May 12, 2024 • 3 min read


A group of bright-eyed entrepreneurs arrived and settled in at a potentially pivotal meeting with a room full of shrewd angel investors. The entrepreneurs were there to pitch the great potential of their emerging businesses, and had high hopes of raising capital to further their cause. The angel investors sat attentively, ready to interview and waiting to be presented with the next big opportunity.


A proptech entrepreneur just finished his pitch. “What’s your strategy?” questioned the angel investor. “What—what’s your growth strategy?” he repeated. “Our aim is to grow revenue by 20% each year,” the entrepreneur replied. “We will do this by offering our solutions to our clients and hiring three business development representatives.” The angel investor had no follow-up questions.


The entrepreneur made a common mistake—he confused strategy with goal-setting. The angel investor's curiosity was not so much in what the entrepreneur hoped to achieve, but in understanding how he hoped to achieve it. A kernel of good strategy, according to author Richard Rumelt, is three-fold:


  1. First, create a diagnosis that defines the nature of the challenge, simplifying the often-complex situation.
  2. Next, produce a ‘guiding policy’ for dealing with the challenge(s).
  3. Then, compile a set of coherent actions that are designed to carry out the guiding policy. 


Exempli Gratia


A perfect example of a great display of strategy can be found in the Battle of Cannae in 216 B.C, in which the Republic of Rome was pushed to near collapse by Hannibal, the General Commander of the Carthage army.


Fifty years prior to the Battle of Cannae, Carthage, a city-state located in modern-day Tunisia, was defeated in war by Rome for control of the southern Mediterranean. Hannibal, fifty years later, now set out for war with the Roman army in an attempt to restore Carthage’s power and honor. 


He took his army to Spain, then Gaul (France), and crossed the Alps into Italy, raiding town after town. The Romans, tired of turning the other cheek, selected two consuls and provided them with eight legions to defeat Hannibal.


The Diagnosis


The battle took place on an open field near a fortress called Cannae by the Adriatic Sea. Fifty-five thousand of Hannibal’s troops were to face eighty thousand Romans. The two armies stood one-half mile apart. The challenge for Hannibal was the shy size of his army in comparison—containing 31% less soldiers than the Romans. 


The Guiding Policy


Hannibal’s guiding policy was rooted in the design of his army’s formation. Hannibal arranged his troops in a broad arc, with his light infantry troops from Spain and Gaul bulging out in the center (see Image 1: Blue = Hannibal). On the side flanks, he placed his heavy infantry and cavalry troops. The guiding policy was to create a facade of retreat to encourage Roman soldiers to charge inward. Upon their charge, Hannibal would entrap the Roman soldiers from all sides. To execute this strategy, he would need his resources (infantry and cavalry troops) to work in unison to carry out a set of coherent actions.


Hannibal v Rome

*Image 1. Blue = Hannibal; Red = Roman 


Coherent actions


As the Roman legions pushed into the center bulge of the Carthaginians, the outward arc reversed inward (see image 2: Red = Roman army). As instructed, the Carthaginians at the front line slowly fell back, not holding the line. Romans, encouraged by the seeming retreat, moved forward to exploit Hannibal’s army’s apparent weakness. Simultaneously, as Hannibal’s light infantry “retreated”, Hannibal ordered his cavalry (placed on the sides of the army) to start their 2-mile arc around the Roman army to attack and defeat the smaller Roman cavalry. 


Hannibal v Rome

*Image 2. Blue = Hannibal; Red = Roman


As the Roman infantry further pushed into the Carthaginian center, the outward arc set by the Carthaginans was reversed inward. As the Romans pushed inward, Hannibal called for reinforcements to hold the line. The seemingly “retreating” troops stopped their retreat and held their ground. Their perceived position changed from panicky barbarians to disciplined troops. 


Hannibal’s heavy infantry then moved in from the flanks, surrounding the Roman army from three sides (see image 2, right side). Hannibal’s cavalry, after defeating the smaller Roman cavalry, rode back in to close the gap from behind the Roman army. The Roman army was so confined in space that the soldiers were unable to lift their weapons. 


This defeat was so great that most southern city-states in Italy declared allegiance to Hannibal following his victory. 


The power of a clever strategy can achieve greater feats than the sum of its goals… and even silence the strength of its opponent.