One of my employees asked me, quite directly, who an entrepreneur actually is. I had been one for thirty years by then and had never once stopped to define it, which tells you something about how much of this is done on instinct.
The first thing to separate out is the title. A chief executive is a job — a set of functions, a place on a chart, a thing you can be appointed to and removed from. An entrepreneur is a way of thinking. The two overlap in plenty of people and are absent in plenty of others, and confusing them is how companies end up with a founder who cannot operate or an operator who cannot start anything.
It is closer to a craft than a curriculum
You can teach business theory, and it is worth learning. You cannot teach the disposition. It sits closer to what a musician or a glassblower has — something you can refine endlessly through practice but cannot acquire by reading about it. I have watched people with excellent training fail at it, and people with none succeed, and the variable was never the coursework.
What the disposition consists of is unglamorous when you write it out: enough ego to keep going while people tell you it will not work, enough humility to admit when they were right or wrong, passion that survives a bad year, optimism that is not delusion, and the energy to sustain all of that simultaneously.
The ships behind you
There is an old story about Cortez burning his ships on arrival so that nobody could consider going home. Whether it happened or not, it describes the condition accurately. The entrepreneur is the person without a fallback, and the absence of a fallback does more work than courage does.
This is also why the advice to start something while keeping your job so often produces nothing. The safety net is not a neutral addition. It changes what you are willing to do on the bad Tuesday.
There are no overnight successes
Almost every one you have heard of took a decade, and the years before the story starts are the ones that made it possible. That gap between the visible version and the actual timeline is what causes most of the damage, because people arrive expecting the visible version and leave when they get the actual one.
Which leads to the only piece of screening advice I have. If the motivation is the money or the recognition, it will not hold. Both of those are outcomes that arrive too late to sustain anyone through the part where they are not arriving. The people who last are the ones who wanted to build the thing.
The cost nobody quotes
Running businesses takes something out of you emotionally, physically, and in whatever you want to call the third category. Timing and luck decide more than anybody comfortable admits. Knowing precisely what you are good at — and being honest about the rest, early enough to hire around it — is most of the difference between the people who keep going and the people who burn out proving they did not need to.