The Right Kind of Asshole

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“Put me anywhere on God’s green earth, I’ll triple my net worth. Mother$u#ker. I will not lose.” —Jay-Z

A unifying trait among the best founders I know is that they are assholes. They are highly opinionated, passionate perfectionists, unable to live with less-than-brilliant ways of doing things. Inside their souls is an itch, a constant, low-volume whining sound that tells them this could be done better.

A unifying trait among the worst founders I know is that they are also—you guessed it—assholes. They are opinionated perfectionists, too.

It is accepted wisdom within Silicon Valley that, as Marc Andreessen puts it, “agreeableness is a problem for innovation.” In my own studies of famous technology entrepreneurs, I have found this statement to be true. To build world-changing companies, to have extreme levels of success, does seem to require an extreme personality. 

What I can’t find anyone saying, and what there appears to be no larger discourse about, is how to harness these personality traits. Used correctly, they can create Steve Jobs-esque personas that enable billion-dollar, long-lasting businesses. Used incorrectly, they can be toxic and ruin startups (and, more importantly, employees’ lives). 

I know of one founder who slept with several of his direct reports and was booted from his own company (though his backers successfully kept his sins away from the press). Naive fool that I am, I thought that would surely spell the end of his career in tech. To my surprise, I ran into him at an industry event last year, once again receiving praise and millions from venture capitalists.

When I back-channeled about why he was involved, his investors said he had the “right type of personality for a founder.” Good grief. His signals of sociopathy were confused for signals of greatness—and, last I heard, his new company had collapsed.

The funding of the wrong type of assholes is an urgent problem, especially as the companies we build gain greater cultural influence, and, with AI reshaping the industry, the stakes seem even higher. If we can better understand that, we can quit giving capital to people with a history of bad behavior and sinking companies, and instead give it to the people who deserve to—and actually can—build the future.

So, what patterns should we look for in identifying the best entrepreneurs? I will warn you, I don’t fully know the answers. However, by open-sourcing what I do know, maybe we can find ones who are slightly better than the assholes we already have.

Signals of grit

I split these characteristics into signals of grit and signals of grift. You may dislike some of these people, but they’ve built great companies.