One of the toughest things for an entrepreneur to do is to cut ties from something they started. It does not matter if it is a positive severing of involvement (e.g. a personally profitable acquisition) or a bad ending (e.g. closing down a venture because it failed), entrepreneurs alway feel like their ventures are their children.

Unfortunately, these thoughts may be the most destructive of any that an entrepreneur may have. At Wasabi Ventures, we are all parents. We all have children that we love and adore. We would do anything for them and often we wear the rose-colored glasses of parenthood that show everything our children do as wonderful. And as entrepreneurs, we also love and adore our “children”, i.e. our companies.  But these emotions blind us from always doing the smart thing. Turning down a lucrative acquisition offer because we don’t want to see someone else run our creation or changing direction as the company is bleeding cash are both examples of this misguided love.

Luckily, there are solutions to this problem.  Having a great advisory board is probably the best remedy.  These independent mentors and assistants are detached enough from the blood, sweet, and tears of running the company that they can offer clear assistance.  Great advisory board members should be like great friends or relatives who can give you feedback about your children.  Sometimes it takes that independent third party coaxing to choose the correct path.

Entrepreneurial success is less about picking your battles than it is about picking your battlefields.

Amateurs focus on tactics–working around the clock, hard-selling, flooding the world with business cards.  The truth is that most battles are won or lost before the opposing forces take the field.

During the Second Punic War, Hannibal beat the Roman army at Cannae by tricking the Romans into fighting on a battlefield of his choosing.  By attacking one of their supply depots and then retreating, and in violation of every rule of warfare, establishing a position in front of a river, he goaded the Romans into attacking.  The Romans saw a battlefield where they could finally corner the wily Hannibal and use the weight of superior numbers to defeat the Carthaginian genius.

The Romans, outnumbering Hannibal 3:1, attacked, trying to drive Hannibal’s army into the river.  Hannibal’s center slowly gave ground, encouraging the Romans to press forward.  At the crucial moment, Hannibal swung the left and right wings of his army inward, completely enveloping the Roman formation.  He utterly annihilated a Roman army of 80,000 men.

By all rights, Hannibal should not have picked a battle against a vastly larger force.  But by picking the right battlefield, he prevailed.  This holds just as true in business as in war.

Google chose the battlefield of making search fast, easy, and better.  This nullified the advantages of Lycos, Excite, Altavista, et al, who had many times the traffic and resources.  Those “portals” could provide an endless array of services, ranging from news to Web-based email.  But on the battlefield of plain old ordinary search, none of those services helped.  In fact, they hindered their efforts to combat Google, whose simple, empty search page completely outclassed the cluttered homepages of its competitors.

The fact that Google’s search results were better was certainly important, but had Google battled its entrenched competition head on, it would have lost.  Google’s genius lay in picking its battlefield.

Pick your battles, but more importantly, pick your battlefields.