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Money Stories · Episode 31

Jack Swift: How AI Is Rewriting the Rules of Leadership

For founders and high achievers rethinking what money is for.

Mike Brown with Jack Swift, CEO of TIFIN · Oct 13, 2025 · 71 min

About this episode

Jack Swift graduated from West Point, served as an Army Ranger and became CEO of TIFIN, an AI fintech platform. Years of pressure wore him down until even the wins stopped feeling meaningful.

He and Mike talk about alignment as a filter for decisions, presence, and what leaders need to understand about AI.

More from Money Stories: all episodes. Mike’s book Be Rich Now covers the same ground in depth.