Most ultra successful people have a very low need for social approval, although society tends to label this incorrectly as a red flag.
The average person is terrified of looking like a fool or bothering people. I’ve met CEOs that will send ten follow-up emails to a dream hire or pitch their idea to a stranger in an elevator without a second thought. This personality type means they can bypass the politeness instinct that slows down everyone else’s career.
Hesitation to ask for help or feedback is a common bottleneck in most professions; someone who isn't slowed by the fear of being annoying can squeeze a year’s worth of progress into a week.
There are very few things in life that shameless persistence won’t give you.
The personality type that showed up most frequently in our research on true outlier founders wasn’t “leader” or “visionary”. It was “difficult”.
As children, we found most never did the group work activity in school. They were often the students who didn’t raise their hand in class but always had something smarter to say. When employed, they asked “why” too many times and frequently pissed off their boss. In the wrong environment these people were marginalized or ignored entirely instead of being celebrated.
When they started their company, suddenly questioning everything became a huge advantage, and refusal to settle pushed their product past "good enough". In a big company they were annoying, but in a zero-to-one environment they cut out months of wasted effort and got to something that actually worked.
We spend too much time looking for founders with charisma and "leadership presence", and not enough time looking for the ones who were kicked out of every system they were part of.
The next wave of iconic founders probably wouldn’t be the ones you’d pick in a boardroom; they are the ones who’d refuse to show up to the meeting at all.