Fantasy Philosophy: Machiavelli vs. Kant?

Fantasy Philosophy: Machiavelli vs. Kant?

Machiavelli, in his book The Prince gives us several incendiary quotes that, one could argue, serve as a reference for modern-day entrepreneurs. Machiavelli’s philosophy epitomizes the struggles of a modern entrepreneur and serves as a guide for surviving that “dog-eat-dog” world.


“It is double pleasure to deceive the deceiver.“

Niccolo Machiavelli


In today’s world of competition, it’s frequently easy to ignore ethics and morals and focus instead on profit margins and bottom lines. Machiavelli serves as a guide for most politicians and some entrepreneurs as he gives them a way to bend the rules to fit their needs.


“The promise given was a necessity of the past: the word broken is a necessity of the present.”

Niccolò Machiavelli


In Machiavelli’s world, morals, ethics, values, promises, are all relative – and all that matters is the victory at the end. But what exactly does that victory entail? Are money, fame, and power the real answer to our quests for our being? As you might have seen in my article on Plato’s Eudaimonia, one can have a fulfilled life if one focuses on reforming society through innovations. Nietzsche takes it to the next level and gives us a clear blueprint for overcoming societal pressures and vices to truly realize one’s inner potential. 


While Plato and Nietzche lay out the high-level framework as to how far we can go, it’s hard to apply these ideas to daily practice. Imagine an average startup entrepreneur, struggling to support his fledgling business, trying to get through his next payroll, or worse – possibly trying to avoid bankruptcy because of his mounting financial obligations. I wrote about “going all-in” a few years ago to explain my journey during the initial phases of my startup; I am sure many of us had similar horror stories involving predator loans, merchant credits, vulture investors, financial consultants, and legal advisors and how we kept looking for the easy way out, only to realize that these shortcuts lead us to worse situations. The last thing an entrepreneur wants to think about while fighting these fires is some idealistic vision laid out by Plato, Socrates, Nietzsche, or any other philosopher for that matter. In times of struggle, all that matters is to figure a way out of the current crisis. At least that’s how I felt when things were hard for me. 


While Machiavelli can claim to provide answers and justifications for breaking promises, being facetious and even being directly unethical at times to win at any cost does not fit my moral compass. In my personal opinion these measures might bring short-term wealth, but do not bring long-term fulfillment. 


What’s the best way to solve this? Let’s apply cartesian skepticism to look at the solution from a different perspective. 


I want to introduce Immanuel Kant, a Prussian German Philosopher from the Age of Enlightenment. Immanuel Kant is one of my favorite philosophers, as he provides a simple blueprint for decision making in his Categorical Imperative doctrine, and I have applied it in several sticky situations with great success over the years.


From Wikipedia –


A categorical imperative denotes an absolute, unconditional requirement that must be obeyed in all circumstances and is justified as an end in itself. It is best known in its first formulation:


“Act only according to that maxim whereby you can at the same time will that it should become a universal law.”

— Immanuel Kant, Grounding for the Metaphysics of Morals


According to Kant, we cannot operate on moral relativism, applying morals where convenient, and ignoring them when they are not. According to his reasoning, we first have a perfect duty not to act by maxims that result in logical contradictions when we attempt to universalize them. 


Kant believed in the concept of perfect duties – in general, precise responsibilities are those that are blameworthy if not met, as they are an essential required duty for a human being.


“Act in such a way that you treat humanity, whether in your own person or in the person of any other, never merely as a means to an end, but always at the same time as an end.”

— Immanuel Kant, Grounding for the Metaphysics of Morals


Simply put,this maxim tells us that we should not consider fellow humans as some “means to an end” – in other words, we should not try to manipulate a fellow human being so that he can return a favor, or help us with a need. We should treat all humans with respect, and assume that they are autonomous and independent, and that their decisions oftentimes have no dependency on our actions.


“Thus the third practical principle follows [from the first two] as the ultimate condition of their harmony with practical reason: the idea of the will of every rational being as a universally legislating will.”

— Immanuel Kant, Grounding for the Metaphysics of Morals


The third formulation says that if everyone follows the first two formulations, there will be no need for laws and regulations. Humans will be able to reach a state of “self-legislation,” where each human will be able to make the right decision by following the first two formulations. 


In business terms, this is the definition of the free market, or at least the utopian vision behind it. If each business works ethically, to win the business of customers, there will be no need for a regulatory body to enforce rules and regulations on these businesses. 


“Act according to maxims of a universally legislating member of a merely possible kingdom of ends.”

— Immanuel Kant, Grounding for the Metaphysics of Morals


The fourth formulation describes a utopian world where each person is autonomous and working on these categorical imperatives, and ultimately making the world a better place (kingdom of ends). Imagine a world where every human acts in full awareness and adherence to their consciousness, acting in adherence to the first two formulations. Such a world would expect every human to be self-legislative, and this universe would not need any laws for social order. In this utopian world, every human being can be trusted completely to make the right decision at all times.


Business and Philosophy


The more I read Kant and Machiavelli and their perspectives on virtues, morals, and ethics, the more I wondered if any of these ideas are relevant to the world we live in. In the current climate, being called a “cut-throat” CEO is  considered a great compliment for an entrepreneur, “shark” investor is a praise for a new banker, and being called a “vulture” is considered a good thing for a financial firm. Is this “dog-eat-dog” world ready for anyone other than Machiavelli? Frankly, Machiavelli seems like our true friend with quotes like these –


The fact is that a man who wants to act virtuously in every way necessarily comes to grief among so many who are not virtuous.

Niccolo Machiavelli


In the above quote, Machiavelli advises against acting virtuously, as most people in the world are not virtuous. However, by subscribing to the theory that some people in the world are not virtuous, some give themselves an excuse to break their own moral or ethical code of behavior. 


I considered the ruthless world we live in, and how philosophy could be of any use in the challenges faced by modern entrepreneurs on a day-to-day basis. Like any other experiment, philosophy is best tested by considering some use cases. 

Pet Walking


Imagine the following scenario – you are a pet owner, and you walk your puppy every morning and evening. You pick up after her every time, with the assumption that all other pet owners are doing the same, and you also know that it’s the “right thing to do.” What if one decides not to pick up after their pet, because some pet owners are not picking up after their pets? If you join the irresponsible pet owners, aren’t you making your neighborhood a worse place? In fact, if some pet owners forget to pick up after their pet, isn’t it the right thing to do to pick it up as well, just because?


In my pet walking example, applying the first formulation will look somewhat like this – “If I can make a universal law that no pet owner should pick up after their pet, I will stop picking up after my pet.” I am sure you will agree that such a law would be absurd – not to mention, our lawns would become unbearable as the result of such a law. 


Applying Kant’s second formulation – “Pick up after a neighbor’s pet without any assumption that the neighbor will return your favor. Do this because this is the right thing to do.”


Applying Kant’s third formulation – “If all responsible pet owners follow the first formulation and pick up after their pet, and also pick up when an owner forgets without any expectation – all our gardens will be perfect!”



Applying Kant’s fourth formulation – “If all responsible pet owners follow the first formulation and pick up after their pet, and also pic kup when an owner forgets without any expectation, there will be no need for laws, regulations, fines, and tribulations to manage this pet waste problem.”


As far irresponsible pet owners are concerned, they might get some satisfaction from letting others take care of their basic responsibilities, but I am hopeful that they might feel guilty eventually, and decide to do the right thing. If they don’t have this basic level of conscience,  their small violations often lead to bigger crimes and ultimately catch up to them. 


If we can trust humans to be “self-legislating” with pet walking, then we should be able to trust humans in general on other matters as well. For the most part, humans don’t need laws – most of us wake up, get dressed, show up to work on time, take care of our families responsibly, and perform our duties as responsible citizens without the threat of punishment from the authorities. All of this comes from our internal core value system, and Kant believes that if we can strengthen that core with clear, non-negotiable guidelines (categorical imperatives), we can solve more complex problems as well.


Competitive Bidding 


Imagine being in a competitive bidding war with another firm, but this other firm has always been unethical with their practices and quotes. One of your staff members advises you to be dishonest and provide a stronger bid in order to help you win the business. The reasoning?  One can only defeat deceit with deceit.


Now let’s revisit the use-case of a bidding war with your unethical competitor, and see if the first formulation helps us. As always, you have two options:



  • Machiavelli’s approach: Submit a dishonest proposal, and stay in the race. Promises are meant to be broken, remember?
  • Categorical Imperative: Stay true to your values, and probably lose the submission to the unethical competitor.



In our example laid out above, if we adopt “It’s OK to be dishonest on a proposal to win against another dishonest bid,” as our maxim, we should be willing to take this as the universal law, and this implies that everyone should be able to cheat on their proposals. This eventually makes the bidding process useless and will make our dishonesty frivolous. 


Loan in Crisis


The company is in a cash crunch because of a terrible year of losses. It would help if the company did whatever it could to survive. One of the ways the CEO could alleviate the problem would be by breaking promises to lenders, customers, and possibly employees.


For this use-case the second formulation helps us. As always, you have two options:



  • Machiavelli’s approach: Pursue your plans to become a wealthy person’s friend, to manipulate this person and extract a personal loan at all costs.
  • Categorical Imperative: Decide to come clean and not pursue this plan, at the expense of failing your business.


In the example above, if we follow Kant’s second axiom, we need to ignore the path that justifies deceit to solicit funds. However, once we decide that such a shortcut is no longer an option,we might think more clearly about following the right course of action, even if that means accepting failure in your business. Or there might be a more viable option, where you explain the perilous state of your business with complete honesty to this wealthy contact,  provide him full details as to the risks involved, and allow him to make the decision. In my interactions with investors, friends, and associates, I have learned that providing the full picture might make you look vulnerable at times. However, being honest, even though it’s inconvenient to do so, allows you to treat your fellow human beings with the respect they most deserve.




Over the years, I am sure I have made some errors in my personal and business life. I can take stock of a few times I might have resorted to Machiavellian tactics at times. In those situations, I am pretty sure I ended up disappointed as a result. I never understood the cause of my disappointment instead of happiness, even when things worked. Thanks to my cartesian skepticism, I came across Kant’s categorical imperative. Kant’s doctrine gave me an unambiguous framework to make the right decisions, even in the most perilous of circumstances. 


Let’s look at our use-cases and ponder the alternative of using Machiavellian tactics instead of Categorical Imperatives.


If one wins an award by making misleading statements, this person would live in fear that the customer might figure out his/her dishonesty eventually. Or even if the customer continues to trust them, he/she might end up failing on the project, as they were not a good fit to begin with. 


Machiavelli’s prompt to “break a promise” might sound simple when the entrepreneur is in a bind. However, such breaches of trust can have a long-term impact on employee morale or put strains on your personal and business relations. More importantly, employees can decide to follow the entrepreneur’s lead and break their promises to the company when the company needs them most. 


If one takes Machiavelli’s approach for deceiving a wealthy associate and taking loans from this person under false pretenses, this person’s subconscious might run into similar problems as he/she broke their morals and ethics and manipulated a fellow human being for his/her selfish ends.


I guess the above assertions about guilt might not apply for a person with no conscience. Machiavelli may speak to those people, lucky ones. However, I am a proud Kantian, and I will be satisfied with a life of minimal wealth, but opulent conscience – not the other way round.

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