The cliche “rules were meant to be broken” is a common one in the world of entrepreneurship. Paul Berberian – a great entrepreneur (and dear friend) almost died yesterday when flying his airplane because he broke three of his rules of flying in a row. Paul got lucky and I very glad he’s alive.
As an investor, I’ve developed some rules. These are not absolutes – I break individual rules on a regular basis. These are not “ethical”, “moral”, or “legal” rules; rather they are functional guidelines for helping create companies that I’ve developed over 20+ years of doing this with 100+ companies. If you are an entrepreneur or executive at a company that I’m an investor in (or a co-investor with me) and have ever had to listen to me blather on about a story of something that has happened at another company to illustrate one of my points, you understand what I mean by “a rule.”
While my rules evolve over time, the core principles don’t. Paul’s post illustrated a point that I hadn’t ever really thought about. When you have a set of rules, it’s ok to break one of them, but it’s probably not ok to break two in a row and it might be fatal to break three in a row. In some recursive parallel universe, I guess that’s a rule.
As a result there are two concepts in play: one of “rules” and one of “additive rules.” (Rule_1 or Rule_2 or Rule_3) is very different from (Rule_1 and Rule_2 and Rule_3). The second case is the one that will get you intro trouble.
Being rigid and slaveishly following rules is stupid. Being flexible and breaking three of your rules in rapid succession might be fatal.