A VC in Vacationland

We all were required to read–at least 50 pages or the Cliff Notes of– Nathaniel Hawthorne’s The Scarlet Letter.  "The scarlet letter was her passport into regions where other women dared not to tread. Shame, Despair, Solitude! These had been her teachers—stern and wild ones—and they had made her strong, but taught her much amiss." 

This is another in my series of anti-VC cliches, ones aimed at giving you real advice on how to manage your start up.

There are more than a few lessons for an entrepreneur in this classic that you never read:

• You will get  to travel to regions others have never explored.  You better, otherwise why go on the quest?
• You will experience periods of deep despair and doubt in your quest.  Be sure you have companions on your journey to help you keep the faith.  Poor Hester never did and that is why her journey was much more difficult.
• Recognize your teachers. Hester had her teachers with her every day, whether she wanted them along or not.  You should know who your teachers are–advisor’s, board members, friends–and be sure you call on them for help.
• You will have a scarlet letter on your chest.  Until you are successful, and that can be defined in many ways (but assume it means you become an industry leader in your space), you will wear that scarlet letter "L" on your front.  It stands for Loser, in case you did not guess.  You will have it until you become a winner. Get used to it.

In the end, Hester never really regains her status in the town, in spite of her lover’s confession on his deathbed. Being an entrepreneur is always being a little suspect–by your investors, friends, customers and your employees. You are the one taking them to places they have never explored.  They are going to be skeptical that once they get there that things may not be any better.  Making sure that this does not happen to any of them is the best end to your story.