The Irrationality of Running a Software Company: Elevating to Rationality Through the Chaos

The Pythagoreans in the 6th century BC clung to the belief that life could be explained through natural numbers—rational, discrete. It was a system built on certainty with observation consistently reinforcing the belief. Geometry, arithmetic, the harmony of music—everything fit neatly within a pattern, a ratio of integers. But this worldview shattered when one of their own proved the existence of an anomaly to their system. The square root of 2—√2—resisted all efforts to express it as a ratio of natural numbers. It was an infinite, unsolvable problem, a number that kept going forever without settling into something definable. It evaded definition. Unable to reconcile this contradiction within their perfect system, the Pythagoreans drowned the philosopher who revealed it. They destroyed the messenger to protect their worldview.

But what if that impossibility—the irrational number—holds a hidden wisdom? Running a software company feels like contending with impossibility. The more you push, the more there is to discover, and the end seems just beyond reach. Yet within this chaos, there is an unexpected clarity: only by elevating yourself to the level of rationality—learning to accept what can’t be controlled or fully solved—can you make sense of what can be seen.

Most of the information founders read online purports to explain it all; neatly fitting into the definitions of how everything ‘ought’ to work. Accelerators and investors talk about ‘the right way’ and yet the journey is still rough. The tyranny of the natural world serves as evidence that the ‘ought’ we strive for is, in fact, an abstraction. Our lived experience is more irrational than it is rational.

Infinite Work, Finite Results: The Search for Limits

Much like irrational numbers, running a software company involves infinite complexity. No matter how many features are built, bugs resolved, or sales meetings held, the finish line keeps moving. The more it is sought, the further off it seems to be. For founders, this feels maddening—why can’t things just work? Why does every solved problem simply reveal new ones? And yet, irrationality is not only unavoidable, it is part of the nature of building something new.

Years ago, I experienced this firsthand during a turnaround at Prognosis - a software company selling enterprise systems to hospitals. Hospital sales cycles are notoriously slow, convoluted by bureaucracy, committees, and entrenched vendors. At times, it felt like chasing √2—progress without resolution.

In one desperate effort to jumpstart momentum, we organized a dinner for potential clients during a major healthcare conference. We partnered with another vendor, rented out Wolfgang Puck’s restaurant in Dallas, and invited our most promising prospects. To our amazement, we received 150 RSVPs. I started doing the math: even a 10% conversion rate meant millions in new contracts. For once, the numbers seemed to add up.

Yet, as the clock struck six, the restaurant remained eerily empty. A few team members shifted nervously, checking their phones and scanning the door. By 6:30, only two attendees showed up. Two. Out of 150. We managed to sit them down, but the night had evaporated into an absurd tragedy. It felt like staring into the endless decimal places of an irrational number, each new digit reminding us how far we were from completion.

What the heck happened? That question haunted me, as it does every founder who grapples with the endless uncertainties of running a software company. The RSVPs were real. The planning was solid. The calls, the confirmations—everything was executed with precision. And yet, success eluded us. Like √2, it defied easy explanation.

The Delusion of Control and the Clarity of Rationality

Here’s the maddening truth: software ventures are inherently irrational - they are resource games mixed within telephone Pictionary where everyone speaks a different language. Founders cling to spreadsheets, forecasts, and KPIs like lifeboats in a storm, hoping that enough data will bring clarity. But the deeper reality is this: the universe of entrepreneurship operates on something closer to irrational numbers—there is no neat ratio of effort to outcome. More data doesnt bring clarity, it brings certainty that clarity is still much farther away. Effort multiplies, returns diminish, and the decimals of uncertainty stretch toward infinity.

In these moments, the balanced founder learns a critical lesson: the limit exists. There may be no exact solution to every problem, but not every problem needs an exact solution. In mathematics, irrational numbers aren’t errors; they are truths—just a different kind of truth; an existential one. They demonstrate that not everything can or should be controlled. Similarly, running a company is not about finding neat solutions; it’s about raising your perspective to see what matters and learning when to let go of what doesn’t. It means finding the limits around irrationality instead of trying to fully define it; stopping the pursuit of clarity at good-enough.

The emotional chaos—the disappointment of empty events, missed targets, or toxic investor dynamics—is inevitable. But so is the opportunity to reframe it. Not every failed dinner event or blown deal is a catastrophe. Sometimes, it’s simply a reminder that the pursuit of control over chaos is an illusion. What matters is the ability to step back and see the patterns within the irrational: which customers still engage, which employees remain committed, and where the real value lies.

The Founder’s Journey: From Frustration to Insight

I’ve often felt tempted to give in to frustration. After all, software ventures offer plenty of dark moments—cash burn, customer complaints, churn, and friction with investors. Yet those moments have taught me how to contend with irrationality. Just because a problem is complex doesn’t mean it’s insurmountable. Like irrational numbers, the path forward in a company may not be perfectly definable, but it can still be navigable.

During the Prognosis turnaround, I often found myself in high-stakes negotiations that stretched on endlessly, much like the decimals of π, without ever quite resolving. I yearned to complete the work; to finish the symphony. Customers would stall, vendors would demand payments we couldn’t afford, and investors would send passive-aggressive emails demanding progress. It was an exhausting exercise in finding clarity amid the noise. But those moments also forced me to step back and ask: what can I control?

In the end, it wasn’t about hitting every target perfectly. It was about aligning the right pieces—the committed employees, the willing customers, the supportive partners—and letting go of the need to control the rest. That is what it means to find the limits of irrationality as a way to arrive at a sufficient definition.

Lessons from the Infinite Loop

So, what’s the takeaway? Founders often believe they need to grind endlessly, as if sheer force will reveal the right solutions. But irrational numbers teach us something else: not all problems are meant to be solved completely. Some require acceptance, patience, and a willingness to focus only on what matters.

In the journey of running a software company, this means:

1. Embrace the irrationality: Not every effort will yield proportional results. And that’s okay.
2. Seek balance through perspective: Your identity is not your company. You are more than the sum of your P&L statements or your latest KPIs.
3. Raise your level of rationality: Learn to distinguish between what you can control and what you must accept. This is not resignation—it’s wisdom.

Like the irrational √2, the journey will stretch endlessly, but that doesn’t mean it’s pointless. There are moments of clarity, breakthroughs that come not from brute force but from insight. The balanced founder recognizes that success is not about taming the irrational but learning to work with it, elevating above the chaos to see what can be seen.

And in the end, all that certainty that we often attack our business problems with fades into the background leaving the founder with an option to lean in finding the next digit in an infinite fruitless quest or embrace the irrational. And if this challenged your worldview of how to scale a software company... at least I live far from the sea.