The Big Customer Trap

Around 2013, Healarium was a small startup building an employee health improvement platform. Gamified goal-tracking for employees, insurance-side dashboards on...

Read More

Docs as Leverage in the AI Era

Documentation used to be optional. In 2026 it is the interface. Every engineering team I have worked with in the...

Read More

Meet Users Where They Are

Around 2012, one of our customers at Radvision was a US prison system. They used our software to schedule 15-minute...

Read More

First Tests at Seed Stage

Most seed-stage teams have either no tests or the wrong twenty. Very few have the right five. “We will add...

Read More

Tech Lead vs Team Lead With AI Agents

Between 2011 and 2014, I was a Python tech lead at Tikal. My team was four people. On any given...

Read More

AI Evals at Seed Stage: The Five to Build First

Most seed-stage teams shipping AI features do not have evals. They have hope. They have a couple of dashboards. They...

Read More

Co-Founders Should Be Complementary, Not Equal

In 2009, seven of us co-founded a startup called Ekkli. In the year and a half we existed, we could...

Read More

The Year a Customer Sat Beside Me

Around 2009, one of our biggest customers stopped going to meetings with our executives. He would fly in, sit down...

Read More

AI Coding Assistants Make Bad Codebases Worse

AI coding assistants do not write good code in bad codebases. They write more of what is already there, faster....

Read More

Who’s Going to Maintain This?

In 2007, I built my first real piece of QA automation in Java. My manager looked at it and asked...

Read More

The 90% Nobody Was Testing

I once helped ship software for CT scanners with about ten percent of it tested. Not because anyone was careless....

Read More

The Deprecation List: What to Kill Before Your Series A

Investors don’t fund mess. Or rather: they fund it, but they price it in. Every piece of unfinished, abandoned, or...

Read More

Code Review at Three Engineers

Most code review advice on the internet was written by people working in teams of fifty. Code review at three...

Read More

When ‘Just Use Postgres’ Stops Being the Answer

I’m the first person to tell founders to just use Postgres. I’m also the first person to tell them when...

Read More

The Five Questions That Decide Your Stack at Seed Stage

Every seed-stage founder I work with has had the same argument with at least one engineer: which framework, which database,...

Read More

Why Your First AI Feature Should Be Invisible

Founders ask me how to launch their first AI feature. My honest answer is usually: don’t launch it. At least,...

Read More

FinOps for Early-Stage Startups: Stop Burning Cash on Cloud

FinOps for Early-Stage Startups: Stop Burning Cash on Cloud Cloud spend is the second-largest controllable cost for most early-stage startups,...

Read More

Technical Debt at Seed Stage: When to Take It On

Technical Debt at Seed Stage: When to Take It On Technical debt has become a dirty term, and I think...

Read More

Hiring Your First Engineer as a Non-Technical Founder

Hiring Your First Engineer as a Non-Technical Founder I get pulled into this conversation more than almost any other. A...

Read More