Serial Entrepreneurs

Now in the midst of my second startup, people often say to me, “Wow, so you are one of those serial entrepreneurs.”

It’s true, I suppose. I didn’t exactly plan it this way, but here I am.

The whole notion is regarded with a great deal of reverence, the latest example of which is here. (Hat tip Brad Feld.)

I’m not disagreeing with any of the sentiments. Lord knows I learned lots of lessons in my first one, MyTrafficNews, that I’m applying to the Legislative Database, LgDb.com.

But allow me to throw one other thought into the mix:

Let’s just say that I wanted to get a big job at a big company. Part of the accepted wisdom is that I would never want to do that, that I could never work in such an environment. There’s probably a grain of truth in that, but lets say that I could set that to the side and get excited about the goals of a large corporation, and would enter that organization in a position that would be interesting. The pay would be great, I wouldn’t have to worry that I’m taking all the risk, and when I went on my paid vacation I could leave the job at the job, and not think about it constantly, the way I do now.

Let’s say that could happen. Here’s the problem: It would NEVER happen. Never.

Why? Because I would feel stifled the first time I had to fill out a form to get a box of paperclips, or whatever?

Well, maybe, but it wouldn’t matter, because I would never get that job. It just wouldn’t happen.

For all the talk from big business about how they need to be more entrepreneurial, bla bla bla, they really all like their gig exactly the way it is. Nobody working within any large corporation is going to hire someone who will come in and upset the apple cart.

“Entrepreneurial” is another word for “Disruptive.” Corporations will issue press releases embracing “market disruptions” but what they really mean is they want to keep doing the same thing in the same ways, and by issuing a press release the execs can feel that they have done what they need to do to react to changes in the markets.

I’m not just blowing smoke here. If you are a person who has a steady career, you should think carefully before becoming an entrepreneur. It’s great, no doubt about it, but you may never be able to go back even if you want to.

(One note about this blog, it’s been quiet for a bit. It will be seeing some big changes and a big announcement soon. Stay tuned!)