Ventures / Venture 3 of 5
The independent CFI's pocket office
Scheduling, progress against checkride standards, endorsements, invoicing, and a beautiful progress page for the student. Built for freelancers teaching in the customer's own airplane.
- Red tape
- Low
- Build effort
- High
- First revenue
- Slower
- Our way in
- Fellow instructors
The opportunity
Why this, and why now.
The established platforms are built for flight schools, with fleets, front desks and dispatch. Independent instructors teaching in a customer's own airplane juggle a scatter of small apps, spreadsheets and paper, and the newer apps aimed at them have few users so far.
A fragmented market with no clear winner is exactly where better design wins. Jon has lived this pain, and he will use the tool himself once his facility opens, which keeps every decision honest.
What we'd build
The first version.
Students and progress
Each student's standing against checkride standards, visible at a glance.
A two-minute lesson log
Record what was covered right after landing, from the ramp.
An endorsement library
Standard wording, verified by Jon, attached to the right student record.
Reminders that matter
Expiring solo endorsements, flight reviews due, and medicals coming up.
Scheduling and invoicing
Availability, bookings and invoices, with payments handled by a standard payment provider.
A student progress page
A beautiful, shareable page showing a student how far they have come.
Less paperwork. More teaching.
On the instructor’s week
Who it's for
The people it serves.
- Freelance CFIs teaching in customers' aircraft.
- Small flying clubs without a front office.
- Jon's own facility as the first and most demanding customer.
- Students who get a clear view of their own progress.
How it pays its way
Ways to make it pay.
- Monthly subscription per instructor.
- Free for students so instructors can invite them freely.
- A facility plan for small schools later.
- Setup help for instructors moving off paper.
Guardrails
Keeping the red tape light.
- Wording verified Endorsements are legal records, so Jon owns and verifies all regulatory wording.
- A complement to logbooks Designed to support required logbook entries until electronic-record requirements are confirmed.
- Your data, exportable Instructors can export everything, any time.
The first 90 days
Four moves, in order.
Map the week
Interview 15 independent CFIs about their paperwork.
Prototype the log
Build the two-minute lesson log first.
Use it for real
Jon runs his own students through it.
Widen carefully
Invite a handful of instructors from his network.
A student who can see their progress keeps coming back.
On students
Questions for Jon
Your take shapes this.
- What paperwork did you dread most as an independent instructor?
- Which apps did you try and abandon, and why?
- Would instructors you know pay monthly for this, and what would make it a clear yes?
Answer any of these, push back, or tell us about a different idea entirely.




