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.

The conventional wisdom that enterprises are blocked by a lack of clean, accessible data is wrong. The true bottleneck is people and change management. Scrappy teams can derive significant value from existing, imperfect internal and public data; the real challenge is organizational inertia and process redesign.

Investor Stacy Brown-Philpot advises that to win large enterprise deals, an AI startup must create a solution so compelling it beats the customer's internal team vying for the same budget. The goal is to access the core 15% budget pool, not the 1% 'play money' budget.

Enterprises struggle to get value from AI due to a lack of iterative, data-science expertise. The winning model for AI companies isn't just selling APIs, but embedding "forward deployment" teams of engineers and scientists to co-create solutions, closing the gap between prototype and production value.

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.

Off-the-shelf AI models can only go so far. The true bottleneck for enterprise adoption is "digitizing judgment"—capturing the unique, context-specific expertise of employees within that company. A document's meaning can change entirely from one company to another, requiring internal labeling.

Many companies struggle with AI not just because of data challenges, but because they lack the internal expertise, governance, and organizational 'muscle' to use it effectively. Building this human-centric readiness is a critical and often overlooked hurdle for successful AI implementation.

Headlines about high AI pilot failure rates are misleading because it's incredibly easy to start a project, inflating the denominator of attempts. Robust, successful AI implementations are happening, but they require 6-12 months of serious effort, not the quick wins promised by hype cycles.

The primary reason multi-million dollar AI initiatives stall or fail is not the sophistication of the models, but the underlying data layer. Traditional data infrastructure creates delays in moving and duplicating information, preventing the real-time, comprehensive data access required for AI to deliver business value. The focus on algorithms misses this foundational roadblock.