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‘The Art of War’: Startup Lessons for Modern Entrepreneurs

One can improve several areas of one's entrepreneurial, business, and leadership skills with the Art of War by Sun Tzu. Let's

The Art of War by Sun Tzu is a book that focuses on military strategy, written about 2,500 years ago. Even though the book is ages old, it is still very relevant to businesses.

While many would claim that it is about the battlefield upon first reading it, but if you look at it from a business or entrepreneurial point of view, you will get a whole different view that you have probably never seen before (1).

Sun Tzu had written the book to entail how to wage war and described it as a path towards either ruin or safety. It describes the path to ensure your victory.

As many of us believe that modern battles don’t happen on battlefields with arms; instead, they happen in boardrooms with ideas. The worldwide market opening has brought several opportunities for local entities to go global. While large organizations with deep pockets can easily do it, but what about small startup entrepreneurs?

You could also wonder how the ancient book can help you as an entrepreneur in a modern time.

However, the fact is that The Art of War lessons is relevant even today for several reasons. Not only in business, but people can apply it to their many everyday life aspects. The strategies in the book by Sun Tzu deal with basic human nature. Hence, we can apply it to a wide variety of current situations, not only business, but politics, science, and even sports (2).

You don’t even have to be a literary expert to understand that if a work survives through millennia, there must be some value in it that is inherent and timeless. If you are looking to educate yourself, The Art of War is not a book you should ignore. After all, several messages in the book have changed people’s lives across continents and centuries.

So far, you must have understood that the book is not merely a collection of battle tactics. It is about psychology, ethics, leadership, and strategy written in a soldierly, strict, and concise manner.

In the article, we have attempted to generalize some book principles that can help you succeed as an entrepreneur, business owner, freelancer, and even an office worker. Let’s take a look at these lessons that could change the way you do business forever.

The Lessons

All of Sun Tzu’s teachings are still relevant to modern entrepreneurs facing fierce competition now more than ever for customers, talent, and market share. Their very survival depends on their strategies, planning, positioning, and leadership, similar to armies a thousand years ago (3).

1. The Attack at Undefended Area

According to Sun Tzu, one needs to ensure success by attacking undefended areas. It is all about finding the weakness of enemies and where they have a presence. The situation is also similar in business. However, the more common thought here is finding the competitor and how we can be there. One of the most common strategies is to start selling where our competitors are not.

When we go to customers where none of our competitors are selling seems to be the easier route. According to Sun Tzu, the idea here is to appear where you are least expected. It allows you to capitalize on a different market subset.

In a war, a smart general also looks for undefended areas. There is an assured success there even though the position value may remain low. In business also, it is always smart to look for new markets and opportunities with few competitors (4).

One also needs to vary ‘solutions looking for a problem,’ and lack of customers.

Ensure success by attacking where the enemy is present and weak.

2. Win-Win Alliance

In ancient times, creative diplomacy was a far better solution than fighting to the death.

One can also apply similar principles to a business partnership. One can find an entity doing business in the same market and build up a mutually benefitting plan. In essence, it would allow you to share each other’s customer base without competition.

As an entrepreneur, you need to learn that your most fierce competitor can also be your best strategic partner, leading to a win-win situation for both parties. It is called coopetition, and it’s often overlooked as a key strategy in business (5).

3. Thorough Preparation Before Battles

According to Sun Tzu, ‘a skillful fighter seeks battles that he knows he can win.’

A smart general always does his research first before going into any battle. He would check the land lay, such as critical high points with the most value, before charging into the fight.

Many startups make an early rush into the battle, assuming that any progress would give them a competitive advantage (6).

But a successful entrepreneur knows his industry inside out and is always aware of any changes that could potentially affect his business, either positively or negatively. Similar to how the natural formation of the country is the best ally for any soldier.

Lining up sources is a critical task, but also is the market timing. Several entrepreneurs get so focused on planning that they never reach the action point. It is often called analysis paralysis, where the person is ready and aimed but never shoots.

The troop of a good general is trained and prepared and never hesitates to act.

People often believe that there is no success guarantee in the business.

However, if one can correctly craft his sales and marketing, one can develop metrics and make decisions. It would guarantee that one knows how much he needs to spend to ‘win,’ where to spend it, and the outcomes based on previous results (7).

As Sun Tzu (8) says in The Art of War, any general who wins the battle had made many calculations before fighting the battle. The general who had lost had made fewer calculations beforehand.

The lesson here is to plan for everything you do and always have backup plans.

4. Strengths and Weaknesses

A winning general is always aware of his troops’ weaknesses and strengths.

Similarly, entrepreneurs must also know and leverage their current team’s competencies while also offering the backup and direction to minimize weaknesses in selecting the target market.

Like every army, all competitors also have weak points. As an entrepreneur, you must watch out for them, pivot them whenever necessary, and lead your team into the fray (9).

When you are well aware of your strengths and weaknesses and your competitors’, you can take advantage of them to further strengthen your own business.

The key lesson here is not to attack your competitors; strong points. You need to analyze their weakest points and how you can take advantage of them. As Sun Tzu says, ‘if one knows his enemy and himself, one would not fear the outcomes of a hundred battles.’

5. Think First, Act Later

He also says that as you seize opportunities, they get multiplied. As an entrepreneur, take advantage of opportunities; more will naturally come. Success promotes further success! As one takes advantage of opportunities that come his way, he builds his expertise, and therefore he prompts further business.

Small wins and some penetrative makes momentum and boost morale for a major assault.

However, there are times when we would need to lose small battles to win the final war.

A successful entrepreneur and army leader know which battles are worth fighting. You would need to accept when something is not working. Don’t allow small battles to take up all your time and energy. It would be much better to use it to plan the next campaign (10).

‘The one who wins knows when to fight and when not to fight.’

An entrepreneur should know that one can’t do everything. And the most successful one knows how to prioritize essential tasks and when to delegate. It is quite often when people spent their energy on fighting ego-battles for little to no reward. However, they need to know that the best is to spend it on moving on.

If you want to be successful, you need to learn to leave your ego and emotions from the equation and focus your energy on tasks with high rewards.

Likewise, no startup or army can manage over three to five goals and priorities without becoming unfocused and ineffective.

‘Spray and pray’ is not a strategy to win any battle. Hence, focus on plucking a key challenge and attack it with all your resources instead of spreading so thin that all your initiatives are jeopardized.

Another point worth highlighting is the decision quality, which is similar to the well-timed falcon swoop, enabling one to strike and destroy his enemy (11).

When an entrepreneur has a sound plan and considers every stage of his strategy, his timing also plays a key role. You need to know when to execute each part of your strategy to have a maximum impact.

A smart general would avoid an army when its spirit is keen. However, he attacks it when torpid and inclined to return. It is the art of mood studies. He would wait for the appearance of unrest and disorder calmly and with discipline among its enemy. It is an art of retaining self-possession.

Likewise, entrepreneurs should not act without thinking first. A successful leader has the self-control to formulate a plan before he acts.

6. A Strong Culture

Sun Tzu emphasizes in The Art of War (13) that a successful leader treats his men as he would his beloved sons, and they follow him into the deepest valley. An entrepreneur should treat the people who work for him as an integral part of his business. He needs to remember the essentiality of staff loyalty (14).

There are also talks about whose army is animated with the same spirit throughout all its rank ultimately wins. It teaches us that our team is most powerful when they are together. We don’t need to give out instances to explain that teams who work together would achieve more than if they are working as individuals.

All the greatest generals in history had one thing in common. They all respected their troops. They never let their men sacrifice themselves to get military advantages. When they care for their soldier, consequently, they also respect their generals.

A leader can only have a victory if his soldiers trust him to make the right decision for them. He commands for respect without ever demanding it and wins his troop over (15).

The lesson to learn here is that it is the environment that encourages people to do something remarkable for others. When there is the right environment, people feel safe, and there is trust and cooperation from everyone.

Similarly, a startup faces insurmountable challenges every day, where everything is at stake. However, people can cooperate and trust each other. Hence, if the same military principles are applied to a startup, we would get an environment where employees can work with each other with a shared success goal.

7. Taking Risks Without Being Reckless

When it comes to war, and even in business, there is no safe position. Charging into a battle with closed eyes is being rash. It can only lead to destruction. Winning in both arena needs the skill and willingness to take smart risks with due diligence, trained resources, and determination.

Sun Tzu also talks about how there is no instance of any country benefiting from prolonged warfare. The same kind of military-level precision is what a startup requires. You cannot go on and on about reaching product perfection before going into the market (16).

That’s why there is the concept of Minimum Viable Product. The key idea is getting the core features together and making the product unique enough and final deployment. Entrepreneurs need to remember that perfection is unattainable.

All we need is to pivot on learning and staying focused on things we already know and things we are going to learn. Then, we can start aiming for perfection to reach excellence.

Another point worth highlighting is that the one who wants to fight first needs to count the cost.

Armies need food, arms, and clothes. When they move, there is a further increase in cost. According to Sun Tzu in The Art of War, a good general knows very well about the extremely high war cost. And, the better general knows when to march the troops and when to keep them in barracks.

Not all leaders have this intelligence, similar to how not everyone can lead a startup.

A startup needs an astute grasp of one’s surroundings, endless days and nights, and a loss of life balance. If one’s heart is empty, the head doesn’t matter as not everyone can pay such a steep price that being an entrepreneur demands (17).

If someone doubts whether they are cut for it or not, it would be wise to stay away from it.

Timeless Reflection

The Chinese military exposition from back in the 6th century continues to hold meaning in modern times. There are multiple translations of the book, each exploring critical topics that have relevance and application across the business, legal, management, and other competitive domains.

There are detailed assessments and planning that show us the elements and factors that can determine our activities’ outcome while stressing the importance of sufficient consideration (18).

The work of Master Sun offers entrepreneurs and innovators several valuable considerations. As an entrepreneur, The Art of War teaches you to create, develop, and grow your business with a selfless collaborative mentality with your customers and company.

While success may include occasional failures, innovating, and not getting the desired target, it may not always mean the approach was a failure, especially when you learn to improve your success chances with the next initiative.

Sun Tzu also advises that it is wise to join hands with allies in a country where there is an intersection of high roads. There is no point in lingering in a dangerous and isolated position.

It means that as an entrepreneur, you should be open to form strong alliances with other startups and trade services to help each other grow.

One of the classic examples is the startup incubator Y Combinator’s startup portfolio. Y Combinator has hundreds of companies, including Dropbox, Heroku, and Snapjoy. The alumni often use each other’s services to advance their customer base and everyone’s growth rate (19).


The Art of War is not only about strategy but more about anti-strategy. His idea is that the impact of strategy and tactics is minimal compared to the impact of leadership, logistics, and discipline.

The profound wisdom is still true in a military concept and a common knowledge.

Businessmen like the concepts of Master Sun because they consider themselves as generals and soldiers of the economy and their competitors as enemies. Because in the end, it is all about decision making and getting all the essential information before making a decision.

Many people worry that they could fail to find the best way to act. At the same time, The Art of War is more about deciding whether taking action is a good idea or not in the first place.

Entrepreneurs can use the writings for real-life application via critical and objective thinking. Or use it as a catalyst to ponder on their conflicts and as an inspiration to find a solution (20).

The book says that ‘when you are strong, appear weak; and when weak, appear strong.’ While the book is talking about it in the military context, you can use it for anything.

For instance, suppose you are good at detecting a lie. It means that you are strong in your ability to avoid getting deceived. And here we apply Master Sun’s advice. For say, someone is dishonest with you, and you let them go and appear weak. It creates an advantage for you since the ‘enemy’ now thinks that he can deceive you again. Meanwhile, you build a strategy based on their new weakness that you now created for that certain someone or ‘enemy,’ their misapprehension of your strength.

In the End

There is no doubt that startup entrepreneurs have a lot to lose and a lot to gain if they play their cards right.

Every day of an entrepreneur is a battle against challenges to reach success.

It will make sense if they wish to learn anything and everything for the board room battlefield. Because it is small and every day learning that makes a big impact in the startup game.

The teachings of Master Sun are still relevant for startups who are facing fierce competition for market share, customers, and talent.

With these lessons in hand, entrepreneurs today can outsmart, overwhelm, and outmaneuver larger firms to capture market share and emerge as victories in their target market.

It is important to remember that whether it is a war or business, approaching any situation mindfully and tactically is necessary. Hopefully, this article has given you some idea of how the book can benefit you and your business.

Let’s take the challenge to be more mindful, pay attention to things that come our way, and put them in the perspective of whether the concept can be adapted to find our requirements. Our idea is that it will allow us to find value in places that we believe.