"Rebelling against authority is an American trait."
This country was founded by outlaws.
Our culture was formed by them. Our economy was built by them. The future will be created by them too.
Outlaws of history are not meant to be for everybody. They are spiky, top-percentile on a trait or obsession that separates them from their peer class. The maverick mentality required to make somebody truly exceptional in any field often alienates them from the crowd.
If you study some of the most iconic entrepreneurs of the last generation, almost all of them went through periods of being completely misunderstood before becoming totally understood.
Henry Ford was called a socialist for doubling worker wages and instituting the 8-hour work day. The wage hike eliminated turnover, attracted the best workers, and seeded the American middle class - which then bought every Model T he could build.
Walt Disney mortgaged his house to finish Snow White (a film projected to lose money). It became the highest-grossing film in history at the time, and Disney used the proceeds to build a studio campus and start work on Pinocchio, Fantasia, and Bambi simultaneously.
Elon split his last $40m in 2008 to save Tesla (running out of cash + weeks from bankruptcy) and SpaceX (three consecutive rocket failures and one launch attempt left before going under). Both companies today are worth a combined $1.5 trillion.
Travis Kalanick launched Uber in cities where the service was explicitly illegal. The Uber playbook - launch first, apologize later, weaponize user demand against regulators - became the template for an entire generation.
We think the best entrepreneurs share two traits: high rebellion (distaste for authority) + high commerciality (creating more value than capturing) = high return on luck.
The quadrant most of venture capital has been competing inside for the last decade has been the upper left. The pattern-matched founder. The Stanford CS dropout, the second-time exit, the well-networked technical hire from a hyperscaler. These are real assets. The industry has bid their valuations up accordingly.
The lower right quadrant produces some of the most fascinating people in history but very little economic value. Pirates. Mafia heads. Criminals. The romantic ideal of rebellion without the discipline that turns it into something (legal) the world can use.
The interesting quadrant is the one in the upper right. The people who scored well on both axes - who had orthogonal paths, refused to do things the way they were supposed to be done, and who built businesses that changed industries.
"It's better to be a pirate than join the navy."
Jobs was an outlaw. So was Rockefeller. So was Disney. So was Ford. So is Bezos. So is Jensen. So is TK. So is Musk.
If people weren’t naturally drawn to these types of individuals, we wouldn’t make them mononyms.
The next era of iconic founders will look no different.
Outlaw is a $10m investment firm that will become the chief capitalist to the upper-right quadrant. We invest as early as possible, and we make it our job to turn these people and their companies into the iconic names of the decades to come.
Below is how we got here, more on what we believe, and why we think now is the right moment to do this.
