The Fastest Way to Build a Profitable Personal Brand
Matt Gray tells Chris Do how a private sobriety journal turned into a millions-follower personal brand, then how he systemized it into FounderOS.
Posted
3 weeks ago
Duration
Format
Interview
educational
Views
16.7K
508 likes
57 · 43
Big Idea
The argument in one line.
Building a profitable personal brand is a learnable systems problem, not a talent contest: ship imperfectly, find the intersection of what you're good at and love, then own an email list and a documented offer instead of chasing views.
Who This Is For
Read if. Skip if.
READ IF YOU ARE…
A founder or coach who already has some traction and organic reach but has never turned it into a documented offer or an email list.
Someone who freezes before posting because of perfectionism and wants a concrete, repeatable way to get past it.
A creator with a real audience (six or seven figures of followers) who is still living deal-to-deal with no owned distribution.
Anyone deciding whether to build on X, LinkedIn, Instagram, or YouTube first and wants platform-specific tactics, not generic advice.
SKIP IF…
You want growth-hacking shortcuts with no patience for the sobriety story and mindset framing the tactics are wrapped in.
You already have a documented offer, an owned email list, and a media team — this talks to the stage before that.
TL;DR
The full version, fast.
Matt Gray, who built FounderOS after growing his own personal brand to millions of followers, argues the biggest blocker to a profitable personal brand is perfectionism, not tactics. His fix: ship imperfectly for 90 days, find the intersection of what you're good at, get paid for, the world needs, and love (his 'ikigai' exercise), then pick one platform and learn its specific packaging rules. Once content is flowing, document a simple offer, get to 15 paying customers, and build an email list you own instead of relying on platform reach. The end state is a personal media company: a team that keeps producing and selling without the founder being the bottleneck.
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Matt Gray introduces himself: 18 years building businesses, an exit at 24, three profitable companies with a combined 14 million-person audience, and FounderOS, his current company helping founders build personal brands.
01:33 – 06:47
02 · From burnout to rock bottom
Being the operational bottleneck cost him more than business success. He describes hiring a CEO or head of ops as a 'magic pill' that didn't work, and the substance use and struggle that preceded his sobriety story.
06:47 – 10:42
03 · The Huberman DM and getting sober
A voice note to Andrew Huberman led to blood work showing his testosterone had dropped from 800 to 200. He quit cold turkey and started journaling daily using The Artist's Way.
10:42 – 14:40
04 · From X to LinkedIn to the conference that changed everything
Posting the same content unedited on X and then LinkedIn grew both audiences. A conference where he watched Alex Hormozi and Cody Sanchez speak convinced him to take his own personal brand seriously.
14:40 – 18:45
05 · Soulful Entrepreneur becomes FounderOS
His first paid cohort, Soulful Entrepreneur, tested well with 15 people but sounded like a yoga studio. Mentor Alex Lieberman's feedback pushed him toward the systems positioning that became FounderOS.
18:45 – 26:58
06 · Building the shipping muscle without perfectionism
Matt's advice for getting started: treat the first 90 days like walking through a gym door, decide if you're camera-first or pen-first, and the conversation turns to a guest, Gil, whose perfectionism is stopping him from posting.
26:58 – 33:21
07 · The two or three people whose opinion matters
Chris walks Gil through an exercise: naming the handful of people whose opinion actually matters, then directly asking them for permission to be bad at something new in public.
33:21 – 49:32
08 · Ikigai, business models, and platform-specific tactics
Matt's ikigai framework for picking a content niche, documenting an offer to reach 15 customers, then a platform-by-platform tour: YouTube packaging, LinkedIn hooks and carousels, X's copywriting culture, and Instagram carousels.
49:32 – 54:47
09 · The handwritten infographics origin story
Matt explains how his viral hand-drawn LinkedIn infographics started as a 25-minute daily experiment after an artist retreat, caught fire, and were eventually handed off to his social media manager Anna, who still makes them.
54:47 – 1:02:42
10 · Signal over noise, and becoming a media company
The metric that matters isn't likes or views but whether a piece gets texted to a friend or shared in a company Slack. Matt introduces the shift from personal brand to personal media company.
1:02:42 – 1:21:25
11 · Waterfall content, owning your list, and cash flow over views
One pillar piece should waterfall into 20-plus derivative posts. Matt argues for owning an email list over renting platform reach, describes contextual lead magnets via ManyChat, tells the Carl Icahn 'happiness is positive cash flow' story, and flags where FounderOS clients' teams typically break.
1:21:25 – 1:32:01
12 · What 'monetization' actually means
Prompted by a guest who says the word is abstract to him, Matt breaks it down: document the offer as a Google Doc, get to 15 customers, then split by price into a Stripe checkout under $2,000 or an application-and-sales-call above it, using a restaurant-menu analogy.
1:32:01 – 1:41:24
13 · Creators vs. founders, and hiring from your audience
Chris contrasts creators, who monetize on views and ads, with founders, who have a product, noting only one of ten polled YouTubers with 10M+ subscribers had an email list. Matt describes hiring most of his roughly 60-person team from his own audience.
1:41:24 – 1:46:39
14 · The chicken-and-egg trap, and closing
Matt's answer to solopreneurs who can't afford help until they make more money: find the single lowest-effort action that produces cash now. The episode closes with a callback to Matt's testosterone numbers and a pointer to founderos.com.
Atomic Insights
Lines worth screenshotting.
Testosterone crashing from 800 to 200 in a 30-year-old male was the wake-up call that started Matt Gray's sobriety, and his personal brand grew out of the recovery process, not a marketing plan.
The first 100,000 followers on X came from posting private morning-pages journaling with zero strategy; copywriting craft only got layered on top later.
Copying the exact same posts from X onto LinkedIn, unedited, grew the LinkedIn audience faster than X itself.
Perfectionism is treated in the conversation as an avoidance strategy, not a standards problem.
Ira Glass's observation on the gap between taste and skill: early creative work is bad because taste outpaces ability, and volume is the only fix.
Most people only care about the opinions of two or three people in their life, yet let strangers online carry that same emotional weight.
90% of YouTube success comes from packaging: the idea, title, and thumbnail, decided before the video is even made.
David Ogilvy's rule still applies to social hooks: you've spent 80 cents of every dollar by the time someone finishes reading the headline.
An email list is estimated to return roughly 32 times the ROI of the next-best marketing channel, because 100% of subscribers receive a message versus 2-5% organic reach on social platforms.
A pillar piece of content should 'waterfall' into 20-plus smaller pieces across platforms instead of creating something new every time.
The real growth signal isn't likes or views, it's whether someone texts a friend or shares a post in their company Slack.
15 paying customers is treated as the practical threshold for product-market fit, the point where an idea becomes a real business.
Offers under $2,000 can sell through a self-serve Stripe checkout; above that, they typically need a sales call.
Of ten YouTubers with over 10 million subscribers polled at a private event, only one had an email list for their audience.
About 85% of Matt Gray's roughly 60-person combined team was hired from people who already followed his content.
The average business takes five to seven years to become truly successful, so personal-brand content strategy should be built for the long term, not a quick win.
Takeaway
The System Behind a Profitable Personal Brand
PERSONAL BRAND SYSTEMS
A sober, systems-driven founder walks through the sequence: overcome perfectionism, find your ikigai, learn platform-specific packaging, then convert attention into an owned email list and a real, priced offer.
01Cold open: who is Matt Gray
Matt Gray spent 18 years building businesses, including an exit at 24 and three companies with 14 million combined followers, before growing his own personal brand.
A profitable personal brand grew out of systems he'd already built for other people's businesses, not a from-scratch marketing plan.
02From burnout to rock bottom
Being the operational bottleneck in his own business cost more than revenue: it cost his mental health and fed a substance problem.
Hiring a CEO or head of ops to 'fix' the business didn't work until he understood the machine he was building himself.
03The Huberman DM and getting sober
A cold two-minute voice note to Andrew Huberman got a real reply and a referral, showing direct, specific outreach can work even with zero prior relationship.
A concrete number, testosterone dropping from 800 to 200, made an abstract health problem impossible to ignore and triggered the decision to quit.
Journaling three pages every morning with no audience, following The Artist's Way, became the raw material his public content was later built from.
04From X to LinkedIn to the conference that changed everything
The exact same posts, copied unedited from X to LinkedIn, grew faster on LinkedIn, showing the value of testing identical content across platforms before assuming what an audience wants.
Watching more established peers on a conference stage was the moment he decided to take his own brand seriously instead of treating it as a side project.
05Soulful Entrepreneur becomes FounderOS
His first paid offer tested with 15 people before he built anything formal, using it as a comedian tests bits before a special.
A mentor's blunt feedback that the original branding sounded 'woo woo' only mattered because it matched something he already sensed himself.
06Building the shipping muscle without perfectionism
Treat the first 90 days of posting like walking through a gym door: the goal is showing up, not producing something good.
Decide whether you're a camera-first or pen-first person before picking a platform, instead of forcing yourself onto a format that fights your instincts.
07The two or three people whose opinion matters
Perfectionism is frequently an avoidance strategy in disguise, not a genuine standard for quality.
The gap between good taste and current skill is supposed to exist early on; the only way to close it is volume, not more editing.
Most people only care what two or three people in their life actually think, yet let anonymous strangers online carry that same weight.
Directly asking the few people whose opinion matters for permission to be bad at something new removes most of the fear of judgment.
08Ikigai, business models, and platform-specific tactics
The ikigai exercise, what you're good at, what you can be paid for, what the world needs, and what you love, filters a content niche before tactics matter.
A simple offer documented as a one-to-two-page doc and sold with a Stripe link can carry a business to its first 15 customers.
90% of YouTube performance comes from packaging (idea, title, thumbnail) decided before the video is filmed, not after.
09The handwritten infographics origin story
A format that performed well came from a low-cost 25-minute daily experiment, not a big production investment.
Once a content format proves itself, it can be documented and handed to someone else on the team without losing what made it work.
10Signal over noise, and becoming a media company
A text from a friend or a share inside a company Slack channel is a stronger signal of content quality than any platform metric.
Moving from personal brand to personal media company means building a team and systems that keep running when the founder steps away.
11Waterfall content, owning your list, and cash flow over views
One long-form piece of content is worth turning into 20-plus smaller pieces across platforms instead of creating something new for each one.
An email list is estimated at roughly 32 times the ROI of the next-best channel because subscribers actually receive the message, unlike a social feed.
Vague job descriptions and missing 30/60/90-day onboarding plans are the most common reason growing content teams break down.
12What 'monetization' actually means
An offer under $2,000 can sell through a simple checkout link; above that price, it usually needs a sales conversation first.
15 paying customers is treated as the practical bar for proving an idea is a real business, not just a hobby.
A business built on views alone behaves like a creator; a business built on a documented offer behaves like a founder, and the difference shapes how it monetizes.
13Creators vs. founders, and hiring from your audience
Roughly 85% of one founder's team was hired directly from people who already followed his content, since they arrive pre-aligned with the values and already know the work.
14The chicken-and-egg trap, and closing
When money is tight, the fix isn't waiting to afford help, it's finding the single lowest-effort action that produces cash right now.
Glossary
Terms worth knowing.
Ikigai
A Japanese concept describing the intersection of what you're good at, what you can be paid for, what the world needs, and what you love — used here as a filter for picking a content niche.
Content waterfall
Turning one long-form piece of content, a YouTube video, newsletter, or blog post, into 20 or more smaller derivative pieces across other platforms.
Contextual lead magnet
A free resource tied to the specific topic of a given post, offered in exchange for an email address, often delivered through an automated DM.
ManyChat
An automation tool that auto-replies to social media comments or DMs, used here to hand out lead magnets in exchange for an email address.
Product-market fit
The point at which enough people are paying for and using an offer that it's proven to work; referenced in this episode as roughly 15 paying customers.
High-ticket product
An offer priced high enough, here above $2,000, that it's typically sold through a sales call rather than a self-serve checkout.
07:45bookAdweek Copywriting Handbook by Joseph Sugarman
42:29tooloneof10.com
44:11toolTapleoX (Taplio)
49:47toolTweet Hunter X
1:05:22toolManyChat
1:11:33channelIcon (documentary about Carl Icahn)
1:11:39channelFounders podcast (David Senra)
1:13:44channelTim Ferriss
1:31:52bookPerennial Seller by Ryan Holiday
1:31:31bookOn Advertising by David Ogilvy / Scientific Advertising by Claude Hopkins
Quotables
Lines you could clip.
16:49
“For the next 90 days, you just walk through the gym door.”
tight, self-contained advice for anyone stuck before starting→ IG reel cold open↗ Tweet quote
25:56
“We have really great taste, but we don't have the skill. So there's that gap between your taste and your skill, and it's enough to cripple you to start.”
the Ira Glass idea, widely relatable to any creative beginner→ TikTok hook↗ Tweet quote
33:07
“You don't have to be great to start, but you have to start to be great.”
three words, sticks immediately→ TikTok hook↗ Tweet quote
1:12:05
“Go and get the money. It doesn't mean you have to be salesy or short-term thinking about it.”
blunt permission-giving line that reframes money-seeking→ IG reel cold open↗ Tweet quote
1:23:03
“Put a menu outside. Set the tables. So that people can walk by, see a menu, like any restaurant, and go, this is interesting, I'd like to work with you.”
full analogy for why an undocumented offer loses customers→ newsletter pull-quote↗ Tweet quote
1:26:30
“I asked ten huge YouTubers, all 10 million plus, how many of you have an email list? Only one person raised their hand. It's terrifying.”
surprising stat with a built-in stakes statement→ TikTok hook↗ Tweet quote
1:03:45
“Your email list is something like 32 times more ROI than the next marketing channel in most founders' businesses.”
a specific, citable number→ newsletter pull-quote↗ Tweet quote
“David Ogilvy said you've spent 80 cents on the dollar by the time people have read the headline.”
classic copywriting principle applied to modern hooks→ newsletter pull-quote↗ Tweet quote
Topic Map
Where the conversation goes.
00:00 – 12:26denseOrigin story and sobriety
12:26 – 33:21denseOvercoming perfectionism and fear of judgment
33:21 – 49:32denseIkigai and platform-specific growth tactics
49:32 – 54:47steadyHandwritten infographics case study
54:47 – 1:21:25densePersonal brand to personal media company
1:21:25 – 1:32:01denseMonetization mechanics
1:32:01 – 1:41:24steadyHiring and team building
1:41:24 – 1:46:39steadyCash-flow mindset and closing
The Script
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Matt Gray is my guest today and we're going to talk about how to build a profitable personal brand. I think we're going to get into a story and we want to start to unpack the things he's been able to do to help a lot of other people. Now normally he speaks to, I think you have a program called FounderOS, that the average person there does what, two to three million dollars a year?
Yep. And then you help build their personal brand. And you have a lot of frameworks and strategies and even AI tools to help them do that.
And we'll get into that in case you want to find out about that. Make sure you stick around. Let's get to know the man first, okay?
Matt, you look like a super chill guy who's got, like, very meditative vibes. Where are you before you do any of this? Like, who is Matt?
Currently living in Bali, Indonesia, and then split my time there and then in Europe, typically in the Dolomites in Italy, mountain biking, and doing my thing there in the summer. And, yeah, I've been building businesses for about 18 years now. Exited a company that I first started when I was 21 and exited at 24.
Since then, I've built three other profitable companies, audiences of 14 million around those companies. And when I was 30, started building my own personal brand. And I scaled that to 3 million people and currently focus most on a company called FounderOS, which really helps founders build.
Profitable personal brands to help them feed their businesses with organic content. So in my own career, as an example, early on, I didn't know operations, didn't know how to build systems. I was the bottleneck in everything I did.
It cost me like not just business success, but cost me like a lot of just like mental health, struggle, addiction, all that kind of stuff. I thought for a while, like I could just hire a CEO or just hire a head of ops, like believing in this vibe of kind of. there's some sort of magic pill, you know, like some person I could bring on that would just finally solve this issue for me.
And having tried that time after time after time, I finally kind of learned the lesson that I need to start wrapping my own head around this stuff, right? Wrapping my head around what does a great operation look like? How do you have clear responsibilities for people?
What's the workflow when you're building maybe a media company? How do you drive people from awareness through to transaction, right? You can't be oblivious to this stuff.
You really got to understand the machine you're building. The same way that people, when they don't know much about a car, bring it to a mechanic and can get screwed. You know, it's the same thing that happens to you in business if you don't understand the machine you're building, right?
You're bound to get screwed. And if you're planning to play the game for the long term, you know, most of us are 50 years, 100 years, what have you. You know, something's going to come up in that ignorance.
Like, well, initially it can be bliss, you know, ends up becoming a real risk. I've seen you grow really, really fast in terms of millions of followers in a matter of like a year, a year and a half, two years. Right.
That is not something that we see every single day. And oftentimes people will send me your content. Like, what's Matt doing?
I'm like, he's doing something good. I could tell he's doing it. What have you learned in the process of taking your account from nothing to like where you're at now?
You have millions of followers and I just checked on X or Twitter. It's like you have 600 ,000. You have a lot of freaking followers on Twitter, which is not easy to do.
Millions on Instagram. What did you figure out in this process? And then we'll, I want to set up the credentials and then we'll like get into like the tactics.
I mean, I started my personal brand around five years ago. the process to getting to that point was kind of actually quite messy. So about eight years ago, I was using substances, drinking too much.
I had become kind of a little bit lost. And I had gotten out of a relationship and had this opportunity to kind of like look myself in the mirror and go like, okay, something's got to change. I had tried to kind of quit 40 plus times.
And knew I needed to get some help. And so I started looking at my phone, starting to think about who do I know? Who can I reach out to?
And I was probably listening to too many podcasts at this point in time. I was like, okay, Huberman could help me. And so I picked up Instagram, you know, sent a voice note to Huberman, two minutes long.
And sure enough, the next morning, randomly, didn't expect this. I had no relationship with him. He got back, sent a voice note and acknowledged the situation I was in.
um kind of told me some of the health issues that were likely to come up if it continued and then made a referral to a guy named dr kyle gillette and was like hey you should go get blood work done with him i think it'll help you understand the impact you're making on your body and so sure enough uh you know a few weeks later had blood work done realized that the substances i was using caused my testosterone to drop from 800 to 200 as a 30 year old male which is super super low and so decided in that moment and something clicked i think it was like this idea of almost gamifying sobriety which for whatever reason worked for me which was like okay it's at this level now if i can just sober up maybe for a few months i can get those levels back and then get back to a level of vitality and so sure enough that's exactly what i did i quit cold turkey stopped drinking and other stuff and Around that time, I got like a kind of a sobriety coach, essentially.
And this individual recommended that I read the book, The Artist's Way by Julia Cameron. And so read the book. For those that don't know, it's this like kind of eight week journey.
There's like a 10 page reading. There's about 10 different prompts at the end of each chapter. And you essentially just write three.
pages of morning pages every single morning when you first wake up. No social media, no nothing. Wake up, write your morning pages.
This was a new habit for me. I had always thought of writing as really scary. I had no idea really how to write that well.
And you didn't need to. This book was really liberating in that sense. You're just writing privately to yourself and just letting it flow.
And so that's exactly what I did. And there was a lot coming out of me. And throughout that experience, I started to realize that I think part of what was going under underneath all these substances was that like the artist in me was kind of being like muffled and suppressed.
And I had just kind of gotten lost in building things in life and struggles or whatever. And hadn't given that artist much of a voice or an opportunity to like exist and create. After going through these 90 days, I just as an experiment was like, oh, screw it.
Why don't I start sharing some of these different lessons and things on X? at the time, Twitter. And it was messy.
I was just putting stuff up there, had no idea how to really do it all, how to look good or how to make it good or whatever. I was just sharing the same way I'd been sharing with myself these random thoughts in these morning journals. And so I started sharing it along that kind of journey.
It was messy at first. Nothing was growing. And I wasn't really in it for the growth.
The whole thing was like just the process of. Just putting this stuff out there. Maybe I could help other people like me.
The kind of creative expression of it all was interesting. There was no grand master plan. And people started to enjoy, though, the things that I was saying.
And there was a little bit of positive feedback, which did feel great, which was like a little bit reinforcing to continue the journey. And along that way, I started to kind of become a little bit more obsessed with like just the craft of writing, like reading. random books, whether it's On Writing by Stephen King and, you know, other books like the Adweek Copywriting Handbook by Joseph Sugarman.
And then that brought me in a little bit more of a wormhole of just like wormholes do, right? Of just looking at hooks and looking at ways of doing it and realize there's like a whole art and a craft behind this that was actually quite fascinating to me. And so I just was both learning the practice of expressing myself more and letting this artist kind of unleash.
while also applying the tactics of copywriting to package it in ways that would travel online and that would be digestible and shareable by folks. And so that was kind of the genesis for then building this audience. And it worked.
And on X grew to 100 ,000 plus. And then just started literally taking that exact same content and just putting it onto LinkedIn. No different edits, no nothing new, literally just putting it over there.
and it actually started growing even faster um linkedin apparently really likes the similar type content that's on x and so that journey kind of continued and it was this gradual process of just iterating and putting myself out there it was only about you know 14 months into that journey then that i started bringing it to short form video um instagram and tick tock and youtube shorts playing around with that looking like an idiot short form videos in the backyard of a porto escondido mexico airbnb i was staring staying at you know then about nearly 18 months into the journey when i started youtube so it's been like a step -by -step um journey but that's kind of how it all unfolded was your intention just to share what you were learning at the time or was there another motivation in terms of building your brand so that you can get people into a program or something or coach them initially it was really just sharing stuff i figured You know, we've learned these things, right?
Where it's like, you know, first -time founders focus on product, second -time founders focus on distribution, right? And actually, when I rewinded this period, this initial sharing on X period, I actually had met you. I went to a sort of a conference hosted by Eric Hsu here in LA.
You were one of the speakers there, along with Hormozy and Cody Sanchez and some others. I was just in the audience. there because i was curious actually a friend steve from prey .com was like hey you should come check this out come with me like it'd be fun i was like screw it so i actually flew from toronto just for that um and uh and went to it and i was just there for the three days for this conference um and it was part of like one of those inflection moments in this whole journey because i started realizing i would was watching hermosi on the stage and then watching cody sanchez and it started to become obvious in my own brain i was like you know matt you haven't built a personal brand but you have been building media companies now for nearly a decade having built herb my second business to an audience of 14 million people organically and produced you know tens of thousands of pieces of content not for me but for that brand and it felt really liberating to some extent to go and take my own brand that much more seriously kind of move from approaching it maybe more in the farm leagues and be like oh no let's go pro um let's give this a shot and so around that time was when i was like okay i'm gonna
Really lean into this more and start viewing it almost like one part art and one part like a sport and just having fun with it all. And the whole journey has really been like this more kind of falling in love with the process and the artistry behind it all. Hence, like a lot of the content there's not that I'm putting out.
It's not there's rules around this stuff. I'm just doing what I enjoy putting out stuff I feel like needs to exist and then listening to the audience. And I feel like that's where a lot of the content strategy has come from is.
listening to folks. They wanted systems. They wanted things to be tactical.
They wanted deep dives and things like content systems to grow on YouTube, or they wanted content systems to go and drive more leads. They wanted to learn how they could go and, you know, nail their brand positioning or brand, you know, statements. And so it was just really kind of listening to these folks and then just responding and helping and serving these people and that kind of compounding over time.
And then sure enough, at some point, about six months into the journey, I was like, I'm going to go and put together something. Let's try and just see if a bunch of people would get on six weeks of Zoom calls with me and learn a little bit more about my own approach to entrepreneurship and how I build companies.
This kind of symbiotic relationship between taking care of yourself. At this point, I'd been maybe almost a year sober. And how when you take care of yourself, it kind of helps your business flourish.
I called the thing Soulful Entrepreneur. Sounded like a yoga studio. Sure enough, I got about 15 people in that from my audience.
And it served as this awesome kind of just testing ground. I felt kind of like a comedian testing their bits before like a Netflix special. Some things bombed, some things really caught on.
And I just paid attention to those patterns, surveying people every week. What did you like most about what I just went through? And what did you like the least?
And just responding to that and adjusting accordingly. And so did that a couple of times. And then that evolved into something more formal.
I ended up listening to a few mentors, one of them, Alex Lieberman, founder of Morning Brew. I had been talking to him every other week and he's like, Matt, you know, this thing is a bit woo woo. And the name, you know, again, sounds like a yoga studio.
I like the systems aspect of what you do. And it wasn't so much that he said this or that his advice was like, you know, what really mattered. I think that most advice, like you got to obviously run it through your own filter.
So when I ran it through the filter that I had, it just clicked with me. Like, yeah, the systems thing that you're saying you think I should lean into, that resonates with me. I like that.
And so that became more of sort of how I started building my brand is around the systems behind entrepreneurship, helping folks build profitable personal brands, helping them do it in a way too that doesn't all come down to them and helping them build the right team, the structure, the workflows. I'm in a strategy behind it all to make it much more simple.
Okay. Is that then the rebrand to founder OS? Exactly.
The systems operating system. Yeah. Okay.
You know, you call it soulful entrepreneur and you live in Bali. You've got the hair for it. You got the vibes.
Whenever I see you on a t -shirt, you're sweating in some tropical environment. You do throw out yoga vibes. You're aware of that, right?
Yeah. And even though you changed the name, is that still a part of your DNA? Yeah.
So, I mean, in some senses there's been a bit of a full circle kind of journey in this world going from like okay i should probably really niche down you know let's be known for this like systems guy stuff right and doing that and then kind of moving the sort of say soulful side of it to the side when people work with me or get to know me There's no splitting these two things, right?
Like I'm one part kind of system so that you can have the freedom that you need in life. But then one part, like, yeah, the soulful side of it, building something that you love that invigorates you and making sure that that artist within you is not ignored. And so, yeah, these days, I mean, there's a much more symbiotic relationship between those two aspects.
I would see my own personal niche, like I have it written down on my own vision board as soulful entrepreneur. Whereas like, you know, my presence online is more of this kind of like. you know, founder operating systems for founders looking to get to $5 million and beyond.
Yeah, well, if your brand is what people say about you or got feeling, my buddy Neil Dhingra, who runs Ford Academy, he's like, oh, you have Matt on. Isn't he that hippie guy? Like, I never thought of you as a hippie guy, but as soon as he said, yeah, he is the hippie guy, isn't he?
Maybe, I don't know. But now that we're talking about all this stuff, it's like, okay, there's that part to it. Okay, here's what I want to do now, because I've teased it, I've promised people.
I don't even think we even need to tell people why they should care about brand. Because if you're this deep into this episode, I'm going to just make the assumption you do care about brand. And people are a reluctant to make stuff.
Help us get over that part first. Let's just say, like, I love the idea. I've not done things because I have all this fear inside of me.
Help me get over that. And then we can move on to the next part, I think. How do you help people get over that?
Yeah, so I think it's kind of breaking it down like it's. That's completely normal, right? Like anything, any important thing you do in life, right?
It's always like that nervous feeling before like starting to get that muscle going. And so I think of it like someone just starting to go to the gym, right? You don't need to worry about gaining a bunch of muscle or losing a bunch of fat initially.
I think if I was advising someone to get fit, it's like, let's make sure like for the next 90 days, you just walk through the gym door, right? And so the analogy then there on like the personal branding side is First off, to know, are you more of a camera first person or are you more of a pen first person, right?
Does it excite you more to start writing with your words and pen? Then maybe get going on a platform like X or LinkedIn with maybe a newsletter eventually. On the other side of things, if you're more comfortable on camera and that's what excites you, then get going on that direction.
Maybe publishing a YouTube every month to start with. And remembering along the way too that the best content strategy is the one that you can stick with. So don't try to go too hard in the paint too fast, right?
Like one step at a time. From there, I think like for the first 90 days, view it as almost like a spiritual exercise of just getting going and building the muscle of shipping. Like as you ship a YouTube video, emotions are going to come up, right?
Oh my gosh, what are people going to think of this? Am I doing it right? Oh, mine doesn't look like Chris's do.
Oh man, like what's my team going to think of this thing, right? All of that stuff's going to come up. And I think it's playing with that voice in your head, right?
And viewing it as a practice, right? The same way that when you go out for a night and you're dancing and you're not a dancer, it's a bit of a practice or the same way that, you know, when you're even hiring early in your company and it's nerve wracking, you're not just not going to hire. You got to view it as a bit of a practice and a skill that you're picking up.
It's a bit uncomfortable. And so same thing. It's like you're likely watching this because you know that it's a valuable thing for attracting talent and driving cash flows and leads and serendipity and new opportunities in life.
Like people know these things because it's the truth. And so not letting those voices creep in your head and stop you from actually shipping the thing and getting started, realizing that, no, that's part of the practice is that there's stuff going to come up. And so, you know, maybe it's having something on the wall where you're just tallying out just the consistency of it and just seeing it as don't worry about the quality of it.
Don't worry about what people say. You're literally just doing this as an internal practice just to start shipping some stuff that you feel good about. Okay.
I'm going to turn this over to our audience here. What I hear you saying is let's just first develop the habit of shipping. Yeah.
and do it in a way that's sustainable and do it or aligned around something that excites you if we accept that as a critical first step what would be stopping each and one of you from doing that do you have anything if you do let's talk about it so matt can address it before we move on what the next step is perfection but what did he just say though he said just get into the habit of shipping yeah not shipping perfectly just shipping something i have to come to terms with Not shipping perfectly.
There was no word about perfection. Can you just ship something? What I'm trying to explain is that perfectionism prevents me from shipping.
It stops me from... Fair enough then. Matt, how do you want to respond to that?
When people are building their brand, something that's going to come up is this idea of... You know, is it good enough? Right.
And perfectionism is something that can often creep into people's brains and stop them from just taking that step. You know, it's something I've been thinking about. Just a quick story on this is that, you know, sometimes this whole content game online, it goes through like these different pendulums and the pendulum swings from a world of kind of super authentic, off the cuff, imperfect content, and then sometimes swings to like more polished content in this day and age.
you know when we're looking at most content online one of the first questions people have when they see something is was this created by ai right and that's the world we currently live in you know rewind five years ago during covid everyone's locked in they start seeing chris's content they're like oh he's got a sure mic and he's got an fx3 and they start getting that and then they're looking at color grades and they're going and they're nerding it out and that was like a wave that we had that's now kind of coming to a halt right and so i would say First off, to deal with, I think it's the right side of the brain that's more logical, maybe getting it wrong, is we're actually living in a day and age right now where the more actually imperfect it is, where you can just feel the humanity and the authenticity behind it, is where humanity is at right now.
They want to know it's you. Even with my own content that was polished for a sec, we're unwinding it. We just started a second YouTube channel.
The rules are no editing, off the cuff, and just keep it real, keep it simple. right and so that's that piece okay on the other side of the perfectionism you know i first off i get it right it's tricky um i've been writing a book now for the last three years and wanting to ship this for a while um and i've been viewing it though as more of an art project not any business or anything and so i'm just giving myself the time to just you know go through the fifth draft go through the sixth draft so i definitely understand perfectionism because i allow myself to be a perfectionist in certain aspects of my life.
This being kind of the one, to be honest. That said, I think when you're going and doing the content side, the thing that's the most important is not where you start, it's the learning velocity. And I think that's true with most things in life.
I think it's actually one of the most important things for us just as humans and founders. to compete over the next 20 years it's just how fast can you learn right because if you can learn you can iterate you can build a better product you can get results you can get cash flows you can reinvest that in areas of your company and also in your own lifestyle and continue to flourish and so i think when you kind of begin this journey and as you're there realizing that if you can just have more of an insatiable appetite to just learn then maybe it allows you to ship something because you're more obsessed with the learning you're going to get from it than the reaction or outcome you're going to get from it um the last thing i'll say on it too is that i've struggled with this again in many areas and i think it's also about a reframe right going from reframing things as this content is a performance where i need to show up and look a certain way to how can i approach this like play and it's about you know i'm just going to show up as i am
You know, no, no performance, not trying to look good, not trying to be perfect. Just like I am who I am. I have things to share that can provide value for someone.
Let's do it. Let's press play. Right.
And trying to just approach it and kind of loosen the grip on the whole experience. That's some things I have a note on my phone called filming checklist. And sometimes when I'm overthinking it, I just read these points in it to kind of, OK, right.
You're all good, Matt. Just turn the camera on and just speak to a friend. Yeah.
So Gil, you are a lawyer. You're also an artist. You play multiple instruments?
Piano and keyboard synthesizer. Okay. Did you get good at playing the piano on day one?
No. Okay. So if a young student wanted to learn how to play the piano, he goes, I don't want to start unless I can play perfectly the first time.
What would you say to them? No, I agree with you. It's just...
No, I'm asking you a real question. What would you say to them? A student says, I love the way you play and perform.
It takes practice. It takes years. But I want to be perfect.
I can't start playing... You can't be perfect on day one. So why does it make sense there, but it doesn't make sense to you in your own life?
It's an interesting question. It doesn't make sense. It does not make sense.
Okay. So I have a theory, and you may not like me for saying it, is I believe your perfectionism is an avoidance strategy. I agree with you 100%.
Okay. So when you can talk to your therapist, say, why am I trying to avoid this? Because we know that everybody who's good at something, they started out really messy at the beginning.
And it's their persistence and how they practice that gets them there. And it's really unrealistic for anybody to say, I'm going to be world -class at something on day one. And to your point, if I may share for your audience, what you are saying is 100 % true because in my own experience, The videos that I do, if you show it to someone else, they would tell you it's above average.
It's not bad what I'm doing. There's something in me trying to avoid. Thank you.
Yeah. And have you seen that Ira Glass interview? He does This American Life.
Ira Glass is the host. And he goes, there's this thing about creativity. And he goes, I want to play for you a clip of me doing an interview.
He hosts one of the most. beloved podcast, okay, very popular podcast, This American Life. And he plays it for you and he's stuttering and stammering through it.
There's a lot of ums and filler words in there. He goes, that was five years after starting. He goes, the problem with a lot of creative people is we have really great taste, but we don't have the skill.
So there's that gap between your taste and your skill is enough for it to cripple you to start. So he goes, I'm still not that good. And he's been doing this for decades.
But people love it. So maybe we shouldn't use our own taste as the barometer for whether or not we're going to do something. Because oftentimes, I don't know about you, when I'm creating something, I'm like, dang, it was so good in my head.
It's just, how do I make this? And we just grind on it. Either it becomes what we want, or we settle and we learn something.
And the next time, we're a little bit better. So it's just this gap between your taste. Because in the world of music, you're at the highest level.
And in the world of content, you're above average. And that is this unbearable gap that you just can't get over. So if you can just let go of that, I think you're going to learn so much more.
I'd love to hear your views on the fear of being judged.
Okay. We can go there if you want. Yeah.
I mean, let me ask you this question. The entrepreneurs that you work with that are part of the founder OS system that are doing two to three million dollars a year. Do they voice these same concerns?
Yeah, I think the interesting thing about all the stuff we brought up, right, is like it doesn't matter whether you're that successful entrepreneur running a 400 million dollar company or you're that person that's, you know, just got a school community to one hundred thousand dollars a month or you're someone just beginning all this journey.
The interesting thing is that when it comes to building a profitable personal brand, what I've noticed is that everyone's kind of a beginner. right and as such yeah all this stuff um comes up um i think it's why too this stuff is a skill right it's a craft and it's complicated and it's messy you know when you look at you know as an example the first mission to the moon i think was like apollo 13 maybe uh people think it was like a straight shot to the moon and then back to earth right but when you actually look at the journey the whole time it was wiggly like this right and so what's the lesson there right It's like 97 % of success is about correction, right?
Not about getting from here A to B, right? The journey of whether it's building a business, the journey of most relationships, the journey of personal branding, it's inherently kind of messy, right? And so how do you ensure that you're course correcting along the way?
Well, you just brought up as an example, you know, you're a piano teacher or so you play piano. And if you were to teach someone piano or if we were to learn a new sport or any new skill or a new language. Right.
You would find a coach or an accountability partner of some sort. And there is a difference in my eyes between a therapist, a friend, a family member and a coach or an accountability partner. Right.
Someone that's like weekly or biweekly, like really checking in. And making sure that you did what you said you were going to do, irregardless of maybe what came up or you're expressing these limiting beliefs and the perfectionism and the worries that come up and being able to then like kind of work through it, but then still commit.
Right. And I think that's inevitably what is needed, I think, in this area. Right.
And where people sometimes downplay because it can sometimes for some people be a natural thing and some people downplay it because, you know, they haven't done it much, so they don't. realize how much fear comes up sometimes just to press publish but then they start to experience that fear and they realize oh damn like now what and they get really in their head and i think if you can find someone to keep you accountable you can find a coach a consultant whatever it is that's right for you you're then able to externalize a bit of that and then have someone that's still making you actually move forward with it and hit the goals that you have in mind wait wait before you do that Can I do my thing and then you add?
Okay, you win. This is her show, man. Yeah, it is.
And to your point, if I may add only one word, P -L -A -Y, play. The power of play is so powerful. When you're playing, you go into the zone and you're creating and you're just flying.
And that fear of judgment and being perfect dissolves. So that's the magic where it happens. So think about it every time you're doing anything.
Play, play, play, play, play, play. And you just lift off. Thank you.
Okay. I want to acknowledge how scary it is to put out content. Because even in me asking you about playing piano, when we practice, we have someone to teach us.
It's very private. You do it in your own home or some small place. It's not on stage in front of 300 people.
Could you imagine just learning scales in front of 300 people? And now I understand there's pain there. OK, so that's a very real thing.
So it's not just imagine. And I want to ask this question in your life, in your circle, people, you know, friends, colleagues, family. How many people do you really care about their opinion?
Can you put a number on it roughly? Of the people in your life that really matter to you, that if they said, I think you're becoming somebody I don't really like that would actually affect you. How many people do you think that might be?
Not very many. Twelve? Not even.
Six?
Probably not. Probably two, three. Two or three.
So we really only care about the opinions of two or three people. And maybe by proxy, when you put it out onto the Internet. some idiot that you don't know is going to say something to you that you're going to take and carry with the weight of the two or three people as if they're saying it to you.
Perhaps. My very practical thing for you is to talk to the three people and say, I'm going to go on an adventure. I'm not going to be very good at it, but I intend to be good over time.
And your opinion means so much to me that I just need space to grow and fail without your condemnation and judgment because I know that'll really derail me. could I get your permission to do this and invite you to give me grace during this time? And if you could do that, that'd be fantastic.
If you give me a support, that would mean even more. Could you do that? Sure, yes.
If you did that, what would they say? I'm sure they would fully support me. They have to.
You matter to them, they matter to you. So if you did that and you have the support of the three people that matter the most to you, don't you think you can conquer the world that way? Absolutely.
But in my case, personally, I think I care about what the people not within my circle say about me than within my circle. But you only care about the opinions of two or three people. Within my circle, yes.
But my worry is about being judged by those who don't know me. What impact would they have on you? In my head?
Not real impact, but in my head it does. How do you separate in your heart or your head? Is there a battle between those two or are they the same?
No, they're not the same. My head is different from my heart. Would your heart care?
No. So your head cares? Yes.
The logical part cares? Correct. What is the logical part saying if you could give it voice?
That you need to be perfect, that you need to show you have no weaknesses. I thought we previously established that in the process of doing something new, it's very natural for it not to be perfect. There's no such thing as perfect beginnings.
Yes, yes. There's like an expression, I hope I say it right. You don't have to be great to start, but you have to start to be great.
So you're trying to find the loophole in that expression.
I think you are. Yes. Are you going to spend the rest of your life trying to find that loophole?
No. Do you believe that, though? I do.
Okay. So your logic says, this is not your heart, by the way, because I don't know how to make hard arguments. I know how to make logic arguments.
So twice now, you've agreed. If a student was trying to learn to play the piano, you're going to suck for a long time. Just deal with it.
And your logic also says you have to start to be great. So when you say the logic part is not connecting, is it the logic part or is it an emotional part? I suspect it's more emotion than it's logic.
But that could just be my logical brain trying to explain that. Tyler, you want to say something? I think perhaps it's because...
he has a very big following who follows him. Like he's a celebrity musician, right? And now he's going to pivot to do something else.
So I think that's, he's already on the public stage, right? He has half a million Instagram. I think that's the difference between like a founder, right, Matt, that has no following and they just have to start.
So they're like, okay, I'll just start. But I think for you, right, do you think that's true? It's like you already have a big following.
People know you as this. really great pianist and musician and now you're pivoting to do something else and kind of maybe sucking at it i'm not saying you suck but like in the beginning right so i think that's that's what i'm noticing maybe is it i don't see it no okay wait take the mic take the mic you're just giving them more reasons yeah don't open it i'm joking thanks tyler thank you for the therapy session by the way I appreciate it.
But you don't think that's it, right? I don't think that is it. It's not like I've been practicing law for a year.
I'm in eight years of my practice now, and I think I'm a great attorney. I'm not sure what it is, but what you last mentioned makes me think whether it's an emotional thing. Yeah, and I'm no therapist, but almost all decisions are emotional.
So we think it's logic, but it's really hard. And it's harder to admit that, especially for guys. because they're like, why am I being so emotional about this?
Get over it. So you and I, we can talk later and try to figure this thing out. But, you know, we're not getting any younger any day, every day.
And I know both of us, sometimes our health is like reminds us of our mortality. So will you be 70 years old before you wake up and say, today's a good day? You know, you age like fine wine, but still you don't want to do this when you're 70, right?
Absolutely right. Yeah. Okay.
Let's get into the next part. OK, so we have to develop the habit of shipping imperfectly. Something doesn't have to be great.
Let's say we get into that rhythm and we start to feel the feelings of like, yes, I can do things. I know this just in my own life. Every time I check off something off a list of a to do list, it feels so freaking good.
It didn't matter if it's like wash the dishes done. It feels like I've accomplished something. Right.
We hold ourself accountable. We have agency. We're doing things.
Let's get into some of the deeper tactics, the things that you have been able to help other entrepreneurs do and build their following. Yeah. So I think, you know, you've got the shipping muscle going.
You're starting to build things. I think the next stage that you want to be thinking about, you know, when you're just getting going is. For me, early on in my journey, it was effective to kind of go and think about, you know, my icky guy.
I come across this in a book, this idea of, you know. your reason for being this japanese philosophy around really kind of like finding like what sets your soul on fire and like your calling in life and it kind of sits at the intersection of really thinking about what you're great at what you can be paid for what the world needs and what you like really love to do the kind of stuff that you lose track of time doing if you're going to be on this journey right like any journey right whether it's building a business a personal brand the greatest returns are going to come from the long -term compounding of the thing right The best folks I've ever met in this space, whether it's yourself or Mosey or Cody Sanchez, and this is one of the biggest things I learned actually five years ago when we first met, was that I could tell the pattern in the one mindset that every single person had and they made decisions around it was they had a long -term mindset with this stuff.
So this Iggy Guy exercise can be really effective because it helps you then make sure that you're building something that is going to make you money, that's going to be fun. And that you could see yourself doing for the long term. I think it's important that then once you've done that exercise, right?
You've gone and journaled maybe 10, 15 things in each of these four quadrants, right? And then started to pick up on some of the patterns in the middle. Then you can start to form that as a more around your kind of initial content strategy, let's say, right?
So for me, that's things like helping founders with systems, building distribution around founders and myself, you know, going and traveling the world. viewing entrepreneurship as a soulful journey, building communities. That's the stuff that sets my soul on fire.
And I've essentially been doing that in some way, shape or form for almost 18 years now. And so I'm building this audience and I'm building now a business too around just my own like natural passion and curiosity. And I'm building a business that I could do and will do until I die.
And so. I think that's a useful exercise because now we're starting to think about the longevity of this all. And now that we've got comfortable with the actual exercise of publishing daily or publishing consistently at whatever schedule makes sense, we're now starting to think about, OK, getting a little more intentional about everything.
Similarly, on the business side of things, right, there's a lot of different business models out there. And at this stage, you may be thinking, well, I actually want to make sure that this is serving. The financial side of it, because I have ambitions to eventually have more of a team around me to get some help so I don't have to just do this all alone.
I think it's looking at what business models make the most sense for what you're trying to do. Are you into building a digital product? Are you into building a software product?
Do you want to have an online community? Do you want to have an in -person mastermind? There's maybe one or two of these business models that are most attractive to you.
And so at that stage, you can start to think about, okay, you've got maybe a business model that's interesting to you. Say it's a mastermind, as an example, and you are really into empowering female founders in LA. It's like, okay, well, now we can kind of mix this icky guy, right, with a business model that seems attractive to you and kind of experiment with mashing these two things together and putting together just even initial Google Doc offer.
Right. Just simply writing a one to two pager. Better yet, if you need some help with that, just enter it into chat to get an initial draft and edit it.
And then whether it's pulling people from the audience, you're just so humbly starting to build and also not being afraid of just hitting up people in your network. You know, nothing better than just looking at your phone contact list, some people that maybe you follow on Instagram, some folks on Twitter or wherever and just.
getting on some calls running that by them and seeing if they're interested right maybe none of them are and good news is you learn and you refine it and maybe some of them are and you get your first customers right but i think that's a way of not just making money which i think is the easier thing it's actually making sure that you're building something that you're going to want to do for 10 20 years you know the average business i think to get real successful can take like five to seven years And so not just focus on making a quick buck, but actually building something that's more enduring as I see that stage.
Well, you were talking about this kind of sweet spot that exists between these four circles, that sticky guy. And if you can figure out your business model and your offer and the audience and the market you want to speak to, that sounds like entrepreneur step. what about the personal branding part how do you build an audience around let's just say i've identified that now how how do i build an audience yeah so let's double click into like the different platforms you can build audiences on and maybe some of the different tactics there so every platform is going to have its own like operating system as to how you go and start building an audience on it okay and so we can deep dive onto a bunch of that on youtube as an example The thing to understand when you're going and growing on YouTube is that 90 % of the success on YouTube is your packaging, right?
It's your idea, title, and thumbnail. And this is where most people screw up. As they're trying to scale, they have an idea, they publish it, the title, thumbnails, and afterthought at the end, and it goes nowhere.
You actually want to start with that, right? You want to start with really thinking about, what are a bunch of ideas I have? And then when I think about titles for these ideas, you know, and researching titles that actually work on YouTube, which you can use tools like, you know, oneof10 .com for this, which is the one that we use internally.
You can go and look at other outliers that exist on the platform, which means, you know, different titles and thumbnails that have performed much better than a given channel's average amount of views. You can then kind of mash up your best ideas with outlier packaging to make sure that you start with the title and thumbnail.
before actually creating a given idea and thereby able to make sure that the first 30 seconds of the video actually fulfill the packaging of the video, that there's a clear structure to it that people understand, whether it's five systems, four steps, so people can follow it right and you get retention. And then ideally making sure as well that there's a good CTA in the video that leads people maybe to join your newsletter via lead magnet or go and maybe work with you in your business.
That's kind of, I think, the 80 -20 of like the YouTube growth approach. On LinkedIn, which is a platform we've grown to about 900 ,000 in the last five years, the key thing on LinkedIn is four aspects. Number one, making sure that you have long form value.
Two is making sure that you have amazing hooks. And so to double click into amazing hooks, right? David Ogilvie, the famous copywriter, said that you've spent 80 cents on the dollar by the time people have read the headline.
And what that means is that you got to get people to read that first sentence, right? You're trying to stop the scroll. And so how do you do that?
The easiest way to think about doing that on LinkedIn, and this is kind of for every platform, you'll see the same pattern. You want to go and you want to actually understand the outliers on that platform. So on LinkedIn, there's a similar tool to one of 10.
It's called Tapleo X. It's a Chrome extension whereby you can go and see. the biggest outliers from the biggest creators again these tools exist for every platform and so essentially this pattern that i just want to double click into is what you're trying to do is you've got these great ideas around this thing that you love to talk about you're trying to get smart now around what actually performs on the platform so i can package these ideas right to work and the issue is when people are thinking about packaging they think they can just wing it but you can't right it's like We all have those friends, right, that will recommend restaurants, right?
And you have that one friend maybe that you always trust their perspective, right? They say, oh, there's this new amazing spot in Santa Monica. You got to check it out.
And why is it that that friend's so good at figuring out that that spot in Santa Monica is actually a banger versus that other friend you have that recommends some spot and you're like, yeah, sure. I mean, definitely not taking that rec out. It's, I think, because they've really refined their palate.
Right. Like they've probably gone to a bunch of spots. They've developed maybe an exquisite sense of taste and they know now like a really, really good spot from a bad spot.
And so early on, what you're trying to do on, say, LinkedIn and really all these platforms is, I think, develop a good palette. And the best way to do that or one of the best ways to do it is to go and start looking at the best people and looking at their best content. and starting to study the patterns like what are the hooks here how have they structured their stuff so we got hook we got long form value there's images as well right so i use a lot of infographics or carousels all even and what actually led to some of my most you know fastest gross on the platform was actually just hand drawing just a little bit of value on a pen and paper with an iphone image every morning for about 20 minutes is again, a little practice and then just sharing those.
And then the fourth thing is then making sure that you obviously have a CTA in it, a call to action that leads people to repost it, which is the number one metric that LinkedIn is looking for. You're getting them to follow you. And then they're again, driving them to a lead magnet, which we can get into the whole lead magnet strategy there.
I'm sure in a second on the X side of things, very similar, right? Every single day on X, I post at 8 AM. And at around 2 p .m.
And the kind of content I'm posting are my best ideas. And then making sure that we're also refining them based on what we're seeing work on the platform. X right now, and it kind of has been this way for about the past year.
It is a squirrely platform. Love it. I think it has some of the best ideas on there.
I think it's got the best copywriting in the world you can find on X. It's typically then what travels to other platforms from my observations. That said.
growing on the platform right now is extremely hard. It's just a tricky, tricky platform. Lots of change, lots going on.
And so the game there I think is changing a lot. I think inevitably though, what always works on the platform is just really good ideas mixed within the right sort of way of packaging it, right? So, you know, whether it's, you know, you can have an idea that's maybe a piece of advice that you got when you were younger.
But maybe it's better to package that in a way that's like, you know, my father always instilled in me, you know, and then something, something, something. And that just being like a good way of leading into the value versus just starting with some story and people are already lost and they scroll by. So it's learning the hooks on X is like the biggest part because it's kind of like the Olympics of copywriting.
And then on Instagram, then when I look at the past six months of performance on my. instagram account that's like around 950k and again has grown to that over the last few years they're all carousels carousels are a format where it's just you know generally a square image that you can swipe through chris does an incredible job of these and oftentimes there's then a cta at the end of it and so you see a lot of reels being made i still push a reel a day on the platform but if we're looking to get up and going and growing on the platform I think carousels are the format of the year so far.
And all of this, like anything on these platforms is subject to change, right? Because platforms evolve, algorithms change. The beautiful thing about some of the things I just laid out is that there are some commonalities between them all, right?
All these platforms require you to have really good ideas. They require you to study what the best people on the platform are doing and really be good and intentional with your hooks. You know, whether it's your first line of your LinkedIn post, a subject line of an email the title of a youtube video there are some commonalities here um and you know amidst all these like little growth tactics we just went over um i think it's also again not losing sight of the fact that there's like the i you know doing things that you love putting out stuff that you love um and you know balancing like the algo with like the art of it all yeah I think the theme across all these things is it usually begins with words and images.
And if you can't get someone to consume the first part, you have zero chance of them consuming the last part. And so whatever the platform leads with is what you need to understand. Okay.
I couldn't write fast enough. You mentioned something on LinkedIn and using an extension on Chrome called Tapleo. Tapleo.
Tap. Yeah. T -A -P -L -I -O -X.
There we go. Yep. Okay.
And there's a similar tool again for X or something called Tweet Hunter X. That's the same thing. When you go to someone's profile on the right side, you see all their best posts ever.
And so same deal. You're kind of developing this exquisite understanding of like, OK, this is what performs best. Right.
So you can imagine that the next time you write, you may see a swipe file you've made of like you've saved all your favorite stuff. And all of that stuff has gotten a million views minimum. Well, now when you're going and trying to bring, you know.
these seven habits that have really helped you over the last year of your life, you can look at how other people have written stuff like that and then leverage that as inspiration as to how you kind of go and format what you're about to go and put out there, which is going to help it kind of at least stand on the shoulders of giants that have put out great stuff and packaged it in a way that helped it take flight online.
One of your standout things, and it's hard to miss if you've been on Instagram, LinkedIn, or X, is these, I would call them crazy infographics that look like you wrote. And I have some questions for you about that because they're really neat.
Even the spacing, the design of them is really neat. And it got me to think, is Matt doing this? Is AI doing this?
Is a designer doing this? And how many versions of this is he doing? So Matt's built a T.
I was at like an artist retreat in Esalen, Big Sur, in like, I think it was October 2023. And after going and building random mosaics and weird artist stuff after that, you know, I got back to building on these platforms. And at the time, you know, LinkedIn was one of those things.
And so it was about January 2024 at this point. I just actually had been sharing again all my same stuff on X onto LinkedIn, like I'd said. And I was like, okay, well, let's spice this up a bit.
One approach that I sometimes have on these platforms is like the J -Lo approach. J -Lo, she can act, she can sing, and she can dance. Kind of.
Kind of. And so it's like this idea of being a triple threat. And I think sometimes that's an interesting way over time as you start to get more comfortable to kind of think about your content strategy and what makes you stand out.
So I had really good hooks. I had great value in them. but there was like something missing.
And so I was like, well, what if I just go and put a drawing together around this concept? I'll time it. I'll give myself like 25 minutes this morning to get this done.
And then take a photo off my iPhone, attach it to the thing and put it live. Sure enough, did this for a week. Things just absolutely caught fire.
And so like most things, when it starts to catch fire, well, I kind of stick with it, right? There's like some good signal there. And as long as you're enjoying it and you're having fun, like, No harm, no foul.
So I did that for another around 100 days. So really putting in the work, really doing this. And again, approaching it more like I just got back from this artist retreat.
When I was younger, I loved to draw. So I was kind of just getting back to just writing neatly. I mean, if you've ever seen me write anywhere, if I really want to try, I can write rather nicely.
So that's what I was doing. It continued to work, continued to go, continued to grow. And then like most things, when we're at that scale, it's time to delegate.
At this stage, I have a couple actually, they're married, that run my social media. And Anna also has really neat handwriting. And so Anna had been seeing these images for some time.
And she said, yeah, I could definitely take this over. Like, beautiful. So that was that.
I just explained the process to her, made a loom around it. She obviously had the whole bank of infographics I'd been making up into that point. And now Anna's the one.
I'm going and creating all of these. And I think she's done it for, again, around like a year and a half now. OK, so they're not AI generated, although most of those that you see online are.
These are just the good old old school handwriting. And that's how we do it. OK, this explains some things.
And I'm going to pull Milko back into the conversation here. Have you seen his work before? No.
OK, that's cool. Don't worry about it, because if I think I was there at the beginning. I'm assuming the things I've seen are not what Anna made, but what Matt made, but I don't know.
But it's almost like a designer architect. Like he's drawing charts and diagrams and illustrations and his writing is, it's crazy because one of my friends was asking me, like, how's he doing? I was like, I think he's just spending a lot of time making them because the spacing is good.
There's not a widow or an orphan in the writing of it. So I say this because this is our zone of genius in design. But instead of using a computer, the analog way, it's like he kind of beats the AI question.
Because I think we like things made by humans and we like imperfection, but not sloppy. And so there's something really beautiful. And I'm not saying he's the only person who's done that, but to my mind, he's one of the first people who did these super intricate infographics made by hand that was so dense that blew up.
That blew up because I was thinking my presumption prior to that was this is too much information. Who wants to read this much right now? But I think you triggered something else, which is the save function.
So people weren't maybe consuming it on the spot. They would like it. Likely they would share it and then they would definitely save it because this is save worthy.
And I think you were hitting the algorithm real hard and it was just sharing it to more and more people. So I want people to think about that. If your content is really good and it looks good, people will save it.
And that's the whole point of it. Yeah, I think something I've learned over time with these two, because I've obviously got a lot of feedback on this specific format, which is handwritten infographics, is that, first off, my feeling on it is that there's something psychological too, just about like human writing has existed forever, right?
It's like so primitive. And so I think there's something like when you're scrolling LinkedIn as an example, you're seeing like this polished thing and a job announcement and then this like beautifully designed Figma intentional perfect spacing thing. And then you just see this weird lighting iPhone photo.
Some of it's dark, some of it's bright. There's like a hand mark here. There's ink there.
Yes, it's decent writing, but there's something so catching to it also because it's this primitive form of. you know, it's handwriting. It's a pattern interrupt.
Yeah. So it's a pattern interrupt. Exactly.
So that's a big thing. And then, yeah, it hits the save function and that gets going. And then weirdly enough, I've had so many people say that they print these out daily, which is really interesting.
So yeah. Is that good? Yeah.
So they print these things for value. And so I think that gets me thinking, you know, with your content, it's kind of. Knowing what like your signal metric is more than like the platform metrics.
Like it's kind of sad in a way, like what the platforms kind of like brainwash us to think sometimes, right? Like it's all about the likes and the comments and the views and all this stuff, right? Versus to me, like one of the things that jazzes me up the most, I mean, yeah, if someone says they're printing off something I made, like that's badass.
That's worth 10 ,000 views to me, 100 ,000 views. Also like just getting a text. Like if I got a text from Chris saying like, man, that image was cool.
That to me is better than like a month of like high performing content. And I have a lot of friends, you know, over the years that, you know, we'll message you something or I'll message them something when I see it. And that matters, that signal is way bigger than any of the noise that you see from just a bunch of likes or comments.
And, you know, my core metric these days is like, if I can, the core signal metric is essentially if I can see on a platform or a friend goes and texts me, sorry, and he's like, Hey, like we just shared this in our company Slack. It was maybe a post I had made or the team had made that they were sharing with the rest of their company.
It's like, that's the signal that we're after. We want a piece of content to be shared with 20 other people inside of Slack. And so kind of understanding maybe what that signal metric is for you beyond just like the platform growth metrics.
The thing I wanted to say, and then give you opportunity to kind of hit any other thing that you think people miss a lot on personal brand building. is what you're saying sounds exhaustive to people. Like, okay, so you're posting this many times, you're doing this, and you're writing hooks.
And people are like, I didn't get into this business to be a social media person. I want to focus on my core business. How do you address that?
Yeah, so we're kind of getting to stage three here, right? Stage one was kind of going and being able to build up the muscle of shipping. Stage two is then starting to go and get, you know.
pick a platform or two and learn the game of the platform and then also what like really sets your soul on fire and make sure that you're getting that early monetization going the reason that stage two is important because as we get to stage three right yes we're trying to get out of this stuff that we don't enjoy and so stage three i would say is it's moving from being a personal brand to a personal media company and so i think that wanting to build a personal brand long term actually in a sense is a bad idea What you're really trying to do is view yourself as a media company.
You're not trying to be a creator that every day is waking up, making things, thinking of ideas, and feeling like it's just this never -ending treadmill. You want to be the CEO of a media company and have the right people underneath you and systems that can help you go and build what you're trying to do so that you could take a week away or a month off eventually and come back and that thing is still cranking along.
And so how do you start to view yourself as this personal media company and build that profitable personal brand, right? Well, first off, obviously at that stage two aspect, you've got to make sure that you have an offer that can scale beyond just like 15, 20 customers, but be able to scale to hundreds depending on the pricing to get you to, you know, real profit numbers per month.
Let's just say 30K plus in profit per month. So when we start making that profit, depending on that route we've gone, right, we've either gone. camera first or we've gone writing first on the camera first side there's going to come a point probably that you want to bring on a social media manager and probably a video editor right so that you're not editing all your own stuff you have more leverage around you someone going and creating the stuff that's ready to post on the given platform and then someone to go and handle the posting for you right so that you can get yourself out of the operations of it all and the workflows and be able to focus on basically being one part CEO of a business that has to keep scaling likely and then have to show up, you know, maybe it's once a month, you know, for a few days to film a bunch of videos in a batch, you know, all at once and then be able to have content now loaded up for the next 60 days and then have that handed off to your media team to then use all that for all the social media content you're going to be putting out.
Similarly, on the writing side, you may go hire a social writer to go and take some of the longer form content you have out there and package it for platforms like X, LinkedIn, carousels on Instagram, and long form LinkedIn posts. And so that you don't need to worry about constantly writing all the time and scheduling stuff on platforms and replying to comments all the time.
You have someone supporting you with all of that stuff. This stuff should get you back if you do it right. You know, we're talking like 30, 40, 60 hours a week that you're not doing that stuff.
You're just the face of the thing. You're the one that has to show up maybe to shoot a video once a month or to maybe write and ideate with your team. But then you have people taking care of the rest.
So then you've got the profit. You kind of understand at least the minimum viable team structure to have this personal media company. Then you need to also have like the systems behind it to make this level of leverage happen.
And so a couple of things there. Number one is something I talk to founders a lot about is having, first off on the content side, a bit of a content waterfall system. In my companies, this idea of like waterfall is a verb, right?
When we see a good piece of content that we've created, typically a long form piece of content, whether it's a YouTube video, a Substack article, a long form LinkedIn post. we'll waterfall that content meaning we'll take that pillar piece of content that you know that's done well and we'll make sure it turns into about 20 plus other pieces of content right it may turn into a few different carousels on instagram we'll turn it into a few instagram reels youtube shorts tick tock videos it may become a couple newsletter videos and also the formation of a youtube video script in the coming weeks right so we're trying to get as much bang for the buck of that kind of kernel of genius that went out into a given piece of content and what this allows you to do is obviously get more output from a given piece of content thereby not having to constantly just create and create and create right because we want to do kind of less but better as we're scaling and so The next aspect, we've got kind of the content side.
That's like one core system. There's a lot there, but that's kind of a quick and dirty of it, is then your nurture layer, right? So you've got this audience growing.
We need to actually go and own that audience, right? You don't want to go and rely on Zuck or on Musk, right? There's something called platform risk.
At any point, you could just get rug pulled and who knows what happens. The real value of building an audience, when we talk about building a personal brand and eventually a personal media company, is owning that audience. Any entrepreneur will tell you the most valuable asset in their business is their email list, right?
Something like 32x more of an ROI than the next marketing channel in most founders' business, right? Like it's your email list that you control. When you send out an email, 100 % of people that you email get it, maybe 60 % open it if you have a good strategy there.
On social media, you post on X, maybe 2 % of people see it. On Instagram, maybe 5%, right? So you don't control that distribution.
Then when you understand the value, right, of really owning and growing your own email list, and it doesn't matter the platform, Substack, you know, Beehive or Kit, doesn't matter, right? Just something. We then want to make sure that we're building that infrastructure right there to go and grab.
that attention and convert it into emails. And this is where most people screw up. They start building an audience.
They get that part down. They have an offer that can sell, right? It's that middle layer of getting people to go from attention through to conversion that they screw up.
One of the best strategies here is what I call contextual lead magnets, right? So you have content going out now. You've maybe picked a few areas of, say, your icky guy.
that you're going to start creating around. So say for me, it's things like personal branding, content systems, and some personal stories, let's say. When I'm going and publishing content in Instagram that month, I'm talking about those three sorts of pillars, right?
I may go and create a lead magnet that is, say, the content waterfall system. That's this powerful system I've made that people can learn about if they go and... DM me on Instagram.
When they DM me on Instagram, it then goes and there's automations in place like ManyChat that can allow you to go and give people a lead magnet in exchange for their email. And now you've brought that eyeball on Instagram into an email you now own that you can now engage with that person for the next three, five, 10 years versus maybe showing up on their feed every couple of weeks.
on Instagram. So it's that infrastructure middle nurture layer that then leads you to having the ability to eventually send out a weekly newsletter in there in the PS section, maybe mentioning the offer that you've created, the business you have, the product, the service, whatever, and start to actually drive leads to your business, which leads to the third layer, which is then monetizing.
And obviously, we're trying to build a profitable personal brand here. And over time, I think the most important metric when you're building a profitable personal brand is essentially like your profit per piece of content, right? Cashflow is king in any business, right?
It's the lifeblood of a business. And as you scale, as you build this media team around you, as you have maybe fancy studios and lighting, you want to make sure that you've got really great cashflow coming in and thereby the content that you're creating is driven around, you know, what. really your dream customers want so i think when you start to kind of see more cash coming in the door one thing i like to do you have more customers survey these people right asking them you know what is it what's your biggest goal this year right um you know what is your biggest challenge right now um what's keeping you up at 2 a .m and if i were to solve anything for you this year what would be the number one thing you'd want my help with So now maybe you're going to your top customers.
Maybe these people are paying you $10 ,000 a year, maybe 5 ,000, maybe 80 ,000, right? Depending on your business. Well, similar fish swim together, right?
So these people that have paid you a lot of money, let's just say 10 to 20 of these survey responses, that's gold inside of those responses, right? Because they're telling you what they want to see more of. And if you can serve those fears or serve those wants, desires, dreams in a really, really solid way, you're likely to go attract more people like them.
If you need even further help coming up with ideas off that, you could simply use Typeform, download the results, upload them to ChatGBT, and ask it to help you come up with ideas to serve this market. And so what we're trying to do essentially is make sure that we're building content around, yes, what we want, but also making sure that we're being conscious of what's actually bringing in cash flows.
Because as I've looked at the patterns here and I've looked at this across 18 ,000 founders that we've helped with just this stuff, the pattern that's oftentimes obvious but counterintuitive initially is that essentially it's not the stuff that gets the most views that makes you the most cash. Oftentimes it's stuff that you wouldn't expect that doesn't get that many views that's actually like the biggest breadwinner.
And so being able to measure that over time is really important. and paying attention to the most important thing, which typically in these brands I think is cash flow. Great.
I think you laid it all out for us. With these entrepreneurs that you work with inside FounderOS, where does it usually break for them? Yeah, the area that breaks most often is, I mean, folks don't have the structure in place for their team.
They don't know who to hire, and they don't know when they've hired someone. the rhythm by which they kind of delegate with this person, how to onboard them and the rhythms that they should be running in their content team. What we help with there and to kind of help everyone in the audience is first off, you need to make sure that you're not guessing at what someone should do when they're coming on board, right?
Like you need to have a really tight onboarding as to what you expect from someone in the first like 30, 60, 90 days of working with them, right? What tasks do you specifically need them to do? And I don't think you should be trusting people's taste out the gate.
That's my own perspective, right? You should be laying out what you do, how you work, get them to execute the task, get them to prove themselves before you start, you know, really requiring them maybe to kind of come up with some crazy new ideas or reinvent the wheel. Too many founders bring people on with vague job descriptions.
and kind of bring them on and tell them to figure it out. And it ends up just failing. And so getting your onboarding right and then writing your job descriptions and what you expect out of the role is key so that the job descriptions as well are not vague.
You've got your values in there, what 30, 60, 90 day success metrics look like. So you're bringing the right people on with the right expectations and then ensuring they hit the ground running. And then along the way, obviously when you brought them on as well.
Like, do you have the right meeting cadences going on board? How do you run those meetings so that you're actually, you know, running a tight team versus things being all over the place and quickly feeling like you got to make some tough decisions and change some things. Perfect.
Before we move on to what Tyler wants to talk about, is there anything that you guys want to ask Matt about this, the four phases? Three. Three.
Content, nurture, or monetize. I want to take a step back because I think the part that gets me and a lot of the people that I work with is getting in your head about views. I really like what you just said about the money, but how do you keep that mindset?
It's not just about the views. Good things can happen even when the views are low and also just that long -term mentality, the marathon, not a sprint, way of going about content.
I'm just going to be real honest about this part. So there's a documentary I watched about six years ago called Icon. It's about Carl Icon, the famous investor.
At one point, I think he owned about 12 % of Apple. And it's an awesome documentary to go check out. And he's this old kind of curmudgeon of a guy, about 88 years old in this documentary.
Loves what he does, though, and he's amazing at it. And he has this pillow in his office and he's just casually talking to the camera, but you can't help but notice what's on this pillow. And it just says, happiness is positive cash flow.
And when I study a lot of people that are successful, there's another podcast I love called Founders, where it just talks about some of the most successful founders of all time. The thing that you can't help but notice is that like, yes, you can be an artist and you can build great products and you can do crazy things. Right.
But like the business runs off of cash. And so at least as I'm building businesses and when I'm talking to other founders about it, the one thing I'm oftentimes trying to just remind people of is like, go and get the fucking money. Right.
And it doesn't mean to go and get the money and then be salesy and then be weird or short term thinking. It's not that at least how I. see it at all, right?
It's about abundance thinking, right? Like, you can have a world where you get the views, you get the cash, you have a badass team, you have fun, it's play, you love your customer, like you can have it all, right? It's not an or conversation, you can be and about how you live your life.
And so when it comes then to, you know, how do you get views out of your brain and focus on the cash? I mean, I just at least come down to like, like, don't you want the money? Like, what do the views do for you?
Right? um you're going to go and spend time on say a friday and go and make some content and you know that maybe when you look at your schedule you really wish that you could also make a hire that would get you out of a couple more things in your company a chief of staff maybe to handle your calendar maybe you want to hire another video editor to help you get out of some more of the you know stuff there right these people they cost money right and so why not go and gain leverage with a given video by focusing it around something that can actually both be fun and serve your customers and make you money.
It's not a sacrifice here. You can have it all. And then thereby make cash, invest that in a great team, get more of your time back and make more great shit that's also abundant in these ways.
Do you find yourself iterating on what you find fun at different parts of things? Yeah. So in terms of like when I approach fun, I think one of the people online that I most admire in this kind of area is Tim Ferriss.
He's the person that inspired me to get into entrepreneurship 20 years ago. And I think when I look at Tim Ferriss, one thing that stands out, at least in my awareness, is that he built a brand around his own curiosity. It's really, in a sense, it's not like a niche in the way that we would typically think about it.
Like, oh, targeting $3 million a year software founders. Instead, what I think he owns is a bit of a psychographic. You know, the kind of person that's like looking to grow, looking to value his lifestyle design, wants to take care of their health, but also try the new things and be a bit of a guinea pig.
He's kind of, he owns that space. And in that sense, it can continue to kind of grow and morph with just his own curiosities. And so when I think about building my brand, and I encourage founders to kind of do this too, I think it's the beauty of building something around more your icky guy, is that it also can just evolve with what you love because you attract.
people that resonate not with like some core niche you have per se they resonate with more of like a core identity right and you know for me that's founders as an example that want to be able to travel and also enjoy taking care of their health and want to have abundance in their lives and spend time with their family but also enjoy making amazing cash flowing business they're high growth but also intentional it doesn't necessarily kind of into like a specific niche it's a bit of a psychographic and so I think in that sense I've built something too that I can keep on pursuing my own passions you know recently as an example made a video where I was just in the dolomites sitting on a rock while on a hike and I just put the tripod down and just press play and just talked about how I think relaxation is important to success and it was mixing kind of a fun part of my life with just pressing play and not really overthinking it so Yeah, that's how I approach it.
I hope that makes sense.
So you talked about content and waterfall system, a nurture layer, monetization. That's where I have no clue. Could you deconstruct that a little bit for us?
What do you mean by monetization? Do you mean when I post things, I get sponsors and they pay me? Do you mean I go after venture capitals to get money from them?
Can you please shed more light about what do you mean by monetization? That's something that's totally abstract for me. Thank you.
All right. Spoken like a true creative, by the way. Yeah, I love it.
He went over this, and the fact that you asked that question is super fascinating to me, but fantastic for asking. Yeah, I love it. Okay.
So, you know, the monetization layer, right? the pot of gold, the gold mine, like we're trying to crack the code on this, right? And yes, it can be like the trickiest layer for folks, especially, you know, creatives oftentimes that, you know, it's really scary asking for money.
And I, you know, Chris has some unbelievable content around that. I know a lot of the creatives I've spoken with always refer back to some of Chris's amazing videos on that front. But to give this a shot, I think I definitely don't recommend that it's ad dollars that you're relying on, although that's fine.
I think that a purely ad -based model is what I'd call like more of a creator than a founder, okay? And there's nothing wrong with any of these things, but creators typically make a business based on views where I see founders build a business based on some sort of offer that they have, right? And so then the question becomes, okay, well, what's your offer, right?
And I think that's where it comes down to what is it that you want to deliver, right? So an offer is, essentially just something that you're delivering to someone that they want to buy at a certain price.
So the most simplistic way to think about this, at least that I think about, is we need to go and create a one or two page Google Doc that is a thing that you are selling, right? And so are you selling a course? Are you selling a mastermind?
Are you selling, maybe it's a SaaS tool that you're going to eventually build, whatever. We need to at least first document like what is the thing. And contrary to what most people tell you, I think you can sell a lot of things off of a Google Doc initially.
You can keep it simple. A Google Doc and a Stripe link can work wonders, at least to get you to your first 15 customers. Okay, why 15 customers?
Why did I bring this up? My brother, who's a product manager and now like a chief product officer of a company. I don't know whether this is like real news or this is fake news, but we're going to get wrong with it, is he told me years ago that 15 customers is product market fit.
And to me, that really settled in my brain. I was like, okay, you just need 15 people, right? I think that's where something sort of starts to transition from like more of like a hobby to then like an offer to like, no, you have a business now, right?
You have something that you sold to 15 people. This is real now. And now we can start to scale this thing, right?
You sell 15 people, you can get to your 100, you may even get to 1 ,000, right? So simply documenting the offer, getting it in front of people, trying to get those first 15 people, I think that's like layer one of monetization, right? Layer two, as we start to now scale it up more, is like that offer becomes a landing page on your website.
It may have a video sales letter attached to it as well that allows people to learn more about what you're doing via video. and then copy around what that offer is. If it's something that people can buy immediately, maybe that's under $2 ,000, they can just click a link to buy and check out with Stripe or whatever payment layer you want to use.
And that's that. If it's above $2 ,000, it may be considered what's called a high ticket product. And thereby, the typical way of selling that is on a sales call.
And so people would then go and click instead of a buy now button. Maybe it's an apply link to work with you. And they'd click that link, maybe fill out a few questions on their stage and what they're looking for and whether it's right for them or right, you know, what you have is right for them or not.
And then either if they qualify, get on a call with you or eventually maybe a salesperson that you hire. And if they don't qualify, you could say that or you could actually go and sell them something that's lower ticket that is right for them. And so it's kind of that layer that we're talking about.
in monetization so milk i'm going to help you okay because i know a lot about her yeah so your offer could be uh i'm going to help you to get into it could be like a portfolio workshop where you're going to get high school students who want to go to art center or otis or one of these private art schools and for four or five thousand dollars over the course of four weeks you're going to review their portfolio you have a system in place you have a framework you'll do some some video like asynchronous courses and you'll do some some uh personal feedback and critique and that's your offer so i think when he said offer at the beginning of this thing that just went right over your head you have to have something you're going to sell or do for for people and it could be one -on -one it could be one to many it could be many to many whatever it is you understand that part okay what does that mean organically can you take the mic I am doing the portfolio workshop organically, meaning people are reaching out to me and they're asking me if they could do a workshop with me one -on -one.
So when you say organically, you mean passively not asking for it. Correct. Let's use the right words.
So now we have to be active and asking for it and creating a sales page or an offer doc. So you understand when he says just do a sales page or sales sheet on Google Docs? That's the ugliest, dirtiest version of this.
You don't even need a website for this. So what you do is like, say, for example, you because I know so much about you, you can say, OK, here's one of my students work. Here's how you make it better.
And at the end of that piece of content, you can say, hey, I have I can help your child get into Art Center. Click on this link or say this word and I'll DM you the link. They go to that doc and the doc says whatever it says, and then they can either pay you or jump on a sales call with you.
And that's how you would do it. That's the monetization that you're missing. So many creative people have a problem asking for work.
They really just rely on word of mouth advertising. And so that's very passive. And that's why we can't control that.
It comes and it goes and we're just like, okay, it's feast and famine all the time, right? You know. So you build a system around this so that you can get more consistently gen deal flow, cash flow.
Yeah, in a sense, like to really, this is a quick analogy, right? It's like you have like a... piece of real estate you bought that could maybe one day be an amazing restaurant right and people know that you're a great chef they see you around this restaurant but there's no menu and they see you they know you're an amazing chef so you have some people sometimes pass by and go hey like you're gonna serve anything or anything is there a way that i could like just get a meal with my wife with you like i i know you're legit that's what you're saying is like organic, right?
You have people kind of coming by and being like, Hey, like, I know you're legit. Like I'd love to do whatever, or they're getting referred to you. What I'm proposing with this offer thing to bring it down to this analogy is like, put a menu outside, right?
Put a sign on the wall, like set the tables, right? So that people can walk by, see a menu, like any restaurant we'd go to. This is interesting.
I'd like to work with you, or I'd like to eat this. And then they sit down and you've got your customers, right? And so your offer is like your menu, right?
You need to start giving people a way to understand how they could work with you because there's a hell of a lot more organic people that are walking by, they're looking at the sign, there's no menu outside, and they're just walking on by. And now you're able to start capturing more of these customers. And then eventually, as you start doing that, you know, at this digital restaurant, you eventually have a person that's actually outside as well.
And they're near the menu. And as people pass by, they look at the menu and they're kind of curious, but then they start walking by, they're like, whoa, whoa, whoa. You want to eat here tonight?
Like when you have any questions? Oh yeah. Is it, you know, is it gluten free?
Yeah. We got a gluten free menu. Come on in.
Yeah. Okay. Oh, you know, I only eat fish.
Yeah. We got sea bass. Come on in.
You know, that's your first salesperson, right? So now your salesperson, you know, has the offer and they can sell it for you. The same way the person outside your restaurant has a sign, has table set and a menu there.
And you can start saying, yeah, we serve this. We don't serve that. And you can start past, you know, getting even more of these organic folks in.
So it's great. And it's. for those creators out there that have that organic traction as you're speaking about and are getting those referrals and are getting that thing, beautiful.
You do have product market fit. You have a business, right? And so imagine the potential if we can just now put that offer out there as a landing page on your website, as something you've gone and documented somehow so that more and more people could discover you because right now you're hiding.
Yeah. Okay, you good?
That's amazing. Okay. I'm glad you said that to no camera.
Oh, absolutely. It's okay. It's okay.
Don't worry about it. We're good. Well, so to draw this string all the way through, you know, I do with a lot of creators who interestingly are startup founders, but they actually have something that most founders don't have, right?
They don't have a product. They have the organic reach, but they don't have a product. So I often have to ask creators, What is the pain point that most of your audience suffers from?
And so we do this exercise of like, what's the pain point? So for me, my channel is about servicing creators. At first, I thought the pain point was copyright strikes, brand deal, contract provisions.
But when I started doing the M &A work and working with creators on exits, I realized that most YouTubers and creators want to get off the hamster wheel. They need to have the product. They need to monetize.
And so really asking your audience, doing the surveys, asking them, you know, I did the scorecard for the hundred million dollar video and I asked them, what's your pain point? What do you want? And they're like, I want off this hamster wheel.
So that means I need a product and I need to monetize. Right. Because they're so reliant on AdSense and brand deals and that if it goes if if they get kicked off of YouTube, then they're done.
And I love what you said, Matt. You know, I was in a room with 10 huge YouTubers a couple months ago, all 10 million plus. I asked all of them, how many of you have an email list?
Only one person raised their hand. It's terrifying. I said to them, so if your channel goes away, you have no way to access your 10 million plus subscribers, right?
So one other question I had for you, because this is something that a lot of founders struggle with, is I think... My favorite phrase right now is capital is very easy to raise. Human capital is very hard to raise.
A lot of creators and founders have a real hard time finding the best talent, right? So when you work with founders, are you actually helping them hire too? And where do you look for those people for them?
So yeah, inside of FounderOS, we help folks hire anything from chief of staffs to social writers, to video editors, to social managers. And so, yeah, we have a whole kind of vetted talent network that way. What I tell founders, though, in general, is that number one, I mean, if you're building a personal brand, no better people to go hire from than ideally like putting it out there to your audience.
Right. I think about 85 percent of my team has come inbound for me putting out messaging that we're hiring certain roles. And then they were really solid and we brought them on board.
And the beautiful thing is when with those folks, what you typically find is like. They're already on board your values. They've been following you for some time.
There's like an aspect of like cultural onboarding that's just happened by nature of them following you online. So typically, depending on your offers and your company and all that, you know, it can be a really good hotbed for A plus talent. The second thing is what I've always noticed is like A players hang out with other A players.
And so when you have a role that's open. It's really good to have a list of like 30, 40, maybe friends, contacts, acquaintances, whatever, that you can go and just even text or email and let them know that you have the role open. Those folks don't need to be doing what you're hiring for.
Like you don't need to go message 40 A -player social media managers to find a social media manager, right? Just go literally email or I like to text, you know, just a bunch of other really solid folks I know, right? you know are really good at what they do they're craftsmen they or they have good taste or um you know they're just really solid because maybe it's their sister a cousin someone they were at dinner with last night that they vetted and they were like oh actually you know what this person i know does that and you know that they have solid judgment solid intuition for it that can potentially bubble up um some really solid potential hires and so that's how on a lot of teams you know my team at founder us is approximately 30 people now a lot of those hires start to come just from their friends, right?
Because great people hang out with other great people. How many people you got right now? At the team?
Yeah. 30 at FounderOS and about 30 at Herb. And 30 what?
30 at Herb, the other company I run. Oh, okay. All right.
So like over 60. 60, yeah. Okay, cool.
Tyler, your question before was something else. Did you give up on that question or no? I do need a social media manager, by the way.
But that's not your question either. This is going to be your last chance. Is it too late to start on X now?
And the second was about your book, right? It's taking you three years to write it. For me, I think three years, most of everything I might be talking about might be outdated.
Okay, so is it too late to grow on X, right? The ultimate question for those that are maybe seeing the platform and all the action going on in it and want to get into it. I don't think it's too late.
I will say it's the hardest platform right now. So when I think about a founder prioritizing and if I was to go down a list of all the things you could do or maybe another platform you could focus on, you know, typically it's like, can we go a lot deeper on what you're already doing? Right.
Again, less but better. Or is there another platform that maybe is a lot more easy that we could get going on? So it wouldn't be the first thing I would go to.
And I'd be careful with it because, yeah, it's very, very, very hard to get started on. So that's that piece on the book side of it. Yeah.
Every book is different. I get a sense. Yeah.
Yours is like this mix of kind of creator CEO. And yeah, I think it depends on what kind of book you're trying to write. Right.
Is it something that's to be more timeless around that subject with timeless principles that even a hundred years from now would still be relevant? Or is it like very much like the algorithm is this right now? And as a creator, then you got to do this to be a CEO, right?
If it's the former, then you don't really need to worry as much. I think about the timing. If it's the latter, yeah, the timing is going to matter a lot.
And I think it's figuring out what kind of book you're writing. Personally, I think a lot of the people that I admire typically try to write the former, which is something more timeless, something that could be a perennial seller, something that will still have a level of relevance even 100 years from now. And examples of this are like On Advertising by David Ogilvie.
or scientific advertising by Claude Hopkins, right? There's some references in there that are pretty old school, but the books are still classics today. And so that's what I would try to default to with a book if you're worried about when it's going to come out and if it's going to matter.
Yeah, try to make it more of a perennial seller and read a book from Ryan Holiday called Perennial Seller that's good on kind of wrapping your head around that concept, I think. The thing I've learned on the book journey that I'll just leave you with too that I screwed up, or not screwed up, It's been the hardest part because really my journey, why it's taken so long is not procrastination or perfectionism, although that's been, you know, it's come up.
It's actually that I didn't have the right sparring partner, an editor. I've had editors. It didn't work out.
And I finally have found someone that's unbelievable. And that's really what I needed all along. I just couldn't find it because I'm really just new to this whole game.
I'd never written a book before. So really make sure you have a good editor that can then help the project move along, help it get out there. I think similar to how whether you're struggling on social media, have an accountability partner, have a coach.
You know, you're struggling with a book. Find an editor. Make sure you're not going solo.
And so for me, too, it's I wish I had met this existing editor three years ago. The book would already be out. Tyler, are you good?
Yeah. You sure? Driggle.
I know Driggle wants to ask. You want the editor? Yeah, I'd be happy to make the intro.
Driggle, you want to say something? Matt, how involved are you with the content strategy for what you guys are doing on YouTube right now? So.
Yeah, I can describe the content strategy and how involved I am. Go for it. Well, just because you say you have a 30 -person team, as I'm trying to scale my own agency, I work with Chris.
And as I scale, I'm having more issues with scaling certain things. I'm trying to assign people to do certain tasks. I just wanted to find out, at least from your perspective, are you still involved with the YouTube strategy or do you have somebody that does that for you?
I have someone that does all YouTube strategy for me. Now, that said, Again, everything I'm building in the team and the systems and be able to remove myself, it's really to get to optionality, right?
It's freedom. But I do love this stuff, right? So I do get involved still sometimes in different aspects because I want to, right?
So, you know, I want to know what ideas we have coming out because I want it to make sure it feels like me and it's the stuff that I would want to watch. So I'll get in there in the first like 10 % in the ideation phase just to see like what we got cooking. And then typically these days to really make sure that it's super dialed, I'll also send just a brief loom video on the concepts and how I'm feeling about them and what comes to mind when I look at the title and the packaging.
So that as we start to kind of get ready for the filming day, my team already knows the kind of things I want to touch on. So it's not some person formulating what I'm going to say that day. It's my thinking, my thoughts and what I genuinely want to show up like.
So in terms of like that process, though, to bring it down to earth with someone that's scaling an agency and looking to. you know figure it out right so they're not getting stuck in the weeds and they're still involved but they're not involved in stuff they don't need to do i think all these things when you look at a business you look at a media company it's an assembly line right it's a machine and when you look at the assembly line of video right it goes from ideation pre -production to production to editing to then distribution analytics and then it's like fed back into ideation right and so when you look at that all like who owns each piece of that process right and if you're trying to get more out of the weeds you want to be making sure probably that you own no more than maybe one or two of those and if you're a founder -led brand a personal brand you're gonna have to be involved in production right because it's your face so you got to make sure then that the other pieces hopefully you have other owners that are owning that piece doesn't mean you can't have an opinion or share an insight or something you'd like to do but you know that
if you were just to vanish for a few weeks and you know go snowboarding somewhere and you know kind of do your thing that the process would still run without you and so you know running this agency getting it to 30k and trying to do it in a sustainable way i'd be looking at you know do i have owners for each step who owns ideation who owns pre -production who owns production who owns editing who owns analytics and can i make sure there's an owner for all those that's not me right and that maybe i can get it to a stage now where I've got owners there.
They're learning from the documentation we have as well as any videos I've made to describe those steps. And I'm now just available on an hour content meeting per week where any questions that come up, opportunities, issues, I can flag them and help with them. But other than that, this team starts to get to a point where its steady state runs without me.
Love that. What are some non -negotiables that you look for when you're hiring people for these positions? So the non -negotiables that we have and that I recommend folks have is, I think, number one, you need people that are extremely reliable, right?
You have dates you're going to be shipping things or shooting dates that are going to happen. These people must ship on time, be reliable, have a history of strong performance. One question I love to ask folks in the interview process is, tell me a time you've done something exceptional.
Right. Like I want to know, like, what have you actually made? What have you put out there?
Let me see it. Show me it. How are you involved in that?
Run me through the process. Why did you make these decisions and really see how this person makes decisions, their judgment, their taste, their intuition. Right.
So extreme reliability. Second thing is we want people that are entrepreneurs. Right.
People that view their area like I'm bringing this person on to run a business unit. Right. So I'm not right.
You know, I'm not bringing as an example, Memo, the editor on my team behind you. He's not just an editor on our team. He is running our editing department and running the second channel we just started.
So he's running a business unit within our business, right? And the kind of people then that you can give the reins for certain outcomes, like, you know, we want this second channel to drive this much cash flow to the company and that person can actually own it. And so you're kind of asking yourself when you're looking at someone, say you're trying to create a million dollar business, you need a few people in there that maybe could run a 500K company.
a couple of people that could run a 250K and then maybe a couple others, but maybe not. And so you're kind of looking at someone maybe and like, would I trust you to run like a 250 to $500 ,000 business? And if it's someone that doesn't hit that mark, they're a bit sloppy, they're rough around the edges, it's like, maybe it's a no.
The next aspect that I look forward to is, I mean, just like raw intelligence, honestly. I think that's something that sometimes gets overlooked in smaller companies, but when you look at big companies, right, they're giving IQ tests. They're looking at where this person graduated from.
They're looking at their marks in school. And so I think just using even, there's a test called BRIC, B -R -I -Q, giving someone an IQ test and making sure that they can, they're smart. Because there's a lot of decisions you're making when we think about, say, editing as an example.
There's so many micro decisions along the way. And also these spaces are being reinvented right now with agents as well, right? And so do you have someone that can go and say, Memo, who's running our second channel, he can use agents to go and look at all these podcast appearances I'm on and long form content I've made and come up with 80 clips a month without even touching and editing software and then just put the polish on it, then just put the packaging on it and make it proper.
Or do you have something like that would just be mind blowing to them and they would never be able to do that? And even in six months when agents are democratized, they're still just like, I just got to do it one by one by hand and my max output is two per month. Like this is a tale of two different companies.
And so you're trying to find those folks that have, I think, the intellectual horsepower to keep up. I want to make sure I ask this. There's a serious question and a super stupid question.
Perfect. To lower the IQ of the room. The serious question is this.
What you're saying makes a lot of sense. If I'm a solopreneur. I want to be able to go and build the content and then have a way to monetize.
And in order to do all this stuff, I do need help, but then I don't have the money to get help. So I keep telling myself if I make enough money, then I'll get the help. Help me get out of that routine because I think I'm voicing it probably for 85 % of our audience right now.
I know our audience, right, Milka? Yeah. They're stuck in this weird loop.
Yeah, so my approach to the weird loop is first things first, you got to get the money. that's how i see it right it's like you're you're building something you're in this loop what's the most important thing you're rebuilding a business okay we got to get some cash right because you get some cash in the door then you can start getting the help you need around you whether it is get that first hire so you're off a bit of the treadmill or it's getting a coach or joining a community or whatever getting the support you need to stay accountable so you're not just spinning your tires and so then it's just looking even just getting a pen and paper out for a second like let's just keep things simple right i know when i get a little anxious or overwhelmed going in just pen and paper, kind of writing things down.
And I don't mean journaling. I mean, even just writing down some bullet points, maybe some to -dos, maybe drawing something helps just me get it in my head, right? What are like maybe the next five, 10 things you think you can do that would drive you some cash flows, right?
Is it getting on 10 sales calls? Is it actually talking to that person that's been saying, hey, I'd love to work with you? Is it...
launching something new because the existing thing's not working right different businesses different cash flow generating activities but always good when you're a bit confused to get grounded and just like what is the highest cash flow move i can make next and so you've now kind of documented some things in your journal some are really bad and been there done that do that all the time and some are actually a kernel of something amazing right You want to then prioritize those things.
And I think a way to think about this, just giving that even more granular, right? If I'm really trying to dial this is what is the lowest effort thing that I think that could produce the easiest amount of cash, right? So like, oh, there's literally someone that emailed you that you just haven't answered yet that wants to work together.
Get on a call, try and close the deal. Let's get this done, right? And so that's...
The next step, because then the cash flow brings you the leverage and the optionality to start investing in some areas that may be able to support you. But without the cash, you're just in this cycle of constantly spinning your tires. You're speaking perfectly logically, like from a business person point of view.
The creative person, God bless you all, can't hear this. They just can't hear it because like. You know them better than I do.
Yeah, I want to do this thing instead. Or when they have money, it's like, well, I'm going to hoard it and I want to use it because money is scarce. So they have a poor money mindset.
Or my friend Erwin McManus would call it a system of thinking that's designed for failure. That's a much bigger, deeper topic to talk about we're not going to be able to solve right now. So I think you may have solved some of that problem in selecting your audience.
If you're a $3 million a year entrepreneur, you've already solved these problems. You don't have to deal with that. You can just help them achieve and scale more.
And so it's a realization I've come to myself. Serving solopreneur creative people has been a massive challenge because there are systems of thinking that it's just so hard to undo. Now, before we run out of time, you created an open loop.
You said you're drinking, you're on substances, you got some blood work done, and your testosterone level was really low relative to your age. How's the testosterone level now? I told you it asked a low IQ question.
open loop bro it's bugging me i'm like yo what happened to that thing testosterone's pumping we're back sobriety works sobriety works i guess yeah yeah okay do you do blood work often every six months okay so you're at where you're supposed to be you're above average below average where are you at we're in the pocket we're okay yeah love it go to the gym there we go lift some weights get some sunshine get some good sleep this is not true i wish that were true yeah It's chemistry.
How are you doing on the testosterone front? Okay. Yeah.
There's two kinds. The kind that I need to grow muscle is not good. Okay.
There's like free testosterone and there's the other testosterone. Whichever one you need to build muscle. But let me try everything I'm supposed to do.
Sleep, diet. Let me try that first. Yep.
Before I get into therapy. Yep. Matt, I appreciate you taking time to talk us through it.
I love the way you present information. You are who you present yourself to be online. You're more clothed today than you normally are, I think, when I see you.
And I appreciate that. Everything you said checks to me. There's a clear logical system.
You are very good at creating systems and you've just proven it to me. And I hope our audience can probably, you probably need to replay this several times and go through this. And if you're ever stuck, you just take the part you're stuck and ask AI.
I understand this. How do I apply this to my line of business? And it will help you.
You don't need to get all the answers from one person. But I like this really high level kind of CEO, executive level looking at a problem. So we understand the architecture of how this is supposed to work.
And then each person is going to have to determine, does this fit for me, what I'm doing, my financial goals, my work ethic, and then find the right answer for them. Now, before we get out of here. People are like, this is super cool.
Is there a lead magnet or is there someplace that we can send them to that they can then go deeper with what you're doing? Yeah, so people can find me, Matt Gray, on all platforms. On my YouTube, you can see a bunch of different topics there.
Go and peruse them. Each video also is accompanied by either a worksheet or some sort of deep dive system that you get for free. So you can go and check those out there as well.
And then if you're interested in going a little deeper on how we work with founders and creators inside of FounderOS. you just go check out founderos .com. Perfect.
Thanks for being here, man. It was awesome. Thank you so much.
Appreciate you. Thank you.
The Hook
The bait, then the rug-pull.
Matt Gray opens by describing an addiction and a testosterone crash that started the whole story, then spends the next hour and a half turning the personal-brand-building process he found on the other side into a repeatable system.
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A creator with 8 million followers and 5.5 years of daily posting breaks his whole content system into two teachable parts: how to stop niching down, and how to build hooks that stop the scroll.
Busy Blooming's Tess Barclay maps YouTube's five creator "departments," makes the case for strategic talking to camera, and takes a rapid-fire Q&A on scripting, titles, niching, and getting over on-camera cringe, all with February 2027's doubled monetization bar looming.
A Forbes-ranked creator breaks growing an audience into six repeatable steps — pick a platform, build credibility without a studio, own a category, mine ideas, read the right metrics, and turn attention into a paid product ladder.
A four-part formula — association, obsession, positioning, world building — for building a personal brand in any category, reverse-engineered from hundreds of the internet's biggest names.
Daniel Priestley returns to The Dept. for a third time to argue that personal brand now beats business brand by 20 to 1 — and to lay out the exact content system that makes the algorithm find your people for you.
A Hollywood showrunner explains why people buy on emotion, not logic — then the host spends an hour turning his rise, collapse, and comeback into nine repeatable principles.
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