Startup Failure Postmortems and Fear
The decisions, incidents, and quiet failures that killed real startups, written down so you avoid them.
30 posts · page 1 of 2
- Startup Failure Postmortems and Fear
The Compliance Audit That Killed the Deal
Enterprise deals die in security questionnaires more often than in pricing negotiations. Here is how the compliance gap shows up and how to close it.
6 min read
- Startup Failure Postmortems and Fear
The Co-Founder Conflict That Killed the Engineering Team
Co-founder conflict is a top predictor of startup failure. When it reaches the engineering team, the damage compounds fast. Here is how it plays out.
6 min read
- Startup Failure Postmortems and Fear
The Cloud Bill That Crashed the Business
Unmonitored cloud spending has killed more than one promising startup. Here is how it happens and what it takes to prevent it.
6 min read
- Startup Failure Postmortems and Fear
The Founder Who Tried to Hire AI Out of a Hole
A postmortem on the pattern of founders using AI tools to avoid confronting the real problems -- and why AI makes bad decisions faster, not better.
12 min read
- Startup Failure Postmortems and Fear
The Engineer Who Left a Year of Bug Fixes Behind
A postmortem on the silent damage an engineer carries when they leave without handing off what they know. What actually gets lost, why bus factor kills quietly, and how to build teams that survive a departure.
12 min read
- Startup Failure Postmortems and Fear
The Vendor Outage That Tested Your Disaster Plan
A postmortem on a third-party vendor failure that exposed a startup's missing disaster recovery plan. What broke, who owned nothing, and how the business relationship with customers changed permanently.
12 min read
- Startup Failure Postmortems and Fear
The Customer Data Leak That Tested Everything
A postmortem on a customer data leak: what happened, how the team responded, and what it actually takes to survive one with the business intact.
12 min read
- Startup Failure Postmortems and Fear
The Wrong Tech Stack Decision That Compounded for Three Years
A postmortem on a technology choice made at the beginning of a startup that became increasingly expensive to live with. What the team optimized for, what they should have optimized for, and how long the cost kept compounding.
12 min read
- Startup Failure Postmortems and Fear
The Hire That Almost Broke the Team
A postmortem on hiring a technically strong engineer who damaged team culture -- what the warning signs were and what the recovery required.
12 min read
- Startup Failure Postmortems and Fear
The Side Project That Became the Main Project (and the Reverse)
Two stories that look opposite and are actually the same. The thing you built on the side took off and ate your main thing. The main thing you built faded and the side thing carries you. Both are about paying attention to what is working.
12 min read
- Startup Failure Postmortems and Fear
The Founder Coding Habit That Killed Velocity
The specific ways that founders who code in their own product slow the engineering team down -- and the discipline required to stop doing it.
12 min read
- Startup Failure Postmortems and Fear
The Open Source Maintainer Who Burned Out
A postmortem on open source maintainer burnout: what builds to it, why the community dynamic makes it worse, and what actually helps before the maintainer walks away from the project.
11 min read
- Startup Failure Postmortems and Fear
The Acquisition That Was Worse Than Death
A postmortem on startup acquisitions that destroy more than they save. What founders get wrong about exit, and what the engineering team experiences after.
12 min read
- Startup Failure Postmortems and Fear
The Layoff That Ended the Founder Engineer Relationship
Layoffs are sometimes necessary. How founders handle them determines whether the remaining engineers stay -- and whether the company survives.
12 min read
- Startup Failure Postmortems and Fear
The Reorg That Broke the Engineering Org
Working notes on the reorg that broke the engineering org. Written for founders, engineers, and operators who want a clear read on startup failure postmortems and fear from someone who has shipped the work.
11 min read
- Startup Failure Postmortems and Fear
The Departure That Took Half the Knowledge With It
A postmortem on what happens when a key engineer leaves and takes the system's undocumented knowledge with them, and how to prevent it.
12 min read
- Startup Failure Postmortems and Fear
The Engineer Who Wrote Off the Codebase: A Postmortem
A postmortem on the moment an engineer decides the codebase is unsalvageable. What leads to that conclusion, when they are right, when they are wrong, and what happens to the company when the decision is made unilaterally.
12 min read
- Startup Failure Postmortems and Fear
The Refactor That Never Ended
Working notes on the refactor that never ended. Written for founders, engineers, and operators who want a clear read on startup failure postmortems and fear from someone who has shipped the work.
12 min read
- Startup Failure Postmortems and Fear
The Performance Regression That Lost the Largest Customer
A postmortem on the performance regression that goes undetected in CI, surfaces in production, and hits the largest customer first. What fails in the detection process, what the customer experience looks like, and what it actually takes to prevent it.
13 min read
- Startup Failure Postmortems and Fear
The Bug That Cost a Year of Trust
A postmortem on a single production bug that eroded a year of customer trust in six weeks. What went wrong, why the fix took so long, and what the team learned.
12 min read
- Startup Failure Postmortems and Fear
The Security Incident That Closed the Series A
A story I have watched play out three times in slightly different forms. A startup builds something good, raises a round, and a security incident kills the next one before it can begin. The cause is always smaller than the consequence.
12 min read
- Startup Failure Postmortems and Fear
The Migration That Ate the Roadmap
The postmortem of a six-month database migration that consumed the engineering roadmap and produced almost nothing visible to users.
12 min read
- Startup Failure Postmortems and Fear
The Outage That Cost the Year
A postmortem on the kind of outage that does more than take the system down for a few hours. It costs customer trust, kills a contract renewal, triggers a board conversation, and changes the company's trajectory. What leads to it, what happens during it, and what the real aftermath looks like.
12 min read
- Startup Failure Postmortems and Fear
The Black Friday That Took Down the Startup
A postmortem on a traffic spike that took down a startup on its biggest day. What failed, why load testing failed to catch it, and what to build differently.
12 min read
More than blog posts.
The Labs folder has the experiments themselves. The Systems folder has the stack and architecture. The Journey folder has the timeline. Pick whichever pulls you.