A Strategy Is Not a Plan - It’s an Insight
Chess is often hailed as the ultimate strategy game, yet its moves are comparatively limited. Go, though simpler in rules, offers infinitely more possibilities—embodying the true essence of strategic thinking. It is about an insight about the board when everything is possible
How Key Insights Win Wars and Startups
Estimated Reading Time: ~25–30 minutes
Table of Contents
Startup Case Studies: Early Strategic Insights That Built Giants
Frameworks for Startups to Find (and Execute) Strategic Insight
Building a “War Room”: Operationalizing Strategy for Early-Stage Startups
Adapting, Not Copying: Why All Frameworks Are Descriptive, Not Prescriptive
Introduction: Strategy as Insight, Not Just Planning
“Everybody has a plan until they get punched in the mouth.” - Mike Tyson
In the world of business, few statements resonate as strongly as Tyson’s metaphor for how carefully laid plans collapse when reality hits. Plans by themselves can be fragile, especially in fast-paced early stages where tactical environments can shift overnight. This is why strategy should never be reduced to a mere step-by-step procedure—it is, at its core, an insight; something that sets you apart.
At Winthewar.co, we work with early-stage startups and executives who want to harness military-inspired thinking, strategies, leadership, and coaching frameworks to helo you gain an edge typically afforded to massive organizations. We believe that understanding the difference between a plan and a strategy, or a deep strategic insight, can spell the difference between mediocrity and lasting success. Instead of getting bogged down in rigid roadmaps, founders and leaders must cultivate the ability to see the battlefield differently—and act accordingly.
In this comprehensive post, you’ll learn why strategy is less about “how we will accomplish X” and more about “why we can win, regardless of changes, if we focus on X.” We’ll delve into military history to see how insight beats brute force and then transition into modern examples—Amazon, Airbnb, and Stripe—where early-stage choices, grounded in a single key insight, fueled stunning growth. By the end, you’ll also grasp how to apply this mindset to your startup at different time horizons using proven frameworks, all while recognizing that these approaches are descriptive—not prescriptive—meaning they must be adapted rather than followed as if ordered by a doctor (more on this later).
Strategy vs. Planning: The Key Difference
Many people equate strategy with planning, often filling whiteboards and Gantt charts with step-by-step instructions for the next several months or years. While planning helps coordinate resources, it lacks the adaptive element that defines true strategy. According to Roger Martin, strategy is a set of choices about where why and how you will compete [1]. In other words, it’s not just the plan but the unique insight that guides your plan. More importantly, it is why this plan over all other available plans.
Richard Rumelt, in Good Strategy/Bad Strategy, underscores the principle that good strategy starts with a diagnosis (an accurate understanding of the challenge, we call this “the problem frame” in the military), a guiding policy (the overarching approach to handle that challenge, this is the unique insight), and a set of coherent actions that flow from the policy (this is aligned actions based on the insight) [2]. This approach stands in stark contrast to standard “vision statements” or “checklists.” A rigid plan often fails when unexpected obstacles arise, while a strategy that’s built around a core insight adapts in real time.
In the military realm, there’s an axiom: “No plan survives first contact with the enemy.” This doesn’t mean planning is futile, but that plans must be flexible and subordinate to the overall strategy. We also believe that the value in making a plan is the process of planning, the mental gymnastics of working through the aligned actions of strategy and assessing the outcome. For the military the mere practice of planning allows for immediate flexibility to new or unforeseen enemy actions. For startups, customers, technology, and market conditions can represent the “enemy” at different points in the journey, and can undermine any static plan. What keeps you on course through these sudden changes isn’t more planning; it’s the deeper reason, a unique insight you have about these factors that you believe above everything else will end with victory — your strategic insight that allows you to pivot or persevere.
“Strategy is about making choices, trade-offs; it’s about deliberately choosing to be different."
— Michael E. Porter
American economist and founder of strategic management
Lessons from Military Strategy: Insight Over Force
Hannibal at Cannae: Turning Strength into Weakness
Hannibal’s campaign against Rome in the Second Punic War provides a classic example of insight beating force head-on. In 216 BC, at the Battle of Cannae, a massive Roman army—twice the size of Hannibal’s—marched forward with the goal of overpowering Carthaginian lines through sheer manpower [2]. Anticipating this tactic, Hannibal arranged his troops in a crescent, placing his weakest forces in the center.
As the Roman legions charged forward, they pressed into the “fleeing” center, overcommitting their formation. In reality, Hannibal was drawing them into a trap. At the decisive moment, Carthaginian cavalry and stronger infantry on the flanks encircled the Roman forces, leading to one of the most catastrophic defeats Rome ever suffered. Rather than simply matching Roman strength, Hannibal leveraged insight—the knowledge of Roman aggression and overconfidence—to flip the script.
For modern founders, the lesson is clear: you do not need to match a larger rival on their strongest terms. Instead, recognize how their primary advantage might become a liability if you shift the playing field. Whether it’s a bloated cost structure, bureaucratic layers, or complacency, an incumbent’s strength can become its undoing if you understand where, how, and why to strike.
This is an example of an insight about the Enemy. Something you can use to disrupt asymetrically. In Asymetric warfare, warriors are looking for ways to create outsized returns on actions against a larger force. They cannot compete head on, they must create opportunities of extreme leverage and mass effects on that singular point of advantage. This for startups can be your wedge. Ultimately if you raise VC your goal is to disrupt the entire larger market, but if you can understand the strategic path from one wedge to another, you can get in an asymetric fight and grow your forces from inside the market picking off more and more strategic positions.
The Battle of Midway: Outsmarting a Stronger Enemy
Fast forward to 1942, and we see another example of strategy via insight rather than brute force. Despite being outgunned, the U.S. Navy turned the tables on the Imperial Japanese Navy at Midway, primarily through codebreaking[5]. American cryptanalysts deciphered Japanese plans to attack Midway, allowing Admiral Chester Nimitz to set up an ambush with his limited carrier fleet. When the Japanese struck Midway as anticipated, they were caught off-guard by American carriers lying in wait, leading to a decisive victory.
This pivotal moment in WWII exemplifies how knowing a critical insight—the future—can compensate for numerical or technological disadvantages. Startups similarly benefit from seeing an emerging consumer trend or competitor weakness before others do. It’s rarely about raising the biggest round of funding or hiring the largest team; more often, it’s about predicting where the market or your competitor will be and positioning yourself accordingly.
Startup Case Studies: Early Strategic Insights That Built Giants
Amazon: Obsess Over Customers, Not Competitors
When Jeff Bezos founded Amazon in 1994, most online retailers aimed for quick profits or growth at any cost. Bezos took a contrarian stance, emphasizing a long-term commitment to customer satisfaction [4]. Rather than focusing on beating individual competitors’ prices or catalogs, Amazon zeroed in on making e-commerce as seamless as possible. Features like one-click ordering, personalized recommendations, and an ever-expanding product range were direct reflections of this obsession.
Crucially, Amazon’s strategy was not “sell books online.” It was “earn customer trust so comprehensively that they’ll buy anything from us in the future.” This insight shaped decisions about logistical investments (warehouses across the country), user-friendly interfaces, and even new revenue streams like AWS that further locked in consumer trust through reliability and innovation. It wasn’t merely a plan to sell a certain number of products; it was a guiding insightthat if Amazon became the place people enjoyed shopping, scale and profitability would follow.
For founders, the Amazon story underscores the importance of identifying the real source of long-term advantage. If you define your strategy around a singular insight—like customer trust—then all subsequent roadmaps, KPIs, and product features fall into place around that goal.
Jeff Bezos’s key insight was the biggest obstacle to mass adoption to online shopping was needing to bridge a new “trust contract” with consumers. For generations customers purchased items in stores from other people, shifting this to a digital transaction meant no one person to blame should that trust contract be broken. We see this need to develop trust with innovations like Airbnb, Uber, or even more broadly with self driving cars. Humans want to have another human to blame or to trust, and with many innovations we have to renegotiate that trust, thats the problem frame, we must ensure trust at all costs is the policy/insight frame, how you do this is the aligned actions. Do you run a little slower not to break things? Not launch until things are set? Or maybe you take risks and launch before it is ready and show that users can trust you by being open to feedback and making change based on their requests.
Airbnb: Brian Chesky’s Insight on Hiring and Founder Focus
Few early-stage founders prioritize talent acquisition as stringently as Airbnb’s CEO, Brian Chesky—his unique hiring philosophy mirrors his underlying belief that top-tier teams shape the long-term success of any startup. A telling example is Chesky’s extreme interview question:
“If you were diagnosed with a terminal illness, would you still want to take this job?”
This seemingly drastic prompt is designed to filter for unwavering commitment and resilience, vital traits for navigating the relentless ups and downs of an early-stage environment. Additionally, Chesky often attempts to dissuade prospective hires by enumerating all the reasons not to join Airbnb—from grueling hours to rapidly shifting priorities—ensuring that only those who remain enthusiastic despite the challenges become part of the dedicated team[1].
Chesky’s founder-mode philosophy extends beyond hiring, reflecting how insight-driven leaders SELECTIVELY AND EFFECTIVELY (important distinction) “micromanage” mission-critical areas. Just as a military commander demands an exceedingly detailed plan for a key operation while delegating the rest, Chesky zeroes in on core levers—such as user trust, product UI/UX, and supply-demand equilibrium. He focuses his time and energy on these pivotal tasks because his experience and strategic insight tell him these are the choke points that can make or break Airbnb’s growth trajectory. Meanwhile, other processes are entrusted to capable teams, allowing Chesky to leverage his own unique perspective to steer Airbnb where it needs to go. This adaptable approach—balancing deep involvement in select areas with a broader trust in specialized teams—illustrates how a founder’s core insight should drive both the company’s priorities, how and who you hire, and the way those priorities are executed.
Stripe: Winning by Serving Developers First
Despite numerous payment gateways existing well before 2010, Stripe carved out a massive market share by focusing on a seemingly niche target: developers. Founders Patrick and John Collison recognized that the biggest pain point in adopting online payments wasn’t price or brand recognition; it was the technical complexity developers faced when integrating clunky APIs, dealing with compliance, and maintaining security [8].
Stripe’s strategy wasn’t “match PayPal’s fees” or “invest heavily in brand marketing.” It was, “offer the simplest, best developer experience, and they will become our champions.” By creating easy-to-use APIs, thorough documentation, and near-instant approvals, Stripe turned developers into its sales force. They integrated Stripe into thousands of new startups, many of which grew to become significant players themselves.
This approach exemplifies strategy as an insight because it tackled a critical chokepoint (developers’ pain) that big incumbents had overlooked. While others poured resources into consumer-facing branding, Stripe addressed the gatekeepers of adoption, reaping exponential growth. Founders can learn from this by identifying a stakeholder or audience whose needs are undervalued by competitors and serving them better than anyone else.
From “How” to “Why”
One unifying theme in the examples above is the difference between “How will we win?” to “Why will we win?”. “How” often produces bullet points on expansion plans or marketing initiatives, but “why” zeroes in on the core rationale behind your ability to stand out and prevail. As Peter Thiel notes, every transformative venture begins with a “secret” or contrarian truth [5]. Amazon’s secret was that customer trust trumps short-term margins; Airbnb’s if you are extreme, be extreme, even when hiring and managing; Stripe’s was that developers actually drive payment adoption decisions.
By framing strategy around a “why,” founders ground their decisions in a central hypothesis about market behavior, technology trends, or user psychology. This “why” not only focuses a startup’s efforts but also guides pivots when initial tactics fall flat, or how you select the RIGHT growth proxy and metrics. If your overarching insight is correct, short-term failures become stepping stones to refine execution. If your insight is wrong, swift feedback loops let you identify the mistakes, shift the hypothesis, and refine it early.
In other words, strategy as insight means you’re not locked into a single plan of action; you’re committed to a perspective. This perspective should inform every product decision, hiring choice, and marketing campaign. Rather than a static roadmap, you have a living thesis that evolves with each new piece of data. Such flexibility is often what separates enduring startups from those that fizzle out once a single approach fails.
In the military we will send recon forces out to help refine the strategic assumptions before a “plan” is even finished. We send these troops out with a set of priority information requirements (PIRs) that we need to answer to turn assumptions into facts. Many times these are helping planners refine those insights and validate them. Think of this recon as your MVP, if you do not have a strategic insight codified how will you know what PIRs to test the assumptions the insight is based on?
"Strategy without tactics is the slowest route to victory. Tactics without strategy are the noise before defeat."
- Sun Tzu
Frameworks for Startups to Find (and Execute) Strategic Insight
First-Principles Thinking: Boil Problems to Their Essence
First-principles thinking involves tearing a problem down to its foundational elements and then rebuilding from scratch, rather than simply iterating on existing solutions [1]. Elon Musk popularized this approach at SpaceX, where he broke down the cost of rockets to their raw materials, uncovering how over-inflated and inefficient traditional aerospace pricing was [8]. But you don’t need to be launching rockets to benefit from this.
For startups, first-principles thinking is about questioning every assumption in your market:
Why do customers prefer X over Y?
Are these preferences rooted in real constraints, or are they artifacts of habit?
Could a new technology or distribution model overturn these assumptions?
By relentlessly questioning what is assumed to be “common knowledge,” founders can stumble upon contrarian insights. Imagine a fintech startup asking why transfers take three days to settle when modern systems should, in theory, enable near-instant transactions. That single question, addressed at its core, can birth an entire innovation. The point is not just to think differently for the sake of it, but to strip away extraneous baggage that might prevent you from seeing the simplest path to capturing or creating value.
The OODA Loop: Be Faster and More Adaptive than the Competition
Colonel John Boyd’s OODA loop—Observe, Orient, Decide, Act—revolutionized modern military strategy [6]. Instead of relying on cumbersome, top-down orders, it emphasizes rapid, iterative learning and adaptation. In aerial combat, the pilot who continuously cycles through OODA faster gains an edge over a slower opponent. The same principle applies to business: the startup that quickly interprets user feedback, reorients its product roadmap, decides on changes, and implements them again can outmaneuver larger, slower incumbents.
Observe: Collect real-time data on user behavior, product performance, and competitor moves.
Orient: Analyze this data to understand emerging patterns.
Decide: Choose a course of action—launch a new feature, pivot your messaging, or double down on a working strategy.
Act: Execute swiftly, then move back to Observe.
This cycle fosters a learning culture where mistakes are quickly identified and corrected. For founders, it means that your strategic insight is never static; you refine it based on market signals. In an environment where consumer tastes and technologies evolve daily, the OODA loop can be your best defense against irrelevance.
Borrowing from Military Strategic Planning
Identify the “Center of Gravity”
Military strategists often refer to an enemy’s center of gravity (COG)—the critical source of strength or cohesion that, if undermined, can lead to a swift collapse [9]. For a large corporation, this might be its vast retail footprint, a flagship product, or a carefully cultivated brand reputation. You are not in the business of undermining a source of strength, instead you are looking for a unique insight, maybe about an industries COG that you believe that can be a strategy. Your center of gravity can be something they missed, but it cannot be focused on the Enemy. You have to be unique, it must be yours. As a founder this is the first risk you must take, a way you see the future unfolding that you are willing to bet the rest of your life on.
What is something you believe about the future that no one agrees with you about? (Peter Thiel)
Why do you believe this is true? What insight or experience gives you trust and confidence in this idea or belief? What other things would need to be true for this idea to be true?
“What Must Be True?” and Other Strategy Questions
An illuminating question for founders is: “What must be true for our strategy to succeed?” [1]. If your plan relies on certain user behaviors, cost structures, or partnerships, list them out:
Do users have to switch from a popular incumbent?
Must suppliers be willing to give you a certain price break?
Are you relying on a regulatory environment that might change?
By identifying these essential conditions, you can test them in smaller experiments, aligning with lean startup principles [10]. If one or more of these pillars proves false, you know immediately to revisit or adjust your strategic assumption. This method prevents large-scale resource wastage on a flawed or overly optimistic plan. It also encourages teams to prioritize critical unknowns—the questions that could make or break your startup’s entire strategy.
Building a “War Room”: Operationalizing Strategy for Early-Stage Startups
One common pitfall is letting grand strategy remain purely theoretical. In the military, generals rely on operations centers or “war rooms” to keep track of live intel, analyze updates, and adjust tactics swiftly. Early-stage startups can adopt a similar practice to ensure strategy as insight remains a day-to-day guiding force.
Set Up a Centralized Strategy Hub
Whether it’s a physical space with whiteboards and dashboards or a digital “war room” (using tools like Notion or Miro), you need a central point where your team can see real-time metrics, user feedback, and competitor developments. This transparency keeps everyone aligned on the tactical steps needed to fulfill your broader strategic insight.Integrate Strategy into Weekly Rhythms
Monday Orient & Decide: Kick off each week by reviewing the latest data—growth metrics, product performance, user testimonials—and then collectively decide on top priorities.
Daily Standups: Short, focused standups can ensure that each day’s tasks link back to the strategic why. It also helps surface issues early, enabling rapid OODA loops.
Friday Retrospectives: End the week by capturing lessons learned—both successes and failures. This fosters a feedback culture, vital for continuous strategic alignment.
Apply First-Principles and OODA in Real Time
Run quick “stress test” sessions on any major initiative. Ask if you’re simply replicating industry norms or if you’ve stripped assumptions down to fundamentals. Align these discussions with an OODA loop framework for faster iteration.Align Rewards with Strategic Goals
If your insight is, for example, “be the most developer-friendly payment solution,” then measure and reward developer satisfaction or the number of successful integrations. Avoid siloed metrics that have little to do with the core strategic advantage.Coaching and Accountability
At Winthewar.co, we emphasize hands-on coaching to help startups maintain discipline in these processes. Having a strategist or coach on board—one who keeps you accountable to your insight—can be invaluable. It mirrors how military leaders rely on advisors and structured after-action reviews to stay objective and consistent.
By establishing these operational practices, you transform strategy from an abstract concept into an everyday habit. This daily discipline, reminiscent of how armies sustain battle readiness, ensures your strategic insight remains front and center—even when day-to-day fires threaten to pull you off-course.
“Strategy is, at some level, the ability to predict what’s going to happen, but it’s also about understanding the context in which it is being formulated. And then you have to be open-minded to the fact that you’re not going to get it right at the very beginning.”
–Martin Dempsey
Adapting, Not Copying: Why All Frameworks Are Descriptive, Not Prescriptive
Ok now that I have given you all of this information to use, here is why you should NOT use it.
A crucial caveat is that every framework, case study, or principle discussed—from Hannibal’s encirclement tactic to Airbnb’s extreme vetting and managment model—is fundamentally descriptive rather than prescriptive. These examples describe what worked in a particular historical or market context, not a one-size-fits-all solution that automatically guarantees success in any situation. So many founders I have coached try to apply what they read or hear “just as” it was done by the person describing it. Like a doctor prescribing medication:
“Take two Jeff Bezos’s written memos, reading them at the begining of any meeting before discussing,
two times a week for 45 days and you will reach 50 million ARR; I have a refill order in if needed." - No One Ever
We tend to prescribe these things that worked for us, or for someone else, because there is no Advice Malpractice lawsuits. We should instead look at all of these things as “a-way” not “the-way” and adapt them or apply them in a way that CAPITALIZES ON THE STRATEGY INSIGHT!
1. Context-Specific History
Military campaigns and startup journeys are incredibly path-dependent. Hannibal’s tactics succeeded against a specific Roman formation with specific cultural mindsets. Airbnb’s trust-oriented approach flourished in a digital era where social media, online payments, and review systems were already normalized. If you copy-paste those tactics blindly, you might miss nuances like different regulatory environments, changes in consumer behavior, or an entirely different set of competitor strengths.
2. Adaptation Over Prescription
Think of these frameworks—first-principles thinking, OODA loops, center-of-gravity analysis—as tools in a strategist’s kit. Tools can be used in many ways, and the user’s skill and the situation’s demands will dictate how effectively they’re applied. Just as a seasoned carpenter selects and adapts tools based on the type of wood, humidity, or design, a savvy founder must tailor these frameworks to their unique market, product, and team dynamics.
Far from being magic pills (take two frameworks and call me in the morning), these strategies require constant iteration and critical thinking. This recognition is at the heart of Winthewar.co. We aim to coach founders to adapt these lessons—rather than adopt them wholesale—so their startups can benefit from proven principles while still differentiating themselves in a saturated landscape.
Insight + Execution = Startup Victory
At Winthewar.co, our core mission is to help founders and executives develop the kind of adaptable, insight-driven strategies that can outmaneuver competitors—even those with far greater resources. From Hannibal’s double envelopment at Cannae to Airbnb’s trust-centric disruption, the unifying thread is always an intellectual edge grounded in a single, potent idea.
Strategy ≠ Plan: A static roadmap can unravel quickly, but a profound why ensures you stay focused and agile.
Military Parallels: Smaller, scrappier forces often triumph by exploiting an enemy’s blind spot or overconfidence. Likewise, startups can beat incumbents through insight rather than brute force.
Startup Case Studies: Amazon’s focus on long-term customer trust, Airbnb’s obsession with safety and community, and Stripe’s developer-first approach were all built on unique insights that guided their decisions and culture.
Frameworks for Action: Principles like first-principles thinking, the OODA loop, and center-of-gravity analysis are descriptive tools. They become transformative only when carefully adapted to your team’s capabilities and market realities.
Operationalize: Consistent war-room practices—daily standups, weekly retrospectives, real-time dashboards—keep your insight woven into every move you make.
Adapt, Don’t Copy: Finally, treat all historical examples, books, and podcasts as inspiration, not rigid templates. Each situation requires a customized approach that aligns with your startup’s distinct trajectory.
In the end, it’s not enough to read about strategy or plan meticulously; you must discover and apply an insight that gives you a unique path to victory. By blending such insight with disciplined execution and a willingness to adapt, you’ll not only survive in competitive markets—you’ll thrive. If you’re ready to explore how these ideas could reshape your startup’s future, consider reaching out to us at Winthewar.co for coaching, accountability, and expert guidancein crafting a strategy truly tailored to your mission.
References
[1] R. L. Martin, Playing to Win: How Strategy Really Works. Harvard Business Review Press, 2013.
[2] R. P. Rumelt, Good Strategy Bad Strategy: The Difference and Why It Matters. Crown Business, 2011.
[3] M. E. Porter, “What is Strategy?” Harvard Business Review, vol. 74, no. 6, pp. 61–78, 1996.
[4] J. Bezos, Shareholder Letters, Amazon.com, 1997–2015. [Online]. Available: https://ir.aboutamazon.com/annual-reports-proxies-and-shareholder-letters/default.aspx
[5] P. Thiel, Zero to One: Notes on Startups, or How to Build the Future. Crown Business, 2014.
[6] J. R. Boyd, A Discourse on Winning and Losing, Air University Library, Maxwell AFB, AL, 1987.
[7] B. Chesky and J. Gebbia, “Origins of Airbnb,” 2008. [Online]. Available: https://www.airbnb.com
[8] E. Musk, “On first principles,” Interview excerpt, Foundation Series, 2012.
[9] L. Freedman, Strategy: A History. Oxford University Press, 2013.
[10] S. Blank, The Four Steps to the Epiphany. K&S Ranch, 2013.