A season of district leaders building real software inside your walls — and the four sizes it could start at.
What you're building
Two layers, one bet
Layer one
The record
An SIS that absorbs the security and privacy complexity districts can't carry themselves, module by module, until the system of record is yours.
Layer two
The garden
A walled space where a district builds its own app against its own data and deploys it safely — no procurement cycle, no year-long security review.
The SIS is the harder engineering. The garden is the bigger idea.
Every district in America has a list of workflows no vendor will ever build, because the market for each one is a single district. That list is where the frustration lives, and it's the one thing a national product can never fix. A walled garden solves all of them at once by not solving any of them. It hands over the shovel.
The obstacle
A garden with nobody in it is just a wall
The practical problem
Districts don't know they're allowed
Thirty years of being buyers taught them that software is something you purchase, evaluate, and complain about. Nobody has shown them the other posture. Access isn't permission, and permission isn't skill.
The harder problem
You can't be the one to show them
A vendor demonstrating how easy it is to build on their own platform is a sales pitch, however true it is. The same demonstration from a practitioner who has sat in their chair is proof. That gap has nothing to do with your product. It's about who's holding the marker.
What's actually at stake
The field settles for less than it should
Other industries raise money on promises to reach other planets. This one argues about seat licenses. If the districts already leaning forward stay isolated, the ceiling stays where it is — and that ceiling is the reason you started a company.
Where I come in
I've been the person in that chair
I spent years as a district practitioner and now run AI strategy across twenty-eight districts. I know what a technology director does with a vendor demo. I also know what happens in a room at two in the afternoon when half of it is stuck on an auth error and morale is the actual deliverable.
That's the job I'm proposing to do. Not to sell your platform — to teach inside it, in front of people who will recognize me as one of them.
You need a gardener, not another billboard.
The plan
Three moves
01
Seat the room
A small roster of district leaders who already want this. Not an audience — a cohort with names, a schedule, and something to build.
02
Ship in public
They build real tools against real workflows, inside your walls, then show the work to an invited room of peers. Proof travels. Pitches don't.
03
Hand it off
Alumni return as co-leads. You end up with practitioners who can run the room without me, and a playbook you own outright.
Choose your size
Four bets
Each one names what you're buying an answer to, and each comes with the result that says stop. A package asks you to believe. A bet tells you when to quit.
Scrimmage
$18K
Two days · 5 districts · 6 weeks out
Five districts, two to three builders each, everyone arriving with a workflow their district actually suffers through. Day one they ship it. Day two we harden it and deploy inside your garden before anyone leaves.
Walk away if
Fewer than three of five have something working and deployed by end of day two.
Preseason
$30K
One month · 5 districts · demo night
The scrimmage plus the three weeks that decide whether anything survives it. Two build clinics, office hours, and a Demo Night on the last Thursday — open to an invited audience who came to watch peers, not a pitch.
Walk away if
Fewer than half the apps are still in use at day thirty.
Recommended
Season One
$66K
Three months · 8–10 districts · $22K/mo
Kickoff retreat, biweekly build clinics, a mid-season teardown where districts critique each other's work, and a Demo Day with a visionary keynote in front of an invited room. Every district ships at least two things.
This is the tier that produces the playbook — curriculum, facilitator guide, recruiting funnel — yours to keep whether or not you ever hire me again.
Walk away if
Fewer than two districts opt into partnership on their own initiative by Demo Day.
Franchise
$108K
Six months · two cohorts · student division
Overlapping cohorts, with alumni co-leading the second. Plus a student division — kids designing the instructional tools they actually want, judged on what teachers would really use, winners deployed in classrooms.
A story about superintendents building software stays inside edtech. A story about fourteen-year-olds shipping tools their teachers adopt does not.
Walk away if
Fewer than three alumni will co-lead a second season without being paid to.
Fees cover design, facilitation, recruiting, and documentation. Direct costs — venue, food, travel, stipends, keynote honoraria — run separately at cost. These are opening numbers, not a rate card.
What's at stake
Two versions of next year
Without a room
The garden stays mostly empty, and the feature that makes you different reads as a checkbox
You compete on SIS features against incumbents with thirty-year relationships
The early adopters keep building alone and nobody sees it
Growth depends on outbound, in a field that doesn't buy that way
With one
Twenty apps live inside your walls, built by the people other districts call for advice
A named annual event with a waitlist
Design partners who arrived on their own initiative, not through a pipeline
Districts running on your infrastructure because that's where they learned to build
Season One, in numbers
Targets you can hold me to
8–10districts on the roster
16–20apps live in your garden
40–60leaders in the Demo Day room
2–3districts converting to partnership
That's $22K to $33K per design partner. One fully loaded rep working the phones costs more than the entire season, converts on a longer clock, and leaves nothing behind when they quit.
Terms
The wall around my day job
Contracted through BlackSage Media, on personal time — no county resources, lists, brand, or hours.
Permanent recusal from any county evaluation or procurement touching your platform.
Cohort one seats outside my professional jurisdiction. Local districts join only on their own initiative, disclosed in writing both ways.
Nobody is asked to buy anything during a season. Commercial conversations happen after, initiated by them, with me absent.
A cohort run by someone with an undisclosed vendor relationship is worthless to you inside a year. One that's papered correctly is worth something for a decade.
Your move
Pick a bet
Six weeks from a yes puts a scrimmage in early October, before districts disappear into the fall. Seven weeks puts it after, and the room gets materially harder to fill.
Cleanest path: run the scrimmage standalone, then decide three weeks later whether to roll into Season One with the fee credited. You risk $18K to learn whether the format works. I risk having to be good in front of a room, which is the part I want.
Three minutes, mostly multiple choice, including a blunt one about the numbers above. Answer those and I'll come back inside a week with the session design, the roster, and a real cost estimate.