My father, a man who spent almost thirty years in the Navy and the rest of his life teaching its future admirals, had a thing for maps. Not the kind you fold up and stuff in a glove compartment, but vast, intricate charts of battles long past. He’d stand before them in his study, a retired Commander in a tweed jacket tracing the ghostly movements of fleets and armies with a wooden pointer.
"Strategy," he’d say, the word carrying the weight of sunken ships and fallen empires, "is the art of the general. But victory? Victory is the business of the quartermaster."
For fifteen years, I worked on Wall Street, a world away from the salt air and historical gravitas of the Naval War College in Newport, Rhode Island where he taught. My battles were fought in spreadsheets and boardrooms, my weapons were leverage and arbitrage. I was an investment banker, which is a polite way of saying I was a professional gambler in a nicer suit. We spoke of "killing it" on a deal and "capturing" market share, but the language was metaphorical, the blood strictly financial. Yet, the longer I spent in that world, the more I saw the echoes of my father's maps in the chaos of the market. The principles that decided the fate of nations at Midway or Austerlitz, it turned out, were the very same ones that determined whether a company, or even an entire industry, lived or died.
The connection was never clearer to me than when I started advising a new breed of entrepreneur: the SaaS founder. These weren't the titans of industry I was used to, the men who moved steel and oil. These were kids in hoodies building empires out of code, waging war not for territory, but for something far more ephemeral and valuable: mindshare. And their campaigns, from the initial launch to the long slog for market dominance, looked an awful lot like the campaigns my father used to diagram.
Let's take a hypothetical, but entirely plausible, example. Imagine a startup, we’ll call it "CogniBooks," that has developed a revolutionary AI platform for accounting firms. Their software doesn't just automate bookkeeping; it predicts cash flow, identifies fraud before it happens, and offers strategic financial advice with the click of a button. It’s a brilliant piece of technology. It’s also completely useless if it just sits on a server. The founders, a couple of coding prodigies and a single, token "business guy," have a strategy: "Build the best product and the customers will come."
My father would have chuckled at that. "A strategy," he'd remind me, "is not a wish."
The Quartermaster's Game: Logistics and Tactics
The first lesson from the war college that applies to CogniBooks is the primacy of logistics. Napoleon famously said that an army marches on its stomach. A SaaS company marches on its code, its servers, its sales team, and its marketing budget. The grand strategy—to revolutionize the accounting industry—is the easy part. The hard part is the logistics, the thousand unglamorous details that make the strategy possible. This is the quartermaster's game.
For a military campaign, logistics means beans, bullets, and bandages. It’s ensuring that the troops at the front have what they need to fight. For CogniBooks, the "front" is the moment a potential customer hears their name for the first time. The logistics are the intricate supply chain that gets them to that point.
First, there's the product itself. Is the code clean? Is the user interface intuitive? Does the AI actually work as advertised? This is the equivalent of ensuring your rifles won't jam in the middle of a firefight. The development team are the armorers, and every bug they fix is a potential disaster averted.
Then there's the infrastructure. Where is the software hosted? Can it handle a sudden surge of users without crashing? A server outage during a product demo is the modern equivalent of your supply lines being cut. The customer won't care that your AI is revolutionary if they can't log in. This is the unsexy, invisible work of building bridges and paving roads before the army can advance.
And then comes the most critical and often underestimated logistical challenge: the go-to-market plan.
This is where tactics come into play.
Strategy is the what and the why while tactics are the how.
How, exactly, will CogniBooks get its revolutionary product in front of the thousands of small and medium-sized accounting firms scattered across the country?
A frontal assault, a massive, expensive advertising campaign, is one option. But like a frontal assault in warfare, it's costly and often ineffective. You're fighting for attention in a marketplace that is already saturated with noise. You're up against the established giants—the Intuits and the Sages of the world—who have fortified positions and massive reserves.
A better tactical approach might be something more akin to an amphibious landing or an airborne insertion. Find a beachhead. Instead of targeting the entire industry at once, CogniBooks could focus on a specific niche: say, accounting firms that specialize in the restaurant industry. They could tailor their marketing message to the specific pain points of that niche. They could attend restaurant industry trade shows, write articles for restaurant trade publications, and offer a version of their software with features specifically designed for restaurant accounting.
This is a tactical decision that serves the larger strategy. By establishing a strong presence in a smaller, less-defended market, CogniBooks can build a base of loyal customers, gather testimonials, and refine their product. They can create a "safe zone" from which to launch their next offensive. The logistics of this tactical move are complex: it requires market research, targeted content creation, a specialized sales approach, and product modifications. But it's a far more efficient use of resources than a broad, unfocused frontal attack.
Branches and Sequels: Planning for Fog and Friction
This brings us to the second, and perhaps most important, concept from the Naval War College: the idea of "branches and sequels."
Dad’s maps were never static. They were covered in arrows, some solid, some dotted, branching off from the main lines of advance. "No plan survives contact with the enemy," he’d quote, a well-worn piece of military wisdom. "The enemy gets a vote." In business, the market gets a vote. And the market is fickle, unpredictable, and often irrational.
"Branches and sequels" is a planning methodology that acknowledges this reality. A "branch" is a pre-planned alternative to the main course of action. What if the initial landing is repulsed? What if the enemy is stronger than anticipated? A good general has a Plan B, C, and D. A "sequel" is a pre-planned follow-on mission for when you succeed. What do you do after you've taken the beachhead? Do you consolidate your position? Do you push inland? Do you exploit the breakthrough and try to encircle the enemy?
For CogniBooks, this means thinking through every possible outcome of their initial launch.
The Main Plan (The "Trunk"): Launch the restaurant-niche version of the product. Gain 50 accounting firms as customers in the first six months. Use their feedback to perfect the software.
Branch 1: The Competitor Counter-Attack. What if, three months after launch, a major competitor releases a similar AI feature? The pre-planned branch might be to immediately pivot the marketing message to focus on CogniBooks' superior customer service and its "built by accountants for accountants" pedigree. It might involve offering a steep discount to the first 100 firms that switch from the competitor. The key is that this response is planned before the crisis hits. The team isn't scrambling to react; they're executing a pre-conceived maneuver.
Branch 2: The Market Shrugs. What if the restaurant niche doesn't bite? What if the initial marketing push results in a trickle of interest, not a flood? The branch plan here could be to pivot to a different niche: law firms, or non-profits, or even internal accounting departments at mid-sized corporations. The research for these secondary targets would have been done in advance. The marketing materials would be 80% complete. It's not starting from scratch; it's a planned withdrawal to a different line of attack.
Sequel 1: The Beachhead is Secure. What if the launch is a resounding success? They hit their 50-firm target in three months instead of six. The sequel plan is ready to go. It might be to immediately begin development on a "Phase 2" of the product, incorporating the most requested features from the initial customers. It might be to launch a second, concurrent campaign targeting a new niche, using the success in the restaurant space as a powerful case study. It might be to raise a new round of funding from a position of strength to accelerate the expansion.
Sequel 2: The Unexpected Breakthrough. What if the AI's fraud detection feature turns out to be the killer app? Customers aren't just saving time; they're saving millions in potential losses. The sequel plan here is to exploit this breakthrough. The marketing message immediately shifts to "The AI that protects your clients." The company could launch a PR campaign based on case studies of fraud detected and prevented. They could develop a stand-alone, lower-cost version of the fraud detection tool to capture a wider market.
This "branches and sequels" approach is the antidote to the "strategy as a wish" mindset. It forces a level of intellectual honesty that is often missing in the optimistic frenzy of a startup. It forces the founders to confront the possibility of failure and to plan for the reality of success. It transforms the business plan from a static document into a dynamic, living war plan.
The Long War
My father used to say that the most dangerous moment for an army is right after a great victory.
Complacency sets in.
Discipline frays.
The enemy, wounded but not defeated, is looking for an opportunity to strike back. The same is true in business. The launch is just the first battle. The war for mindshare, and ultimately for market share, is a long, grinding campaign.
The giants of the industry, the ones CogniBooks is trying to unseat, aren't going to just surrender. They will react. They will copy features. They will cut prices. They will use their massive marketing budgets to drown out the upstart's message. They will use their established relationships to lock in customers.
This is where the lessons of the war college become a matter of survival. The company must continue to rely on superior logistics—a faster development cycle, better customer support, a more efficient sales process. It must continue to use clever tactics: finding new niches, forming strategic partnerships, using guerilla marketing techniques. And it must constantly be wargaming, constantly thinking in terms of branches and sequels, anticipating the competition's moves and planning its own counter-moves.
The war for market share is a war of attrition. It's not won with a single, brilliant product launch, just as a war is not won with a single, brilliant battle. It's won by the side that can sustain the fight, that can adapt to changing conditions, that can out-think and out-maneuver the competition over the long haul. It's won by the side that understands that strategy, in the end, is not about having the perfect plan. It's about having the right process for dealing with a world that is messy, unpredictable, and relentlessly hostile to even the best-laid plans.
I left Wall Street a few years ago. The game, for me, lost its appeal. I wanted to build things and I lost faith in fiat noise once I found the Bitcoin signal. But I still see the maps. I see them in the pitch decks of the founders I advise. I see the lines of advance, the fortified positions, the logistical supply chains. And I see the ghosts of my father's lessons, the timeless principles of strategy and tactics, playing out in a new kind of warfare, fought with code and clicks instead of cannons and cavalry. The battlefield has changed. The nature of the war has not. And victory, as it always does, belongs to the quartermaster.
Here’s to the revenue logisticians out there.
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