10 Lessons Machiavelli Can Teach Founders

The only constant as a founder of a startup is change. The wisdom of historical figures can offer unexpected insights. Niccolò Machiavelli, a name that often conjures up notions of cunning, deception, and the ruthless pursuit of power, may not be the first mentor that comes to mind for startup founders. Yet, beneath what many interpret as Machiavellianism — synonymous with unethical or deceitful behavior — lie fundamental truths that can guide the modern entrepreneur through the treacherous yet rewarding journey of building a startup.

Who Was Niccolò Machiavelli?

Niccolò Machiavelli (1469–1527) was a Renaissance political philosopher, diplomat, and writer, best known for his work “The Prince.” Born in Florence, Italy, Machiavelli lived through tumultuous times, witnessing the complexities of political power plays firsthand. His most famous work advises rulers on maintaining power by any means necessary, leading to the term “Machiavellian” being associated with manipulation and unethical behavior. However, a deeper understanding of his writings reveals a pragmatic realist who understood the human condition and the dynamics of power and leadership — concepts that are very much applicable to the modern business world.

Lessons for Startup Founders

1. The Importance of Adaptability

Machiavelli emphasized the necessity of adapting to changing circumstances, famously advising rulers to be as flexible as the winds of fortune. In the startup ecosystem, adaptability is equally critical. Market conditions, consumer preferences, and technological advancements change at an unprecedented pace. Founders who heed Machiavelli’s counsel to adapt swiftly and effectively can navigate their companies through volatile waters, seizing opportunities that less adaptable competitors might miss.

2. Realism Over Idealism

Machiavelli was a proponent of dealing with the world as it is, not as we wish it to be. For startup founders, this means a grounded approach to business. While vision and ambition are vital, they must be tempered with a realistic assessment of the market, the competition, and one’s capabilities. By embracing realism, founders can make strategic decisions that are informed, pragmatic, and more likely to result in sustainable growth.

3. The Value of Being Feared and Loved

One of Machiavelli’s most famous dichotomies is the choice between being feared or loved as a leader. He suggests that while it is ideal to be both, being feared is safer than being loved if one must choose. In the context of startups, this does not advocate for tyranny but underscores the importance of respect and authority. Founders should strive to build a culture where their leadership inspires trust, respect, and a degree of admiration, ensuring that the team will follow when tough decisions need to be made.

4. Fortune Favors the Bold

Machiavelli believed in taking initiative and being bold. “Fortune is a woman,” he wrote, “and it is necessary, if you wish to master her, to beat and ill-use her.” This controversial analogy aside, the underlying message for entrepreneurs is clear: success often requires boldness and the willingness to take calculated risks. Startups are inherently risky ventures, and founders who wait for opportunities to fall into their lap will likely be overtaken by those who actively pursue their goals.

5. The Significance of Appearances

Machiavelli acknowledged the importance of appearances and public perception. For startups, brand image, founder reputation, and company culture are not superficial concerns — they are essential to attracting investment, recruiting talent, and acquiring customers. Founders must be mindful of how they and their startups are perceived, managing appearances to build and maintain trust, credibility, and a positive public image.

6. Strategic Use of Resources

Machiavelli advised rulers to be judicious in using resources, a lesson particularly relevant for startups, where resources are often limited. Effective allocation of time, capital, and human resources can be the difference between success and failure. Founders need to prioritize ruthlessly, invest in areas that offer the highest returns, and be willing to cut losses on initiatives that do not deliver as expected.

7. Building Strong Alliances

The importance of alliances was not lost on Machiavelli, who understood the power of strategic partnerships in consolidating power and influence. Similarly, startups can accelerate their growth and enhance their market position through strategic partnerships, collaborations, and networking. Building a solid ecosystem of allies can provide startups with resources, expertise, and channels to market that would be difficult to achieve independently.

8. The Art of Decision-Making

Machiavelli highlighted the importance of decisiveness in leadership, arguing that indecision is often more damaging than making a wrong decision. In the fast-paced world of startups, founders are frequently faced with making decisions under uncertainty. Embracing Machiavelli’s advice means accepting the inevitability of making mistakes but understanding that the ability to make decisions swiftly and confidently can propel a startup forward. Through making decisions, learning from their outcomes, and adjusting course, founders can navigate their companies through the complexities of growth and competition.

9. Maintaining Control Over Your Destiny

Machiavelli was a firm believer in the power of human agency over fate. While acknowledging the role of fortune, he argued that one could bend the arc of destiny in one’s favor through cunning, strategy, and willpower. This underscores the importance of proactivity and the pursuit of agency for startup founders. Rather than being passive recipients of market forces or external circumstances, founders should actively seek to shape their environment, influence stakeholders, and create opportunities for their venture. This proactive stance involves reacting to market trends and anticipating or creating them, thereby maintaining control over the startup’s destiny.

10. The Importance of Learning from History

Though not a lesson explicitly stated by Machiavelli, his work is a testament to the value of historical insight. By analyzing the rise and fall of rulers and empires, Machiavelli extracted timeless principles of power dynamics and leadership. Similarly, startup founders can benefit enormously from studying the successes and failures of those who have come before them. The startup ecosystem is rich with case studies, cautionary tales, and blueprints for success. Founders who take the time to learn from history — both their own experiences and those of others — can avoid repeating past mistakes and leverage proven strategies to their advantage.

Final Thoughts

Niccolò Machiavelli’s teachings, often misunderstood as a playbook for deceit and manipulation, contain invaluable lessons for startup founders. By looking beyond the misconceptions and understanding the core principles of adaptability, realism, strategic boldness, and effective leadership, entrepreneurs can draw on Machiavelli’s wisdom to navigate the challenges of the startup world. In the end, Machiavelli teaches us not about the virtue of ruthlessness, but about the pragmatic realities of achieving and maintaining success — a lesson as relevant today as it was in the Renaissance.