The irritation
Three weeks before the 2024 NFL season, I decided to test whether leagues would pay for a personalized ESPN-style recap full of their own matchups, standings, storylines, and trash talk.
ProductRetired2024 · Retired
League Lingo
A retired SaaS product that turned Sleeper league data into weekly AI-written fantasy-football newsletters, emails, and PDFs.
- Current state
- Retired — 2024 · Retired
- Jack’s role
- Product design, Full-stack engineering, AI editorial systems, Operations
- Find it in the workshop
- Archive Yard · Fantasy pennant marker
Built because…
The real build story.
What I built
Commissioners pasted a Sleeper league ID; Django and Python pulled rosters, scores, standings, and player data; OpenAI generated configurable recaps, rankings, projections, and roast pieces; then the system delivered email newsletters and PDFs on a schedule.
The hard part
The promised automation became weekly editorial labor: correcting stat errors and hallucinations, changing prompts, writing new article scripts, and trying not to break older formats. The Sleeper-specific data model also made ESPN and Yahoo expansion expensive.
Under the casing
Proof, not decoration.
Build evidence02 items
- Sleeper league sync feeding scheduled AI newsletters, email, and PDF output
- A shipped Django SaaS with users, payments, and a detailed public postmortem
- Django
- Python
- PostgreSQL
- OpenAI API
- Sleeper API
- SendGrid
- AWS S3
- Heroku
Scope of work
What I owned.
- Product design
- Full-stack engineering
- AI editorial systems
- Operations
No victory-lap math
Outcome and lesson.
Where it landed
League Lingo shipped on time and had a handful of paying users, but the quality did not justify the original price or the maintenance burden. I reduced the price, stopped the service around Week 9, and published the failure honestly.
What stayed
AI does not remove the editorial product. Accuracy, variety, source structure, and scalable data modeling mattered more than the novelty of generated copy.
Field notes
This project has a physical address.
In the playable workshop, League Lingo lives in the Archive Yard as a fantasy pennant marker. You can inspect it without unlocking anything.