The 'Mad Men' era of relying on a creative director's gut feel is obsolete. Many leaders still wrongly judge marketing creative based on their personal taste ('I don't like that picture'). The correct modern approach is to deploy content and use the resulting performance data to make informed decisions.

Data's role is to reveal reality and identify problems or opportunities (the "what" and "where"). It cannot prescribe the solution. The creative, inventive process of design is still required to determine "how" to solve the problem effectively.

The market for financial forecasts is driven by a psychological need to reduce uncertainty, not a demand for accuracy. Pundits who offer confident, black-and-white predictions thrive because they soothe this anxiety. This is why the industry persists despite a terrible track record; it's selling a feeling, not a result.

Barry Diller's key lesson from failure is that experience breeds cynicism, which corrupts good decision-making. He advises leaders to constantly fight this tendency and "scrub their instincts clean." Maintaining a degree of naivete is crucial for accurately judging new ideas without being biased by past negative experiences.

After nearly crashing his plane by abandoning his flight plan on a whim, Jim Clayton learned a critical lesson: in high-stress situations, your senses can be wrong. He applied this to business, relying on data and strategic plans over impulsive emotional reactions during predicaments.

Founders often start with strong intuition but lose it after achieving success. This occurs because long-held societal conditioning, which teaches individuals to distrust themselves and outsource authority to experts, resurfaces and mutes their inner voice.

Intuition is often overridden in professional settings because it's intangible. A bad decision backed by a rational explanation is often more acceptable than a good one based on a "gut feeling," which can feel professionally risky.

Diller’s process for navigating the unknown isn't about brilliance but relentless iteration. He describes it as taking "one dumb step" at a time, bouncing off the walls of bad ideas and mistakes, and course-correcting. This embraces looking foolish as a prerequisite for finding the right path.

Entrepreneurs are natural risk-takers. Relying solely on logic, which is designed to keep you safe by recalling past failures, stifles the very creative and intuitive superpowers that drive entrepreneurial success.