I’ve been helping Jaspar do a lot of hiring for Smarter Social Media lately. The process has been fascinating. As entrepreneurs we are both predisposed to want to hire people with an entrepreneurial mindset. We are looking for someone who can see the vision. Someone who will take a smaller salary today to be part of something significant. Someone who will work long, hard hours to build a great company.

All of these things come standard with an entrepreneurial personality and they are essential for  early employees to posses in any bootstrapped company. The problem is the other qualities of entrepreneurial personalities: strong will (aka stubbornness), the need to lead and a preference for vision over execution, are all qualities of terrible employees. Employees need to be flexible so they can take orders, they need to be team players and they need to take the CEO’s vision and execute on it relentlessly. Herein lies the problem with hiring the entrepreneurial type.

Not all entrepreneurial personalities are created equal however. In the course of my contact with entrepreneurial employees I’ve noticed two distinct categories: wannabes and hasbeens. Let’s start with the wannabes – these people think they are entrepreneurs. They plan to one day start their own venture and are working inside a startup to gain experience. At their best they are sponges eager to learn and grow. At their worst they are arrogant and rigid. They posses all the qualities of a spoiled child, wanting their way or no way and being completely unwilling to put in the hard work to accomplish the vision (even if the vision is theirs to begin with). For the most part wannabes make terrible employees. They are the quickest to claim ownership of your firm’s successes, and the quickest out the door when times get tough.

Hasbeens are an entirely different breed. They are ex-entrepreneurs. Their previous venture most likely failed, otherwise they wouldn’t be working for you (of course, in some rare cases they are back for the fun of it.) Generally they are the humblest and hardest working of all employees. Why? Because they’ve been on a tour as an entrepreneur. They are intimately familiar with the stress that only someone leading a firm can understand. They’ve managed employee emotions, cash flow, bottom lines, boards and everything else that comes with the job. They understand the position that you are in. On rare occasion they have a chip of resentment on their shoulder because they didn’t make it. But with their resentment comes respect, something most wannabes lack entirely.

So if I have my pick between a 23 year old bright eyed, ambitious, “I hope to be an entrepreneur” and a 35 year old, humble, “I failed as an entrepreneur”, I’m taking the 35 year old every time.

  1. September 14, 2010

    I always take the 35 year olds too!

  2. July 21, 2011

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