Build a Company That Won’t Break Your Heart
Lessons from a different Machiavelli than the one you know and fear
What kind of startup CEO do you want to be? In a presentation to entrepreneurs this week, I challenged them to think beyond the old-school, “machiavellian” approach to leadership. You don’t have to be a tyrant to succeed. In fact, I’m convinced that the alternative—leading by assembling people and resources together, by creating what one author calls “power with” rather than “power over”—results in a more resilient, meaningful, and ultimately successful company.
Background
This week I had the pleasure of speaking at the UTA Center for Entrepreneurship and Technology Development’s weekly speaker series, EpicMavs. It’s an event for students, faculty, and local entrepreneurs here in Arlington. For more takeaways from the presentation, check this post out on collaboration and effective leadership.
This post shares the core lessons from that conversation, plus a few extra reflections. It might challenge the way you think about building a company.
The Worst Places to Work
I started the talk by asking the audience: “Tell me about some of the worst places you’ve ever worked—or that you’ve seen your parents or family or friends work. What made them so rotten?” I wasn’t surprised by the immediate flood of examples:
Bad managers who criticize every idea.
Toxic environments that suck the life out of everyone.
Terrible cultures where you never quite feel you belong.
Leaders who micromanage or dump work on people.
Organizations with zero structure, where no one knows what they’re supposed to do, but everyone gets blamed if something goes wrong.
Next, I asked, “Now, tell me more about the leaders of those places. What were they like? What were their so-called ‘leadership traits’?” Again, a wave of answers:
They were dominant and narcissistic.
They were power-seeking.
They lacked empathy.
They loved to micro-manage.
In other words, the leaders were acting a lot like the classic interpretation of Machiavelli’s “Prince”—the authoritarian, top-down boss who has to be feared to stay in control.
Machiavelli 1.0 → 2.0
Chances are you’ve heard the phrase “It’s better to be feared than loved.” That comes from Machiavelli’s famous The Prince, written in the early 16th century, which is basically a manual on how to be an iron-fisted monarch. But Machiavelli also wrote another book called Discourses on Livy, published after his death, where he argues that a republic—not a monarchy—is actually a better route if you want your legacy to outlast you.
This bit of Machiavelli is often forgotten. So in my talk, I proposed that most of us have only heard the “Machiavelli 1.0” version. We’ve been taught that leadership is a top-down function. But if you look closer, you see “Machiavelli 2.0”: the idea that real longevity comes from building something collective, not from being the ultimate boss.
Unfortunately, the corporate world hasn’t fully caught up. Many companies still operate like little monarchies, with the CEO as the Prince or Princess and everyone else as the subjects. The “fear or love” approach might get you short-term results. But in my experience, it can lead to what one entrepreneur described to me as “a fat wallet and a broken heart.”
The Two Kinds of Startup CEO
1) The “Power Over” CEO (Machiavelli 1.0)
This is the leadership style we’ve all been taught in some shape or form:
Spot the opportunity, like an arbitrage play in the market. This is the opportunity discovery perspective of entrepreneurship.
Lock down resources (capital, labor, trade secrets, etc.) so nobody can snatch them away.
Maintain power over these resources by controlling them (and the people) carefully, guarding your intellectual property, and outmaneuvering any competition.
Win by beating everyone else, establishing a monopoly or near-monopoly, and extracting as much profit as possible from customers, suppliers, and employees.
If this is the CEO’s mindset, you can guess the kind of skills that get cultivated:
Sharp power plays
Aggressive competition
A tendency to micro-manage or keep people in line
A “my way or the highway” approach
And you can guess the kind of organizational culture that flourishes: an environment rife with fear, suspicion, politicking, and, often, burnout.
2) The “Power With” CEO (Machiavelli 2.0)
But here’s the other way—what political scientist and management guru Mary Parker Follett called power-with. Instead of treating entrepreneurship like a hunt for fleeting opportunities to exploit, think about creating opportunity through storytelling, relationship-building, and collective learning, or what some authors call entrepreneurial assembly. It goes something like this:
Tell a Story. You start with a “contingent vision”—a flexible story about what you want to build and why it matters.
Gather Allies. You go out and share that story, paying attention to what resonates with people. You adapt your vision to pull in new resources, partners, perspectives, and skills. Instead of trying to get power over them, you’re building power with them.
Assemble Generously. As you collect these resources—people, funding, expertise, connections—you begin to weave them together into a working business model. More importantly, you’re creating a new social network of folks who share a sense of ownership and passion for what you’re building.
Success, in this model, is about leaving your ego at the door and crafting a system where everyone can win. If Machiavelli 1.0 is all about the single, central figure controlling everything, then Machiavelli 2.0 is more like a legislator or a collaborative conductor, orchestrating a broad, vibrant ensemble.
Three things to remember about Machiavelli 2.0 style entrepreneurship, or entrepreneurial assembly, or the power with way, or maybe entrepreneurship as legislating:
Tell stories. Tell stories about what you could build, and how the world could change if you built it. Hold these stories loosely, and avoid being protective of what you think is your “intellectual property;” >95% of the time, it’s not what will make or break you.
Gather allies. Pay attention to what gets people excited. Figure out what resources, skills, knowledge, and networks they would be willing to put toward their vision of your project, and what it would take to make them excited to share that with you.
Assemble generously. As you meet people, start to weave them together; look for ways, even seemingly unrelated to your project, to add value to them or connect them with people that can.
If you do all that, I believe you’ll become a better leader, establish a better culture, and run a more successful business--or even better, build a new network.
Will You Be a Tyrant CEO? Or a Legislator?
At this point in the talk, I asked everyone to think about their own projects, which included software, a bakery, a data initiative, and other ideas still rattling around in their heads. Then, I posed two sets of questions:
What would the Machiavelli 1.0 (the tyrant) version of this look like? How would it feel to run (or work at) that kind of business?
What would the Machiavelli 2.0 (the legislator) version look like? How does that feel different?
Students articulated what “power over” culture might be (fear, paranoia, short-sighted gains) versus the “power with” approach (collaboration, shared excitement, real ownership). There wasn’t consensus in the room—I am a professor, after all, so I couldn’t let us all agree on everything—but I hope students took away that what style of leadership they deployed, though certainly dependent to the context they might be operating in, was largely their choice.
Let’s be real: you’ll still find big-name entrepreneurs who preach the “1.0” style and we can point to their success stories—think Jack Welch, Donald Trump, Peter Thiel. But I would argue that if you stick to that “power over” script, you might end up with money in the bank but a whole lot of regrets about the cost to yourself, your people, and your community.
But I have seen that entrepreneurs who do these three things—tell stories, gather allies, and assemble generously—build a radically different kind of company. If you do that, your culture will be more collaborative and your leadership style will evolve from “command and control” to “co-create and empower.” And if you ask me, that’s a more exciting path to take—one that can still yield impressive commercial success, but with far less heartbreak along the way.
Show notes and further reading
On Machiavelli 2.0 leadership
Lead Together by Tania Luna. A light-hearted, fictionalized presentation of Mary Parker Follett’s concepts of power over and power with (2023). Also see Amy Edmonson’s The Fearless Organization (2018), Dacher Keltner’s The Power Paradox (2017), and Matthew Stewart’s “The Management Myth” (2006).
Machiavelli’s Discourses on Livy (1531).
On different kinds of entrepreneurship:
“Discovery and Creation: Alternative theories of entrepreneurial action” by Sharon Alvarez and Jay Barney (2007).
“An Assembly Perspective of Entrepreneurial Projects: Social networks in action.” By David Obstfeld, Marc Ventresca, and Greg Fisher (2020).
“Bricolage and beyond: Bringing modern entrepreneurship theories to bear on policy entrepreneurship” by Mark Hand and Colin Birkhead (2023). Introduces classic versus modern conceptions of entrepreneurship on pp. 6-11.
On Machiavelli 1.0 leadership
