February 6, 2024

Having spent more than a decade as an operator at LinkExchange, Tellme Networks, and Zappos, and then the last decade representing Sequoia on the boards of some exceptional and legendary companies, I have learned much from outlier founders.

June 8, 2026

Every MBA cohort gets introduced to the Pareto Principle somewhere in the first year: 20% of your inputs produce 80% of your outputs, or 20% of your customers generate 80% of your revenue. It’s interpreted as 20% of your effort yielding 80% of the result. Do less, get more. The pattern is real. The math […]

June 1, 2026

My son is finishing his last week as a high school freshman. While cramming for finals, he was listening to “Non-Stop” from Hamilton. He complained he didn’t have enough time and asked me how to think about it. I smirked because we had talked about the same topic in 2023, and I first wrote about […]

May 4, 2026

Tobi Lütke at Shopify, Luis von Ahn at Duolingo, and Sebastian Siemiatkowski at Klarna all traveled a familiar road. A bold internal memo becomes a public artifact. Headlines follow. Then, months later, a clarification or a walkback. Klarna paused its hiring freeze. Duolingo walked back the replacement framing. Shopify softened its language without abandoning the […]

April 27, 2026

Dan Lorenc, Co-Founder and CEO of Chainguard, is creating new norms for AI adoption at his company. We are all seeing early results of AI adoption, but those results are uneven. We thought this was a useful framework that others could benefit from, so asked Dan if we could share it publicly.  In short, they […]

April 20, 2026

Every time I land in the UK, I catch myself hesitating at the curb. Look right, not left. Walk on the left side of the street. It feels unnatural…until it doesn’t. After a few days, that behavior fades into the background, and my actions become automatic. Defaults are the quiet architecture of how we think […]

April 6, 2026

In 1977, Charles and Ray Eames released a short film called Powers of Ten. It begins with a couple at a picnic in a Chicago park. Every ten seconds, the camera pulls back by a factor of ten. The blanket becomes a field, the field becomes a city, the city becomes a continent, until Earth […]

March 30, 2026

We’ve been taught to tell simple narratives. They are catchy and memorable. Let’s be honest. They work. Good narratives compress complexity into clarity and conviction. They give founders the language for their vision, recruiting, and fundraising. They give investors a shared vocabulary for pattern recognition. When Sam Altman or Dario Amodei framed their company’s mission […]

March 23, 2026

This past week, I co-hosted a pre-game show with Sarah Guo before Jensen Huang’s GTC keynote in San Jose. Three panels, twelve guests, covering open models, agentic AI, and physical AI. Backstage, one founder told me his biggest competitor is no longer another AI lab. It is an open-source project built by a single Austrian […]

March 9, 2026

In the past few weeks, I’ve spoken with several founders about how much AI coding tools are creating enormous leverage for the people who actually take the time to master them. We need new frameworks for development. Waterfall was used for the mainframe and PC era and gave way to agile in the internet and […]

March 2, 2026

This past Friday, I posted on X: “As a founder, you can get a lot of things wrong. But if you’re unwilling to die, it will eventually work out…Be optimistic, and try to be right. But even if you’re not right, don’t die.” I expected modest engagement. Instead, it struck a nerve. Many founders reached […]