Success brings knowledge, but it also creates a bias against trying unconventional ideas. Early-stage entrepreneurs are "too dumb to know it was dumb," allowing them to take random shots with high upside. Experienced founders often filter these out, potentially missing breakthroughs, fun, and valuable memories.

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.

A 2022 study by the Forecasting Research Institute has been reviewed, revealing that top forecasters and AI experts significantly underestimated AI advancements. They assigned single-digit odds to breakthroughs that occurred within two years, proving we are consistently behind the curve in our predictions.

Corporate creativity follows a bell curve. Early-stage companies and those facing catastrophic failure (the tails) are forced to innovate. Most established companies exist in the middle, where repeating proven playbooks and playing it safe stifles true risk-taking.

The Miami Heat's superstar trio only won championships after adding Shane Battier, a 'no stats all-star.' His value came from making others better—setting screens and ensuring team cohesion. This highlights the critical role of 'glue players' who enable superstars to shine, a contribution often missed by traditional metrics.

To drive adoption, changing the default from opt-in to opt-out is far more effective than simply reducing friction. When a company automatically enrolled new employees into a 401(k) plan, participation jumped from 50% to 90%, demonstrating the immense power of status quo bias.

The "bitter lesson" in AI research posits that methods leveraging massive computation scale better and ultimately win out over approaches that rely on human-designed domain knowledge or clever shortcuts, favoring scale over ingenuity.

After discovering the 'Winner's Curse' was causing them to overpay for oil leases, Arco engineers faced a problem: bidding less meant losing auctions. Instead of illegal collusion, they published a scientific paper on the phenomenon. This educated their competitors, reducing the likelihood of anyone overbidding and making the market more rational.

When driving major organizational change, a data-driven approach from the start is crucial for overcoming emotional resistance to established ways of working. Building a strong business case based on financial and market metrics can depersonalize the discussion and align stakeholders more quickly than relying on vision alone.