In my opinion, the most important thing to consider before plunging into starting a business is to question yourself, whether you are really built to be an entrepreneur. I am not talking about skill sets, savyness or even luck, but rather whether your personality and personal traits are geared towards coping with all the struggles and nuances of what comes with being an entrepreneur. It almost seems like the common answer nowadays as entrepreneurship becomes more and more popular and success stories become even more dramatic, entrepreneurs are inclined to think, “I have a great idea, and I should pursue it.” But what comes after this is a long endless battle with finding a cofounder, deciding the right responsibilities, negotiating the right equity splits, finding the right source of funding, determining the right product/ marketing fit, hiring… and so much more. So, what if despite of that you were able to persevere and manage to grow the company? You’ll soon realize the skill set that is needed for each stage of the company is different, and you might be fired by your own investors even before you had a chance to prove yourself. This is where personality comes to the test and becomes the most important question of all. Will you be able to thrive in facing these never ending difficulties? Do you like to manage all the surrounding nuances and be willing to give up at least half your time not working on the product and presumably what you are passionate and good at, but deal with business necessities like funding and hiring? Are you going to be happy as the relationship with your comrades in the business gradually moves towards a hierarchy?
At some point, it becomes not a question if ability, but will you be happy making these choices. It is easy to grow and learn new expertise along with the business, but having the ability to cope with it does not guarantee being in this position will bring you personal fulfillment.
I felt this particularly strongly in the Lew Cirne case. I believe that fundamentally Lew did not want to be the CEO, he was the technical innovator who established the product, but as the business needed other skill sets, he was forced to either learn it himself or to put more experienced people in place. He chose the latter because of his lack of confidence and conviction to step up and this was further proved by watching his timid disposition in the video where he spoke. He did a spectacular job managing his business, but what stood in the way to me was his own lack of conviction to be the leader that his company needed him to be, even if it was not the leader he himself wanted to be. I think this demonstrates a great lesson that the most important step before we start on a venture would be having the self awareness to say no if it we could foresee that it is not the type of situation that we will be happy in.