Pittsburgh Ventures

Being a big fan of Woody Allen’s early films, it is with hesitation that I present to you this named rule and its follow-on twin.

Rule #2728:  If the founder of a startup reminds you of Woody Allen, run away…

My father-in-law always says that it is too bad that comedy isn’t easily monetized, otherwise the family would be sipping tall drinks on in the sand of some far-away beach.  But those same qualities that make it easy to laugh at Woody Allen don’t give investors a great deal of confidence.

Rule #2729:  When you know more about a business before a call with the founders than you do after, these are likely neither founders nor a business you want to invest behind.

Founders can be their own worst enemies – as Woody Allen often is in his movies.  Watching the holes he digs for himself in business, in love, and in life make your toes curl inside your shoes – you feel for him.  That is what makes him so darn funny.  Don’t spin your business in such a complex way, off on so many tangents, that you leave investors confused and lost – trust me, this isn’t good for your prospects to get money.  Investors want to see that you think clearly, and can convey what you do to customers, employees, and other future investors.

Remember, in probably his best role, as Virgil Starkwell in Take The Money And Run, Woody Allen couldn’t get money out of a bank because he couldn’t get out of his own way.  Don’t be a Woody Allen.