One of the things I've always known about myself when it comes to my position as a founder is that the second I have to sit down and fill out an expense report for the HR department, I'll know it's time to go.
The "Why Entrepreneurs Don't Scale" articled really hit home in this regard. I agree with everything that the author included as reasons that founders have a hard time adjusting to a company, with the exception of one omission: that it's perfectly alright if a founder doesn't make the transition. Becoming a multi-decade CEO isn't the only definition of success for an entrepreneur.
I also don't think it has anything to do with personality or innate habits--when it comes down to it, the skill sets for a CEO of a startup vs. a CEO for an established company are very different. For a startup, the skills are more similar to a Project or Program Manager, and the elements mentioned in the article serve them well. A CEO of a big company is entirely different, and in other circumstances it would take many years for a Project or Program Manager to be promoted to CEO. Founders of companies are expected to make that transition in a much shorter time, so it's really no surprise that they don't make the transition that often.
And anyway, who wants to be in charge of things like setting company policies for expense reimbursement? It's much more fun to build things from nothing and be creative :)
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