My father was an accumulator of cliches. I have so many in my head and they come out without even trying. I really wish I could ask him some more. Someday I should start writing them down. One of those cliches I use almost weekly with regards to a new founder or community leader. It involves the creation of a “Pro/Con” list to help you make a decision.

But first a little context.

The cliche my dad shared with me goes like this, “Son if you have to make a pro/con list to decide if you want to have a child, you are already done. The list of cons far outweighs the list of pros when you put it in the format of a bulleted list. Having a child is a decision that defies bulleted logic”.

Now, let me spin that into entrepreneurship.

If you have to make a pro/con list to decide on whether you want to be a founder of a startup or a community leader, you are already done. The cons far outweigh the pros. Starting a company with little information or confidence in the outcome defies logic. Deciding to spend valuable time trying to grow your local startup community with little confidence of the outcomes defies logic. 

If you need logic to decide whether you should quit your job and go without pay for months in order to start your company, I would posit that you do not have the DNA of an entrepreneur.

In 1999 I sold off the assets of a corporate venture fund and was deciding what to do next. I had left the MapQuest board of directors and that entity had yet to go public and later be acquired by AOL. I smartly developed a two-track game plan.

Track One: Get a Job. This involved networking with fellow venture capitalists, former partners, distributors and business friends. This effort also involved looking inside my current corporate master (R. R. Donnelley & Sons) where Jim Donnelley offered to put me in the printing operations track. Thanks for that support, Jim. I also networked with the local Chicago headhunters.

Track Two: Start a New Company. I had an idea of rolling up all of the Tier 2 mapping companies (there were still 20+ of these spread all over the US) and combining the paper versions with a web service (rebuild MapQuest) where the combination would create a 1 + 1 = 3 product mix.

I worked them both in parallel.

Guess which one won?

If you guessed the job – you win a bottle of Yoohoo next time I see you.

You see the startup did not have a chance when I started getting job offers. The known kicks the ass of the unknowns every time. Entrepreneurship is a journey that defies logic. That is not to say that you don’t use logic and data to make startup decisions. You should.

But if the original decision to “leap” is based on a pro/con list, then you shouldn’t birth that baby.

I miss you Dad.  Send some more cliches my way when you have a chance.