What does it take to leave a skyrocketing career at a billion-dollar defense startup to serve your country?

Matt Weiss made that exact choice, and it shaped everything about how he leads today.

In this episode, Matt shares his unconventional journey from rejecting Goldman Sachs and joining Anduril as one of their earliest employees, to walking away from it all to become a Marine Corps Intelligence Officer. Now, he's co-founding Circuit, an AI company bringing cutting-edge technology to manufacturing companies across America's heartland.

This conversation dives deep into what the military teaches about leadership, why decision-making must live close to the problem, and how real innovation is born from discipline, humility, and relentless feedback. From Gen Z leadership and the military recruiting crisis to AI, manufacturing, and building companies in the heartland, this episode is a masterclass in long-term thinking.

If you want to understand what leadership really looks like under pressure and how greatness is built when no one is watching, this episode delivers.

Key Takeaways

🟦 Leadership is learned through responsibility

🟦 Discipline compounds over time

🟦 Innovation breaks regression to the mean

🟦 Service builds resilience

(00:00) Intro

(01:36) Matt's Background and Career

(03:50) Joining Anduril

(05:39) Transition to Military Service

(08:52) Writing the Book on Military Recruitment

(15:18) Leadership Lessons from the Military

(19:36) Business Ventures and Mentorship

(23:35) Connecting Legacy Systems with AI

(27:52) Targeting Large Enterprises

(28:43) Military Leadership Lessons

(35:38) What is Greatness

(40:31) Where to Find Matt

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