The Best Founders Think They Are Destined to Win
He asks founders if they think they are better than other people, and he cares less about the answer than about how hard they try to convince him.
mondaymorning.substack.com · Screening for ManiacsThe paperwork was routine. A founder had a $6 million investment offer, with the usual condition that he would earn his stock gradually over time. Reviewing it with the Antler investor who screens founders for a living, the founder said, "if they want my shares to vest over four years, they don’t understand that I will die before this is less than a $10B company"
The investor keeps that story as his prime example of narcissism, and he means it as praise. In his view, founders need crazy confidence, big egos, and a sense that they are meant for more. As he puts it, "To do something that changes the world, you first have to believe you’re capable of it and destined for it"
So he asks questions designed to invite an immodest answer. He asks, "Do you believe you’re a natural leader, or is that something you learn?" He asks, "Do you find that if you wanted to, you could win any argument?" And he asks, "If you’re honest with yourself, do you feel like you’re better than others?"
He admits the debate over the timeline was absurd. What mattered was the sentiment behind it. He writes, "actual answers do not matter as much as observations of character." What he watches for is whether the founder is assertive, opinionated, and unusually enthusiastic, and whether the founder is trying to make him believe it rather than "saying the socially acceptable thing for an interview"
Questions people ask
Isn't narcissism a red flag for a boss?
It can be. Psychologists distinguish grandiose confidence, which can help a founder recruit, raise money, and persist, from exploitative or abusive behavior, which drives good people away. The investor is screening for the first kind, assertiveness and persuasion, not for a license to mistreat staff.
What does it mean for shares to vest over four years?
It means the founder does not own all of his stock on day one, but earns it month by month over four years. If he quits early, he leaves the unearned shares behind. Investors use it to keep founders committed for the long haul.
Do humble founders ever succeed?
Yes, many do, especially in businesses that reward careful execution, deep technical work, or long customer relationships. The argument here is narrower, that tackling an extremely ambitious startup requires an unusual tolerance for disbelief, and that often looks like overconfidence from the outside.