The Nature and Character of War

Why founders and investors repeatedly prepare for an environment that no longer exists.

I. The Problem with Startup Advice

Startup founders are surrounded by advice. Some of it comes from founders who have already built successful companies. Some comes from investors, advisors, board members, accelerators, podcasts, and the broader startup community. And, all of it sounds authoritative and comes across with a high level of confidence.

It usually sounds familiar. Launch early. Raise as soon as possible. Stay lean. Hire ahead of growth. Do things that don’t scale. You need enterprise sales. You need PLG. Ignore competitors. Obsess over competitors. Build community first. Build your product first. Build in stealth. Build in public. Once product-market fit appears, pour fuel on the fire.

What makes this advice powerful is not merely that it is repeated. It’s that it usually comes attached to real success. A founder who built a large company in a previous startup cycle explains how a specific decision changed their business’s trajectory, and an investor points to patterns observed across multiple breakout companies. The advice carries the authority of lived experience.

And yet one of the most common failures in startup ecosystems is not a lack of advice but too much of it, combined with too little of an understanding of context. Founders often inherit tactics that worked under a particular set of market, capital, and technological conditions and then treat those tactics as if they describe the permanent logic of company-building. Investors do something similar when they turn the visible features of previous winners into criteria for finding the next ones.

The result is a familiar yet underrecognized problem where founders and investors repeatedly prepare for an environment that no longer exists. They absorb lessons from the last cycle and carry them into a different one. They confuse what was contingent on context with what is enduring. They take strategies shaped by a particular competitive landscape and mistake them for universal principles.

A useful way to think about this problem comes from an unlikely source. In On War, Carl von Clausewitz drew a distinction between the nature of war and the character of war. Though developed in the context of military conflict, that distinction offers an unusually precise way of understanding why startup advice ages badly, why venture capitalists often overlearn from previous cycles, and why both founders and investors need a more disciplined way of thinking about strategy and context.

II. Clausewitz’s Distinction: Nature and Character

Clausewitz’s central insight is that war has an enduring nature, but a constantly changing character.

By the nature of war, he meant the underlying features that make war what it is: a contest between opposing wills, conducted for political purposes, under conditions of uncertainty, friction, danger, and chance. These are not temporary features tied to a specific century or technology. They persist whether the conflict is fought with muskets, tanks, aircraft, or drones.

By the character of war, Clausewitz meant the way war presents itself in a particular time, place, and context. The character of war changes with technology, organizational evolution, doctrine, culture, geography, and the identity of the actors involved. Napoleonic warfare did not look like the First World War. The First World War did not look like the Second. Contemporary conflicts increasingly involve cyber systems, autonomous platforms, and ubiquitous sensors. The visible form changes. The underlying nature remains.

That distinction matters because strategists often confuse the two. They study the most recent conflict, absorb its surface lessons, and then prepare as though those visible features define war itself. In doing so, they risk mistaking transient conditions for permanent truths.

The same error appears in business, and particularly in startups. Within startups, there is an enduring logic of competition and an ever-changing set of tactics, tools, and market conditions through which that competition plays out. And as with military strategy, people are tempted to convert recent success into timeless doctrine. And there, too, the cost of doing so can be severe.

Clausewitz’s framework is valuable not because startups are literally warfare, but because both domains involve strategy under uncertainty, adaptation by intelligent opponents, and the constant need to distinguish between structural realities and temporary conditions. That is exactly the distinction startup ecosystems often fail to make.

III. The Nature of Startup Competition

Startups, like wars, have an underlying and unchanging nature.

At the most basic level, startups are contests between adaptive actors. A founder is not building in a vacuum. Customers respond. Competitors respond. Incumbents respond. Distribution channels shift. Platforms change incentives. Investors alter the constraints under which companies operate. The economics of markets change. Every serious startup enters an interactive environment where each move reshapes the landscape for everyone else.

Startups also unfold under conditions of deep uncertainty. In the earliest stages, founders usually do not know with confidence whether the problem they are building their company around is truly significant, whether the market for solving it is large enough, whether the proposed solution is compelling, whether the buyer is the right one, whether adoption will spread, or whether the market itself will develop in the direction they expect. Early-stage startup-building is not simply execution against a known blueprint. It is exercising judgment under incomplete information and extreme uncertainty.

Then there is friction. Everything takes longer than expected. Customer behavior doesn’t line up with what they say they want. The product reveals problems that were invisible at the whiteboard. Hiring introduces complexity faster than clarity. Distribution channels that appeared promising become crowded or expensive. In startups, as in war, reality pushes back quickly.

Chance matters too. Timing, regulation, talent availability, capital markets, technological readiness, competitor missteps, and just plain luck all shape outcomes in ways no founder can fully control. Good judgment matters enormously, but so does entering the market at a moment when the market is susceptible to the kind of company being built.

Finally, startups are deeply human endeavors. They depend on leadership, morale, persuasion, endurance, and the ability to keep making decisions under pressure when there is no certainty. Teams become tired. Founders become emotionally attached to ideas that don’t fit the market. Organizations begin telling themselves stories they want to be true. Human behavior is not an accidental feature of startup building. It is part of its nature.

Taken together, these features form the enduring logic of startup competition. Markets change. Tools change. Business models change. But startups remain contests of adaptation under uncertainty, constrained by finite resources and shaped by timing, resistance, and judgment.

IV. The Character of Startup Competition

What changes, often dramatically and continually, is the character of startup competition.

The character of startups is shaped by the specific environment in which companies are built: the cost of starting, the speed of shipping, the dominant distribution channels, the availability of capital, the expectations investors hold, the saturation of customer attention, the maturity of infrastructure, and the technical capabilities available to even very small teams.

The startup environment of the early consumer internet days was different from that shaped by cloud infrastructure and SaaS. The SaaS-heavy 2010s were not the same as the product-led growth era. Neither looks exactly like the current moment, in which AI is lowering development costs, compressing product cycles, reducing the scarcity of certain technical capabilities, and potentially eroding the defensibility of features that once looked durable.

Each of these periods encouraged different tactics. In one environment, rapid fundraising might create a decisive advantage, while in another, it might encourage premature expansion. During one period, self-serve, bottom-up adoption might be the cleanest path to scale. In another, trust, integration, and workflow ownership might require a more direct and deliberate go-to-market motion. In one cycle, talent could be assembled cheaply and quickly. In another, even small hiring mistakes could become existential.

This is why startup advice so often sounds contradictory. The contradiction is frequently real, but it does not always reflect confusion. It often reflects the fact that different advice was rational in different competitive environments.

What founders and investors are really arguing about, much of the time, isn’t the nature of startups but their character. The danger begins when the tactical recommendations that emerged from one context are treated as though they belong to the permanent logic of all startup building.

V. Fighting the Last Startup Cycle

Clausewitz’s distinction matters because it explains why startup ecosystems are so prone to fighting the last cycle.

The most dangerous advice is rarely obviously wrong. More often, it is advice that once worked under a previous character of competition and is now repeated as though it were part of the enduring nature of startups. That is how tactical lessons harden into written-in-stone law.

When this happens, founders start to imitate visible behaviors without understanding the conditions that made them effective. Investors begin to search for echoes of prior success rather than for the capabilities required in the present environment. Entire categories of companies can be funded, built, and advised according to assumptions that are no longer true.

This is not just a problem of stale tactics. It is a problem of strategic misdiagnosis. A founder using old advice may end up optimizing for the wrong bottleneck. An investor using old patterns may back the wrong teams or pressure the right teams in the wrong direction. Both sides can become attached to a script that no longer matches the terrain.

That is the deeper relevance of Clausewitz. His framework offers a way to separate what is durable from what is temporary. It encourages more disciplined judgment about which lessons transfer and which do not. And it suggests that much of what passes for startup wisdom should be treated not as law, but as history.

VI. Why Founder Advice So Often Becomes Obsolete

Advice usually doesn’t travel in the form in which it was originally learned. It often arrives compressed and out of context.

A founder who succeeded in one environment rarely passes along a full account of the conditions that shaped that success. What gets transmitted is a distilled version of the lessons learned. The contextual nuance turns into raise earlier, stay leaner, launch sooner, hire sales now, avoid sales entirely, focus on virality, go enterprise, ignore enterprise, build community first, or push monetization later. The advice may be sincere. It may even have been correct at some point. But it was correct somewhere else, under a different set of conditions, against a different set of constraints. By the time it becomes common startup advice, much of that context has been stripped away.

It decays because startup narratives are written after the fact. Success creates the illusion of inevitability. The story of a company becomes coherent in hindsight. A founder identifies the decisive moves they made: the early launch, the aggressive fundraise, the refusal to pivot, the unusual hiring decision, the obsession with a specific metric. But lived reality is rarely that clean. Most successes are shaped by a mix of judgment, timing, luck, market structure, buyer behavior, competitor weakness, and changing opportunity. The final narrative highlights the visible move and quietly removes the rest of the context.

It decays because advice is survivor-filtered. The ecosystem mostly hears from the companies that made it through. For every founder who says an early large round unlocked speed and market leadership, there are ten others for whom too much capital too early created the illusion of progress and the burden of expectations before the business had found the right direction. For every founder who says manual early effort built durable customer insight, ten others simply built a labor-intensive company that looked like a software business from a distance. The advice survives because the company survived, not necessarily because the lessons transfer.

It decays because once a tactic becomes widely known, it changes the environment in which it operates. A playbook often works in part because it is scarce. Once it becomes common, the advantage fades. When every company tries to build an audience before product, or run the same product-led motion, or optimize for the same fundraising markers, what was once differentiating becomes crowded and expensive. Success generates imitation. Imitation changes the character of the market. And ultimately, the advice loses effectiveness.

It decays because startup advice is often formed inside a financing cycle. Founders built during periods of abundant capital learn one set of habits, such as hiring quickly, depending on capital for speed, raising before capital is necessarily needed, and using capital as strategic leverage. Founders shaped by tighter environments learn a completely different set of lessons, such as preserving runway, earning conviction before scaling, delaying fixed costs, and building with smaller teams. Neither worldview is universally right or wrong. Each is partly a rational adaptation to a particular capital regime. Trouble begins when those adaptations are reintroduced later as timeless laws.

That is why so much startup advice becomes misleading precisely when it sounds most confident.

Take the claim that venture capital should be raised as early as possible. Sometimes that is correct. When the market is moving quickly, distribution is open, and additional capital will finance real learning or meaningful acceleration, early fundraising can be strategically valuable. But when capital arrives before clarity, it can distort priorities, encourage performative growth, and reduce the space a company has to discover what problem it should actually be solving.

Or take the instruction to focus relentlessly on growth. Growth matters. But growth of what, and at what stage? Early top-line movement can conceal confusion as easily as it can signal product-market fit. A company that does not yet understand its user, its use case, or its retention dynamics can easily mistake activity for progress.

Even the celebrated advice to do things that do not scale is conditional. It is sound only when the unscalable work produces learning that can later be translated into a scalable system. If the manual effort merely props up a model whose economics or behavior never improve, it’s not a strategy, it’s camouflage.

In Clausewitzian terms, the mistake is always the same: tactics born from a particular character of competition are mistaken for truths about the nature of startup building itself.

What, then, should founders do?

The first step is to assess all advice through a contextual lens. The relevant question is not whether advice is good in the abstract, but under what conditions it would be true. That single question restores context. It forces the founder to ask what assumptions are embedded in the recommendation, like the kind of buyer, the kind of budget climate, the kind of distribution channel, the kind of capital market, the level of product maturity, the degree of urgency in the customer, and the level of certainty in the business.

The second step is to pay attention to warning signs. Advice should be handled carefully when it is delivered in universal language, when it travels too easily across very different types of companies, or when it is most attractive precisely because it relieves the discomfort of uncertainty. Startup advice in the form of folklore is often compelling because it offers the emotional comfort of a script. It turns ambiguity into ritual. But action is not the same thing as strategy.

The third step is to anchor decisions in present reality. The founder’s actual task is to diagnose the situation in front of the company to determine what remains unknown, where the real resistance lies, what kind of learning is currently most important, what constraints are temporary, and what constraints are structural. Once that diagnosis is clear, advice can be interpreted contextually rather than simply obeyed.

This is a more Clausewitzian posture toward company-building. It does not reject precedent. It just refuses to accept it whole. It assumes that strategy must fit the campaign being fought, not merely resemble one that was previously won.

VII. The Investor Version of the Same Error

The same confusion appears on the investor side, but in a more consequential form because it becomes institutional.

When founders inherit outdated advice, one company may be pushed off course. When investors inherit and internalize outdated advice, entire portfolios can be shaped by stale assumptions about what good founders, good companies, and good strategy look like.

Venture capital is especially prone to this problem because it relies heavily on pattern recognition. Firms look for echoes of prior success, such as familiar founder profiles, familiar markets, familiar go-to-market motions, familiar signs of “velocity,” and familiar stories that fit prior winners. Pattern recognition is not irrational; it is one of the few tools the venture capital asset class has. But it becomes dangerous when it is detached from the conditions that made the earlier pattern meaningful.

Investors also become imprinted by cycles. Those formed in periods of easy capital may internalize speed, fundraising strength, and organizational aggression as indicators of quality. Those formed in harder markets may overcorrect toward austerity, early revenue, and default to survival, even when a category requires longer product development or more deliberate market creation. In both cases, what is being treated as wisdom is often the residue of a particular regime.

Then there is the problem of advisory pressure. Investors are expected to be helpful. A board seat creates an implicit obligation to contribute. But that obligation can produce a subtle failure in which advice is given not because the investor has superior contextual knowledge, but because silence feels like abdication. The result is guidance that is too tactical, too confident, or too detached from the company’s actual context.

This matters because founders usually possess an advantage that investors do not, which is proximity. Founders see the customer conversations, the product friction, the quality of demand, the internal confusion, and the timing of learning. Investors see more companies, but each individual company at a much lower resolution. That broader view can be valuable. But it becomes harmful when the lower-resolution perspective overrides the higher-resolution one simply because it carries status.

This is how investors end up pressuring companies into scripts that no longer fit. A firm whose identity was forged during one period may continue to push fundraising benchmarks that made sense then but not now. A partner who saw one go-to-market motion generate outlier returns may recommend it broadly, even where buyer behavior, product complexity, or market maturity point elsewhere. A board member may prefer a familiar narrative because it is easier to understand and easier to sell internally, even when the company’s actual path is messier and less legible.

Clausewitz’s framework suggests a different role for investors.

The enduring part of venture investing is not a fixed playbook. It is the challenge of allocating capital under uncertainty, identifying teams capable of adaptation, and helping companies think clearly in interactive competitive environments. Everything else is like the founder archetypes that look promising in a given moment, the metrics downstream investors reward, the openness of distribution channels, the cost of talent, the tolerance for burn, and the credibility of particular market narratives are contingent.

That distinction should change both underwriting and advising.

On the investing side, it means looking past superficial resemblance to previous winners. The stronger question is not whether a founder looks like someone who won the last cycle, but whether the founder appears able to navigate a changing one. Can this person learn quickly? Can they separate signal from noise? Can they update beliefs without losing strategic coherence? Can they make hard decisions under uncertainty? Those qualities speak more directly to the nature of startup competition than any passing preference for a particular biography or style.

On the advising side, the most useful investor behavior is usually less prescriptive and more diagnostic. Good advice clarifies trade-offs, sequencing, and assumptions. It helps founders reason. It asks what must be true for a strategy to work, what remains unknown, what bottleneck actually matters, which decisions are reversible, and what evidence would change the recommendation. That kind of advice respects the founder’s contextual knowledge while still contributing a broader pattern-based perspective.

Just as important is knowing when not to give advice. Investors should be cautious when the founder has materially better information than the boardroom about the relevant decision, when the recommendation derives mainly from a prior cycle whose assumptions no longer hold, or when the firm’s desire to be useful is greater than its confidence that the recommendation actually fits the company’s present reality. There is a significant difference between helping a founder reason and pressuring a founder to imitate past startup successes.

One of the most damaging habits in venture is the conversion of anecdote into obligation. A famous company hired a head of sales at a certain stage, raised a particular round, delayed monetization, or pushed aggressively into enterprise. The example then becomes normative. The investor is no longer sharing precedent but implying that the founder is behind if the same moves are not made. This collapses the distinction between historical example and present strategy.

The better investor role is narrower and stronger at the same time, becoming narrower in tactical prescription and stronger in strategic discipline. The aim should be to create clarity without imposing scripts, to help founders distinguish enduring realities from temporary conditions, and to resist turning a portfolio’s past into another company’s future.

VIII. A Better Use of History

The implication is not that advice is useless or that history has nothing to teach. It is that both founders and investors have to treat advice historically and contextually, as something that emerged from a particular competitive environment and must be tested against the one in front of them.

That is the enduring value of Clausewitz’s distinction. It forces a separation between what is structural and what is circumstantial. It reminds founders that startups are always shaped by uncertainty, friction, adaptation, and the pressure of limited resources. It reminds investors that no cycle grants permanent authority to its playbooks. And it offers both groups a more disciplined way to think about strategy in markets that change faster than their stories do.

Startup ecosystems are unusually prone to borrowing confidence from the past. A company succeeds, a narrative forms, a tactic hardens into doctrine, and the doctrine gets exported into a new environment that no longer shares the conditions from which it came. This is how founders end up taking obsolete advice from successful operators. It is how investors end up funding and coaching as though the last cycle were still underway. It is how founders and investors essentially end up fighting the last war.