Why I’m Not a Serial Entrepreneur

Yes, I’ve owned my own company. Twice. And I have the scars to prove it. I sold the last company because I realized that as long as I owned it, I would remain single. Yes, I was married to my company and my mental health was almost completely determined by the state of the bank account.

Inc. magazine has a great article that talks about the dark side of entrepreneurship. You can read The Psychological Price of Entrepreneurship here. It provided the spark for this blog post, as I have developed my own hypothesis about entrepreneurs, especially in Silicon Valley. Most are what society would consider odd. OCD, narcissistic, compulsive, addicted, Aspergers (another post on this theme).Because in many ways you can’t be a balanced individual and be successful at a startup. It takes so much energy, so much focus, and so much suspension of reality to make a big-idea-that-no-one-else-believes-in actually work that you have to be on the edge of “normal” to survive.

Yes, there are exceptions. Yes, there are nice, regular Joes (and Josephines) that start great companies. But I won’t be one of them because now I know myself much better. I don’t have the emotional capacity to share between family and a start-up, mostly because I don’t have much emotional capacity to begin with. Since I now have a family, I know I’ll never be able to survive the rigors of the roller coaster ride of emotions that come with starting something from scratch.

So how do some people become successful serial entrepreneurs? My hypothesis is that serial entrepreneurs cope in one or both of two ways. One, is that they figure out how to partition their life between home and work, both physically and emotionally, or they are single. Two, is that they become relatively self-supporting or self-financed after their first company. And maybe the second reason one is the key for me.

I was raised to be very conservative with my money, and that is, quite frankly, a terrible disadvantage in start-ups. You need to be willing to accept long odds because the potential returns are worth it. You as an individual (or a small team) can accept the long odds much better than a big company with big resources, and that is the primary reason smaller companies grow – they are more nimble and take more risks. My problem is that I just can’t handle the suspense nor the potential stress of that risk. However, if I think about it rationally, I know I would survive. Heck, I’ve told myself many times the worst case would be moving back in with my parents. I just couldn’t handle it emotionally.

I have the drive, the vision, the intellect, the network, and the management skills to be a serial entrepreneur. But not that final, important quality – emotional stability around money-at-risk. Sure does feel good to admit it.

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Categories: Deep Thoughts, Family, Technology

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