Andrew and Jay trade stories and strategies around one of the most pivotal parts of entrepreneurship: risk.

Jay recounts signing the papers for a commercial building just weeks before the world shut down in 2020—and how faith, clarity, and conviction helped him stay the course. Andrew reflects on leaving his teaching job, taking out his first major equipment loan, and learning to distinguish between high-stakes risks and small, reversible bets.

Together, they explore:

• How to tell if a risk is worth it—and when it’s not
• The difference between existential bets and strategic discomfort
• Why every major leap should be built on a bedrock of small, disciplined moves
• Learning from others’ scars instead of earning your own
• How lean thinking shapes their approach to change, investment, and uncertainty