Unlike shares purchased with personal capital, stock options are often treated like "house money." This incentivizes CEOs to make excessively risky bets with shareholder capital because they capture all the upside but are not punished for failure, leading to poor capital allocation.

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The CEO distinguishes 'betting' from 'gambling.' He defines gambling not by the activity but by its structure: creating an artificial risk where the house has stacked odds. In contrast, trading on natural, pre-existing risks in a fair, market-based system is fundamentally different.

Charlie Munger, who considered himself in the top 5% at understanding incentives, admitted he underestimated their power his entire life. This highlights the pervasive and often hidden influence of reward systems on human behavior, which can override all other considerations.

While bonuses tied to revenue incentivize employees to perform specific tasks, they are purely transactional. Granting stock options makes team members think holistically about the entire business's long-term health, from strategic opportunities to small cost savings, creating true psychological ownership.

Gifting non-performance-based shares to all employees doesn't foster an 'owner mindset.' True ownership thinking is better cultivated through incentives tied to specific, controllable outcomes, like targeted cash bonuses. Standard equity compensation often just becomes another part of the salary package, disconnected from individual impact.

Musk's performance-based compensation sets a precedent for other CEOs to approach their boards with ambitious growth targets in exchange for significant equity increases. This challenges the traditional one-way dilution model for founders and executives.

Barry Diller dismisses the common belief that stock options retain employees, calling it "hogwash." He argues people stay for opportunity and engaging work, not because they are waiting for options to vest. His approach is to provide opportunity and pay for performance in cash, empowering employees to invest if they wish.

Corporate leaders are incentivized and wired to pursue growth through acquisition, constantly getting bigger. However, they consistently fail at the strategically crucial, but less glamorous, task of divesting assets at the right time, often holding on until value has significantly eroded.

Spinoza's concept of "canatus" (striving) highlights how misalignment between individual goals (e.g., a CEO's reputation) and the organization's goals (shareholder returns) creates agency problems that damage the entire enterprise, underscoring the critical need for incentive alignment.

When a private equity investment thesis is primarily built around a single person (e.g., a star CEO), it's a sign of weak conviction in the underlying business. If that person fails or leaves, the entire rationale for the investment collapses, revealing a lack of fundamental belief in the company's industry or competitive position.

Exercising stock options is an investment decision, yet employees are rarely given the same information as investors. Employees should reframe this and request access to the company's data room to make an informed choice, pushing for greater transparency and fairness in startup equity compensation.

Executive Stock Options Encourage Reckless "House Money" Risk-Taking | RiffOn