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Failures — the failure database

Every failure documented with the same four questions. These pages taught me more than any success ever did.

Post-mortem

2022

A hire I hadn't earned the right to make

“Senior hires need scaffolding to succeed — a team, a process, real scope.”

What happened

Hired a VP-level leader before the company had the systems or scale for that role to succeed. They left within four months.

Why it happened

I hired for the company I hoped to be in a year, not the company I actually was. The role had no team, no process, and no clear mandate underneath it.

The lesson

Senior hires need scaffolding to succeed — a team, a process, real scope. Hiring ahead of that scaffolding sets good people up to fail.

What I’d do differently

I’d hire one level below what feels urgent, and build the scaffolding a senior hire needs before making the senior hire.

Post-mortem

2020

Shutting down my first startup

“A great product with no distribution plan is a hobby, not a company.”

What happened

After two years, we shut the company down. We had a working product and a handful of loyal users, but never found a repeatable way to acquire customers.

Why it happened

We fell in love with the product before validating that the market had a scalable way to find it. Distribution was an afterthought until it was the only thing that mattered.

The lesson

A great product with no distribution plan is a hobby, not a company. Distribution has to be designed in from month one, not bolted on after launch.

What I’d do differently

I’d spend the first month mapping three plausible acquisition channels and running the cheapest test on each, before writing a single line of product code.

Post-mortem

2019

A bad co-founder split

“Founder agreements aren't paperwork — they're the highest-leverage conversation two people will ever have about a company.”

What happened

Parted ways with a co-founder after eighteen months, at real cost to the team’s trust and momentum.

Why it happened

We never wrote down what we each expected from the role, the equity, or the decision rights when we started. Ambiguity festered until it became resentment.

The lesson

Founder agreements aren’t paperwork — they’re the highest-leverage conversation two people will ever have about a company. Skipping it doesn’t remove the disagreement, it just delays it.

What I’d do differently

I’d write and sign a real founder agreement — roles, vesting, decision rights, an exit process — before writing any code, no matter how good the relationship feels on day one.

Failure stories often teach more than success stories. That's why this page exists.