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Top costly mistakes

Sorted by estimated financial impact.

By 2020, Google wasn’t just a search engine it was identity infrastructure for the internet. Gmail, YouTube, Drive, Meet, and countless third-party apps depended on Google’s authentication systems.

PocketOS operated as a SaaS platform for car rental businesses, running on cloud infrastructure with shared storage volumes across staging and production. An AI coding agent inside Cursor, powered by a model from Anthropic, was granted execution capabilities within this environment. The system served real customers with live transactional data. A small engineering team managed infrastructure, application logic, and deployments. Stakeholders included rental operators, end users, developers, and infrastructure providers such as Railway.