Growing up without facing challenges or failure makes it difficult to handle adversity as an adult. Adversity is the core foundation of sustained success because it builds resilience. Coddling children, such as with eighth-place trophies, robs them of the chance to develop this crucial life skill.

To raise children who thrive outside "the system," parents must shift from preventing failure to encouraging resilience. This means getting kids comfortable with losing through competition, de-emphasizing grades, and prioritizing work ethic and real-world experience over trophies.

Success requires resilience, which is built by experiencing and recovering from small failures. Engaging in activities with public stakes, like sports or public speaking, teaches you to handle losses, bounce back quickly, and develop the mental fortitude needed for high-stakes endeavors.

Vaynerchuk attributes his success to early experiences of 'losing'—as an immigrant, a poor student, and an average athlete. These experiences eliminated his fear of failure, a critical trait for entrepreneurs who must constantly take risks and face judgment.

Resilience isn't about avoiding failure but about developing the ability to recover from it swiftly. Experiencing public failure and learning to move on builds a crucial 'muscle' for rebounding. This capacity to bounce back from a loss is more critical for long-term success than maintaining a perfect record.

Modern parenting that shields children from failure with participation trophies actually teaches indifference and fear. The key is to teach kids that losing is not only acceptable but good. A child who learns to love losing builds the resilience needed for the real world.

Crying after a loss indicates that a child cares deeply, which is a positive trait that should be encouraged, not suppressed with phrases like 'it's just a game.' This passion is a foundational element for developing a competitive spirit and resilience. Teaching kids that competition doesn't matter can lead to apathy and depression.

Using his sports fandom as a metaphor, Gary Vaynerchuk explains that the day after his favorite teams (Rangers, Yankees) won championships, he stopped following them as intensely. The real fun and engagement are in the losing, the striving, and the adversity of the journey—not the fleeting moment of success at the end.

Supporting a perennially losing sports team builds resilience and a love for the struggle, core traits of an entrepreneur. Deriving self-esteem from a winning team is a crutch, whereas embracing the pain, grind, and hardship of losing builds the character necessary to succeed in business.