Essays

AI teammates are microservices again. Buy the outcome, not the org chart.

Five jobs AI cannot take from you, and how I got back in the game.

Kalanick is back. What his return says about founders who never stopped.

What investors actually back at the earliest stage: you, not the product.

AppSignal bootstrapped for 13 years, then took $22M. Why the math changed.

LLMs reopened markets VCs had written off. How to be contrarian and right.

The founder who made me sign an NDA over lunch. Nobody steals ideas.

A Charleston team was told to aim small. Why the ceiling is the point.

Build for recognition and it twists every call nobody sees.

After the failure, nobody answers who you become. You will it.

Three keys to crisis PR, and how Astronomer changed the conversation.

Leaving SF showed me how much ambition is set by your zip code.

Windsurf walked away from a $3B OpenAI deal. What it cost the team.

Durov gave up his company, his country, and his freedom of movement.

My first startup fell apart. What Sisyphus gets wrong about the boulder.

The exit you chase for years, and the hangover once you catch it.

11x allegedly inflated ARR and invented customers. The tell founders miss.

The well-meant founder habit that quietly wrecks a capable team.

When to pull the trigger on your first hires, and who comes first.

Charging early proves more than demand. The second reason matters more.

The one situation where growth rate is the wrong number to watch.

The LEAD framework for picking a CEO when the answer is not obvious.

Five kinds of trend, and which ones are worth building a company on.

Pitch raised $137M and gave it back. How Renklint changed course.

Arc killed a working product at a $550M valuation. Ego is the real cost.

When to stop raising and treat the rejections as the answer.

Graham versus Sacks on Zenefits, and where optimism becomes a lie.

The three ways to build, and how I worked the call for Megaphone.

Cofounder conflict kills 65% of startups. Eight mistakes to avoid upfront.

The Oilers power play works because they do not need to talk.

Being comfortable looking cringe is an underrated founder weapon.

How transparent to be with your team, and what a leak actually costs.

Opinionated cultures win the way politicians do: inspire the base.

In the details is not micromanaging. Chesky, Jobs and the difference.

What the OpenAI weekend taught about leading through a real crisis.

Bezos said customer centric a thousand times. Repeat yourself.

Taking the higher valuation can cost you the round after it.

You are waiting too long. Six signs the decision is already made.

Build in public or in stealth, and how to take the best of both.

Raise prices to lose the customers who were never yours.

Six things founders give up that they should have kept.

The six tradeoffs every founder makes, learned inside Uber and Airbnb.

Five paths worth exploring before you accept a down round.

Going all in is the most personal and most strategic call you make.

Only 41% split evenly. When an uneven split is the right call.

What to offer your first employees, and how to negotiate it.

What founders actually pay themselves, and what it does to runway.

Why I left the company I founded, and eight other reasons founders go.