We Were the Pirates, Now We’re the Port Authority I knew something had curdled in startup-land when my feed lit up with dunk-tweets about @im_roy_lee and @cluely. Here is a young, hungry, ambitious hacker who is unafraid to push social and technological boundaries and ultimately assembles a team and aggregates capital to do just that. Everyone here recoiled as if some cosmic line had been crossed and a taboo had been broken. The judgment wasn’t the typical, ignorant condemnation outsiders used to hurl at us; it was tech patrolling its own fiefdom, insisting that this kind of weirdness shouldn’t be allowed past the gate. The calls were coming from inside the house. This reaction would have astonished the founders we once idolized. The companies of yesteryear all pushed boundaries to the point of being seen as heretical. What bound those heretics together was a willingness to be misunderstood, and a community that, even if skeptical, still rooted for the possibility they might be right. But success metastasizes. Two decades of bull markets and the movie The Social Network later, the pirates now own and police the ports. Some of this is inevitable. Institutions accumulate scar tissue; they remember Icarus. If we keep on this path, we run the risk of snuffing out the flames of ambition. We’ll force true innovators into speakeasy corners instead of on parade floats where they belong. The frontier will reboot elsewhere, and we’ll be puzzled why we missed it. We cannot allow the Paradox of Tolerance to worm its way into humanity’s brightest shining beacon. We must celebrate the crazy ones, the rebels, the troublemakers, because they are the ones who end up changing the world.

Intimacy is inversely proportional to scalability.

I’ve been evaluating people using my @diabrowser /skill. It’s called /graham and It’s scary good. Watch me test it on a few victims live (incl. @nikitabier )

Something’s rotten in startup land. When did we become orthodox? We used to celebrate mavericks. Now we only accept founders and startups from Innovation™️ University. We used to be pirates—now we’re the Port Authority. Stop gatekeeping disruption and raise the black flag! 🏴‍☠️

It's easier to turn attention into capital than it is to turn capital into attention.

We will have driverless minivans. We will not have driverless convertibles.

I regret to inform you that an agentic browser will not be a thing. Two reasons: 1. The browser is a labor AND leisure tool 2. Cost and willingness to pay

One year ago, we bet the company we could will a new category of software – an AI browser – into the world. Today, the @nytimes wrote, “@diabrowser illustrates that the humble web browser may be the path to making AI more natural to use.” So surreal, v proud of our team 🥹😭

Venture capital is rocket fuel. Useful only if you're building a rocket. Put it in a car and it blows the engine.