Jackson McGregor: Redefining Masculinity, Purpose & The Lost Art of Brotherhood

In this episode of the Cut The Sh*t Podcast, Lewis Kross sits down with Jackson to have an open, honest conversation about what masculinity really means in today’s world.
They dive deep into accountability, purpose, and the loss of rites of passage that once helped boys become men. The discussion touches on how shame and guilt often lie beneath anger, how disrespect shapes identity, and why the absence of true masculine guidance is leaving men directionless.
Jackson and Lewis also explore the balance between masculine and feminine energy, the role of community and brotherhood, and how authentic connection and fear can become powerful tools for personal growth.
This episode challenges stereotypes around toxic masculinity, celebrates emotional strength, and reminds men that leadership starts from within.