Failures & lessons learned
Mistakes in underinvesting in foundational engineering practices that later produce catastrophic outages and delays.
Many startups overlook core engineering foundations, misjudging their long-term impact, until fragile systems buckle under pressure, costly outages erupt, and growth stalls, forcing painful, learnings-filled pivots and costly rebuilds.
Published by
Henry Griffin
August 12, 2025 - 3 min Read
In many ambitious ventures, the initial sparkle of speed and lean operations crowds out the quieter discipline of solid foundations. Teams chase features and user metrics, outsourcing or deferring critical engineering practices that seem expensive or unnecessary in the short term. Yet foundational strands—version control discipline, automated testing, meaningful monitoring, and resilient deployment pipelines—act as the unseen scaffolding of any scalable product. When these are neglected, small bugs become stubborn confusions, incident response becomes chaotic, and the cost of later fixes multiplies. The outage emerges not as a single catastrophe, but as a cascade of avoidable friction that undermines trust, slows customer growth, and drains developer morale.
The core mistake is treating foundational engineering as optional rather than essential. Startups often price the risk of outages as a distant problem, assuming a big rewrite will be feasible later. This mindset ignores the compounding effect of technical debt, especially when rapid iterations ride on fragile environments. Smaller teams justify skipping reviews, eschewing automated tests, or delaying observability investments, hoping to preserve velocity. Unfortunately, speed without stability creates brittle systems that cannot adapt to real user load or evolving data models. As outages accumulate, leadership faces a hard reckoning: either allocate resources now, or endure a more expensive, more disruptive reconstruction later that erodes market confidence.
Foundations mispriced risks creating fragile, costly systems.
When engineering foundations are underfunded, every change becomes a potential fault line. Without robust testing, a new feature may regress critical paths, hidden errors surface only under pressure, and debugging climbs to near-heroic effort levels. Observability—not just dashboards but actionable alerts and structured incident playbooks—remains sparse, leaving teams blind to the exact causes of failures. This opacity forces guesswork, delays root-cause analysis, and delays remediation while customers endure degraded service. The longer the delay, the more entangled the problem becomes, and the more fragile the product appears to external users who have high expectations from otherwise ambitious promises.
A related risk is underfunding automation and release practices. If continuous integration and continuous deployment are treated as nice-to-haves or afterthoughts, deployments become manual, error-prone rituals with inconsistent rollback options. When incidents arise, rollback speed matters as much as feature velocity. Without automated tests that cover critical paths, feature flags that actually work, and canary deployments that reveal issues early, teams are forced into firefighting rather than systematic improvement. The cumulative effect is a culture of reactive maintenance, where engineers spend more time patching problems than building new capabilities, eroding trust inside the team and with customers.
Early neglect of reliability compounds into expensive outages.
Leaders who undervalue reliability often mistake it for a luxury rather than a baseline requirement. They imagine that a lean approach can weather outages by sheer talent, but talent without guardrails is brittle. Early investments in load testing, chaos engineering, and resilient architectures multiply over time, turning potential catastrophes into manageable incidents. Prioritizing reliability requires a conscious budget, dedicated time, and measured experimentation. The payoff is not perfect perfection but predictable performance under typical and peak conditions. Teams that commit to these disciplines align product velocity with system stability, enabling sustainable growth rather than sudden, traumatic interruptions.
The appetite for speed often erodes during outages, teaching a harsh lesson about cost of inaction. When incidents occur, teams scramble to patch the most visible symptoms, leaving deeper architectural flaws untouched. This short-sightedness creates a cycle: fixes are temporary, documentation remains sparse, and new features continue to press on fragile infrastructure. The healthier approach embeds reliability into the product from day one: design for failure, diversify critical services, and keep a living record of incidents and resolutions. Such practices empower teams to run experiments, learn quickly, and prevent recurrence, even as product demands evolve.
Incident discipline transforms how a company grows.
The moment a system fails, the true value of foundational engineering is revealed. The organization discovers that uncoordinated teams, inconsistent coding standards, and patchwork monitoring amplify the impact of faults. Recovery becomes a complex sprint where engineers chase after the root cause while users experience degraded performance. The absence of reliable incident response protocols means valuable time is wasted during critical moments. Documented runbooks, known-stakeholder contact lists, and defined escalation paths transform chaos into controlled, repeatable processes that shorten downtime and restore confidence more quickly.
In such environments, post-incident reviews become the essential engine for learning. Without them, teams repeat mistakes, focusing on quick quarantines rather than systemic fixes. Effective reviews identify not only what broke, but why the underlying architecture allowed a fault to propagate. They reveal gaps in dependency mapping, configuration management, and release coordination. The best teams turn these insights into precise, actionable improvements—refactoring risky components, adding redundant pathways, and improving rollback capabilities—so future incidents are smaller and quicker to resolve.
From underinvestment to durable, scalable engineering culture.
Establishing incident management as a core capability resets the operating rhythm of a startup. It teaches the organization to treat outages as signals with learnable content rather than embarrassing failures. Teams develop a common language for communicating severity, scope, and impact, which reduces blame and accelerates collaboration. With clear postmortems and tracked improvements, engineers gain confidence to push changes with decreased fear of cascading failures. The culture shifts from reactive firefighting to proactive resilience, enabling faster feature delivery without compromising reliability.
As reliability practices mature, teams begin to measure the true cost of downtime and the value of preventive work. They allocate dedicated budgets for SRE resources, invest in standardized testing frameworks, and establish service level objectives that guide decisions. This shift aligns engineering with business outcomes: customers experience steadier performance, revenue is less vulnerable to outages, and the organization learns to prioritize investments based on concrete risk reduction rather than intuition. The resulting resilience becomes a differentiator that supports sustainable growth, not a liability that derails progress after the initial hype fades.
The journey from underinvestment to durable practice is gradual and context dependent. Startups that succeed in this transition do not suddenly transform; they adopt incremental improvements that compound over different phases of growth. They start with essential guardrails—version control discipline, automated tests for core paths, and reliable deployment pipelines—and progressively layer in more sophisticated reliability strategies. As teams mature, they codify patterns for disaster recovery, incident response, and post-incident learning. This evolution yields a culture where engineers feel empowered to innovate without sacrificing system stability or customer trust.
The enduring lesson is that foundational engineering is not a barrier to agility but its engine. By funding core practices early, organizations remove the friction that converts guesses into outages and delays into lost opportunities. The payoff is a product that scales smoothly, a team that learns quickly, and a business that can endure the inevitable tests of growth. In this mindset, the cost of fixing mistakes soon after inception dramatically undercuts the cost of letting fragile systems navigate the market, turning risk into resilience and potential into predictable performance.
