Having spent the better part of 15 years in and around startups, one thing I’ve observed is that the best entrepreneurs I’ve seen have a tendency to double down where they’re strong, and either ignore or hire around where they’re weak. Example strengths could be vision-casting, product insight, or sales. I’m sure there are others, but those tend to be what stand out.
If entrepreneurs are exceptional in an important area, their strength usually makes up for all of their obvious weaknesses.
Another interesting thing I’ve noticed is that a person’s character has very little to do with success and failure. This is not to say that “nice guys finish last”, it’s just that it doesn’t seem to matter much. The clear strength is what ends up mattering in the end.
‘Often, although not all the time, a founder’s strength is in getting people to believe completely nonsensical things. Many times, although not always, people who are good at this also have flawed characters. It doesn’t seem to matter, although sometimes founders go too far and end up as a Theranos.
Completely ignoring weaknesses is not a great strategy, not because it leads to failure, but because it can create dysfunctional cultures. Dysfunctional cultures succeed all the time, but eventually they need to repay the debt that built up over the years, and sometimes that slows a company down at an important time. It’s always better to hire around your weaknesses.
Doubling down isn’t an obvious thing to do. Most of our academic and professional lives are spent trying to skill up where we are weak. How many reviews focus on “feedback and areas for improvement”?
Perhaps ironically, being well rounded usually makes people a better manager, leadership team member and employee. Only founders, or founding teams, seem to be able to get away with this. Organizations can only handle a small number of these asymmetric contributors, and tend to manage out others who exhibit this behavior.
I think this phenomenon is true because startups require some type of force that propels them from birth into what they will ultimately become. That force tends to come from a founder who is asymmetrically skilled.
If you are a founder, find your superpower and double down.