Jack Swift: How AI Is Rewriting the Rules of Leadership - Money Stories Ep 31

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Oct 13, 2025

Jack Swift, a former Army Ranger and West Point graduate turned AI fintech leader, shares his transformative journey. He discusses how his definition of success shifted from achievement to alignment, emphasizing the importance of mindfulness and creativity in leadership. Jack reveals fascinating insights on how AI can enhance human potential and the need for adaptive leadership in a fast-changing world. He also talks about redefining wealth as the ability to serve and his work with Sangha, promoting conscious leadership practices.

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ANECDOTE

Childhood Poverty Shaped Purpose

Jack Swift describes growing up in Hope, Arkansas surrounded by poverty which instilled compassion and a desire to serve.
A grocery-store moment when his mom denied apple juice cemented his drive to never lack access to food again.

ANECDOTE

West Point Survival Moment

Jack recounts West Point's shock to his system and the pressure of passing 'rock math' to stay at the academy.
He and a teammate nervously checked posted grades and celebrated when they passed, marking a crucial survival moment.

ANECDOTE

Ranger School's Mind-Body Lessons

Jack describes Ranger School's extreme conditions: 63 days, one meal a day, two hours' sleep on average.
He learned the difference between mind and body and how each dictates action under severe stress.

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Jack Swift followed the path to success with precision.

He graduated from West Point, served as an Army Ranger, and grew to CEO of TIFIN, a category-defining AI fintech platform valued at $842M.

Jack spent years building a successful life. He had the titles, the income, and the momentum.

Over time, the long hours and constant pressure wore him down, until even the wins stopped feeling meaningful.

He realized he was building from fear instead of alignment, and it was costing him his health, his clarity, and his sense of purpose.

On this episode of Money Stories, Jack shares how his definition of success changed, what AI is revealing about human potential, and why presence has become his most valuable asset.

We dive into:

• How Jack rebuilt his life around clarity, not achievement

• Why alignment is now his filter for every decision

• The inner practices that shaped a billion-dollar company

• What leaders need to understand about the role of AI

• Why creativity, not control, is the new edge

• How to build coherence, not just culture, and why that changes everything

About Jack Swift

Jack Swift is a leader who has spent his career operating at the edge of performance and transformation. A West Point graduate and former Airborne Ranger, his foundation in the military shaped a leadership style built on discipline, resilience, and purpose. After his service, Jack brought those same principles into the world of finance and entrepreneurship, guiding companies through growth and reinvention. He helped scale Janus Henderson’s institutional business, co-founded Pacific Current Group, and later led TIFIN, an AI-driven fintech platform that is redefining how wealth and asset managers use AI. Today, Jack advises AI companies, Brightwave and Grid.aero, is Co-Founder of Sangha and serves as a Board Director for Lockton Companies and Bow River Capital.

Connect with Jack

Website: jackcswift.com

Linkedin: https://www.linkedin.com/in/jack-c-swift/

Check out his book coming out early next year titled Level 7 Leadership: Leading in the Age of AI

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