The Entrepreneur's Dilemma - Letting Other People Muck Around in Your Stuff to Make it Better

The USV guys and I had lunch with a great company that, probably more so than a lot of other companies, because of the relationship between its founders, exemplifies a startup's growth from something emotional to more of a business.  OK, so not to say that businesses can't be emotional, they are, and I know the founders and management team are very emotionally invested in this company.  However, there comes a point in every company's life where the founder has to let go--at least enough to allow other people to get in there and help create something bigger than the founders themselves.  I don't envy founders that face this, because I know I was never able to do this well myself, to the detriment of the things I had created.

When I was at Fordham, I started a monthly business newspaper: The CBA Business Journal.  While I had lots of writers and a couple of people helping me on layout, it was mostly me putting it all together.  There were so many little things that were just easier for me to do that the incremental effort it required of me to show someone else how to do it.  Most of the time, it was never going to get done exactly how I wanted it to get done anyway, so I just wound up doing most things myself.

The problem was, not only did I not scale, but there was no continuity without me.  Nothing got done if I was busy with a test.  I never figured out how to build a machine that ran on its own power.  When I graduated, it died, not because there wasn't anyone around willing or capable of picking it up, but because I never made the personal and psychological sacrifices necessary to ensure it would last well beyond my time at Fordham.  I never imagined The CBA Business Journal without me.  That was a problem.  The question is how do you do that?  This is one of the most fascinating aspects of the creation of a business from my perspective.

I think it would be interesting to hear from entrepreneurs how they psychologically, especially in their first venture, start letting go of the reins for the greater good of the business and start imagining the business without themselves.  When you do you realize you need a CEO?  When do you decide to leave a business?  This, I imagine,  is especially hard for people whose personalities are intertwined with the business and the community around that business.  So, if anyone has run a startup and accomplished the passing of the torch effectively or otherwise, I'd love to hear from you via comments and trackbacks.