The $500 CLI: Why Version 1.0 Was a Disaster [And How Procrastination Almost Killed It]
If you read the first three parts of our series, you know the broad strokes: We took a lean "Notion + GitHub + Amazon SES" setup, faced a massive Q4 Black Friday surge, hired a smart $500-a-month student developer, and coded our first Markdown-to-HTML converter script to survive. On paper, it sounds like a slick, heroic startup success story. In reality? Version 1.0 of our CLI tool was a total technical trainwreck. Below are links to articles from that series to give you a backstory:
The $0 Email Engine: How I Used Notion, GitHub, Amazon SES to Outsmart Email Service Providers
Monolithic Campaigns: How Micro-Tasking Cures Email Burnout
From Raw HTML Dumps to a CLI: How We Built LLazyEmail
It wasn't a disaster because my student developer failed. It was a disaster because of three hard technical and psychological pillars that hit us right in the face.
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