David is not Goliath, and should not be
When you are doing something truly disruptive, you are in a David versus Goliath situation (and this is especially true for technology). The story of David is highly instructive for anyone who aspires to do world-changing things, and its lessons go much deeper than an inspirational tale of the little guy beating the big guy.
Let’s begin with the obvious: David wins by not playing by Goliath's rules. He doesn't out-muscle Goliath, instead fighting a lightweight, guerrilla style insurgency. David is Exhibit A for the theory that speed, wits, and the ability to adapt can trump size, resources, and heavy armament. After felling Goliath with his slingshot, he beheads him with his own massive sword (a gory but potent bit of symbolism often left out of the retelling).
However, David’s selection as champion of the Israelites and his rise to field commander were unconventional, even revolutionary acts in themselves. In fact, almost every key event of David’s ascendancy was highly unlikely. It began when the prophet Samuel sought out Jesse of Bethlehem, believing that one of his sons would become king of the Israelites. Samuel rejected each of Jesse’s grown sons in turn before Jesse reluctantly presented David, his youngest son and a mere shepherd. Anointed by Samuel, David went to the court of King Saul, initially as his armor-bearer. Yet it was as a musician that David made himself indispensable to Saul, healing his afflictions with his sublime harping. When war broke out with the Philistines, David was not even asked to fight at first, instead going home to tend his father’s sheep. When David arrived at the front to answer the call, he faced fierce opposition from within the Israelite ranks, chiefly from his own brothers. I suspect that when Saul, not renowned for his piety, gave David permission to face Goliath, he was not 100% faithful, but instead thinking “this is so crazy it just might work.”
After numerous trials, including his betrayal by Saul, David was crowned King David. He ruled unconventionally and brilliantly, true to his essence, and in doing so established the House of David and the true throne of Israel. Famed as a warrior, he never forgot that he was also an artist, and crafted psalms as powerful in their own way as his armies. This is not to say that David’s reign was a wholly peaceful one, or that his better judgment always prevailed. He made his share of prideful mistakes, and suffered no shortage of tragedies, none more painful than the deaths of two of his sons. However, David proved willing to build on his failings, and never stopped bucking convention. When the time came to choose a successor, he passed over his heir apparent for Solomon (originally the product of adultery with the wife of one of David’s commanders). Solomon, of course, built the great temple of Jerusalem, composed the Song of Songs, and became synonymous with surpassing wisdom. Ultimately, the line of David exemplifies the divine ascendancy of the unlikely.
For technology entrepreneurs, the story of David is a highly attractive one, and the modern-day parallels are striking. You can think of David’s slingshot as one of the original disruptive technologies – it’s lightweight, requires minimal training, and utilizes off-the-ground commodity hardware. It is likewise fitting that the term “Philistine” has come to mean someone without any appreciation for art and learning, and this is especially true concerning the perception of software, perhaps the most misunderstood and underappreciated form of technology at the institutional level. Of course, David himself is the most inspiring part of the story, a young, fearless, brash, but supremely talented leader who emerges from the least likely of places with the most counterintuitive blend of skills.
However, those who would follow in David’s footsteps must beware the catastrophic, yet often subtle pitfalls along the path. It is paramount that as David wins, he doesn't become Goliath. For leaders who emerge from the tornado of the hyper-growth phase, this is deceptively easy to do, and the annals of technology are piled with the cautionary examples of companies born from innovation that faded into irrelevance by allowing themselves to become the hated establishment. David must be true to who he is, not by consciously choosing to remain small and irrelevant, but by resisting Goliath’s arrogance and vulnerabilities - even while embracing growth and influence.
I spend a lot of time working with large and important institutions to help them solve their biggest problems. This tremendously rewarding, and as the sense of partnership and investment in their mission develops, it is tempting to want to be of them as well as work with them. Yet you can only help them if you are true to David, and this requires you to maintain the unique identity and vantage point of the constant outsider. And this is why massive institutions need the help of entrepreneurs, even if they don’t realize it at first. This is inevitably a bumpy process, because the cultural bias is to keep David in a limited role, away from the front. Eventually, though, it becomes clear that in order to do radically different things, they need radically different competencies and perspectives. If it was simply a matter of finding better top-down management, they could promote from within. To enlist a warrior psalmist is a different thing entirely.
Of course, embracing unconventional wisdom is only the first step. The far greater hurdle is how to institutionalize agile and independent thinking without becoming doctrinaire and inflexible about it – an ironic but all too common mistake. Interestingly, this applies to both the century-old brand name that seeks to embrace entrepreneurial culture and the scrappy startup that suddenly finds itself with thousands of employees. Once again, David rides to the rescue. Consider the fundamental challenge faced by US Special Operations Command, a four-star headquarters with almost 60,000 personnel, charged with maintaining supremacy in lightweight, unconventional warfare. Former commander General Bryan Brown, who enlisted as an infantry private and retired as one of the great visionaries of special operations, once remarked that USSOCOM needs its poets too. David knew it all along.