Chase Maddox Guitar Academy: The $59 Jazz Skool

Chase's Guitar Academy is Chase Maddox's jazz guitar community on Skool, with 212 members on two tiers, $59 and $79 per month, behind a seven-day free trial. It sits at rank 13 in the Skool Games Music top 50 and posted the strongest 30-day recurring revenue change on Skool's public leaderboard of any Music room we broke down this week. The page does something none of the other Music rooms in that group do: before it asks for money, and before the trial even starts, it asks you to take a sixty-second test.

Who is Chase Maddox?

Chase Maddox is a jazz guitarist and teacher who runs Chase's Guitar Academy on Skool as @chase-maddox. His Skool bio reads "I help people learn jazz guitar and am the co-founder of JazzMemes, the largest online community for jazz with 600K+ people", which is the audience engine sitting behind this community.

Chase Maddox

Founder of Chase's Guitar Academy, a 212-member jazz guitar community on Skool priced at $59 or $79 per month with a seven-day free trial. His Skool bio reads "I help people learn jazz guitar and am the co-founder of JazzMemes, the largest online community for jazz with 600K+ people". The academy's about page carries an endorsement attributed to guitarist George Benson. He runs the room with one other admin.

How Chase's Guitar Academy sells

It sells a system as the antidote to abundance. The opening line names the frustration precisely, inconsistent progress and not knowing what to play, and the second line names the cause: you have too much free material and no order to put it in.

For jazz guitar specifically that is the right enemy to pick. There is more free instruction in this style on the internet than any player could work through in a lifetime, and the reason a serious learner stalls is not scarcity, it is sequence. Positioning against YouTube rather than against other courses reframes the purchase from "another lesson" to "the order to do them in".

Then it does the thing that makes this page distinctive. Rather than describing the system, it starts running it on you immediately, with a sixty-second level assessment that assigns you a track.

What the about page actually says

The Chase's Guitar Academy about page is reproduced in full below. Numbers mark the five lines doing the work; hover one for why.

Why start with an assessment instead of an offer?

Because "I do not know what to play" is a sorting problem, and an assessment solves it in front of the buyer instead of promising to solve it later. Sixty seconds of questions produces a track, and a track is a personalised answer that the reader now owns before paying anything.

Three things happen at once. The buyer gets proof that a structure exists, because a structure is what produced their result. They get a small commitment on record, which makes the next step feel like continuing rather than starting. And the community gets a segmented member on day one, which means the seven-day trial can be spent playing a tune at the right level rather than browsing a library.

Compare that with the standard trial. Most free trials hand over everything and hope the buyer finds the right shelf, and the members who fail to find it are the ones who cancel on day six. An assessment turns the trial from a tour into a task.

The cost is real but small: someone has to build the question set and the tracks it maps onto, and the mapping has to be honest or the result is worse than no assessment at all. For what a trial does and does not cover on this platform, see the Skool free trial explained.

What separates $59 from $79

One thing separates them: Premium adds weekly live classes, guest artist masterclasses and feedback from Chase. Everything else is identical, since both tiers get the full curriculum, the community and the same path through standards, soloing, comping and chord melody, and the page is clear about that rather than blurring it.

Both per-day figures check out, since $59 across thirty days is $1.97 and $79 is $2.63. That is worth saying because per-day framing is usually where sales pages quietly round in their own favour, and this one does not.

The structure is a clear version of a rule that keeps showing up across our breakdowns: the recorded material sets the floor price, and the founder's attention is what an upgrade actually buys. A $20 gap for live access and personal feedback is a modest ask, which suggests the upgrade is being used to sort the committed rather than to maximise revenue. See how Skool membership tiers work for the mechanics of running two prices in one room.

The guitar lane is three different products

The three guitar rooms in the Music top 50 sell three different things: jazz standards sorted by level, a fixed 52-week curriculum with public accountability, and Grateful Dead repertoire behind an entry room and a capped VIP tier. It would be easy to file them together. They are not competing.

Genre, structure and commitment shape all differ, which is why three guitar rooms can sit inside one top 50 without cannibalising each other. A jazz player wanting standards is not the buyer for a Dead songbook, and a player who wants weekly sorting is not the buyer for a fixed 52-week march. If you are entering a crowded instrument niche, that is the lesson: pick the repertoire and the structure, not just the instrument. See how to niche down a Skool community.

The funnel, step by step

A large free jazz audience feeds a sixty-second assessment, the assessment feeds a seven-day trial with a specific task in it, and the trial feeds two prices that differ by one deliverable.

The top of this funnel is a meme page. A jazz audience of the size the founder describes costs nothing to reach and shares nothing in common with a paid learner except the subject, which is exactly why the assessment sits between them: it converts an amused follower into a sorted prospect in under a minute.

The formula you can copy

Name the enemy your buyer already believes in. For anyone learning an instrument in 2026 that enemy is not a lack of material, it is the absence of an order to work through it in. Sell the sequence.

Put a diagnostic in front of your offer. Anything that returns a personalised result in under two minutes will outperform a paragraph describing your method, because the reader experiences the method instead of reading about it.

Then make your upgrade buy the one thing you cannot record. Curriculum, community and library belong on the floor tier. Live time and your own eyes on someone's playing belong above it, and a modest gap between the two prices sorts the committed without punishing anyone. For how founders arrive at those numbers, see how to price a Skool community, and for the other end of the guitar lane, see our breakdowns of 52 Week Guitar Player and Grateful Mike's two-room guitar ladder.

Frequently asked questions

What is Chase's Guitar Academy on Skool?

Chase's Guitar Academy is a private Skool community for jazz guitar players run by guitarist Chase Maddox. It has 212 members, two admins and 2,284 posts, and costs $59 per month for Standard or $79 per month for Premium after a seven-day free trial. Members take a sixty-second level assessment, get assigned a track of real jazz standards, and work through soloing, comping and chord melody. Premium adds weekly live classes, guest masterclasses and the founder's feedback.

How much does Chase's Guitar Academy cost?

Standard is $59 per month and Premium is $79 per month, both after a seven-day free trial with no charge on the day you start. The page frames those as under $2 and under $3 per day, which is accurate. Prices on Skool are set by the community owner and can change, so check the live page before you join.

Who is Chase Maddox?

Chase Maddox is a jazz guitarist and teacher and the founder of Chase's Guitar Academy on Skool. His Skool bio states that he is co-founder of JazzMemes, which he describes as the largest online community for jazz with more than 600,000 people. His community's about page carries an endorsement attributed to guitarist George Benson, which we report as the page's own claim.

Is jazz guitar hard to learn?

Jazz guitar is harder than most popular styles for a specific reason: the chord vocabulary and the improvising vocabulary have to be learned together, and both are larger than in rock or blues. A player needs extended and altered chords, several ways to voice each one, the ability to hear and follow a harmonic sequence in real time, and a repertoire of standards to apply it all to. What makes it feel impossible is usually not difficulty but disorder, which is why structured routes through a fixed set of tunes are the standard answer.

Can you teach yourself jazz guitar?

Yes, and plenty of players have, but self-teaching in jazz fails in a predictable way. Learners accumulate scales, shapes and licks without ever playing complete tunes, so they know a great deal and can play very little. The usual fix is repertoire-first, meaning you learn actual standards from the beginning and pick up theory as each tune demands it, which is the approach this community's page describes when it promises real tunes rather than scale drills.

What is the difference between the $59 and $79 tiers?

The curriculum, the community and the path through standards, soloing, comping and chord melody are identical on both. Premium at $79 adds weekly live jazz guitar classes, guest artist masterclasses and feedback from Chase Maddox himself. In other words the extra $20 a month buys live time and a person's attention, not more material.