In this follow-up episode of Forge, Josh and Kenton continue the conversation about failure, resilience, and the long road of learning that comes with building a business.
After reflecting on the collapse of Kenton’s early real estate momentum in the previous episode, the discussion turns toward what came after.
The years that followed were not defined by a single event, but by the slower and often more difficult process of rebuilding confidence, culture, and leadership from the inside out.
Kenton shares how the internal impact of that season lingered longer than the external circumstances. Even as the company continued to operate and grow from the outside, the weight of that earlier failure shaped the way he made decisions, interacted with his team, and carried the responsibility of leadership.
Josh and Kenton explore how pride, fear, and lost confidence can quietly isolate leaders at the very moment when they need their people the most. They discuss the surprising reality that many team members are often willing to rally around a struggling leader, but only if they’re allowed into the process.
The conversation also turns toward the nature of risk. Entrepreneurs often celebrate bold moves and big swings, but fewer people talk openly about the emotional resilience required when those swings miss. Kenton reflects on how early success created a sense of certainty that later setbacks challenged, forcing him to develop a deeper understanding of resilience and self-awareness.
Throughout the episode, the discussion moves beyond business tactics and into the mindset required to continue moving forward. Josh and Kenton talk about the difference between regret and bitterness, why honest post-mortems matter, and how leaders can learn to separate criticism of their role from criticism of their identity.
They also reflect on the importance of creating environments where others can take risks without fear of catastrophic failure, whether in business, leadership, or even parenting.
This episode is ultimately about growth through adversity, and the quiet maturity that develops when leaders learn to analyze failure without being defined by it.
Original theme music composed and performed by Ben Smith
Produced by Seth Steward Productions
Co produced by Kalen Wookey
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