Commandos, Soldiers, and Police: How Startups Evolve and Mature Over Time

Navigating the necessary—and sometimes painful—transitions as your startup grows from exploration to execution

In his classic 1993 book, Accidental Empires, Robert Cringely presents a framework that remains as relevant today as ever—describing the evolution of companies through three distinct stages: Commandos, Infantry, and Police. Jeff Atwood famously highlighted this concept in his 2004 article, "Commandos, Infantry, and Police,” a post I discovered through Gabriel Weinberg’s insightful compilation of mental models. Over the years, this framework has resonated deeply with my own startup journey, first at ZestyAI and now at Paxton AI.

Commandos: Creativity as a Destructive Act

When you're a Commando, you're landing behind enemy lines, navigating uncharted territory, and operating with minimal resources. It's exhilarating but nerve-wracking, defined by speed, creativity, and a near-total absence of structure. At ZestyAI, our earliest days felt exactly like this—we had no idea which direction to take. Initially, we tried our hand at creating an online solar marketplace, PowerScout, but quickly realized it wasn't viable. This pivot triggered a frenetic phase of rapid experimentation—mortgage marketing, lead generation across various industries—until we stumbled upon risk modeling for the property insurance industry. The thrill of invention, the fear of failure, and the relentless pursuit of something meaningful defined the essence of this Commando phase.

Our first sale, and soon after our Series A funding at ZestyAI, were unforgettable milestones—validations that transitioned us from the exhilaration of unbounded exploration into the disciplined execution required of Soldiers.

Soldiers: From Chaos to Structure

Success inevitably introduces the Infantry phase, characterized by scale, operational structure, and repeatable processes. Suddenly, the words PTO policies, OKRs, and performance reviews entered our vocabulary—necessary yet initially uncomfortable transitions for those accustomed to pure creative freedom. For me personally, this transition marked one of the most challenging stages of my career. Moving from the autonomy of being the solo AI engineer who knew every line of code to leading a team meant navigating intense periods of context-switching, balancing technical execution, client expectations, investor updates, and team management simultaneously.

At this critical scale-up stage, the tension between innovation and discipline is palpable. Commandos, fueled by novelty, can quickly grow restless, craving the next frontier. But Infantry—the disciplined troops—must step in to refine, stabilize, and systematically expand upon the creative chaos Commandos leave behind.

Infantry—the second wave of personnel—arrive to consolidate the gains Commandos achieved through rapid prototyping and exploratory leaps. Their mission: convert rough prototypes into robust, reliable products, institute repeatable processes, and establish an operational framework essential for scalable growth. At ZestyAI, this meant formally defining policies, structuring OKRs, and implementing rigorous performance reviews.

For a Commando at heart, this shift toward formality and structure can feel restrictive, even stifling. Yet, without Infantry, the startup’s growth stalls. As Zesty scaled toward our Series B, my role evolved dramatically. Leading a team of 20 talented individuals, I found great fulfillment in mentorship, team building, and seeing collective efforts yield impressive results. Yet, gradually, I found myself distanced from the immediate, hands-on creativity that had initially fueled my passion.

Police: Stability, Scale, and Structure

Eventually, organizations require the Police phase: professionals committed to stability, reliability, and sustainable long-term growth. Unlike Commandos exploring uncharted territory or Infantry expanding operational scale, Police focus on securing existing gains and protecting established territory. Their world involves meticulous risk management, compliance, quality control, and careful coordination. Their mission is not innovation, but continuity and optimization at scale.

I encountered the Police phase early in my career at established institutions like McKinsey and the Federal Reserve. At such scale, risks are carefully managed, processes deeply formalized, and changes slow and measured. This environment attracts individuals with lower risk tolerance, deeply invested in preserving the organization’s brand and reliability—qualities essential to mature organizations yet fundamentally different from startup life.

The Cycle Begins Again: Launching Paxton AI

After reaching Series B at ZestyAI, the Commando in me felt an irresistible urge to return to the frontline. This led me to found Paxton AI just as generative AI began to reshape the technological landscape. Armed with the invaluable lessons from my ZestyAI journey, Paxton’s early days were both invigorating and somewhat familiar. I had learned the importance of prioritizing rapid iteration, customer validation, and agility above premature formalization and overly rigid processes.

Paxton progressed rapidly from pre-seed to seed funding and then quickly to Series A in just two years—a much faster journey than my initial startup. Having learned the complexities of juggling creative innovation and structured management at ZestyAI, I quickly recruited a highly capable VP of Engineering at Paxton. This allowed me to shift more strategically into the CTO role, focusing primarily on product vision, strategic initiatives, and the exciting challenges of scaling innovation in a rapidly evolving AI landscape.

Embracing the Journey

Every successful startup must gracefully manage transitions through Commandos, Soldiers, and Police, clearly recognizing the strengths and inevitable limitations of each phase. Misalignment during these critical junctures can introduce friction, slow growth, or even derail the startup entirely. Effective leadership involves embracing new roles, fostering the right culture for each stage, and knowing precisely when to delegate or transition responsibilities.

Reflecting deeply on my journey, this framework provides not merely an analogy but genuine clarity. Understanding these complementary roles—Commandos, Soldiers, and Police—enables entrepreneurs to anticipate transitions, build teams deliberately, and effectively guide their startups from thrilling ideation through disciplined execution and ultimately mature, sustainable growth.

The critical lesson? Identify clearly which stage you’re in, immerse yourself fully, and stay keenly aware of when your leadership style must evolve or when it’s time to empower others to lead. Much like successful military campaigns, startups require the right people, in the right roles, deployed strategically at precisely the right moments.