Crushing It

Real conversations with leaders navigating risk, resilience, and growth in high-stakes environments.

Hosted by former FBI agents and Bawn founders, Crushing It features candid conversations with founders, executives, and advisors navigating growth, cyber risk, and high-stakes decisions.

Featured Episode

Navigating Compliance in the Age of Cybersecurity

Featuring Kate Williams, Partner, Risk Assurance & Advisory – Maxwell Locke & Ritter

Startups are being asked to prove compliance far earlier than they expect—often before they feel ready. Kate Williams explains how SOC 2 readiness, audit timing, and emerging AI risks are reshaping how growing companies earn trust and scale responsibly.

Watch / Listen

What We Cover

Crushing It explores the real decisions, risks, and lessons behind leadership and success—especially when the stakes are high and the path forward isn’t obvious.

Leadership and decision-making under pressure

Risk, trust, and credibility in complex environments

The realities behind growth and success

Lessons learned from setbacks and near-misses

Responsible AI by 2030: Transparency, Trust, and the Risks We Can’t Ignore

Xiaochen Zhang offers a deep dive into responsible AI, revealing why transparency, accountability, sustainability—and missing talent and tools—will define AI’s future.

Watch / Listen

Navigating Compliance in the Age of Cybersecurity

Kate Williams explains why compliance expectations are showing up earlier for growing companies—and how SOC 2 readiness, trust, and emerging AI risks are reshaping how leaders scale responsibly.

Watch / Listen

Playing the Long Game: Risk and Resilience from the World of Golf

Former FBI agent JJ Costigan explains how preparation, discipline, and leadership keep high-stakes environments on course.

Watch / Listen

Turning Risk Into a Business: MGAs Reshaping Insurance

Somil Jain discusses how Managing General Agents (MGAs) turn complex risk—cyber, AI, and emerging tech—into real, scalable insurance businesses.

Watch / Listen

Why Crushing It Exists

Crushing It was created to go beyond the highlight reel. Too often, we see success without hearing about the risks, missteps, and hard decisions that made it possible. This podcast focuses on those moments—where judgment mattered, pressure was real, and the outcome wasn’t guaranteed. It’s about what leaders learn when the stakes are high.

About the Hosts

Jonathan Trimble

Jon is a former FBI Special Agent and cybersecurity executive whose career focused on intelligence, analytics, and technology development. A graduate of the U.S. Coast Guard Academy, he brings a strategic, systems-level perspective to how leaders understand risk and make decisions in complex environments.

Robert Cochran

Rob is a former FBI Special Agent who led and supported extensive international cyber investigations involving complex threat actors and cross-border risk. A graduate of the U.S. Military Academy at West Point, he brings an operational, real-world lens to conversations about resilience, accountability, and leadership under pressure.