Contrary to the belief that wealth enables better leadership, Bouaziz argues it can be a 'trap.' He has observed successful founders get distracted by newfound wealth, pulling their attention from the business and causing it to stagnate. This period of underperformance often continues until a crisis or board pressure forces them to refocus on their core responsibilities.

The money from generational wealth often disappears by the third generation because the true asset—the financial knowledge and mindset that created it—is not effectively transferred. The knowledge is more valuable than the cash.

Wealthy parents who endlessly provide for their adult children may inadvertently signal a lack of faith in their abilities. This can lead to depression and a sense of incapability, as the financial support is perceived as a message that they are seen as losers.

Massive wealth imposes a hidden 'social debt'—a crushing weight of expectations that dictates how heirs must live, who they can marry, and what values they must hold. As the Vanderbilt family story shows, this can destroy independence and happiness, effectively making heirs prisoners of their fortune.

Instead of a fixed inheritance plan based on age, adopt a flexible strategy that scales financial support up or down based on a child's productivity and life choices. This approach, inspired by Morgan Housel, rewards effort and responsible behavior while avoiding subsidizing unproductive lifestyles.

Wealthy upbringings can be a disadvantage for aspiring investors by dulling the intense drive required to endure the profession's challenges. David Rubenstein argues that those from modest backgrounds often possess a 'hunger' and resilience that is critical for success, as they have more to prove and can better handle frequent setbacks.

While well-intentioned, providing prolonged financial support to adult children communicates a belief that they are incapable of succeeding on their own. This cripples their self-esteem and ambition, making the enabling parent the root of the problem.

Providing children with a high standard of living inadvertently sets that lifestyle as their baseline expectation. This becomes a curse, as they may feel like a failure if they can't replicate it or be prevented from pursuing a fulfilling but less lucrative career.

The traditional model of inheritance is suboptimal. Giving money to your children when they are old provides far less utility than giving it to them in their 30s or 40s. A financial gift at that stage can fundamentally change their life trajectory by helping with a down payment or easing the cost of raising children.