Large enterprises navigate a critical paradox with new technology like AI. Moving too slowly cedes the market and leads to irrelevance. However, moving too quickly without clear direction or a focus on feasibility results in wasting millions of dollars on failed initiatives.

Unlike traditional software development, AI-native founders avoid long-term, deterministic roadmaps. They recognize that AI capabilities change so rapidly that the most effective strategy is to maximize what's possible *now* with fast iteration cycles, rather than planning for a speculative future.

AI agent platforms are typically priced by usage, not seats, making initial costs low. Instead of a top-down mandate for one tool, leaders should encourage teams to expense and experiment with several options. The best solution for the team will emerge organically through use.

Instead of making one large, transformative bet on AI, Macy's is testing it across numerous departments (supply chain, HR, marketing) in small trials. This "pokers in the fire" approach allows for broad learning and discovery of value without overinvesting before the technology is fully mature or scaled.

The rapid pace of AI makes traditional, static marketing playbooks obsolete. Leaders should instead foster a culture of agile testing and iteration. This requires shifting budget from a 70-20-10 model (core-emerging-experimental) to something like 60-20-20 to fund a higher velocity of experimentation.

Small firms can outmaneuver large corporations in the AI era by embracing rapid, low-cost experimentation. While enterprises spend millions on specialized PhDs for single use cases, agile companies constantly test new models, learn from failures, and deploy what works to dominate their market.

In the AI era, the pace of change is so fast that by the time academic studies on "what works" are published, the underlying technology is already outdated. Leaders must therefore rely on conviction and rapid experimentation rather than waiting for validated evidence to act.

In the fast-moving AI sector, quarterly planning is obsolete. Leaders should adopt a weekly reassessment cadence and define "boundaries for experimentation" rather than rigid goals. This fosters unexpected discoveries that are essential for staying ahead of competitors who can leapfrog you in weeks.

In a rapidly evolving field like AI, long-term planning is futile as "what you knew three months ago isn't true right now." Maintain agility by focusing on short-term, customer-driven milestones and avoid roadmaps that extend beyond a single quarter.