Money acts as a "non-specific amplifier," much like alcohol or power. It doesn't fundamentally change your character but magnifies your existing traits—both good and bad. Insecurities become more pronounced, generosity becomes super-generosity, and a "micro asshole" becomes a "mega asshole."

Unlike first-time founders who struggle for attention, successful repeat founders face the opposite problem. Prospects tend to agree with their ideas due to their reputation, creating 'happy ears' and masking the truth until a payment is requested.

Successful individuals earn 'idiosyncrasy credit,' allowing them to deviate from social norms. However, observers often make the mistake of assuming these eccentricities were necessary for success. In reality, these behaviors are often tolerated or hidden until success provides the freedom to express them.

Founder Donald Spann found that being underestimated as a Black entrepreneur could be turned into an advantage. When you easily surpass the low expectations others might have, it creates an outsized positive impression, making it easier to build rapport and gain respect in business settings.

We project our paths to happiness onto others, forgetting values are individually conditioned. One person's dream (entrepreneurship, multigenerational living) is another's nightmare. This awareness fosters humility and prevents giving prescriptive, biased advice about how to live wisely.

Founders often start with strong intuition but lose it after achieving success. This occurs because long-held societal conditioning, which teaches individuals to distrust themselves and outsource authority to experts, resurfaces and mutes their inner voice.

The real danger for leaders comes during great success, when it is easy to become detached from reality. Avoiding the bubble created by executive perks requires a conscious effort to stay grounded, as this is when judgment is most at risk.

Mentalist Oz Perlman landed more airtime on CNBC than any CEO by tailoring his performance to the network's world: stocks, bonds, and markets. By making his craft relevant to their audience's interests, he became indispensable. To capture attention, obsessively focus on the other person's context and needs.

People's relationship with money is deeply personal, shaped by everything from childhood memories to cultural background. When discussing finance, two people may be using the same words but speaking different 'languages.' Recognizing that a dollar sign can evoke freedom for one person and anxiety for another is key to effective communication.