Ethical Review of Social Sciences

Durham & Thunmann, 2025. Published under a Creative Commons Attribution 4.0 International (CC BY 4.0) license.

https://doi.org/10.70150/2654b605.

THE MACHIAVELLIAN CHALLENGE TO BUSINESS ETHICS

GEORGE BRAGUES*

Abstract:

No political philosopher is better known in the business world than

Niccolo Machiavelli. His fame resting on The Prince, the

Renaissance Italian writer has often been featured in the popular

business press, mostly to show the relevance of his realpolitik

world-view to the sorts of issues that a contemporary manager is

apt to face. However, the popular view of Machiavelli as a hard-

headed thinker has been challenged by scholars pointing to his

advocacy of republics in the Discourses on Livy, his other great

work. Interpreted along these lines, Machiavelli can be invoked to

support participatory structures in business along with the

cultivation of publicly spirited virtues. We argue that the common

perceptions of Machiavelli are actually on a better track. His

analysis of republics uncovers weaknesses germane to business

that render The Prince more suitable to commercial life. As such,

Machiavelli’s overriding point is that in a competitive arena, such

as that of modern-day business, individuals holding leadership

positions, or aspiring to them, must be prepared to go beyond

conventional morality and live by a different and, indeed, icy set of

rules. Being good in business, Machiavelli warns, will only lead to

personal ruin.

Machiavelli goes further than this, calling for a trans-valuation of

values, wherein the praiseworthy quality of leaders are redefined

so as to take into account the competitive realities of business. In

this new ethic, virtue is connected to acquisitiveness, moral

flexibility, image management, and reaches its culmination in the

entrepreneurial task of founding a great company.

Keywords: Machiavelli, Leadership, Virtue, Vice, Image

Management, Entrepreneurship

JEL Codes: A12, A13, B10, B31, M00, M10, M12, M13, M14

Introduction

To the extent that businesspersons currently look to

philosophers at all for guidance on their affairs, none

is regarded more highly than Niccolo Machiavelli.

Conduct an online search for books on Machiavelli

and business and one will find numerous books with

the Italian thinker’s name cited in the title, ranging

from general handbooks like Machiavelli on

Leadership: Why Machiavelli’s Rules are as Timely

and Important Today as Five Centuries Ago (Ledeen,

1999), Machiavelli on Management: Playing and

Winning the Corporate Power Game (Griffin, 1991)

to works geared to more specific audiences, whether

marketers, Machiavelli, Marketing and Management

(Harris, 2000) or women, The Princessa: Machiavelli

for Women (Ruben, 1988) and Machiavelli for Women

(Smith, 2022). While at times, as in What Would

Machiavelli Do: The Ends Justify the Meanness

(Bing, 2002), the reader is presented with the

caricature of Machiavelli as an unabashed amoralist,

the popular business literature does not revive the

initial estimation of the Renaissance Italian thinker,

which prevailed for centuries after his death, that saw

him as a teacher of evil. Indeed, Alistair McAlpine

somehow manages to infer the point that, “a leader

must be trustworthy” (1998, p. 3), that he or she must

be “unscrupulously fair” (ibid.), and “always resist the

temptation to exchange old friends for new, no matter

how attractive these friendships may appear” (p. 4).

Still, as corroborated in an analysis of Machiavellian

business manuals (Galie & Bopst, 2006), the advice

offered tends to echo widespread understandings of

Machiavellianism – that is, as a philosophy that

checks idealist impulses by recognizing the

competitiveness of human existence and enjoining the

necessity of morally questionable tactics in the pursuit

of one’s goals. This conception of Machiavelli’s

thought is also common in the scholarly literature, as

described by Maity et al (2023) through a bibliometric

analysis of existing studies. Nowhere in Machiavelli’s

corpus is the reader more susceptible to being morally

startled than The Prince (1985), a how-to guide for

rulers published posthumously in 1532. It is the work

that is typically referenced whenever the attempt is

made to apply Machiavelli to business.

Machiavelli did, however, write other books. These

include The Art of War, History of Florence, and even

poetry and plays, the most recognized of these being

the comedy Mandragola. Beyond The Prince, his

most important political work is the Discourses on the

First Ten Books of Titius Livius (henceforth, referred

Associate Vice-Provost, University of Guelph-

Humber, Toronto, Canada.

george.bragues@guelphhumber.ca.

to as the Discourses), in which Machiavelli uses the

ancient historian’s account of Rome’s development as

the background for his own analysis of republican

government. Reading these books, particularly the

Discourses (1970), one meets with a different

Machiavelli than that conveyed in The Prince,

someone more animated by public spiritedness and

moral seriousness. Indeed, the forcefulness of this

figure in the over-all frame of his corpus is such that

it has become fashionable among scholars in the

history of ideas and political philosophy to view

Machiavelli as a champion of classical republican

ideals of liberty, participatory democracy, and

devotion to the common good, the latter exemplified

in the individual practice of the civic virtues (Pocock,

1975; Skinner, 2000). In this interpretation,

Machiavelli is situated within a tradition that goes

back to Aristotle and Cicero and forward to James

Harrington, Robert Sidney, and the civic humanism

that allegedly informed the American founding. This

view has arguably supplanted an earlier opinion, one

which had served to overthrow the old-fashioned

conception of Machiavelli as advocating vice, that

depicted him as foreshadowing Max Weber’s

conception of social science as a value free analyst of

the means necessary to achieve the ends politicians

happen to choose (Olschki, 1945).

Modern-day

proponents of Machiavelli’s significance to commerce

could theoretically invoke this approach by

substituting the ends of businesspersons for those of

politicians. Still, their recommendations would still be

compelled to acknowledge the moral dubiety of the

means that Machiavelli proposes. By contrast, anyone

holding to the now more favored republican view

would face a challenge in making Machiavelli

relevant to business. Thus, it has been argued that his

thought cannot properly be applied to business where

the predominant motives of pecuniary self-interest

necessarily collide with the self-denying imperatives

of republicanism (Ramsey, 2000, p. 159). Others

sympathetic to the republican interpretation of

Machiavelli insist that any application of his thought

to business must take into account his condemnation

of the corrupt mores that plagued the governance of

Renaissance Italy, which would translate today into a

concern with corporate corruption (Galie & Bopst,

2006; Cousins & Reina, 2016).

Is the latest academic current on the mark or do the

Machiavellian business primers do a better job of

gauging the Italian thinker? Unsophisticated as the

latter often are, the popular literature at least has the

virtue of faintly grasping that Machiavelli is up to

something dodgy that fundamentally defies the norms

of traditional morality. Nothing about Machiavelli’s

republican leanings rules this out, as I shall argue

For an overview of the many interpretations that have been offered

of Machiavelli, see Berlin (1972)

below. My contention is that the analysis of republics

in the Discourses underlines the relevance of the hard-

headed counsel offered in The Prince to the running

of a business. What the leadership gurus, however, fail

to perceive is that Machiavelli is not merely insisting

that a competitive arena like business demands that

those in leadership positions, as well as those aspiring

to them, be prepared to transcend orthodox moral

dictates and operate by a more icy set of rules. I

maintain that Machiavelli’s purpose is much grander

– his thought points to a trans-valuation of values,

wherein the virtues and vices of leaders are redefined

so as to take into account the competitive realities of

business. This new value system -- amenable to the

ambitious in business but antithetical to the socially

conscious mindset encouraged in contemporary

business ethics -- comes down to the following advice:

Adopt a general strategy of doing good, as

conventionally defined, combined with a willingness

to depart from that course whenever necessity and

interest requires it, while making sure to rationalize

these deviations to onlookers by framing one’s actions

within a compelling narrative.

1. Republics Vs. Principalities

The Prince begins with the assertion that all

governments have either been republics or

principalities. For us living in the 21

century,

accustomed to differentiating between democracies

and authoritarian regimes of one kind or another,

Machiavelli’s dichotomy does not strike us as

unusual. But to someone in his time, it would have

appeared odd because the time-honored typology,

going back to Aristotle’s (1984) The Politics,

organized regimes into three kinds – to wit,

monarchies in which authority was exercised by one

individual, aristocracies in which the few ruled, and

democracies where the many held sway (1279a22-

1279b10). In cases which the ruling element pursued

its own interests rather than the common good,

monarchy was understood to have turned into a

tyrannical regime, aristocracies became oligarchies,

and democracies transformed into anarchic mob-rule.

In the Discourses, Machiavelli acknowledges this

categorization, but he insinuates that the gulf between

the good and bad trio is significantly less than his

philosophic predecessors recognized (D.i.2, pp. 106-

109).

His reasoning is as follows: history shows that the

first governments were led by single individuals.

Though originally selected for their wisdom and

justice, these monarchs eventually gave way to

hereditary governments. Presumably, this was

Henceforth, references to the Discourses will be designated by the

letter, “D”, followed by the book and chapter headings, and then the page

numbers specific to the translation selected.

because rulers naturally favored their offspring and

because it rendered more certain who would be the

successor, thereby reducing destabilizing power

struggles upon the death of the leader. But among the

heirs of a monarch, there would invariably be those

that lacked the skills and integrity of the founding

sovereign. As these lower calibre successors would

abuse their power to indulge their every whim, the

elite classes were prompted to stir up and join forces

with the populace in bringing down the tyrannical

order. Consequently, the elites were seen as liberators

and the general public assented to be ruled by them.

This gave rise to aristocracies that initially promoted

the public interest, with memories still fresh of the

oppression suffered during the period of one-person

rule. As time passed, however, and the proceeding

generations took helm of the aristocracy, this ruling

group also succumbed to greed and overweening

ambition. Not having had any direct experience of the

damage caused when leaders put their own interests

above those of the community, they became oligarchs

and went about exploiting the common people. The

populace, in turn, rebelled against the oligarchs and set

up a democracy which, again, served to promote the

common good while the generation that created it was

still alive. Yet once that generation passed, the

democratic regime degenerated into individual licence

and widespread disrespect for authority. The chaos

and lawlessness that ensued drove people to look to a

single individual to restore order and stability. In this

way, we are brought back full circle to a monarchy and

the cycle starts again and continues ad infinitum,

unless something beyond the three basic frameworks

can be established. From Machiavelli’s standpoint,

therefore, the empirical record indicates that sticking

to the Aristotelian typology would pose a mental block

to the design of lasting forms of governance.

Machiavelli espies his alternative scheme in the

historical experiences of Sparta and Rome. If the

former did it by design of its legendary founder,

Lycurgus, and the latter achieved it through an

evolutionary process, both republics wisely mixed

elements of all three of Aristotle’s regimes (D.i.2, pp.

109-111). Sparta reflected monarchy with its two

kings, the aristocracy through its Senate, the

Gerousia, and democracy via its ephors. Likewise,

Rome had its dual consuls as its component of

monarchy, the Senate as its aristocracy, and the

Tribune of the Plebeians as its democracy. By having

all three in the same political order, the excesses of

each were checked and balanced, precluding any of

the sectional interests these embodied from

dominating the laws and policies of the state, and

forcing them to accommodate their legitimate

concerns. With no party capable of lording it over

anybody else, no one was ground down into an

oppressed status where they had little to lose by

subverting the entire political system. This is why,

Machiavelli claims, Sparta endured for over eight

centuries and Rome survived as a republic for

approximately 450 years.

A republic, then, is defined by Machiavelli as a

regime in which authority is shared amongst the

various constituencies in society. Its opposite is a

regime in which authority is not shared, but resides in

a single individual, namely, a principality. Despite

one-person rule being vulnerable to tyranny,

Machiavelli considered principalities an alternative

worthy of consideration because those had proven

capable of forming the basis of enduring order. If we

restate Machiavelli’s classification of regimes in

business terms, a principality would be equivalent to a

sole proprietorship or a corporation in which all the

significant decisions are made by the CEO – or more

precisely, an autocratic CEO. A republic would be

analogous to a partnership, assuming the various

partners are equally involved in decision-making. Or,

it could be equivalent to a corporation in which the

CEO (the monarch) depends on the counsel and

support of other top executives along with the heads

of functional or operating units (the aristocratic elite),

and the CEO is closely monitored by the Boards of

Directors along with the leading shareholders (also,

the aristocratic elite), with employees and ordinary

shareholders (the demos) also having some notable

influence on the firm’s affairs. This is not too far from

prevailing conceptions of good corporate governance

as well as the recommendations offered by advocates

of a more participatory culture within companies.

With respect to politics, there can be little doubt that

Machiavelli favors republics over principalities. The

most obvious sign of this is that a principality, being

dominated by the monarchical element, is not so

disposed to embody the checks and balances that

Machiavelli praises. He studied the Romans because

the ancients offered better political models than his

contemporaries, and what especially attracted him to

the past was the greater devotion to liberty then

displayed. It was no coincidence for Machiavelli that

the ancient world also contained more republics than

the contemporaneous political scene. “The study of

history reveals”, Machiavelli says, “the harm that

servitude has done to peoples and to cities” (D. ii. 2,

p. 274). Where individuals are deprived of liberty,

they have less incentive to marry and procreate,

dissuaded as they are by the prospect that their

children might be taken away from them and put into

slavery. Nor can they be so certain that their offspring

will have an opportunity to rise in social position.

Moreover, economic productivity is adversely

impacted by the absence of liberty, since people

cannot be sure of keeping the fruits of their labor and

investment – which, by the way, goes against the

thesis cited above that Machiavelli saw commercial

self-interest as necessarily at odds with a well-

constituted republic (D.II.2, p. 280; Ramsey, 2000).

He explicitly concedes that principalities, as opposed

to republics, cannot maintain the people’s freedom

(D.i.6, p. 156).

His preference for republics also comes to light in a

revolutionary discussion comparing the political

judgment of princes to that of the public. Before

Machiavelli, political philosophers and historians

were generally sceptical of conferring political

authority on the populace because it was thought that

they are readily swayed by momentary and erratic

passions. The people, so it went, could not summon

the wisdom to manage political affairs properly. This

view is expressed in Plato’s The Republic, where the

ideal regime put forward is rule by a philosophic elite

(1968: 473c-e). Even the more democratic Aristotle

(1984) argued that the best order, in theory at least, is

one in which one or a few virtuous individuals govern

without hindrance (1284a3-11 & 1284b25-34). He

only settled for a mixed regime as a practical

compromise. Let us not forget either that Cicero’s

(1991) devotion to the Roman Republic was based on

the notion that the aristocratic part reflected in the

Senate ought to be predominant over the populace (pp.

78-79). Machiavelli contests this, first, by insisting

that the ancient thinkers put too much stress on the

matter of who is at the helm, rather than the

institutional constraints in which the ruling element is

required to operate. Where institutions buttress the

rule of law, princes and the people are equally

salutary, in that both are constrained from acting

chaotically on their emotional biases (D.i.58, pp. 252-

254).

Indeed, when both are unshackled from the rule of

law, principalities are the more dangerous regime. A

raucous populace can be calmed by a judicious person,

but a vicious prince must be dealt with by eliminating

them from power. And when both the prince and

people are free to wreak havoc, the latter at least have

a better intention: “The brutalities of the masses are

directed against those whom they suspect of

conspiring against the common good; the brutalities of

a prince against those whom he suspects of conspiring

against his own good” (D.i.58, p. 257). In the case

where both are bound by laws, the people again

emerge as the superior option, for they are actually

wiser than princes in making better predictions about

the outcomes of alternative policies. “Not without

good reason is the voice of the populace likened to that

of God” (D.i.58, p. 255). In a debate, Machiavelli

remarks, the public almost always sides with the

sounder position and, in elections, it generally selects

the best candidates. By Machiavelli’s estimation,

there were only four elections that the Roman public

could legitimately regret the votes it cast over the four

and a half century period of the republic. As to why

the public is a more accurate prognosticator than a

single individual, Machiavelli unfortunately says too

little, though he does allude to the fact that a prince is

more apt to be biased by stronger passion. What he

means, one may surmise, is that the populace

assimilates a much wider diversity of emotions than

an individual, so that it is more difficult for a particular

feeling to dominate in skewing a judgement. In this

way, Machiavelli can be said to have foreshadowed

the wisdom of crowds thesis (Surowiecki, 2004).

Beyond that, however, the Machiavellian brief for

republicanism is of limited applicability to business.

The liberty which republics foster may indeed be

conducive to population growth, but the main

beneficiary of that is the political community, whether

by increasing the pool from which to draw an army for

self-defence, augmenting productive factors, or

assuring there are enough young people to finance a

publicly funded old-age pension scheme. It is less

clear how much a firm gains from encouraging its

employees to raise children, for while family

responsibilities might spur individuals to work harder

and more conscientiously, they also could draw

loyalty away from the company. Though a free society

certainly helps businesses prosper, the ideal of liberty

poses a tension to the way firms are internally

organized as hierarchies in which people agree to take

direction from others (Coase, 1937).

More significantly, Machiavelli argues that one-

person rule works best when an existing government

needs to be fundamentally reformed or when a new

regime is being founded. The business parallel to this

would involve an autocrat-CEO in corporate

turnaround situations or during the early, more

entrepreneurial, stages of a company’s development.

Machiavelli’s reasoning here is that any organization

will have narrow interests benefiting from the status

quo who cannot be persuaded to acquiesce to change

on any reasonable terms. Such interests can only be

overcome by a resolute individual willing to use

coercive measures. In this connection, Machiavelli

praises Cleomenes for successfully reforming Sparta

by first killing all the ephors and everyone else who

stood in his way (D.i.9, pp. 133-134). Since firms are

accountable to the laws of a larger community,

Machiavelli would obviously not advise a

restructuring CEO to commit murder, though he

would recommend that those inextricably tied to the

old order be somehow made to leave. Start-ups also

face vested interests, that is, the existing firms whose

business will be negatively impacted should the new

enterprise flourish. Were this formidable opposition to

be managed by a sizable group in which every aspect

of strategy had to be discussed, the inevitable

differences in opinion would hinder agreement (D.i.9,

p.132). A single entrepreneurial CEO can act more

decisively.

The possibility is left that Machiavelli’s

republicanism still serves as a model for healthy and

established companies. Favoring this is Machiavelli’s

claim that republics are more conducive to expansion

than principalities (D.ii.2, p. 275). By having a greater

say in the community’s affairs, the public more

eagerly assumes the sacrifices involved in enlarging

the state’s boundaries. Similarly, in business, if a

corporation wants to increase market share, enter new

markets, and introduce new products, it needs the

support of middle-managers, employees, and ordinary

shareholders. They are all more apt to “buy in” to the

company’s growth plans if outlets are available to

express their voices. That said, one must still wrestle

with Machiavelli’s contention that republics should

imitate Rome in making provisions allowing for the

appointment of a dictator for a limited term.

Machiavelli extols this practice: “of Rome’s various

institutions this is one that deserves to be considered

and ranked among those to which the greatness of

Rome’s vast empire was due” (D.i.34, p. 195). What

made dictatorship so necessary was that the Roman

Republic’s growing influence in Italy caught the

attention of neighbouring governments and led them

to join forces against it. In other words, dictatorship

helped Rome manage the challenge of heightened

political competition.

Do Machiavellian principles equally mandate the

practice of dictatorship for companies dealing with

economic competition? Nobody can doubt that

competition between states can impact a larger

amount of people and descend into violence in a way

that intra-firm rivalry does not. Still, though not giving

rise to wars and tectonic shifts in geopolitics, the

casualty rate for companies engaged in market

competition is notably higher than it is for states

enmeshed in international conflict. Not a single

company remains as a component of the Dow Jones

Industrial Average from the beginnings of that index

in 1896, with General Electric being the last original

member until it was dropped in 2018 (Phillips, 2018).

Looking back to the Fortune 500 list in 1955, only

fifty-one companies, about 10% of the original group,

were still in the 2020 rankings (Perry, 2020).

Meanwhile, among the leading states in 1955, only the

Soviet Union has disappeared, while Germany has

returned to its pre-World War II boundaries.

Considering that states have a coercive apparatus at

their disposal to ensure the allegiance of its citizens,

whereas companies are limited to persuading

customers to support its products and services, the

relative permanence of governmental institutions is

understandable. Yet if the political arena was

sufficiently competitive for Machiavelli to advocate

provisional dictatorships, the more precarious rivalry

witnessed in the economic realm makes it all the more

necessary to accept an autocratic office in the running

of companies. As Machiavelli points out, such an

office is compatible with a republican structure, so

long as the autocrat is selected by representative

bodies for a limited term and a specific purpose

(D.i.34, pp. 194-195). Are these not the terms of

modern-day CEO’s? Do they not essentially assume a

temporary dictatorship over the firm for the purposes

From here forward, citations from The Prince will be designated by

the letter “P”, then the chapter, followed by the page number specific to

the translation used.

of maximizing shareholder value, doing so by

appointment of the Board of Directors acting for the

shareholders?

2. Virtú and Acquisitiveness

Thus we are brought back to The Prince, where the

popular business literature on Machiavelli has focused

all along. More so in a new venture, but still

significantly so with established companies operating

in a competitive space, a princely authority must take

command. How an individual acquires and maintains

this power is the overriding theme of the first half of

The Prince. It turns out, however, that the individual

who masters this subject is not simply the possessor of

a valuable method, skill set, or technique, the optimal

use of which poses moral questions. In Machiavellli’s

eyes, the maestro of power is nothing less than the

pinnacle of virtue. This stunning claim becomes

evident in following Machiavelli’s use of the word,

“virtú”, Italian for virtue, a word for which translators

have usually substituted, “skill”, or “ability”, and

sometimes, “courage”, “valor”, “strength of purpose”,

or “manliness”. While the last four are somewhat

more positively evaluative than the first two, they still

fall short of what the term “virtue” would designate,

insofar as ordinary conversation occasionally

associates them with morally despicable characters, as

when someone notes that Osama Bin Laden had

strength of purpose or insists that terrorists display

courage. The reason, one suspects, that virtú has

almost always not been consistently rendered into its

English equivalent, virtue – Mansfield’s (1985)

translation being the exception – is that the

implications of doing so are so morally startling.

In the broadest sense, as Machiavelli outlines, a

person can obtain sole authority either by inheriting it

or without the advantage of family connections.

Clearly, the first instance, what Machiavelli calls a

hereditary principality, is what takes place in family

businesses, which to this day still make up a

significant proportion of the world’s firms (EY

Global, 2023; Conway Centre, 2024). Machiavelli

observes that maintaining power in hereditary

situations is relatively simple because those serving

under the new head are accustomed to the family’s

authority (P.ii, pp. 6-7).

All this individual needs to

succeed is a modicum of talent and a willingness to

uphold the company’s traditions. Not having much in

the way of opposition to deal with, the newly minted

boss is not forced to upset anyone. The assumption of

a family business thus poses few moral dilemmas. At

the same time, with Machiavelli making no reference

to virtue at this stage of his analysis, it is apparently

not a role either by which one can express any

estimable traits.

It must be admitted that Machiavelli’s reflections

run counter to the well-known fact that family-run

enterprises have an unusually high casualty rate once

the founder has left the scene. Only about 30-40% of

US family-owned businesses survive through the next

generation, and just 10-15% make it to the third

(Beckhard and Dyer, 1983; Applegate, 1994 as cited

in Finch, 2005; Smith Family, 2024). In Machiavelli’s

defence, this might be the consequence of heirs failing

to heed his advice to retain the traditional modes of

operating and being liable instead of implementing

sweeping change in order to put their imprint on the

operation (Miller, Steier, & Le Breton-Miller, 2003,

pp. 521-523). But it might also reflect the

obsolescence of the old ways, the necessity of greater

than average skill at the top of a business, in addition

to the vulnerability of a family business to poor

succession planning and conflict between kin about

strategy. Far from being a calm moral sea, these

battles can render family businesses into ethical

minefields. Successfully navigating these will also

demand more than ordinary virtues, contrary to what

Machiavelli suggests.

Of non-hereditary principalities, Machiavelli

distinguishes four types: mixed, civil, new, and

wholly new. Where someone is already prince, but

then adds to their power by conquering another

already existing state, we have what Machiavelli calls

a mixed principality (P.iii, pp. 7-16). The business

equivalent here is obvious: a take-over. Especially

since the merger and acquisitions wave of the late

1980’s, and continuing more recently with the

ascendance of private equity, take-overs have come

under an ethical cloud because of the painful

restructuring that acquirers typically undertake,

shedding the targets’ underperforming operations,

eliminating jobs, in the process harming the local

community (Di Norcia, 1988; Morgenson & Rosner,

2023). Always the realist, Machiavelli is well-aware

that some will have to be hurt for, “it is a natural and

ordinary necessity … that one must always offend

those over whom he becomes a new prince” (P.iii, p.

8). Addressing himself entirely to the self-interest of

princes, Machiavelli counsels them not to hesitate

whatsoever in eliminating anyone standing in the way

of transforming their new possession into a viable

entity.

Machiavelli’s discussion highlights another oft-

cited problem with mergers and acquisitions, namely

that the synergies aimed at often go unrealized

because of a cultural clash between the two firms

(Buono, Bowditch, & Lewis, 1985; Weber &

Camerer, 2003; Goksoy, 2019). Machiavelli alludes to

this in noting that a prince’s difficulties with a new

territory are always greater to the extent one confronts

different customs and language (P.iii, pp. 9-11). Not

surprisingly, he does not even remotely touch the idea

that this cultural divergence is best managed by

promoting dialogue between members of the two

original entities in the hopes of removing invidious

stereotypes, identifying common ground, and

generating mutual respect for outstanding differences.

Implied instead are two more hard-nosed approaches,

with either the CEO maintaining a regular presence at

the headquarters of the acquired company or setting

up a corporate version of a colony. Where the CEO is

onsite regularly, any disruptive activity can be dealt

with quickly, rather than festering to the point where

one can only temporize with it. If staff members want

to enter into the CEO’s good graces, they will

appreciate having easy access to see him or her; and if

they are not inclined to ingratiate the CEO, there will

be greater cause for fear, precisely because the boss is

within striking distance. The flaw in this method,

though, is that the CEO runs the risk of neglecting

matters at the home base. Aware of how this dilemma

can manifest itself in the political area, Machiavelli

prefers the colonization strategy. In the business

realm, this can be accomplished by the CEO

substituting a number of key people from the previous

management team with a group loyal to one’s self.

While those displaced surely suffer, their numbers are

relatively small and, with their no longer being on the

scene, they cannot readily join forces against the CEO.

Meanwhile, the people that were not forced out of the

company will be glad to still have a position and will

tread carefully lest the same fate that befell their old

colleagues strikes them. Cultivating fear is the

Machiavellian way to manage integration risk. It is

also the way leading to virtue, for it is in the chapter

on mixed principalities that the word virtú first makes

it appearance in a descriptive context. Thus, the

Romans are praised for their virtú, in part for their use

of the colonization tactic to assimilate alien territories

into its empire (P.iii, pp. 11-13).

From hereditary and mixed principalities,

Machiavelli turns his attention to new principalities.

Here, rather than appending the new to the old, an

outsider takes control of an established principality.

This is what happens, say, when a new CEO is brought

in to run Bank of America but comes from Goldman

Sachs. According to Machiavelli, the incoming leader

will either face a situation in which individuals are

accustomed to having freedom or lacking it. Again, to

apply this to the world of commerce, the new CEO

might be heading to a firm where power was

previously decentralized, the organizational structure

was relatively flat, and employees were not closely

monitored and instead given latitude to follow their

own paths. On the contrary, the incoming CEO can be

walking into a situation where power had been highly

centralized, a hierarchical order-taking environment

prevailed, and employees were tightly supervised and

expected to meet stringent performance standards. A

company with staff habituated to an autocratic style of

management will, Machiavelli suggests, present little

opposition to a newly appointed CEO (P.v, pp. 20-21).

The latter merely need to remove anyone closely

associated with the former CEO so that employees

will not have someone else to rally around.

The difficulties are far greater if the workforce is

used to permissive and consultative managers. To

counter this, Machiavelli suggests the already cited

tack of making one’s presence felt in the company.

The princely CEO should not be aloof or allow

themselves to become isolated, and nor eagerly

delegate tasks to others. They ought to involve

themselves in every aspect of the business to signal

that nothing is done without their sanction. Another

option, Machiavelli states, is for the prince to allow

the people to direct themselves, co-opting a few of

them to forge a loyal governing elite, while ensuring a

tribute is paid. Translating this into business, a CEO

could proceed similarly by leaving the employees’

freedoms and prerogatives untouched, promoting

some ambitious individuals from outside the top rungs

of the organization, and then giving this fresh elite

profit targets to meet. Owing their position to the

CEO, their loyalty will be assured and, because they

come from within the company, their authority is more

likely to be accepted by their colleagues.

However, in further reflecting upon this relatively

benign approach, Machiavelli insists upon the greater

wisdom of destroying the free state: “whoever

becomes patron of a city used to living free and does

not destroy it, should expect to be destroyed by it; for

it always has as a refuge in rebellion the name of

liberty and its own ancient orders which are never

forgotten” (ibid.). The Spartans, Machiavelli

observes, tried setting up oligarchic elites when they

took over the republics of Athens and Thebes, but

failed. The virtuous Romans, by contrast, famously

destroyed Carthage and succeeded in holding it. One

shudders to think how this advice might be put into

business practice, but the reference to Carthage, razed

to the ground by the Roman General Scipio Africanus,

does not mean that a Machiavellian CEO has to wipe

out the company’s offices and facilities. The profit

imperative of business clearly rules out the destruction

of physical capital. It is the firm’s human capital with

which one must deal. With Machiavelli indicating that

a prince must assure, “the inhabitants are broken up or

disbursed” (P.v, p. 21) the CEO intent on following

the Italian thinker will have to literally “clean house”,

by firing the more dispensable employees, or,

particularly if they are essential to the operation,

reassigning them within a revamped organizational

structure so that old bonds and alliances are broken. In

this reorganization, the princely CEO would also be

well-advised to eradicate all vestiges of the old

participatory structures. The number of committees

must be pared down, their membership restricted, their

jurisdiction narrowed.

This anti-democratic counsel is reversed when

Machiavelli addresses civil principalities, understood

as a regime in which a citizen rises to become prince

of his own community (P. ix, pp. 38-42). In business,

this would correspond to the circumstance where the

incoming CEO is promoted from within the

organization. For Machiavelli, the overriding issue

here for the prince is whether they ought to found their

support upon the great or upon the people – stated in

business terms, whether to rely on the top executives,

large shareholders, the board of directors or,

alternatively, upon the rank and file employees and, if

it is a large publicly traded corporation, the many

small shareholders. Machiavelli recommends building

on the latter, since the popular element is easier to

satisfy. The elite are ambitious and are willing to take

advantage of employees, say by working them hard to

impress superiors, as well as ordinary shareholders by,

for example, arranging lavish pay packets. Ordinary

workers and shareholders merely desire not to be

exploited by the company’s elites. The ambitions of

the elites are hard to quench without creating hostility

in the rank and file, at which point one is unable to

count on the latter should adversity strike the

company. That, in turn, renders the CEO vulnerable to

the machinations of elites aiming to replace him. By

contrast, a CEO can readily gain the support of those

at the middle to lower rungs of the organizational chart

by preventing their exploitation. Should the CEO

inspire the employees and shareholders as well, both

productivity and the stock price will rise, leaving him

or her virtually impregnable. Indeed, the ideal way to

accomplish this, Machiavelli insinuates, is to initially

gain the leadership role with support of the elites (P.ix,

p. 40). Then, once one has assumed office, one shifts

allegiances to the popular element, which, having

expected the incoming CEO to ingratiate the upper

ranks, will be especially thankful that the new leader

is looking out for their interests. In this manner, the

CEO can harness the people’s energies to motor the

company’s growth, capturing a benefit of the

republican framework without actually having to be

constrained within it (D.i.16, p. 156).

Machiavelli’s examination of the various

principalities reaches its summit in Chapter VI of The

Prince. The subject is wholly new principalities, in

which it is not simply that the prince is new, but the

regime itself has only recently come into being. In

politics, this is the founding of a nation. In business, it

represents the start of a company. Nothing is more

daunting, Machiavelli says, than instituting new

modes and orders, for the founder has enemies in all

those that benefit from the status quo (P.vi, pp. 23-24).

The founders’ base of support is lukewarm at best, for

those standing to benefit from a regime change fear

the repercussions of resisting the old order. Then, too,

there is the innate conservatism of human beings to

overcome, that tendency to be sceptical of anything

beyond the range of one’s experience. Entrepreneurs

face similar challenges, having to deal with

competitors who would rather quash an upstart, rather

than let it grow to the point where it can seize

dominance of the marketplace. Banks and investors,

too, are wary of providing financing, as are friends and

family to which the budding entrepreneur often

resorts. To staff the new venture, one usually finds that

the most promising individuals already work at other

companies, from which one must woo them, while

assuaging their qualms of leaving behind a decent

position and potentially rupturing established business

relationships. Not only that, customers wonder how

the young company’s good or service fulfills a need

they never imagined or how it could possibly be better

than the competing firm to which they have long been

loyal.

Given the long odds, Machiavelli argues that the

success of founders cannot possibly be owing to

fortune or luck, except in being afforded an

opportunity. Their success must principally be due to

virtue. Accordingly, Machiavelli summons, “the

greatest examples”: Moses, Cyrus, Theseus, and

Romulus, respectively, the founders of Israel, Persia,

Athens, and Rome (P.vi, p. 22). Were we to come up

with an analogous list of great business founders, it

would have to include John D. Rockefeller, Henry

Ford, Sam Walton, Bill Gates, Steve Jobs, and Elon

Musk. Through their “excellent virtue” (P.vi, p. 23),

they not only serve as role models, but illuminate why

the more common forms of acquiring and maintaining

power lend themselves to the expression of human

excellence, even if a paler version of that manifest in

founding a new polity. In successfully integrating an

acquisition or improving the profitability of an old

sleepy firm, a CEO imitates part of the skill set

possessed by a legendary business founder. On the

Machiavellian view, the exalted virtue of this figure is

like a sun that shines on the performance of lesser

business leaders.

All this begs the question why founding is the font

of virtue, especially insofar as the lustre of that activity

is conceived as dignifying the numerous instances of

morally dubious power plays outlined thus far.

Machiavelli never systematically defends the

superiority of founding. His reasons are scattered

throughout his writings. To begin with, he notes that

seeking resources is natural to human beings. “And

truly it is a very natural and ordinary thing to desire to

acquire” (P. iii, p. 14). The founder takes this impulse

to extraordinary heights by giving birth to something

heretofore not seen. Machiavelli completes that last

quoted sentence as follows: “and always, when men

do it who can, they will be praised or not blamed; but

when they cannot, and want to do it anyway, here lie

the error and the blame” (P.iii, pp. 14-15).

Recognizing how acquisitiveness is ingrained in the

human psyche, public opinion will not begrudge a

person who builds a fortune and, indeed, will admire

them if they do so under difficult circumstances. But

public opinion, Machiavelli claims, is not so

forbearing when someone tries and fails. Every moral

lapse and character weakness is then highlighted,

while the similar failings of a successful acquirer are

overlooked– and even the illustrious class of founders,

Machiavelli implies, are impelled by the

precariousness of beginnings to cut moral corners (P.

xvii, p. 66). Like it or not, people judge things by the

outcome: “let a prince win and maintain his state: the

means will always be judged honorable, and will be

praised by everyone” (P.xvii, p. 71). To this,

Machiavelli adds that originators of religions and

states are in fact held in the highest esteem (D. i.10, p.

134). Though not put on the same pedestal, the

memory of those who erected great businesses is

preserved in our day. To be sure, all this assumes that

human opinion is the measure of virtue, instead of

God, nature, or reason. And Machiavelli does, in fact,

hold that morality is humanly constructed. He adopts

Polybius’ contention that justice arose at the origins of

societies when individuals perceived that it was

ultimately in their self-interest to promote norms of

reciprocity by praising those who adhered to them and

blaming those who violated them (D. i.2, p. 107). On

this understanding, human opinion does arguably

become the measure of virtue.

3. Revaluing the Virtues and Vices

Machiavelli may be right that public opinion looks

fondly, and gives the benefit of the moral doubt to,

individuals who have flourished in worldly affairs.

Even so, if we are to take our bearings by opinion as

Machiavelli does, it must also be acknowledged that

people admire qualities that do not necessarily go hand

in hand with the art of acquisition, such as generosity,

humanity, faithfulness, and honesty. Machiavelli well

knows that the commendation of these traits is implicit

in everyday ways of moral speaking. He realizes, too,

that philosophers -- St. Thomas More, for instance --

have envisioned utopias where such traits would

animate the social order. But Machiavelli thinks it

more appropriate to focus on what he calls, “the

effectual truth” (P. xv, p. 61) – namely, to what works

in practice, as opposed to what is merely imagined in

theoretical speculation. “And many have imagined

republics and principalities that have never been seen

or known to exist in truth; for it is so far from how one

lives to how one ought to live that he who lets go of

what is done for what should be done learns his ruin

rather than his preservation” (ibid) What

Machiavelli’s statement here connotes is that

businesspersons who orient their conduct around what

ought to be done – as all business ethicists prescribe –

are essentially opening themselves up to be suckers

and victims of the unprincipled people that abound in

the world. To the extent that the highest praises are

bestowed on founders, and flows downward to

common acquirers, it logically follows for

Machiavelli that no practically relevant teaching on

virtue can recommend a course of action that

ultimately leads to one’s downfall. Consequently,

Machiavelli counsels princes to be flexible in their

behaviour, respecting ordinary moral values when

circumstances permit, but transcending them when

interest requires it. This is Machiavellian virtú in a

nutshell. Virtú does not efface traditional virtue, but

preserves it (Mansfield, 1996, pp. 6-52). Still, in its

opposition to time-honored moral understandings,

virtú constitutes an attempt to bring about a

revaluation of values in which acquisitive human

personalities, like those seen in business, will cease to

feel alienated and guilty about taking the measures

needed to assure their success.

Spelling out what this means, Machiavelli first

redefines liberality, the virtue that concerns how a

person deals with money. It is hard to find a time and

a place in which grasping, penny pinchers have been

held in high regard and where generosity has not been

praised. No one, to be sure, is expected to be

extravagant to the point of depleting their own

resources. Nevertheless, it is commonly thought that

each should be ready to give in accord with their

means. Machiavelli, though, appeals to the prospect of

financial ruin to argue for stinginess (P. xvi, pp. 63-

65). Generosity only benefits a leader, he says, if it is

noticed. But as people are not necessarily going to

discern kindness if the bounty is small, generous

leaders must give lavishly in order to secure a good

reputation. Eventually, to finance this, they are forced

to deprive money from some of the people they

oversee in order to shower it on others. A CEO, for

instance, who donates large sums to local charities,

with a view to generating positive media coverage, is

subsequently compelled to reduce departmental

budgets and forgo the customary hike in the stock

dividend, with the result that shareholders and

employees grow to hate the CEO. If, on the other

hand, the CEO is parsimonious, fewer sacrifices will

be required, and, as time passes, he or she will come

to be seen as generous precisely for leaving people

alone. In the Machiavellian recasting, generosity is not

taking.

Machiavelli then shifts his discussion of the virtues

and vices of leaders to the distinction between mercy

and cruelty. Few things, particularly in our times,

shock the conscience more than cruelty; and few

things are more endearing than mercy. Machiavelli, by

contrast, asserts that the value of these depends on the

mode of their employment (P. xvii, pp. 65-68). Mercy

is badly used if it precludes decisive action to remedy

a situation that would otherwise dangerously

intensify. Indeed, for Machiavelli, the more merciful

tack is to carry out the harsh measures necessary to

prevent matters from worsening, since the cruelty will

be felt by few, whereas the cessation of the turmoil

will be enjoyed by many. Mercy is ill used, too, if it

renders one indulgent to the excesses of one’s

officials, as may happen when a CEO looks away as a

member of his or her executive team bullies other

staff. The CEO’s lieutenants are more effectively

utilized, Machiavelli astonishingly suggests, if they

are delegated the dirty work and then dispensed with

once they have served their purpose. In Machiavelli’s

most shocking illustration, he relates the story of

Remirro de Orco, who had been brought in by Cesare

Borgia to restore order and stability in Romagna (P.

vii, pp. 29-30). Sparing no brutality, de Orco quickly

accomplished his assigned task, making a reputation

for himself, though at the price of igniting hatred in

the public. Desiring that this ill-will not carry over to

him, and also that de Orco not outshine him, Borgia

hacked him into two pieces and left his body in a

public square with a bloody knife beside it. “The

ferocity of this spectacle left the people at once

satisfied and stupefied” (P.vii, p. 30).

Timing matters as well, according to Machiavelli.

Cruelty is best done all at once because the pain will

eventually be forgotten (P. vii, pp. 37-38). Stretching

it out in smaller doses, in the hopes that this will create

less heartache, actually fosters hatred because victims

are constantly reminded of who is behind their

suffering. The opposite tack is recommended for acts

of kindness. People granted significant benefits will

only be impressed by something bigger the next time,

whereas a series of smaller gifts delivered over time

can more easily be made to ascend in value to meet

expectations, in addition to continually reinforcing in

the beneficiary’s mind the goodness of the benefactor

(ibid.). What this might entail for business managers

can be readily imagined: give minor, regular raises to

employees and, whenever the economy slows down,

calculate all the labor cost reductions necessary to

make it through the downturn, and announce the

layoffs all at once.

It is mid-way through his analysis of cruelty and

mercy that Machiavelli issues his notorious answer to

the question whether it is better for a leader to be loved

or feared. He indicates that it would be ideal to be

both, but as circumstances usually force one to choose,

the optimal course is to be feared, rather than loved (P.

xvii, pp. 66-67). Love places followers beyond the

leaders’ control, while fear puts obedience in the

hands of the leader. This becomes obvious,

Machiavelli notes, when difficulties arise and

sacrifices are required. Having shown the leader

affection and promised to always stand at their side

when times are good, people will just as quickly

abandon him or her when the times turn rough. “For

one can say this generally of men: that they are

ungrateful, fickle, pretenders and dissemblers, evaders

of danger, eager for gain” (P.xvii, p. 67). Relying on

fear hinders this ugly side of human nature from

hurting the prince because the threat of pain makes it

in people’s interests to obey in every circumstance.

Now an argument could be made, as Cicero did

approximately 1,500 years before, that Machiavelli

underestimates the power of love to bond individuals

to leaders and spur people to rally around them in their

hour of need

. Cicero (1991) also pointed out that fear

is apt to spark hatred, the breeding ground for revolt

(p. 75). Machiavelli’s counter to this is that it is

possible to avoid hatred while being feared, so long as

one punishes people only with good reason, refrains

from using one’s authority for sexual purposes, and,

most importantly, one avoids seizing people’s

property. In other words, a corporate leader can

successfully rely on fear to maintain their authority if

their forceful acts can be justified, they steer clear of

any behaviour that might be construed as sexual

harassment, and they refrain from denying employees

and shareholders monetary benefits due to them.

Justice -- understood in the ordinary sense as respect

for property and persons in addition to giving each his

due -- is the Machiavellian antidote to the hatred that

fear might instil.

Machiavelli immediately reverts back to the

questioning of ordinary moral notions in analyzing

honesty and fidelity to promises, also commonly

regarded as part of justice. Most people and

philosophers, excepting strict Kantians, have agreed

that the duties of honesty and faithfulness are not to be

adhered to absolutely, but that if a breach is required,

it must be to help others. Hardly anyone thinks that an

individual hiding a Jewish family in their house in

early 1940’s Germany was obliged to tell the truth to

a Nazi official that came knocking at their door asking

whether they know the whereabouts of any Jewish

persons. Machiavelli concurs that the obligation is not

unconditional, though for reasons of the leader’s self-

protection. It would make sense to tell the truth and

keep promises if everyone else did, Machiavelli

admits, but in the competitive universe in which

humans are continually trying to get an edge at others’

expense, that faithfulness cannot be expected. Thus,

Machiavellian leaders must become master

dissemblers and be willing to break promises when it

ceases to be in their interest to adhere to them (P. xviii,

pp. 69-71). One need not be especially clever,

Machiavelli believes, to come up with a plausible

rationalization, which can be rendered all the more

credible if one succeeds and continually sermonizes

about the sanctity of honesty and faith. “Men in

general judge more by their eyes than by their hands

… [e]veryone sees how you appear, few touch what

you are” (P.xviii, p. 71). Whatever the merits of this

advice in politics, its value in business may certainly

be suspected, even on Machiavelli’s self-interested

grounds, if only because a liar and promise breaker

will eventually find no one willing to associate and

deal with them. So too, what Machiavelli says is based

on the idea that politicians ultimately play on a stage

before the populace. “For the vulgar are taken in by

the appearance and the outcome of a thing, and in the

world there is no one but the vulgar” (ibid.). But

For a more detailed comparison of Machiavelli and Cicero, see

Colish (1978).

businesspersons mostly play a game in which they

interact with other businesspersons, who certainly

have financial incentives to look beyond appearances

before entering a transaction.

Be that as it may, the appearance-reality distinction

that Machiavelli draws is the key to understanding the

contradictory spectacle of putting in a good word for

the traditional virtues and simultaneously invoking

virtú to designate something opposite that is highly

worth emulating. According to Machiavelli, the

traditional virtues properly belong to the realm of

appearance, while virtú is meant to characterize the

reality of a prince who knows how to shift to and from

the old verities and then cover it up effectively without

provoking hatred and opposition. Besides disguising

it with rationalizations, success, and appeals to the

common good, Machiavelli recommends that princes

cultivate an image that is as far from levity,

indecisiveness, spinelessness, and unsteadiness as it is

close to seriousness, resoluteness, courage, and

steadfastness (P, xix, p. 72). They ought to keep a low

profile in their day-to-day administrative tasks so that

the grand enterprises they rarely undertake can shine

all the more brightly. No matter what they do, it should

be done well. Nor should leaders shy away from

seeking fame, which for businesspersons means

getting lionized on the cover of Fortune magazine,

writing articles for The Wall Street Journal, and

publishing books to shares one’s life story,

experiences, and leadership wisdom. Business leaders

can also burnish their image by recognizing the

virtuous (as understood by orthodox standards),

rewarding those who work hard, perform their

functions exceptionally well, and make signal

contributions to the company’s growth. Finally, as a

way to demonstrate concern for the happiness of

employees, Machiavelli urges managers to host

parties during holiday periods, sponsor special events,

and give away prizes in contests (P.xxi, pp. 87-91).

Whether or not all this image management can work

is the big question left hanging from Machiavelli’s

discussion and upon which his entire teaching on

leadership stands or falls. It cannot be illuminated

much by social science studies that attempt to examine

the performance of Machiavellian types versus non-

Machiavellians (Christie and Geis, 1970; Gable and

Topol, 1991; Ricks and Fraedrich, 1999). This

research, in which the connection between

Machiavellianism and business success comes to view

as mixed, identifies a Machiavellian based on how a

person answers a series of questions on the so-called

Mach IV or Mach V scale. No consistent adherent of

Machiavelli would dare admit to others that they are

guided by his teachings. To do so, after all, would be

to raise doubts about one’s trustworthiness, making it

more difficult to obtain the co-operation of others in

the advancements of one’s projects. Leaders,

especially, depend on others to follow their direction

and thus can least afford signaling any kind of

opportunism. For this reason, the true Machiavellian

will not disclose their own Machiavellianism. Though

disclosure, responses can be faked (Fehr, Samson,

Paulhus, 1992: 102 citing Skinner, Giokas, &

Hornsstein,1976; Skinner, 1982). A proper empirical

test of Machiavelli’s counsel must imitate his

historical approach in closely scrutinizing the deeds,

statements, and reputations of well-known business

leaders and gauging whether the successful ones were

distinguished by acting in crucial moments with virtú,

while preaching, and being generally presumed to

exemplify, conventional virtue.

Conclusion

While present-day business ethicists differ on a

wide variety of issues, there is a broad consensus that

selfishness ought to be inhibited in the commercial

arena and that business leaders should instead be

consciously driven by a more altruistic set of motives.

We find that Machiavelli fundamentally disagrees

with this consensus -- despite his advocacy of

participatory forms of governance, and the publicly

spirited virtues that go along with it, in the Discourses.

For he concedes that the participatory structure of

republics is ill-suited to organizational contexts that

are in need of radical reform or which must be started

anew. In these cases, Machiavelli insists a princely

leader is necessary. In acknowledging, too, the utility

of temporary dictatorships in republics, he can be

taken to support the temporary dictatorships that the

CEO’s of our day essentially assume in established

and well-functioning companies.

Thus directed to The Prince for business counsel,

we see Machiavelli trying to establish a novel

conception of morality, encapsulated within the notion

of virtú, in which human excellence is equated with

acquisitiveness. This ideal is personified most fully in

the individual who originates new modes and orders,

the founder of a great business. Still, in this

revaluation of values, Machiavelli retains traditional

understandings of virtue that emphasize self-restraint

and altruism. But this is something merely for

business leaders to simulate in normal circumstances.

In more exceptional circumstances, when self-interest

demands it, the moral orthodoxy must be set aside for

the expression of virtú. Machiavellian CEO’s

seemingly devote themselves to the most exalted

principles of business ethics, and leave everyone

convinced that they are doing so, but really operate as

ruthless capitalists.

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