THE PITFALL PRINCIPLE*

Monkey caught in a bamboo trap beside a tiger in a bamboo forest; Japanese text reads 猿罠に陥り 虎安んず 山中閑居画.

A young monkey looked down from the high branches at the mighty tiger resting below. Filled with clever schemes, the monkey spent days weaving a net of vines, digging a deep pit, and laying a feast of sweet mangoes at the edge to lure the beast.

When the trap was set, the monkey clapped its paws in delight, eager to prove its superiority. It dropped from the canopy to admire its handwork, stepped too close to the precipice, and slipped on a rogue peel.

With a yelp, the monkey plunged straight into the deep pit, landing tangled in its own vines. Below, the tiger opened one lazy eye, yawned, ate the mangoes left on the brink, and walked away into the jungle.

FINAL THOUGHT

“Whoever digs a pit will fall into it, and a stone will come back on him who starts it rolling.” — Proverbs 26:27

Entrepreneurs: Often you spend spend months crafting elaborate strategies, complex financial models, and hyper-designed funnels to “trap” a market or outsmart competitors, only to become hopelessly entangled in your own bureaucratic overhead or rigid assumptions. 

Investors: It is wise to not become so obsessed with airtight terms, complex hedging, or forcing a portfolio company into a rigid thesis that you blind yourself to reality, falling victim to the very structures you created to mitigate risk. True mastery lies not in orchestrating elaborate traps for the future, but in staying agile, aware, and firmly planted outside the pits of our own making.

Be mindful of those who are over-engineering for personal gain. Time will often reveal the truth and the crafty will lead themselves into to self-sabotage.

— Early Boykins III