Yesterday we had our portfolio company summit with the CEOs of most of our active investments in our office.  It is always a really fun day because there are great discussions about a far ranging set of topics from hiring to business models.  This year as an opener we went around the room and everyone talked briefly about a lesson learned in the last 12 months.   There were a ton of really good insights there and some really funny ones, such as “it is better to have a hole than an asshole” (about having the courage to fire a key contributor with an attitude problem).

But if one paid close attention there was also a fascinating pattern.  One CEO would say something like “we learned that AB testing really works.”  And then a couple of people later, another CEO would say “we learned that building what we ourselves wanted in the product gave us the best results.”  Or more starkly put, one CEO learned to do more AB testing and the other to do less.  Can both be right?

The answer is yes and it is exactly why startups are hard!  You can do too much AB testing and you can do too little AB testing.  I have to come to think of this as Scylla and Charybdis problems.  And there are a great many of them.  You can be too early to a market or too late.  You can raise too much money or not enough.  You can hire too fast or too slow.  You can spend too much time on corporate culture or not enough.  And so on.  Navigating between the two is hard and also means that someone else’s lesson may not apply to you!

The challenge to find the right course will become a new mini series here on Continuations.  I will pick one of these and explain how you can go wrong on either side.  Please let me know your own favorite examples to be included in this.