frequently. Atomic Habits provides the identity-based habit framework that underpins the bi-weekly ritual discipline Gray describes. |
| Nielsen Norman Group -- F-Pattern Reading | Research on how people actually read online content. Useful for newsletter formatting decisions: short paragraphs, front-loaded value, bold key phrases, and scannable structure all align with observed reading behavior. |
Source Material
Part 1 -- 0:00 to 1:30:00
00:00
You want to implement this in your workflow today. Then we're going to get into how a 30 minute voice memo becomes 30 days of content for me, and then I'm going to show you some examples of me going and then waterfalling that content to take the voice memo that I make simply from recording on my phone through an app that all of you guys have and then going and turning that into newsletters and then into all the content you see from me on things like Instagram carousels on Instagram stories across X and LinkedIn where I've built a combined audience of now over 3 million people, hence probably how many of you found this workshop here today. And then we're going to talk a little bit about how I'm actually converting then all those eyeballs into clients, which I know is super important to you guys, because none of you guys want to be spinning your tires making content for nothing, right? You guys are running businesses, you're founders, you're looking to build something impactful, you want to monetize, inevitably, which I understand, and so I'm going to show you guys how I think about that, which I think rather unconventional, and we're going to get to that in the fifth step towards the end of the workshop today, you're going to want to stay tuned and get into why most founders I think are creating 50x more content than they really need to be making.
04:32
This is the exact content ritual that I've been doing now once a month produces generally over 30 days of content for me for all platforms in my voice. This is anti AI. Now let's rewind for a second and show you a little bit about kind of how I got to this point in my journey. I was 21, I started my first company, Bit Maker, and in that company we trained full stack software engineers, got them jobs at tech companies like Shopify, Facebook, Google, and it was a wild ride. There's one point in that business that I got a knock on the front door of that business, it was two enforcement agents from the Canadian government. They thought that I was operating a university when really what this was was just a technology boot camp. We're not giving people grades, we're getting them jobs, and 95% of the graduates from this intensive in-person boot camp I had started were getting jobs within one month of graduating, so I knew that I had to do something, because these guys told us that we were going to have to shut down the business in one month. Ended up that night collecting every single email of different folks that I had gone and come across over the previous two years building the business -- venture capitalists, software engineers, different mentors, people in the Toronto and Canadian tech community. I stayed up for 16 hours, no sleep, emailed every single person on that list, to the tune of over 3200 people. For 24 hours, the story of the government trying to shut down this business called Bit Maker was trending across Twitter in Canada and the US. One week later, on a phone call with the Minister of Training, Colleges and Universities in Canada. 48 hours after that call, one week after being threatened to be shut down, we were back in business.
09:12
So, what I'm going to show you guys now is how to go and get over the content hamster wheel, and let's get into the five pieces now of this authenticity machine. Step one: the five authenticity questions. The basis of what we're trying to do here is tap into our soul, not slop. We live in a day and age, right, where so many people are just coding everything or Chat GPT, all the stuff, and you and I have seen that slop everywhere, right? It shows up in those common sentence patterns that you read a post and you go within seconds, "Oh, this isn't actually that human." You have those people that show up in a way that feels super genuine, feels resonant, makes you feel some type of way. It's those sorts of people that inevitably you want to work with. I've gone and surveyed folks that joined Founder OS. 72% of the people that join said it was your energy, your vibe, it got me to join Founder OS. When I go, and I've worked with over 17,000 founders over the last five years, same pattern shows up in their businesses and their brands as well. Inevitably, our founder energy is the most resonant, the most contagious element that we have -- your energy, right, your soul, your resonance truly is like your competitive advantage as a founder.
14:06
What I will typically do is put these questions on my phone. I'll typically have a Google Doc with questions on them, and off I go on my walk, right? And so what I'm typically then going to do is pick a question. So, what I want you guys to do right now is we're going to run through this as a demo. Go and pick one question here. All right, let's just say, you know, I picked question two. Right, where in the business are my standards too low right now? We're now going to go and actually complete the voice memo content ritual. If you have an iPhone, which is what I use -- I'm just going to type in Voice Memo. I've got this voice memo app that pops up. This is exactly how I've been creating my content for social, my newsletter -- it's also how I've been putting some of the final touches on my book. I find when I get stuck, right, what I'd rather do is just get out of the room, right, get outside, go for a walk, and just start then answering the question or thinking through it and vocalizing it to the voice memo app.
17:51
The more we can just get the voice out of us, the more content obviously we're going to have, and so when I'm thinking about going and recording my voice, guys, one thing that I used to get tripped up on with my content is that for many of you the core kind of content you're looking to create is educational content, and one of the core pieces of educational content is being specific, so as you're going and talking through your answers to these questions, the core thing we want to do is get into the why and the how to do things, so as you're answering a question like where did you simplify your business, the more specific you can be there, and the more that you get into specifically how you simplified it versus just some surface level stuff, the more attractive, the more resonant your content is going to be, because it just feels super raw and real, and it has depth to it.
26:12
Have a writer doing it? No. Fancy AI I'm using to write that? No. It's really my voice. I've probably gone through 20 different copywriting books from the best of the best -- David Ogilvy, Gary Halbert, Joseph Sugarman -- and the core things they'll tell you in these books is that the best copywriting is: you write like you speak. That's interesting, right, and that's always fascinated me. And to actually just speak is exactly what the voice memo content ritual is all about.
30:35
That document I just showed you becomes over 25 newsletters. I've been publishing newsletters daily. What I'm simply doing is just making sure it's formatted nicely, right, trying to keep the paragraphs pretty tight, maybe bolding aspects that stand out, maybe adding a meme or two, just to keep it light, bit fun. I'm simply going and taking my raw voice, not here to go and polish it too much, want it to really just sound like me, very much trying to just have a conversation with the reader. What it creates, right? If society is moving more towards slop, do I go and be the anti that, and move way more towards soul?
35:24
I found this more easy, fun, so much more impactful too, in terms of just the kind of people that I'm attracting to my businesses, because people can really feel me through this content. I think that that's something that is missing right now. Right, so many people are just getting lost in slop. I was seeing one of my favorite creators the other day was sharing a podcast he had recently recorded with a big name. I could tell in the carousel that he had made that every single piece of copy was from Chat GPT with the same old patterns. It kind of turned me off, to be honest, and I won't look at that guy's content anymore.
39:27
When we look at this, right, this is an example of creating around 40 carousels, and then what I'm doing then is going and editing all these, so I've come up with all of the hooks for it, and then it's simply going and backfilling my voice and what I've said around these things into this format, so it's no AI-generated stuff, it's not any net new content or new words, it's just taking my words and putting them into these structures. So in that sense, again, that voice from the pillar piece of newsletter content gets translated to all this other content. Many of you here, who here is making short form video, or looking to make short form video across their different platforms?
44:14
This is the IG reels engine, and I kind of approach this a bit like a sport, right? When I go and I record in one go in a given morning, my goal is to get, say, 45 or so done in one three hour go, so that I then have my content for the next sort of 45 days all scheduled, so it's batched on one Friday morning, and then I'm good to go. The same sort of pattern I showed you with the voice memo ritual, right, where I'm able to record my voice for 30 minutes to an hour, and then that becomes my newsletters for the next 30 days or so.
49:05
When we focus the content waterfall on having a pillar piece of long form content, for most of you, I think that should be a newsletter that's taken from your voice memo. Voice memo, newsletter, and then if you're more writing first, you're likely going on platforms like X and LinkedIn. You can use TypeFury to schedule your X content. On LinkedIn, the beautiful thing is you can more or less just take a bunch of the long form writing in a newsletter and just put that onto LinkedIn and then add just probably a high value image to it and ship it. If you're going on platforms like YouTube or Instagram -- for YouTube, a lot of what's going on here is I'm simply just taking a newsletter subject that I've talked about and using that newsletter as the outline for a YouTube video.
53:53
Essentially, when people go and say, comment on a post, "PRODUCER," I'm going to go and send people a core lead magnet for that given post, so we go and we look at my content -- these are examples of over the last four years, I've made about 154 different lead magnets. So essentially, when people go and say comment on a post, I'm going to go and give them this magnet, right, that gives them a lot of value, allows them to go deeper, but in exchange for this lead magnet, folks are leaving their email and their phone number. So I'm essentially able to drive people from the audience, say on Instagram, to the DMs, and in exchange for their email and phone number, give them this lead magnet. Then I'm able to go and market to folks in my newsletter and drive them to Founder OS if it's right for them.
58:15
Showing you guys here, right, is like this framework that's honestly been insanely transformative for me, right, helping me go and take my real thoughts, my real voice, translate that to my newsletter, bring that to my carousels, my stories, YouTube videos, you name it, and be able to create that resonance online, right, create a brand that people gravitate towards, that's magnetic. Founders need support. They need actual help from someone that's been where they're trying to go. They don't need to make all the mistakes that are common when you're building these kind of founder-led brands. So that's exactly what I built with Founder OS.
1:06:36
We have 20 questions to help you with your own authentic version, and it looks like a lot of you guys are into this. I've included here the Claude prompt as well, so you're easily able to then take that voice memo you record and then use Claude to then transcribe your voice, like we showed you, right, and then move that to your newsletter, and then it kind of goes through the steps as well that we want to take, then waterfalling that content. Okay, from there I actually described to you how we think about contextual lead magnets, some of the anti-AI rules that I think are really important, and we summarized all of that for you there.
1:10:45
Question from the chat: I feel that due to the saturation of the yapping format and the lead magnet strategy, it's lost its efficacy in driving reach or sales, respectively. Do you think there is a way to implement the strategy into a different format? Well, guys, I think as we're thinking about creating content, one approach I think a lot about is you don't need that many different formats when you're making content. Oftentimes what you're trying to do is just find your core few formats. For YouTube, as an example, you just need like three formats to be successful. Ryan Trahan has this format where he's like, I tried every Airbnb category -- I survived 50 hours. He's just coming back to those three proven formats. Dan Coe's videos are how-to and step-by-step. Dan Martell has most people and then tried 500 AI tools. When you look at my channel -- how-to videos, building systems, and level-based. Block out so much of the noise in terms of all of these different things you could make. Oftentimes, when I'm thinking about the core of my content, it's the intersection of what excites me, what are my best customers looking for from me, and what is working well across my social media.
1:24:51
Kenisha is saying, I love that you don't feel the need to design your lead magnets in Canva. Guys, like the weird thing I found after building online businesses for like 16 years is that more raw still more are generally consumed by people. You have probably seen it, right -- maybe you've seen like a really beautifully designed Instagram Reel, so well done that it almost felt like a commercial or an ad. Your brain's almost subconsciously trained just to scroll right through it. On the other side of it, you may see me just in a raw video show my notebook and an image on it, kind of just be talking real like I am with you here. You stop because it's like, oh shit, this just feels like an off-the-cuff real thing. I know that on LinkedIn, some of our best content we've ever posted are literal images that I've drawn in my notebook -- just things like these kinds of images where it's just a bunch of value in a post, and it's me just going and drawing that with my own pen and paper. That forms best. It's not some insane graphic. It's just paper. It's 100,000 impressions, right. And this is what's helped grow our LinkedIn to over 918,000 organic followers, with 500,000 organic impressions a week, without spending a dime on ads.
Part 2 -- 1:30:00 to end of workshop
1:30:00
Do you have all your systems interconnected digitally, like with Notion or something, for example, or is it better to have independent processes? Yeah, so we have like a social media manager that would then have the different independent systems, right, for say YouTube, and how we do things there, Instagram, X, LinkedIn. But in terms of like some crazy interconnectedness, the only main thing that's interconnected is the content waterfall, right? This idea of taking that newsletter, like I showed you, and then waterfalling that to the platforms. But there's not anything crazy. I hate Notion, by the way. So I'm just going to put that out there. I think it's overly complex. Too many people are lost in Notion Docs on Notion Docs. I'm simply a Google Workspace kind of guy, and no crazy Notion systems for me. I don't like it. I find it confusing. I think too many people using that are overcomplicating their content operation.
1:38:28
Helen's asking: Matt, how did you develop the authenticity questions? Well, I think first off, like the authenticity questions are just a bunch of questions that I've kind of gone and gathered over the last while. I actually just shared an authenticity worksheet with you guys. You know, these sorts of questions -- the ones I just shared -- are just kind of questions that, I don't know, when I've gone about my life, these are just questions that feel like they stand out to me and help me kind of open up. Being vulnerable, being open on social media -- I know it probably doesn't come naturally to you, it doesn't really come naturally to me either, if I'm being open. And so that's why I find having really good questions is key, and that's also why the voice memo system is also really helpful to me as well, because it allows me to just like open up. I like to walk, because it just creates this forward momentum. I'm looking at nature, looking at the sky, and I'm just trying to just let it flow.
1:42:50
When I think about the album only I can make, I think it's being open about this tension that we exist in as founders -- this idea that one personality that we may have wants to lock in and build and create our dreams and is obsessed, but there's also this kind of personality that we have as founders that wants to chill, wants to rest, wants to escape into nature for three days and unplug and leave our phone behind and just be in expansive adventures with our friends and just enjoy life and screw work, and I don't think it's that one or the other is right or wrong. I think it's that both of these worlds can exist at the same time. You can be both an obsessive successful founder and want to screw off into nature or want to sleep in on a Sunday or take a week or take weekends off -- both of these things can be true. So if I was to say the album only I can make, the theme of the album I'm currently making is embracing the tension.
1:44:00
Something to share on core offer and positioning, on guaranteed alignment. I think overall is like making sure that your content, your core offer, and your delivery are all aligned. Many people have a scarcity mindset when they're building, right? They think that they have to do something to be successful. And I think the bigger question you want to ask yourself is, what would I do if I knew I would be successful? Six years ago, I was working on a business called Open Send with two other friends of mine. The business had a clear line of sight to be worth hundreds of millions of dollars. But for about those first five months building this business, I was thinking in my head, do I really want to be doing this? Is this really what I'm supposed to be doing, building an identity resolution software? My mind kept on going and saying, yeah, Matt, you're going to make a boatload of money off this thing. But my heart, my soul -- oh man, I feel like I'm just selling my soul doing this. I wrestled with this for about three months, and what I ended up realizing after talking with a coach and then in a therapy session -- my therapist, Jenna -- she said, Matt, we call this the whole-body yes. The whole-body yes is when your mind is telling you yes, your heart is telling you yes, your soul is saying yes. You have yes across those three kind of centers. In my mind, working on Open Send -- my head, sure, I was going to make a bunch of money off it. But in my heart and soul, I was like, hell no, this is not it.
1:48:30
When I think about offer and positioning, right, I think it's sure making an irresistible offer, sure, nailing your positioning, having the right structure to it, making sure it's clear and compelling. I also think it's about making sure it's truly aligned and resonates with you, and something that you actually want to go put out there to the world. That's my quick take. Oftentimes, crafting an offer really is that simple. On one side, energetically, I think you want to be putting something out there to the world that you can see yourself doing the next decade versus selling something that feels like you're selling your soul. And at the same time, want to just keep it simple. Oftentimes what I see is founders put together these really complex offers, and it's impossible for anyone to understand what the heck it is.
1:53:04
Gabriel is asking: how did it click to you at the core of it? Well, I do a board meeting, as I've talked about, every single month. So this is like my June 2026 board meeting. And so every single month I do this meeting with myself, where I'm checking in on what are my personal goals, my business goals, and then I'm doing a reflection on what went well, what didn't go well, and what did I learn. And for me it clicked when I started thinking about, okay, well, what is my 10 year vision, right? And I really wanted to go and create the greatest founder community and experience that's ever existed. One of the ways it clicked, Gabriella, was I was working with a coach, and coach kind of mirrored to me that my systems and what I was sharing with him on the call were really unique and different, well organized, simple to understand, well documented. He had never seen that before from anyone, and this is someone that worked with some of the most successful founders out there. He went from Casey Neistat to Sean Perry, and a bunch of other legends. I didn't realize, because I thought all founders had this kind of documentation. All founders had these levels of systems. I thought it was normal. It became obvious to me through my coach, Ryan, that this was not normal. These systems are actually really different. It was actually from having this coach that I learned that the systems I was making were really valuable, and it encouraged me to go and make more systems and start to think about sharing those systems more.
1:57:35
The stuff that I work on every single day, every week, every year is stuff that I would do even if I was retired, right, because I could retire, but this is the kind of stuff I love to do. And I think maybe you can even tell that, right? This workshop was probably scheduled for 60 minutes, and here we are 126 minutes into it, and still having a good time. In life you want to find those things that you lose track of time doing, kind of like me right now on this workshop, helping you guys. When I got started, I told myself that the business must feel like play -- no worrying, because worrying is a disease. I must be removed from any annoying task. Do things that are fun. There has to be a path to getting into $10 million profit a year. I need to make something that people want. I need to control 98% of it, thereby no co-founders. I need to love the problem, love the customer, and have distribution product fit. I'm going to make something that's true to these criteria, and so it was getting clear on those criteria.
2:01:49
So I kind of told myself that I was going to just go in every single week, every month, just optimize my ikigai and build a life, build a business around that, so that every day I was doing stuff that set my soul on fire, that I love, because I think one of my core purposes of being here on earth is to unlock my full potential and unlock the potential of millions of other high performers, creative folks, builders, dreamers, just like you guys, so I owe it to myself to lean into my calling, and I owe it to you guys to develop a level of mastery in these things that set me apart, so that I can evolve as a human, and hopefully help many of you guys also level up in some small way.
2:06:23
Well, guys, this has been a lot of fun. We've covered a lot here. I appreciate you guys being a part of this. Yeah, we got some kangaroos to go see on the beach now, and so appreciate you guys all being here. You guys should definitely go and check your emails over the next three days, right? You're going to get the recording, you're going to get the authenticity kit again, right, and some other good stuff. Thank you so much for your time, guys. Means a lot. I'll see you guys on the inside. Love y'all.
AI Implementation Prompt
This prompt was generated from workshop content. Copy and paste into a new AI session to work with this material.AI Implementation Prompt
CONTEXT This prompt is based on The Authenticity Machine, a live workshop hosted by Matt Gray of Founder OS on June 23, 2026. Matt Gray is a Canadian entrepreneur who built his first company, Bit Maker, trained full-stack software engineers, and placed them at companies like Shopify, Facebook, and Google. He grew a second company brand to 14 million people over 12 years without building a personal brand, then reversed course at age 30 and has since built a combined audience exceeding 3 million across Instagram, X, and LinkedIn while serving more than 17,500 founders through his program Founder OS. The Authenticity Machine is a five-step content operating system that converts a 30-minute voice memo recorded on a walk into 30 days of platform content across newsletters, YouTube, Instagram, X, and LinkedIn, all in the founder's original voice without AI generation or a content team. The system is explicitly anti-AI at the creation stage: Claude and similar tools are used only to transcribe and format, never to write or rewrite. The five steps are: (1) select five to ten authenticity questions and record a voice memo on a walk, (2) transcribe using a specific Claude formatting prompt, (3) edit the transcript lightly into a newsletter draft, (4) waterfall the newsletter across platform-specific formats, and (5) close every piece of content with a contextual lead magnet that captures email and phone and routes into a nurture sequence and offer. KEY PRINCIPLES 1. Soul not slop. AI-generated content is now identifiable on sight. Authentic founder voice is becoming scarce and therefore more valuable. Every piece of content should be distinguishable as coming from one specific person. 2. Voice memo first. Speaking generates content faster and more authentically than writing. The voice memo is not a draft -- it is the primary creative input. Everything else is formatting and distribution. 3. Newsletter as the anchor. Every social platform is rented. The newsletter is the only content asset the founder fully owns. Build the newsletter first; all other formats are downstream. 4. The content waterfall. One voice memo produces 12-plus newsletters. Each newsletter produces one YouTube video, six Instagram Reels, and a set of X and LinkedIn posts. The creative decision happens once every two weeks. 5. Contextual lead magnets. Lead magnets convert when they match the content that delivered them. Every post needs a keyword that triggers delivery of a directly relevant resource. The resource captures email and phone and routes into a nurture sequence. 6. Two or three core formats per platform. Successful creators succeed by mastering a small number of repeatable formats, not by chasing every format or trend. Identify the formats that sit at the intersection of what excites you, what your dream clients want, and what performs on your platform. 7. Raw outperforms polished in the current content season. Audiences are trained to scroll past high-production content that reads as advertising. Unpolished, high-signal content stops the scroll because it reads as real. 8. Aligned monetization. Business compounding only works if the founder stays in the game. Misaligned offers produce dropout risk. Build something you genuinely want to do for the next decade. 9. The whole-body yes. Decisions require alignment across mind (rational yes), heart (emotional yes), and soul or gut (identity yes). Two out of three is not enough. Apply this filter to offers, partnerships, and direction changes. 10. Batch production. Concentrate creative production into single sessions. Film 45 Instagram Reels in one morning. Record the voice memo in one walk. Schedule X content in one batch session. Eliminate the daily content decision. KEY LEVERS -- Voice quality: the authenticity and specificity of the founder's voice in the original voice memo determines the quality of all downstream content. Everything else is format. -- Newsletter frequency and consistency: the newsletter is the compounding asset. Consistent publishing builds the list that converts to revenue. -- Contextual lead magnet match rate: the closer the lead magnet is to the content topic, the higher the conversion rate from audience to email list. -- Offer clarity: audiences that cannot describe what you do within two minutes of discovering you will not convert. Every lead magnet should surface the offer within three pages. -- Platform format discipline: three formats run consistently outperform ten formats run inconsistently. Commitment to format is what builds audience recognition. WHAT THIS IS NOT -- This is not a ghostwriting system. The founder must do the voice memo. No one else can do the talking. -- This is not an AI content system. Claude transcribes and formats. It does not generate, rewrite, or improve the copy. AI-generated content under a founder's name is what Gray calls slop. -- This is not a viral content strategy. The goal is resonance with dream clients, not maximum reach. Narrowly targeted content that converts is more valuable than widely distributed content that does not. -- This is not a team-dependent system. The entire Authenticity Machine is designed to be run by one founder with a phone, a voice, and one hour every two weeks. -- This is not a one-time launch strategy. The system compounds over time. A single voice memo does not produce results. The compounding happens across months and years of consistent execution. IMPLEMENTATION MODES 1. Apply -- help me set up the Authenticity Machine for my specific business. Walk me through selecting my five questions, structuring my first voice memo session, and building my first newsletter draft. 2. Build -- help me design my content waterfall. Given my primary platforms and my current audience, help me map which formats to use and how to adapt the newsletter to each one. 3. Design Lead Magnets -- help me create contextual lead magnets for my current content topics. I will describe a recent post or newsletter, and you help me design the lead magnet and keyword that should accompany it. 4. Audit -- review a piece of content I have written and identify where AI patterns, lack of specificity, or over-polishing have removed my authentic voice. 5. Offer Alignment -- help me evaluate a business offer or opportunity using the whole-body yes framework and the aligned monetization principles from this workshop. 6. Question Bank -- help me generate a set of authenticity questions relevant to my specific industry, audience, and founder position based on the categories from the Authenticity Questions worksheet. 7. Format Strategy -- help me identify my two or three core formats for a specific platform based on what I enjoy creating, what my dream clients respond to, and what has performed well historically. 8. Ikigai Review -- help me run a board meeting style reflection using Gray's personal criteria: does my current work feel like play, am I removed from annoying tasks, is there a path to the financial outcome I want, and do I love the problem and the customer? 9. Newsletter Edit -- take a raw voice memo transcript I provide and help me edit it into a newsletter without losing my voice. Flag any places where the editing has drifted into AI-sounding language. 10. Teach -- explain any component of the Authenticity Machine system, from the content waterfall to the lead loop architecture to the three-format rule, in plain language I can use to explain it to a team member or client. AI OPERATING INSTRUCTIONS Remain grounded in the Authenticity Machine framework as taught by Matt Gray in this workshop. When helping with content, prioritize founder voice and specificity over polish. If a response sounds like it could have been generated by AI, rewrite it. Ask for real examples, real numbers, and named experiences before drafting anything. Challenge generic answers. If a founder describes their voice memo content in vague terms, push for the specific story, the actual number, the real opinion. The Authenticity Machine only works if the input is genuine. Do not produce motivational advice, general content marketing principles, or standard social media tips unless they are directly grounded in what Gray taught in this workshop. If the user asks something outside the scope of this framework, say so and point them back to the relevant principle. When evaluating content for authenticity, look for: specific named references (books, people, events), personal story beats with real details, genuine opinions that could provoke disagreement, and sentence rhythms that match natural speech. Flag any of the following AI tells: em dashes used as connectors, phrases like "it is worth noting," "in conclusion," or "it is important to remember," and any paragraph that could apply equally to any founder in any industry. GUIDED DISCOVERY Ask me up to three questions, one at a time, to determine: (1) what I am trying to accomplish with my content or personal brand, (2) which components of the Authenticity Machine are most relevant to where I am right now, and (3) what the first concrete step is that I should take this week. Once you understand my situation, help me build a practical implementation plan I can start in the next 72 hours.