A mentor isn't someone who provides step-by-step instructions. The most powerful learning comes from finding someone you admire and closely observing their every move, how they speak, and how they behave in the face of obstacles, rather than seeking direct guidance.

When a founder advises a successor to 'make decisions that energize you,' it's a strategic directive, not a wellness tip. It serves as a guardrail against the 'death by a thousand cuts' that comes from compromising core beliefs just to make others comfortable, thereby preserving the vision.

In an era without standardized reporting, Green created her own information advantage. She personally inspected assets like rail yards, talked to workers, and even found disgruntled associates of sellers to uncover hidden flaws. This deep, primary-source due diligence was her key differentiator from other investors.

Early ventures into legally ambiguous or "get rich quick" schemes can be an effective, albeit risky, training ground. This "gray hat phase" forces rapid learning in sales, marketing, and operations, providing valuable lessons that inform more legitimate, scalable businesses later on.

Instead of traditional classroom training, Stone would take new salespeople on live sales calls. They'd observe him, attempt a pitch themselves, and receive immediate feedback. This rapid, immersive cycle built competence and confidence quickly, even for those without a college degree.

When Green trapped a short-seller, she could have financially ruined him. Instead, she charged a modest premium because he had always treated her respectfully. This demonstrates a strategic choice to preserve reputation over maximizing a single transaction, a rare tactic among the Gilded Age's ruthless barons.

The founder hired an experienced CEO and then rotated through leadership roles in different departments (brand, product, tech). This created a self-designed, high-stakes apprenticeship, allowing him to learn every facet of the business from experts before confidently retaking the CEO role.

When transitioning leadership, you must allow your successors to make mistakes. True learning comes from fixing failures, not just replicating successes. As the founder, your instinct is to prevent errors, but you must permit 'fuck ups' for the next generation to truly develop their own capabilities and own the business.

The young founder hired an experienced executive who became a mentor and effectively his boss. He learned more from observing this leader's actions—how he interacted with people and approached problems—than from direct instruction. This demonstrates the power of learning through osmosis from seasoned operators.