Episode 253:54
Postmortem: What Broke
May 4, 2026
The failures episode. Stuck deploys, full disks, dead ends, and the rebrand scars — documented as promised.
EP. 25 — Listen Now
Show Notes
Segments
- 00:00 — The promise from Episode 01: failures get documented harder. Time to pay up.
- 11:20 — Infrastructure week from hell: rate-limited deploys, a disk at 97%, and a git identity that silently blocked everything.
- 25:40 — Product dead ends: features built for an imagined user and killed on contact with a real one.
- 37:10 — What each failure changed about the system — the only reason postmortems matter.
Key takeaways
- Every silent failure had a loud signal somewhere — instrument the boring things.
- Sunk cost is the most expensive subscription an operator can hold.
- A failure that changes the checklist was tuition; one that does not was just loss.