Marcus Aurelius was the most powerful man in the world. He commanded armies, governed an empire, and faced threats that would have broken most people. He also wrote a private journal that he never intended anyone to read — and in it, he was brutally honest about his own failures, fears, and the daily struggle to live according to his values.
Marcus Aurelius was the most powerful man in the world. He commanded armies, governed an empire, and faced threats that would have broken most people. He also wrote a private journal that he never intended anyone to read — and in it, he was brutally honest about his own failures, fears, and the daily struggle to live according to his values.
That journal became the *Meditations*. And I have returned to it more times than I can count — not as a historical curiosity, but as a practical manual for the thing I spend most of my time doing: building companies and backing the people who build them.
The Obstacle Is the Way
Ryan Holiday, who has done more than anyone in the modern era to bring Stoic philosophy to a practical audience, distilled one of the Stoics' central insights into a single phrase: the obstacle is the way. The idea comes directly from Marcus Aurelius, who wrote: "The impediment to action advances action. What stands in the way becomes the way."
I have tested this idea against twenty years of building, and I believe it is true. Not in a motivational-poster sense, but in a deeply practical one. Every significant obstacle I have encountered in building Pypestream — and there were many — contained within it the information I needed to solve the problem. The customer who told us our product was not good enough was pointing us toward the product that was. The investor who passed was clarifying exactly what we needed to prove before the next conversation.
The Stoic insight is not that obstacles are secretly good. It is that your response to obstacles determines your trajectory far more than the obstacles themselves. This is not a comfortable idea. It removes the comfort of blaming external circumstances. But it is an enormously empowering one, because it means that the variable you can control — your response — is also the most important variable.
Amor Fati: Love What Is
The second Stoic principle I return to constantly is *amor fati* — love of fate. Nietzsche popularized the phrase, but the idea runs through Stoic philosophy from Epictetus to Marcus Aurelius. The practice is this: not merely to accept what happens, but to actively embrace it. To want it to have happened, because it happened, and because your response to it is now the thing that defines you.
This sounds like resignation. It is the opposite. *Amor fati* is the foundation of radical agency. When you stop spending energy wishing things were different and start spending that energy on what you can actually do, you become dramatically more effective. The founder who spends six months grieving a failed product launch is six months behind the founder who spent those six months learning from it.
I watched this play out in real time during the early years of Pypestream. We had built what we believed was a genuinely transformative product — an AI-driven customer communication platform that we were convinced would change how enterprises operated. The market was not ready. The sales cycles were brutal. The early feedback was mixed. There were moments when the rational thing would have been to pivot or quit.
What kept us going was not optimism. It was something closer to the Stoic practice of *premeditatio malorum* — the premeditation of evils. We had already imagined the worst. We had already made peace with the possibility of failure. That peace gave us the freedom to keep building without the paralysis of fear.
The Dichotomy of Control
Epictetus, who was born a slave and became one of the most influential philosophers in history, built his entire teaching on a single distinction: some things are in our control, and some things are not. What is in our control: our judgments, our desires, our actions. What is not: our reputation, our wealth, the opinions of others, the behavior of markets.
This distinction is the most useful framework I know for managing the emotional volatility of building a company. Founders are, by nature, control freaks. We want to control outcomes. But outcomes are not in our control. What is in our control is the quality of our thinking, the rigor of our execution, and the integrity of our decisions.
When I am working with a founder who is spiraling — consumed by anxiety about a competitor's move, a fundraising timeline, a key hire who might leave — I come back to this distinction. What is actually in your control right now? What is the highest-quality action you can take today? Everything else is noise.
The Practice, Not the Philosophy
The mistake most people make with Stoicism is treating it as a philosophy to be understood rather than a practice to be lived. Marcus Aurelius did not write the *Meditations* as a philosophical treatise. He wrote them as daily reminders to himself — notes to return to when he was tired, when he was angry, when the weight of his responsibilities threatened to overwhelm his judgment.
The modern equivalent is whatever practice allows you to return to your values under pressure. For me, it is a morning journal — fifteen minutes before anything else, writing down what I am grateful for, what I am anxious about, and what the most important thing I can do today is. It is not sophisticated. But it creates the space between stimulus and response that Viktor Frankl identified as the source of human freedom.
Frankl, who survived the Nazi concentration camps and wrote *Man's Search for Meaning*, arrived at the same insight as the Stoics through a very different path: "Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom."
That space is what we are building when we practice Stoicism. Not detachment. Not indifference. The capacity to choose, even under pressure.
What This Means for Founders
The founders I most want to back are not the ones who have never failed. They are the ones who have failed and come back with something the failure taught them. The ones who can sit in the uncertainty of the early stages without needing it to resolve immediately. The ones who can receive hard feedback without becoming defensive, and who can hold conviction without becoming rigid.
These are Stoic qualities. And they are, in my experience, far better predictors of long-term success than any metric on a pitch deck.
Marcus Aurelius never ran a startup. But he understood that the quality of your inner life determines the quality of your outer work. That the person you are when things are hard is the person you actually are. And that the practice of becoming that person is the most important work there is.
Richard Smullen is the co-founder of Keller Winston and the founder of Pypestream, Inc.
