You post consistently. Your content gets engagement. People tell you it’s valuable. But when you launch something, sales disappoint.
The problem isn’t your content quality. It’s the system that turns readers into buyers.
Matt Gray built his business around that system.
By the third quarter of 2024, Matt was generating over $620,000 in monthly recurring revenue.
Seven hundred forty people pay $7,800 annually for his premium community. That’s one tier in a seven-product ladder. His profit margins exceed 70 percent (no advertising needed).
Somewhere between a person’s first $29 purchase and their $7,800 commitment, something shifts. Not in what Matt sells them. In how ready they become to buy it.
The Shift That Took Matt Gray from Revenue to Real Leverage
Matt’s story with Founder OS starts with what came before it.
By 2021, he’d built Gray Enterprises and Herb to 14 million community members. Annual revenue reached $13 million. His team numbered over 50 people.
From outside, this looked like success. Inside, it created constant pressure.
Every revenue increase demanded more staff. More customers meant more operational complexity. The business generated impressive reach without creating leverage.
The earlier chapter matters for context: in 2014, he sold Bitmaker coding school to General Assembly. He was 26 years old at the time. He’d taught himself to code after getting kicked out of his family home at 18.
“I realized no one was coming to save me. I had to change.”
He’d escaped one constraint. Then created another.
In late 2023, Matt launched Founder OS. He built it for founders experiencing what he’d just lived through. Operators already earning between $30,000 and $500,000 monthly who’d built something real and felt stuck inside it. Revenue without freedom. Growth without leverage.
He positioned it as an operating system for businesses.
The target wasn’t people trying to start. It was people trying to stop being the bottleneck in what they’d already built.
He set the annual membership at $7,800 with no monthly payment option.
The reasoning: monthly subscriptions create a recurring decision point.
With subscriptions, every 30 days members subconsciously ask “should I keep this?” That question alone drives churn, even when people are getting value.
Annual pricing eliminates that friction. The decision happens once.
The $7,800 price point also filtered deliberately. It’s high enough that only serious operators would pay it.
Those who invest that much typically implement what they buy. Implementation creates results. Results create retention. The price itself became a qualification mechanism.
Members received extensive deliverables. Access to 180+ documented systems. Forty live implementation sessions monthly. That works out to 8-10 sessions weekly. Twenty-four hour response time on questions. Custom AI tools trained on 2 million words from Matt’s frameworks.
The revenue doesn’t come from advertising or sales teams. It comes from content that builds trust before asking for anything.
Matt creates 3-5 long-form posts each week. His team transforms each post into 25+ smaller pieces. One post becomes threads, carousels, reels, newsletter segments, and blog content. This generates around 2 billion impressions annually without spending a dollar on ads.
The content does two things simultaneously. It teaches his frameworks. And it demonstrates those frameworks working in real time. People watch the system operate before they consider buying it.
That approach built his newsletter to over 100,000 subscribers. When those subscribers see an offer, 3-5 percent click through. Typical newsletters see 0.3-0.5 percent.
He also runs free workshops called CEO Coffee Break. Just genuine help around implementation.
Between 10-15 percent of attendees book consultation calls afterward. Those calls convert 7-10 percent to paid programs.
The pattern repeats: teach first, prove it works, let people decide they want help.
By the time someone books a call, they’ve already learned from him for months. The decision feels natural.
Results came quickly. Within one year, 740 members joined.
That generated $5.77 million annually from this single product. Monthly churn stayed below 7 percent. Members stayed an average of 14 months or longer.
The community is one product in a larger system. Each product prepares someone for the next.
From $29 to $68,000: How His Product Ladder Multiplies Revenue
By Q3 2024, Matt was generating $620,000 in monthly recurring revenue. The $7,800 community accounts for most of it. Six other products make up the rest.
This is how the full system works:
Free newsletter with over 100,000 subscribers.
Courses at $29-$97.
Intensive programs at $997-$2,997.
Core Founder OS program at $5,000-$10,000.
Annual community at $7,800.
Velocity advisory at $29,000 yearly.
Mastermind at $68,000 yearly.
Most of those 740 community members didn’t start at $7,800. They started at $29 or $97. That first purchase crossed a threshold. They moved from browsing to buying.
Once someone spends $29, paying $97 feels smaller. After $97, the $997 intensive becomes conceivable. Each step prepares them for the next.
The financial multiplication matters. Take 100 customers who each pay $5,000 once. That’s $500,000 in revenue. Now take those same 100 customers through the ladder. They spend an average of $12,000 over time. That’s $1.2 million in revenue. Same acquisition effort. 2.4 times the revenue.
That multiplication works because moving someone from $29 to $7,800 costs nothing extra. They’re already in the system. They already trust the teaching. They’ve seen results from earlier purchases. The ladder turns single transactions into relationships.
Matt spends zero on advertising. His profit margins exceed 70 percent. At $620,000 monthly revenue, typical businesses allocate $180,000-$310,000 to ads. That’s 30-50 percent of revenue going to customer acquisition.
Matt keeps that entire amount. Over a year, that’s $2.16-$3.72 million more in retained profit. The longer he operates, the wider that gap becomes.
The content catalog compounds this advantage. He’s been publishing since 2012. Thirteen years of frameworks. Old posts still drive new subscribers. New content references old ideas. Everything interconnects.
A competitor starting today faces a 13-year deficit.
The margin advantage becomes even more powerful at scale. Matt runs this same model across Gray Enterprises and Herb. Fourteen million people. $13.8 million annually. Same 70+ percent margins. Four hours of work daily. The architecture replicates.
That portfolio validates what he teaches. He’s not theorizing about systems. He’s running them across multiple businesses. Students see documented proof.
How to Build (and Test) Your Own Monetization Engine in 90 Days
Matt’s 100,000 subscribers and 13-year catalog seem impossible to copy. They are. But the conversion architecture isn’t.
He started with architecture that worked for 100 customers. Then he scaled it to 740.
Start with one good post each week. Share frameworks, case studies, or system breakdowns. Turn each post into 8-10 smaller pieces. A thread for X. A carousel for LinkedIn. A newsletter excerpt. A blog post. A short video or story.
Pick two platforms. LinkedIn plus one other works well.
Target 1,000 newsletter subscribers in 90 days. Use a valuable framework as your lead magnet. Track whether you’re attracting the right people.
Remember that first purchase I mentioned earlier? The one that moves someone from browser to buyer? Start there.
Create a $29-$97 product that solves one specific problem. This shows you who actually buys versus who just browses. That information matters more than the money you make.
Goal: 20-50 sales.
Track who buys. What do they have in common? These people become your warmest list for the next level.
After 50+ low-ticket sales, launch a $997-$1,997 program. Offer it only to previous buyers. Goal: 10-20 sales.
Then build your $3,000-$5,000 main program. Each level unlocks when the previous level proves demand exists.
Let customers choose themselves through their purchases.
When you launch your group program or community, price it annually at $3,000-$5,000 minimum. This filters for people focused on results. They do the work because they’ve invested real money.
Lower prices attract people who quit easily. Higher prices attract serious buyers who get results and stay.
You can test this in 90 days.
Week 1: Design your ladder on paper. Write down what you’d charge for complete transformation. Your $5,000-$10,000 flagship. Work backward. What’s 20 percent of that value? That’s your $997-$1,997 tier. What’s 10 percent? That’s your $97-$297 tier. What’s 2 percent? That’s your $29-$47 tier.
Build only the bottom tier first. Test if it sells.
If a $29 product doesn’t sell 50 times, a $5,000 product won’t either. Test small. Scale what works.
Don’t Chase Followers. Build a System That Converts Them.
Most creators chase audience size because it feels like progress. But 100,000 followers with zero sales doesn’t pay bills.
Matt’s first 100 customers at $29 generated $2,900 – more immediate cash than years of audience building that never converted
Build conversion architecture first. Then feed it with content.
Expensive offers need warm traffic. Build trust first. The ladder proves value at each step.
Matt’s system works because each piece helps the others. The pricing filters for people who do the work. The trust makes premium pricing believable. The ladder multiplies what each customer spends.
Remove any piece and it breaks.
That moment before someone decides to spend $7,800? It starts with a $29 purchase you design this week. The decision happens in the months before they see the price. Through products that prove value. Through pricing that filters for serious people. Through content that teaches while showing it works.
You don’t need Matt’s audience. You need his architecture.
Design your product ladder this week. Test whether your $29 offer sells before building anything else. The structure converts. Then you scale.