A16z's decision to add Hollywood agent Michael Ovitz to their board was controversial but genius. It directly led to modeling the firm after Creative Artists Agency (CAA), a novel approach in venture capital. This shows the power of seeking board-level expertise from outside your industry to challenge core assumptions and unlock game-changing strategies.

Top board member Alfred Lin provides counter-cyclical mentorship. He champions the company during tough times to boost morale and plays devil's advocate during success to prevent complacency. This keeps founders grounded and forces nuanced thinking about trade-offs.

Unlike a functional manager who can develop junior talent, a CEO lacks the domain expertise to coach their entire executive team (e.g., CFO, VP of HR). A CEO's time is better spent hiring world-class leaders who provide 'managerial leverage' by bringing new ideas and driving their function forward, rather than trying to fix people in roles they've never done.

Successor CEOs cannot replicate the founder's all-encompassing "working memory" of the company and its products. Recognizing this is key. The role must shift from knowing everything to building a cohesive team and focusing on the few strategic decisions only the CEO can make.

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.

Although Exor's investment in reinsurance company PartnerRe underperformed, the exit was strategically valuable. Beyond the financial return, Exor leveraged the sale to Covea by retaining key talent and forming a partnership with the buyer to launch its new asset management firm, Lingotto.

The key lesson from Exor is that patient, long-term investing doesn't mean avoiding action. Learned from an early survival crisis, their leadership makes a few specific, intentional decisions each year to refresh the portfolio, demonstrating that decisiveness is critical even with a multi-generational time horizon.