Machiavelli Had it Easy is an engaging text for the emerging discipline of governance. Gaps arise when directors and managers come together from diverse vocational and cultural languages and interests. Compressed information streams in the digital age, yet few reconcile silos of business, legal expertise and regulatory public-interests for informed decisions. This text presents research and a market-tested decision-framework for comparative law, market practice, and human nature in the vital strategic-oversight role of governance. Informed by cognitive science, business practice and legal duties, one conclusion is that bias and self-interests are instinctive but reconciling best-interests is not. Too often lessons learned from centuries of law are overlooked. The chapters are a dozen inquiries into recurring problems in the boardroom. Part one is an entry-level technical reference of law and governance principles. Unique appendices of keywords and case notes will aid those new to markets governed by the western rule-of-law and those tripping on gaps in comparative jargon. Part two is a series of practical hot-topics in the context of law and governance; part three looks to next steps in accountability and liability. The text will help accountants, engineers, lawyers, and business operations and market-policy experts from around the world work together, and; professors, professionals and students anticipate change. After drilling through accountability and liability for hybrid organizations, typical crises are revealed to be from a lack of aligning interests and related information churn. Conclusions of the how and why of governance systems link the human condition and the rule-of-law in the digital age.